Denver (DEN) to Chicago (MDW), Jan 19, 2027: round trips from $238, one way from $128

Denver (DEN) to Chicago (MDW), Jan 19, 2027: round trips from $238, one way from $128 on Axel, checked Nov 13, 2026. Lowest published fares: $238 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 19–23, 2027; $128 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 19, 2027; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Hotels in Chicago for these trips

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 nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Jan 19–20, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 a night · 4★ Freehand Chicago, $73 a night · 5★ Sofitel Chicago Magnificent Mile, $253 a night
• Hotels in Chicago for these nights (Jan 19–21, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $74 a night, $147 for 2 nights · 4★ Freehand Chicago, $73 a night, $145 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $232 a night, $463 for 2 nights
• Hotels in Chicago for these nights (Jan 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $73 a night, $220 for 3 nights · 4★ Freehand Chicago, $72 a night, $217 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $233 a night, $699 for 3 nights
• Hotels in Chicago for these nights (Jan 19–23, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $80 a night, $318 for 4 nights · 4★ Freehand Chicago, $74 a night, $295 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $227 a night, $909 for 4 nights
• Hotels in Chicago for these nights (Jan 19–24, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $393 for 5 nights · 4★ Freehand Chicago, $75 a night, $374 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $299 a night, $1,496 for 5 nights
• Hotels in Chicago for these nights (Jan 19–25, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $476 for 6 nights · 4★ Freehand Chicago, $74 a night, $445 for 6 nights · 5★ Nobu Hotel Chicago, $398 a night, $2,388 for 6 nights
• Hotels in Chicago for these nights (Jan 19–26, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $551 for 7 nights · 4★ Freehand Chicago, $74 a night, $518 for 7 nights · 5★ Nobu Hotel Chicago, $403 a night, $2,821 for 7 nights
• Hotels in Chicago for these nights (Jan 19–27, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $634 for 8 nights · 4★ Freehand Chicago, $74 a night, $591 for 8 nights · 5★ Nobu Hotel Chicago, $406 a night, $3,249 for 8 nights
• Hotels in Chicago for these nights (Jan 19–28, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $709 for 9 nights · 4★ Freehand Chicago, $74 a night, $663 for 9 nights · 5★ Nobu Hotel Chicago, $404 a night, $3,636 for 9 nights
• Hotels in Chicago for these nights (Jan 19–29, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $784 for 10 nights · 4★ Freehand Chicago, $74 a night, $735 for 10 nights · 5★ Nobu Hotel Chicago, $401 a night, $4,008 for 10 nights
• Hotels in Chicago for these nights (Jan 19–30, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $868 for 11 nights · 4★ Freehand Chicago, $74 a night, $814 for 11 nights · 5★ Nobu Hotel Chicago, $400 a night, $4,395 for 11 nights
• Hotels in Chicago for these nights (Jan 19–31, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $943 for 12 nights · 4★ Freehand Chicago, $74 a night, $892 for 12 nights · 5★ Nobu Hotel Chicago, $398 a night, $4,771 for 12 nights
• Hotels in Chicago for these nights (Jan 19 – Feb 1, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $1,026 for 13 nights · 4★ Freehand Chicago, $74 a night, $964 for 13 nights · 5★ Nobu Hotel Chicago, $394 a night, $5,120 for 13 nights
• Hotels in Chicago for these nights (Jan 19 – Feb 2, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $80 a night, $1,115 for 14 nights · 4★ Freehand Chicago, $74 a night, $1,037 for 14 nights · 5★ Nobu Hotel Chicago, $393 a night, $5,498 for 14 nights

All hotels in Chicago

Route overview: Denver to Chicago (MDW) flight deals

2027-01-19 · one way · Axel-exclusive $128

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.

2027-01-19 → 2027-01-20 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-20 09:20:00 → DEN 2027-01-20 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-19 → 2027-01-21 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN120: MDW 2027-01-21 10:50:00 → DEN 2027-01-21 12:30:00; nonstop; 160 minutes. Local airport times.

2027-01-19 → 2027-01-22 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-22 09:20:00 → DEN 2027-01-22 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-19 → 2027-01-23 · Axel-exclusive $238

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN598 / WN32: MDW 2027-01-23 10:10:00 → DEN 2027-01-23 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2027-01-23 10:10:00 → MKE 2027-01-23 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2027-01-23 12:45:00 → DEN 2027-01-23 14:20:00.

2027-01-19 → 2027-01-25 · Axel-exclusive $238

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN1523 / WN2509: MDW 2027-01-25 10:05:00 → DEN 2027-01-25 14:15:00; 1 stop(s) via OMA; 310 minutes. Local airport times.
  • WN1523: MDW 2027-01-25 10:05:00 → OMA 2027-01-25 11:40:00; layover at OMA: 115 minutes.
  • WN2509: OMA 2027-01-25 13:35:00 → DEN 2027-01-25 14:15:00.

2027-01-19 → 2027-01-26 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-26 09:20:00 → DEN 2027-01-26 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-19 → 2027-01-27 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-27 09:20:00 → DEN 2027-01-27 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-19 → 2027-01-29 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-01-29 09:20:00 → DEN 2027-01-29 11:00:00; nonstop; 160 minutes. Local airport times.

2027-01-19 → 2027-01-30 · Axel-exclusive $238

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN598 / WN32: MDW 2027-01-30 10:10:00 → DEN 2027-01-30 14:20:00; 1 stop(s) via MKE; 310 minutes. Local airport times.
  • WN598: MDW 2027-01-30 10:10:00 → MKE 2027-01-30 11:00:00; layover at MKE: 105 minutes.
  • WN32: MKE 2027-01-30 12:45:00 → DEN 2027-01-30 14:20:00.

2027-01-19 → 2027-01-31 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4606: MDW 2027-01-31 16:25:00 → DEN 2027-01-31 18:10:00; nonstop; 165 minutes. Local airport times.

2027-01-19 → 2027-02-02 · Axel-exclusive $247

• Southwest Airlines WN1698: DEN 2027-01-19 14:10:00 → MDW 2027-01-19 17:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN264: MDW 2027-02-02 09:20:00 → DEN 2027-02-02 11:00:00; nonstop; 160 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 18, 2027 · Return options
• Jan 20, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Denver (DEN) to Chicago (MDW) · Jan 19, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
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