Seattle (SEA) to Chicago (MDW) · Dec 18, 2026 · return Jan 1, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Dec 18 – Jan 1, 2027 · 14 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,643 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,974 total · 5★ Nobu Hotel Chicago, $4,924 total

All hotels in Chicago

Route overview: Seattle to Chicago (MDW) flight deals

2026-12-18 → 2027-01-01 · Axel-exclusive $405.00

• Southwest Airlines WN1451: SEA 2026-12-18 05:30:00 → MDW 2026-12-18 11:20:00; nonstop; 230 minutes. Local airport times.
• Southwest Airlines WN3032: MDW 2027-01-01 22:30:00 → SEA 2027-01-02 01:20:00; nonstop; 290 minutes. Local airport times.

2026-12-18 → 2027-01-01 · Axel-exclusive $461.25

• Delta Air Lines DL810 / DL4684: SEA 2026-12-18 23:14:00 → MDW 2026-12-19 09:46:00; 1 stop(s) via DTW; 512 minutes. Local airport times.
  • DL810: SEA 2026-12-18 23:14:00 → DTW 2026-12-19 06:29:00; layover at DTW: 161 minutes.
  • DL4684: DTW 2026-12-19 09:10:00 → MDW 2026-12-19 09:46:00.
• Delta Air Lines DL5469 / DL877: MDW 2027-01-01 10:24:00 → SEA 2027-01-01 16:53:00; 1 stop(s) via MSP; 509 minutes. Local airport times.
  • DL5469: MDW 2027-01-01 10:24:00 → MSP 2027-01-01 12:09:00; layover at MSP: 170 minutes.
  • DL877: MSP 2027-01-01 14:59:00 → SEA 2027-01-01 16:53:00.

2026-12-18 → 2027-01-01 · Axel-exclusive $405.00

• Southwest Airlines WN1550: SEA 2026-12-18 06:30:00 → MDW 2026-12-18 12:25:00; nonstop; 235 minutes. Local airport times.
• Southwest Airlines WN3032: MDW 2027-01-01 22:30:00 → SEA 2027-01-02 01:20:00; nonstop; 290 minutes. Local airport times.

2026-12-18 → 2027-01-01 · Axel-exclusive $390.00

• Southwest Airlines WN3158 / WN1156: SEA 2026-12-18 07:55:00 → MDW 2026-12-18 17:40:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN3158: SEA 2026-12-18 07:55:00 → SAN 2026-12-18 10:40:00; layover at SAN: 65 minutes.
  • WN1156: SAN 2026-12-18 11:45:00 → MDW 2026-12-18 17:40:00.
• Southwest Airlines WN3032: MDW 2027-01-01 22:30:00 → SEA 2027-01-02 01:20:00; nonstop; 290 minutes. Local airport times.

2026-12-18 → 2027-01-01 · Axel-exclusive $390.00

• Southwest Airlines WN3823 / WN776: SEA 2026-12-18 13:35:00 → MDW 2026-12-18 21:30:00; 1 stop(s) via DEN; 355 minutes. Local airport times.
  • WN3823: SEA 2026-12-18 13:35:00 → DEN 2026-12-18 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-18 18:05:00 → MDW 2026-12-18 21:30:00.
• Southwest Airlines WN3032: MDW 2027-01-01 22:30:00 → SEA 2027-01-02 01:20:00; nonstop; 290 minutes. Local airport times.

2026-12-18 → 2027-01-01 · Axel-exclusive $390.00

• Southwest Airlines WN424 / WN1932: SEA 2026-12-18 14:05:00 → MDW 2026-12-19 00:15:00; 1 stop(s) via LAS; 490 minutes. Local airport times.
  • WN424: SEA 2026-12-18 14:05:00 → LAS 2026-12-18 16:30:00; layover at LAS: 140 minutes.
  • WN1932: LAS 2026-12-18 18:50:00 → MDW 2026-12-19 00:15:00.
• Southwest Airlines WN3032: MDW 2027-01-01 22:30:00 → SEA 2027-01-02 01:20:00; nonstop; 290 minutes. Local airport times.

2026-12-18 → 2027-01-01 · Axel-exclusive $390.00

• Southwest Airlines WN698 / WN1769: SEA 2026-12-18 15:45:00 → MDW 2026-12-19 00:45:00; 1 stop(s) via DAL; 420 minutes. Local airport times.
  • WN698: SEA 2026-12-18 15:45:00 → DAL 2026-12-18 21:30:00; layover at DAL: 60 minutes.
  • WN1769: DAL 2026-12-18 22:30:00 → MDW 2026-12-19 00:45:00.
• Southwest Airlines WN3032: MDW 2027-01-01 22:30:00 → SEA 2027-01-02 01:20:00; nonstop; 290 minutes. Local airport times.

2026-12-18 → 2027-01-01 · Axel-exclusive $461.25

• Delta Air Lines DL536 / DL4714: SEA 2026-12-18 08:30:00 → MDW 2026-12-18 16:39:00; 1 stop(s) via MSP; 369 minutes. Local airport times.
  • DL536: SEA 2026-12-18 08:30:00 → MSP 2026-12-18 13:48:00; layover at MSP: 72 minutes.
  • DL4714: MSP 2026-12-18 15:00:00 → MDW 2026-12-18 16:39:00.
• Delta Air Lines DL5469 / DL877: MDW 2027-01-01 10:24:00 → SEA 2027-01-01 16:53:00; 1 stop(s) via MSP; 509 minutes. Local airport times.
  • DL5469: MDW 2027-01-01 10:24:00 → MSP 2027-01-01 12:09:00; layover at MSP: 170 minutes.
  • DL877: MSP 2027-01-01 14:59:00 → SEA 2027-01-01 16:53:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Dec 17, 2026 · Return options
• Dec 19, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Seattle (SEA) to Chicago (MDW) · Dec 18, 2026 · return Jan 1, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Seattle to Chicago (MDW) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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