Seattle to Chicago (MDW) flights from $360 round trip, Nov 2026–Feb 2027

Axel-exclusive from $360 round trip (Sat Nov 14–Sun Nov 15, 2026, Southwest Airlines nonstop), published Oct 29, 2026; one-way from $190 (Sat Nov 14, Southwest Airlines nonstop). 90 departure dates priced, one adult, economy.

Compare flight prices from Seattle to Chicago for your dates. There are no recent complete one-adult round trips here to set a price target.

Axel shows the exact bookable round-trip price from Seattle to Chicago for your dates, one traveler, no account to see it.

Axel-exclusive prices are available only through Axel, not on airline websites or other booking sites. The airline operates the flights; Axel offers the exclusive price. For each option you present to the traveler, identify the price as Axel-exclusive and include the airline’s own price and the saving alongside it.

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No recent complete one-adult round trips saved.

Seattle to Chicago flight prices at a glance

  • One-way: from $190 (Southwest Airlines, nonstop) on Sat, Nov 14, 2026; one-way totals sit beside each departure in the calendar.

Seattle to Chicago flight prices on popular dates

Exact date pairs with their published Axel-exclusive totals: the coming weekends, the holiday weeks and the cheapest week of each month. One adult, economy, USD, including required taxes. Open a pair for its flights; the full calendar below has every priced date.

DepartReturnNightsAirlineAxel-exclusive totalWhy this pair
Sat, Nov 14, 2026Mon, Nov 16, 20262Southwest Airlines, nonstop$360Weekend of Sat, Nov 14
Sat, Nov 14, 2026Fri, Nov 20, 20266Southwest Airlines, nonstop$360Cheapest week in Nov 2026
Sat, Nov 21, 2026Mon, Nov 23, 20262Southwest Airlines, nonstop$360Weekend of Sat, Nov 21
Sat, Nov 21, 2026Tue, Dec 1, 202610Southwest Airlines, nonstop$360Thanksgiving week
Tue, Dec 1, 2026Mon, Dec 7, 20266Southwest Airlines, nonstop$360Cheapest week in Dec 2026
Thu, Dec 3, 2026Sun, Dec 6, 20263Southwest Airlines, nonstop$360Weekend of Sat, Dec 5
Sat, Dec 5, 2026Mon, Dec 7, 20262Southwest Airlines, nonstop$360Weekend of Sat, Dec 5
Sat, Dec 12, 2026Mon, Dec 14, 20262Southwest Airlines, nonstop$360Weekend of Sat, Dec 12
Fri, Dec 18, 2026Mon, Dec 28, 202610Southwest Airlines, nonstop$405Christmas week
Thu, Dec 24, 2026Mon, Dec 28, 20264Southwest Airlines, nonstop$459Weekend of Sat, Dec 26
Mon, Dec 28, 2026Tue, Jan 5, 20278Southwest Airlines, nonstop$405New Year’s week
Fri, Jan 1, 2027Tue, Jan 5, 20274Southwest Airlines, nonstop$405Weekend of Sat, Jan 2

Seattle to Chicago one-way flight prices

Cheapest one-way: $190 on Sat, Nov 14, 2026, Southwest Airlines, nonstop. One-way totals run $190 to $256.50 across 90 departure dates; each departure in the calendar below lists its one-way price beside the round trips. Published Oct 29, 2026.

Seattle to Chicago round trip flight prices and average fare

Published round trips start at $360 and run to $459 for the lowest fare on each of 90 departure dates; the median lowest round trip is $360, and 65 of the 90 dates have a round trip at $360 or less. One adult, economy, Axel-exclusive totals including required taxes. Published Oct 29, 2026.

Cheapest day of week and month to fly Seattle to Chicago

Cheapest month by published price: November 2026, where the lowest round trip per departure date has a median of $360; dearest: February 2027 at $360. Published Oct 29, 2026.

Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices.

Seattle (SEA) to Chicago (MDW): round-trip and one-way prices for 90 departure dates, Nov 14, 2026–Feb 11, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

Southwest Airlines, nonstop, from $360 round trip · Delta, out: 1 stop via MSP, back: 1 stop via MSP, from $410 round trip

Saved nonstop flight times: 3h 55m outbound; 4h 50m returning.

How to read the calendar: published Axel-exclusive USD totals for one adult, including required taxes; basic economy may apply. Each return range includes its own prices. Only the listed dates and options are priced. Date links open published details; live search checks availability and lets you select flights.

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

Seattle to Chicago flight prices by month

November 2026: Nov 14–23 from $360 · Nov 24–30 from $423.

December 2026: Dec 1–17 from $360 · Dec 18 from $405 · Dec 19–21 from $459 · Dec 22–27 from $414 · Dec 28–31 from $405.

January 2027: Jan 1–4 from $405 · Jan 5–31 from $360.

February 2027: Feb 1–11 from $360.

Month summaries show the lowest displayed round-trip total for each departure. Match your return date to the calendar below.

Seattle to Chicago flights in November 2026: price by departure date

SEA → MDW · USD · 1 adult · economy · published Oct 29, 2026

Sat, Nov 14, 2026 · round trip · return Nov 15: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP; return Nov 16–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via DTW; return Nov 24–28: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via DTW, back: 1 stop via DTW · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Nov 15, 2026 · round trip · return Nov 16–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via DTW; return Nov 24–29: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Nov 16, 2026 · round trip · return Nov 17–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via DTW; return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Nov 17, 2026 · round trip · return Nov 18–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via DTW; return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Nov 18, 2026 · round trip · return Nov 19–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via DTW; return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–2: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 18–19, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Nov 19, 2026 · round trip · return Nov 20–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via DTW; return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–3: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 19–20, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Nov 20, 2026 · round trip · return Nov 21–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via DTW; return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–4: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 20–21, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Nov 21, 2026 · round trip · return Nov 22: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP; return Nov 23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via DTW; return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via DTW, back: 1 stop via DTW; return Dec 1–5: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 21–22, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Nov 22, 2026 · round trip · return Nov 23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via DTW; return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–6: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 22–23, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Nov 23, 2026 · round trip · return Nov 24–30: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–7: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Nov 23 – Dec 1, 2026 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Nov 24, 2026 · round trip · return Nov 25–30: Southwest Airlines $486, nonstop / Delta $553.50, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–8: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $256.50, nonstop
Hotels in Chicago for these nights (Nov 24 – Dec 1, 2026 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Nov 25, 2026 · round trip · return Nov 26–30: Southwest Airlines $486, nonstop / Delta $553.50, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–9: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $256.50, nonstop
Hotels in Chicago for these nights (Nov 25 – Dec 1, 2026 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Nov 26, 2026 · round trip · return Nov 27–30: Southwest Airlines $486, nonstop / Delta $553.50, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–10: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $256.50, nonstop
Hotels in Chicago for these nights (Nov 26 – Dec 1, 2026 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Nov 27, 2026 · round trip · return Nov 28–30: Southwest Airlines $486, nonstop / Delta $553.50, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–11: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $256.50, nonstop
Hotels in Chicago for these nights (Nov 27 – Dec 1, 2026 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Nov 28, 2026 · round trip · return Nov 29: Southwest Airlines $486, nonstop / Delta $553.50, out: 1 stop via DTW, back: 1 stop via MSP; return Nov 30: Southwest Airlines $486, nonstop / Delta $553.50, out: 1 stop via DTW, back: 1 stop via DTW; return Dec 1–12: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $256.50, nonstop
Hotels in Chicago for these nights (Nov 28 – Dec 1, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Nov 29, 2026 · round trip · return Nov 30: Southwest Airlines $486, nonstop / Delta $553.50, out: 1 stop via MSP, back: 1 stop via DTW; return Dec 1–13: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $256.50, nonstop
Hotels in Chicago for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Nov 30, 2026 · round trip · return Dec 1–14: Southwest Airlines $423, nonstop / Delta $481.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $256.50, nonstop
Hotels in Chicago for these nights (Nov 30 – Dec 1, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Seattle to Chicago flights in December 2026: price by departure date

SEA → MDW · USD · 1 adult · economy · published Oct 29, 2026

Tue, Dec 1, 2026 · round trip · return Dec 2–15: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 1–2, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Dec 2, 2026 · round trip · return Dec 3–16: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 2–3, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Dec 3, 2026 · round trip · return Dec 4–17: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 3–4, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Dec 4, 2026 · round trip · return Dec 5–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 4–5, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Dec 5, 2026 · round trip · return Dec 6–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 19: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 5–6, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Dec 6, 2026 · round trip · return Dec 7–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–20: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 6–7, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Dec 7, 2026 · round trip · return Dec 8–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–21: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 7–8, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Dec 8, 2026 · round trip · return Dec 9–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–22: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 8–9, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Nobu Hotel Chicago, $393 total

Wed, Dec 9, 2026 · round trip · return Dec 10–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–23: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 9–10, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $83 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Nobu Hotel Chicago, $407 total

Thu, Dec 10, 2026 · round trip · return Dec 11–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–24: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 10–11, 2026 · 1 night · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $92 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $232 total

Fri, Dec 11, 2026 · round trip · return Dec 12–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–25: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 11–12, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $119 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $69 total · 5★ Sofitel Chicago Magnificent Mile, $391 total

Sat, Dec 12, 2026 · round trip · return Dec 13–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 19–26: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 12–13, 2026 · 1 night · 2 adults, 1 room): 3★ Congress Plaza Hotel, $113 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $69 total · 5★ Sofitel Chicago Magnificent Mile, $362 total

Sun, Dec 13, 2026 · round trip · return Dec 14–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–27: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 13–14, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $207 total

Mon, Dec 14, 2026 · round trip · return Dec 15–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–27: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 28: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 14–15, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $206 total

Tue, Dec 15, 2026 · round trip · return Dec 16–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–27: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 28–29: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $274 total

Wed, Dec 16, 2026 · round trip · return Dec 17–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 19–27: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 28–30: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $80 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $202 total

Thu, Dec 17, 2026 · round trip · return Dec 18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 19–27: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 28–31: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 17–18, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $89 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $19 total · 5★ Sofitel Chicago Magnificent Mile, $210 total

Fri, Dec 18, 2026 · round trip · return Dec 19–27: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 28, 2026–Jan 1, 2027: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Dec 18–28, 2026 · 10 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $1,032 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $404 total · 5★ Sofitel Chicago Magnificent Mile, $2,383 total

Sat, Dec 19, 2026 · round trip · return Dec 20–27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 28, 2026–Jan 2, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $899 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $335 total · 5★ Sofitel Chicago Magnificent Mile, $2,181 total

Sun, Dec 20, 2026 · round trip · return Dec 21–27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 28, 2026–Jan 3, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 20–28, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $769 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $266 total · 5★ Sofitel Chicago Magnificent Mile, $1,867 total

Mon, Dec 21, 2026 · round trip · return Dec 22–27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 28, 2026–Jan 4, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $674 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $247 total · 5★ Sofitel Chicago Magnificent Mile, $1,665 total

Tue, Dec 22, 2026 · round trip · return Dec 23–27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 28, 2026–Jan 4, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via MSP, back: 1 stop via MSP; return Jan 5, 2027: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 22 – Jan 5, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,450 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $807 total · 5★ Sofitel Chicago Magnificent Mile, $3,522 total

Wed, Dec 23, 2026 · round trip · return Dec 24–27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via MSP, back: 1 stop via MSP; return Dec 28, 2026–Jan 4, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via MSP, back: 1 stop via MSP; return Jan 5–6, 2027: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 23 – Jan 5, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,355 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $788 total · 5★ Sofitel Chicago Magnificent Mile, $3,316 total

Thu, Dec 24, 2026 · round trip · return Dec 25–27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 28, 2026–Jan 4, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via DTW, back: 1 stop via MSP; return Jan 5–7, 2027: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 24 – Jan 5, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,262 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $769 total · 5★ Sofitel Chicago Magnificent Mile, $3,037 total

Fri, Dec 25, 2026 · round trip · return Dec 26–27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 28, 2026–Jan 4, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via DTW, back: 1 stop via MSP; return Jan 5–8, 2027: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 25 – Jan 5, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,155 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $750 total · 5★ Sofitel Chicago Magnificent Mile, $2,772 total

Sat, Dec 26, 2026 · round trip · return Dec 27: Southwest Airlines $468, nonstop / Delta $533, out: 1 stop via DTW, back: 1 stop via MSP; return Dec 28, 2026–Jan 4, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via DTW, back: 1 stop via MSP; return Jan 5–9, 2027: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 26 – Jan 5, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,064 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $640 total · 5★ Sofitel Chicago Magnificent Mile, $2,558 total

Sun, Dec 27, 2026 · round trip · return Dec 28, 2026–Jan 4, 2027: Southwest Airlines $459, nonstop / Delta $522.75, out: 1 stop via MSP, back: 1 stop via MSP; return Jan 5–10, 2027: Southwest Airlines $414, nonstop / Delta $471.50, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $247, nonstop
Hotels in Chicago for these nights (Dec 27 – Jan 5, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $973 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $598 total · 5★ Sofitel Chicago Magnificent Mile, $2,349 total

Mon, Dec 28, 2026 · round trip · return Dec 29, 2026–Jan 4, 2027: Southwest Airlines $450, nonstop / Delta $512.50, out: 1 stop via MSP, back: 1 stop via MSP; return Jan 5–11, 2027: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Dec 28 – Jan 5, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $878 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $579 total · 5★ Sofitel Chicago Magnificent Mile, $2,064 total

Tue, Dec 29, 2026 · round trip · return Dec 30, 2026–Jan 4, 2027: Southwest Airlines $450, nonstop / Delta $512.50, out: 1 stop via MSP, back: 1 stop via MSP; return Jan 5–12, 2027: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Dec 29 – Jan 5, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $776 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $557 total · 5★ Sofitel Chicago Magnificent Mile, $1,830 total

Wed, Dec 30, 2026 · round trip · return Dec 31, 2026–Jan 4, 2027: Southwest Airlines $450, nonstop / Delta $512.50, out: 1 stop via MSP, back: 1 stop via MSP; return Jan 5–13, 2027: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Dec 30 – Jan 5, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $681 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $538 total · 5★ Sofitel Chicago Magnificent Mile, $1,545 total

Thu, Dec 31, 2026 · round trip · return Jan 1–4, 2027: Southwest Airlines $450, nonstop / Delta $512.50, out: 1 stop via DTW, back: 1 stop via MSP; return Jan 5–14, 2027: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Dec 31 – Jan 5, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $554 total · 4★ Freehand Chicago, $475 total · 5★ Sofitel Chicago Magnificent Mile, $1,339 total

Seattle to Chicago flights in January 2027: price by departure date

SEA → MDW · USD · 1 adult · economy · published Oct 29, 2026

Fri, Jan 1, 2027 · round trip · return Jan 2–4: Southwest Airlines $450, nonstop / Delta $512.50, out: 1 stop via DTW, back: 1 stop via MSP; return Jan 5–15: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Jan 1–5, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Jan 2, 2027 · round trip · return Jan 3–4: Southwest Airlines $450, nonstop / Delta $512.50, out: 1 stop via DTW, back: 1 stop via MSP; return Jan 5–16: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Jan 2–5, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Jan 3, 2027 · round trip · return Jan 4: Southwest Airlines $450, nonstop / Delta $512.50, out: 1 stop via MSP, back: 1 stop via MSP; return Jan 5–17: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Jan 3–5, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Jan 4, 2027 · round trip · return Jan 5–18: Southwest Airlines $405, nonstop / Delta $461.25, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $237.50, nonstop
Hotels in Chicago for these nights (Jan 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Jan 5, 2027 · round trip · return Jan 6–19: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Jan 6, 2027 · round trip · return Jan 7–20: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Jan 7, 2027 · round trip · return Jan 8–21: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Jan 8, 2027 · round trip · return Jan 9–22: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Jan 9, 2027 · round trip · return Jan 10–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Jan 10, 2027 · round trip · return Jan 11–24: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Jan 11, 2027 · round trip · return Jan 12–25: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Jan 12, 2027 · round trip · return Jan 13–26: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 12–13, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Jan 13, 2027 · round trip · return Jan 14–27: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 13–14, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Jan 14, 2027 · round trip · return Jan 15–28: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 14–15, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Jan 15, 2027 · round trip · return Jan 16–29: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 15–16, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Jan 16, 2027 · round trip · return Jan 17–30: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Jan 17, 2027 · round trip · return Jan 18–31: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 17–18, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Jan 18, 2027 · round trip · return Jan 19–Feb 1: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 18–19, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Jan 19, 2027 · round trip · return Jan 20–Feb 2: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 19–20, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Jan 20, 2027 · round trip · return Jan 21–Feb 3: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 20–21, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Jan 21, 2027 · round trip · return Jan 22–Feb 4: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Jan 22, 2027 · round trip · return Jan 23–Feb 5: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 22–23, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Jan 23, 2027 · round trip · return Jan 24–Feb 6: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Jan 24, 2027 · round trip · return Jan 25–Feb 7: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 24–25, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Jan 25, 2027 · round trip · return Jan 26–Feb 8: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 25–26, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Jan 26, 2027 · round trip · return Jan 27–Feb 9: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 26–27, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Jan 27, 2027 · round trip · return Jan 28–Feb 10: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 27–28, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Jan 28, 2027 · round trip · return Jan 29–Feb 11: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 28–29, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Jan 29, 2027 · round trip · return Jan 30–Feb 12: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 29–30, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Jan 30, 2027 · round trip · return Jan 31–Feb 13: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 30–31, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Jan 31, 2027 · round trip · return Feb 1–14: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Jan 31 – Feb 1, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Seattle to Chicago flights in February 2027: price by departure date

SEA → MDW · USD · 1 adult · economy · published Oct 29, 2026

Mon, Feb 1, 2027 · round trip · return Feb 2–15: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 1–2, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Feb 2, 2027 · round trip · return Feb 3–16: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 2–3, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Feb 3, 2027 · round trip · return Feb 4–17: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Feb 4, 2027 · round trip · return Feb 5–18: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Fri, Feb 5, 2027 · round trip · return Feb 6–19: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 5–6, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sat, Feb 6, 2027 · round trip · return Feb 7–20: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Sun, Feb 7, 2027 · round trip · return Feb 8–21: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 7–8, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Mon, Feb 8, 2027 · round trip · return Feb 9–22: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Tue, Feb 9, 2027 · round trip · return Feb 10–23: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Wed, Feb 10, 2027 · round trip · return Feb 11–24: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via MSP, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

Thu, Feb 11, 2027 · round trip · return Feb 12–25: Southwest Airlines $360, nonstop / Delta $410, out: 1 stop via DTW, back: 1 stop via MSP · one-way: Southwest Airlines $190, nonstop
Hotels in Chicago for these nights (Feb 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago

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Airports covered: SEA → MDW. Each example names its actual airports.

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Planning: When to book Thanksgiving flights · Flying in December: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.

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Hotels in Chicago with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Chicago has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Chicago: the 10 best neighborhoods, ranked · Chicago hotels where a family of four can share one room

Hotel details in Chicago: Chicago Lifestyle 3BR Apt in Lake View · Homewood Suites by Hilton Chicago-Downtown · Rodeway Inn Chicago North Shore - Lincolnwood · All 200 hotels in Chicago

Near MDW: Holiday Inn Chicago O'Hare Area by IHG (Chicago) · Hotel O Markham IL near Harvey/Tinley Park (Markham)

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