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Seattle → Chicago

Jan 21, 2027 · return Feb 4, 2027

SEA → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
12:15 amSEA
3h 50m
Nonstop
6:05 amMDW
Southwest Airlines
8:45 pmMDW
4h 50m
Nonstop
11:35 pmSEA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
11:20 amSEA
3h 50m
Nonstop
5:10 pmMDW
Southwest Airlines
8:45 pmMDW
4h 50m
Nonstop
11:35 pmSEA

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Thu, Feb 4

Delta Air Lines
8:30 amSEA
6h 9m
MSP · 1h 12m
4:39 pmMDW
Delta Air Lines
9:30 amMDW
7h 25m
DTW · 1h 8m
2:55 pmSEA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
2:05 pmSEA
8h 10m
LAS · 2h 20m
12:15 am+1MDW
Southwest Airlines
8:45 pmMDW
4h 50m
Nonstop
11:35 pmSEA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
3:45 pmSEA
7h
DAL · 1h
12:45 am+1MDW
Southwest Airlines
8:45 pmMDW
4h 50m
Nonstop
11:35 pmSEA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
1:35 pmSEA
5h 55m
DEN · 1h
9:30 pmMDW
Southwest Airlines
8:45 pmMDW
4h 50m
Nonstop
11:35 pmSEA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
7:55 amSEA
7h 45m
SAN · 1h 5m
5:40 pmMDW
Southwest Airlines
8:45 pmMDW
4h 50m
Nonstop
11:35 pmSEA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Delta Air Lines
11:14 pmSEA
8h 32m
DTW · 2h 41m
9:46 am+1MDW
Delta Air Lines
9:30 amMDW
7h 25m
DTW · 1h 8m
2:55 pmSEA

Round-trip total · 1 adult · Taxes included

Make this trip yours

SEA ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-21 → 2027-02-04Southwest AirlinesWN4975 / WN3032$360.002026-10-29T02:06:31Z
2027-01-21 → 2027-02-04Delta Air LinesDL536 + DL4714 / DL4711 + DL728$410.002026-10-29T02:06:31Z
2027-01-21 → 2027-02-04Southwest AirlinesWN970 / WN3032$360.002026-10-29T02:06:31Z
2027-01-21 → 2027-02-04Southwest AirlinesWN424 + WN1932 / WN3032$345.002026-10-29T02:06:31Z
2027-01-21 → 2027-02-04Southwest AirlinesWN698 + WN1769 / WN3032$345.002026-10-29T02:06:31Z
2027-01-21 → 2027-02-04Southwest AirlinesWN3823 + WN776 / WN3032$345.002026-10-29T02:06:31Z
2027-01-21 → 2027-02-04Southwest AirlinesWN3158 + WN1156 / WN3032$345.002026-10-29T02:06:31Z
2027-01-21 → 2027-02-04Delta Air LinesDL810 + DL4684 / DL4711 + DL728$410.002026-10-29T02:06:31Z

2027-01-21 → 2027-02-04 · $360.00

  • Southwest Airlines WN4975: SEA 2027-01-21 00:15:00 → MDW 2027-01-21 06:05:00; nonstop; 230 minutes. Local airport times.
  • Southwest Airlines WN3032: MDW 2027-02-04 20:45:00 → SEA 2027-02-04 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $410.00

  • Delta Air Lines DL536 / DL4714: SEA 2027-01-21 08:30:00 → MDW 2027-01-21 16:39:00; 1 stop(s) via MSP; 369 minutes. Local airport times.
    • DL536: SEA 2027-01-21 08:30:00 → MSP 2027-01-21 13:48:00; layover at MSP: 72 minutes.
    • DL4714: MSP 2027-01-21 15:00:00 → MDW 2027-01-21 16:39:00.
  • Delta Air Lines DL4711 / DL728: MDW 2027-02-04 09:30:00 → SEA 2027-02-04 14:55:00; 1 stop(s) via DTW; 445 minutes. Local airport times.
    • DL4711: MDW 2027-02-04 09:30:00 → DTW 2027-02-04 11:45:00; layover at DTW: 68 minutes.
    • DL728: DTW 2027-02-04 12:53:00 → SEA 2027-02-04 14:55:00.

2027-01-21 → 2027-02-04 · $360.00

  • Southwest Airlines WN970: SEA 2027-01-21 11:20:00 → MDW 2027-01-21 17:10:00; nonstop; 230 minutes. Local airport times.
  • Southwest Airlines WN3032: MDW 2027-02-04 20:45:00 → SEA 2027-02-04 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $345.00

  • Southwest Airlines WN424 / WN1932: SEA 2027-01-21 14:05:00 → MDW 2027-01-22 00:15:00; 1 stop(s) via LAS; 490 minutes. Local airport times.
    • WN424: SEA 2027-01-21 14:05:00 → LAS 2027-01-21 16:30:00; layover at LAS: 140 minutes.
    • WN1932: LAS 2027-01-21 18:50:00 → MDW 2027-01-22 00:15:00.
  • Southwest Airlines WN3032: MDW 2027-02-04 20:45:00 → SEA 2027-02-04 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $345.00

  • Southwest Airlines WN698 / WN1769: SEA 2027-01-21 15:45:00 → MDW 2027-01-22 00:45:00; 1 stop(s) via DAL; 420 minutes. Local airport times.
    • WN698: SEA 2027-01-21 15:45:00 → DAL 2027-01-21 21:30:00; layover at DAL: 60 minutes.
    • WN1769: DAL 2027-01-21 22:30:00 → MDW 2027-01-22 00:45:00.
  • Southwest Airlines WN3032: MDW 2027-02-04 20:45:00 → SEA 2027-02-04 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $345.00

  • Southwest Airlines WN3823 / WN776: SEA 2027-01-21 13:35:00 → MDW 2027-01-21 21:30:00; 1 stop(s) via DEN; 355 minutes. Local airport times.
    • WN3823: SEA 2027-01-21 13:35:00 → DEN 2027-01-21 17:05:00; layover at DEN: 60 minutes.
    • WN776: DEN 2027-01-21 18:05:00 → MDW 2027-01-21 21:30:00.
  • Southwest Airlines WN3032: MDW 2027-02-04 20:45:00 → SEA 2027-02-04 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $345.00

  • Southwest Airlines WN3158 / WN1156: SEA 2027-01-21 07:55:00 → MDW 2027-01-21 17:40:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN3158: SEA 2027-01-21 07:55:00 → SAN 2027-01-21 10:40:00; layover at SAN: 65 minutes.
    • WN1156: SAN 2027-01-21 11:45:00 → MDW 2027-01-21 17:40:00.
  • Southwest Airlines WN3032: MDW 2027-02-04 20:45:00 → SEA 2027-02-04 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $410.00

  • Delta Air Lines DL810 / DL4684: SEA 2027-01-21 23:14:00 → MDW 2027-01-22 09:46:00; 1 stop(s) via DTW; 512 minutes. Local airport times.
    • DL810: SEA 2027-01-21 23:14:00 → DTW 2027-01-22 06:29:00; layover at DTW: 161 minutes.
    • DL4684: DTW 2027-01-22 09:10:00 → MDW 2027-01-22 09:46:00.
  • Delta Air Lines DL4711 / DL728: MDW 2027-02-04 09:30:00 → SEA 2027-02-04 14:55:00; 1 stop(s) via DTW; 445 minutes. Local airport times.
    • DL4711: MDW 2027-02-04 09:30:00 → DTW 2027-02-04 11:45:00; layover at DTW: 68 minutes.
    • DL728: DTW 2027-02-04 12:53:00 → SEA 2027-02-04 14:55:00.

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