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Seattle → Chicago

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SEA → MDW1 adulteconomy

24 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:30 amSEA
3h 55m
Nonstop
12:25 pmMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
12:15 amSEA
3h 50m
Nonstop
6:05 amMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
12:15 amSEA
3h 50m
Nonstop
6:05 amMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:30 amSEA
3h 55m
Nonstop
12:25 pmMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:55 amSEA
7h 45m
SAN · 1h 5m
5:40 pmMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
2:05 pmSEA
8h 10m
LAS · 2h 20m
12:15 am+1MDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
1:35 pmSEA
5h 55m
DEN · 1h
9:30 pmMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Show 8 more flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
3:45 pmSEA
7h
DAL · 1h
12:45 am+1MDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
1:35 pmSEA
5h 55m
DEN · 1h
9:30 pmMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:55 amSEA
7h 45m
SAN · 1h 5m
5:40 pmMDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:45 pmSEA
7h
DAL · 1h
12:45 am+1MDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:05 pmSEA
8h 10m
LAS · 2h 20m
12:15 am+1MDW
Southwest Airlines
10:30 pmMDW
4h 50m
Nonstop
1:20 am+1SEA

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 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

Fri, Nov 27 – Fri, Dec 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

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
12:15 amSEA
3h 50m
Nonstop
6:05 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
8:30 amSEA
6h 9m
MSP · 1h 12m
4:39 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:30 amSEA
3h 55m
Nonstop
12:25 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:05 pmSEA
8h 10m
LAS · 2h 20m
12:15 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:55 amSEA
7h 45m
SAN · 1h 5m
5:40 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
1:35 pmSEA
5h 55m
DEN · 1h
9:30 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
3:45 pmSEA
7h
DAL · 1h
12:45 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way 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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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN4975$190.002026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1550 / WN3032$360.002026-10-29T02:06:31Z
2026-11-20 · one wayDelta Air LinesDL536 + DL4714$220.002026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Delta Air LinesDL536 + DL4714 / DL4711 + DL728$410.002026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4975 / WN3032$423.002026-10-29T02:06:31Z
2026-11-20 · one waySouthwest AirlinesWN1550$190.002026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4975 / WN3032$360.002026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1550 / WN3032$423.002026-10-29T02:06:31Z
2026-11-20 · one waySouthwest AirlinesWN424 + WN1932$175.002026-10-29T02:06:31Z
2026-11-20 · one waySouthwest AirlinesWN3158 + WN1156$175.002026-10-29T02:06:31Z
2026-11-20 · one waySouthwest AirlinesWN3823 + WN776$175.002026-10-29T02:06:31Z
2026-11-20 · one waySouthwest AirlinesWN698 + WN1769$175.002026-10-29T02:06:31Z
2026-11-20 · one wayDelta Air LinesDL810 + DL4684$220.002026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3158 + WN1156 / WN3032$345.002026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Southwest AirlinesWN424 + WN1932 / WN3032$345.002026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3823 + WN776 / WN3032$345.002026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Southwest AirlinesWN698 + WN1769 / WN3032$345.002026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3823 + WN776 / WN3032$402.752026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3158 + WN1156 / WN3032$402.752026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Southwest AirlinesWN698 + WN1769 / WN3032$402.752026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Southwest AirlinesWN424 + WN1932 / WN3032$402.752026-10-29T02:06:31Z
2026-11-20 → 2026-11-23Delta Air LinesDL810 + DL4684 / DL4711 + DL728$410.002026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Delta Air LinesDL536 + DL4714 / DL4711 + DL728$481.752026-10-29T02:06:31Z
2026-11-27 → 2026-12-04Delta Air LinesDL810 + DL4684 / DL4711 + DL728$481.752026-10-29T02:06:31Z

2026-11-20 · one way · $190.00

  • Southwest Airlines WN4975: SEA 2026-11-20 00:15:00 → MDW 2026-11-20 06:05:00; nonstop; 230 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $360.00

  • Southwest Airlines WN1550: SEA 2026-11-20 06:30:00 → MDW 2026-11-20 12:25:00; nonstop; 235 minutes. Local airport times.
  • Southwest Airlines WN3032: MDW 2026-11-23 22:30:00 → SEA 2026-11-24 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-20 · one way · $220.00

  • Delta Air Lines DL536 / DL4714: SEA 2026-11-20 08:30:00 → MDW 2026-11-20 16:39:00; 1 stop(s) via MSP; 369 minutes. Local airport times.
    • DL536: SEA 2026-11-20 08:30:00 → MSP 2026-11-20 13:48:00; layover at MSP: 72 minutes.
    • DL4714: MSP 2026-11-20 15:00:00 → MDW 2026-11-20 16:39:00.

2026-11-20 → 2026-11-23 · $410.00

  • Delta Air Lines DL536 / DL4714: SEA 2026-11-20 08:30:00 → MDW 2026-11-20 16:39:00; 1 stop(s) via MSP; 369 minutes. Local airport times.
    • DL536: SEA 2026-11-20 08:30:00 → MSP 2026-11-20 13:48:00; layover at MSP: 72 minutes.
    • DL4714: MSP 2026-11-20 15:00:00 → MDW 2026-11-20 16:39:00.
  • Delta Air Lines DL4711 / DL728: MDW 2026-11-23 09:30:00 → SEA 2026-11-23 14:55:00; 1 stop(s) via DTW; 445 minutes. Local airport times.
    • DL4711: MDW 2026-11-23 09:30:00 → DTW 2026-11-23 11:45:00; layover at DTW: 68 minutes.
    • DL728: DTW 2026-11-23 12:53:00 → SEA 2026-11-23 14:55:00.

2026-11-27 → 2026-12-04 · $423.00

  • Southwest Airlines WN4975: SEA 2026-11-27 00:15:00 → MDW 2026-11-27 06:05:00; nonstop; 230 minutes. Local airport times.
  • Southwest Airlines WN3032: MDW 2026-12-04 22:30:00 → SEA 2026-12-05 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-20 · one way · $190.00

  • Southwest Airlines WN1550: SEA 2026-11-20 06:30:00 → MDW 2026-11-20 12:25:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $360.00

  • Southwest Airlines WN4975: SEA 2026-11-20 00:15:00 → MDW 2026-11-20 06:05:00; nonstop; 230 minutes. Local airport times.
  • Southwest Airlines WN3032: MDW 2026-11-23 22:30:00 → SEA 2026-11-24 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $423.00

  • Southwest Airlines WN1550: SEA 2026-11-27 06:30:00 → MDW 2026-11-27 12:25:00; nonstop; 235 minutes. Local airport times.
  • Southwest Airlines WN3032: MDW 2026-12-04 22:30:00 → SEA 2026-12-05 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN424 / WN1932: SEA 2026-11-20 14:05:00 → MDW 2026-11-21 00:15:00; 1 stop(s) via LAS; 490 minutes. Local airport times.
    • WN424: SEA 2026-11-20 14:05:00 → LAS 2026-11-20 16:30:00; layover at LAS: 140 minutes.
    • WN1932: LAS 2026-11-20 18:50:00 → MDW 2026-11-21 00:15:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3158 / WN1156: SEA 2026-11-20 07:55:00 → MDW 2026-11-20 17:40:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN3158: SEA 2026-11-20 07:55:00 → SAN 2026-11-20 10:40:00; layover at SAN: 65 minutes.
    • WN1156: SAN 2026-11-20 11:45:00 → MDW 2026-11-20 17:40:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3823 / WN776: SEA 2026-11-20 13:35:00 → MDW 2026-11-20 21:30:00; 1 stop(s) via DEN; 355 minutes. Local airport times.
    • WN3823: SEA 2026-11-20 13:35:00 → DEN 2026-11-20 17:05:00; layover at DEN: 60 minutes.
    • WN776: DEN 2026-11-20 18:05:00 → MDW 2026-11-20 21:30:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN698 / WN1769: SEA 2026-11-20 15:45:00 → MDW 2026-11-21 00:45:00; 1 stop(s) via DAL; 420 minutes. Local airport times.
    • WN698: SEA 2026-11-20 15:45:00 → DAL 2026-11-20 21:30:00; layover at DAL: 60 minutes.
    • WN1769: DAL 2026-11-20 22:30:00 → MDW 2026-11-21 00:45:00.

2026-11-20 · one way · $220.00

  • Delta Air Lines DL810 / DL4684: SEA 2026-11-20 23:14:00 → MDW 2026-11-21 09:46:00; 1 stop(s) via DTW; 512 minutes. Local airport times.
    • DL810: SEA 2026-11-20 23:14:00 → DTW 2026-11-21 06:29:00; layover at DTW: 161 minutes.
    • DL4684: DTW 2026-11-21 09:10:00 → MDW 2026-11-21 09:46:00.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN3158 / WN1156: SEA 2026-11-20 07:55:00 → MDW 2026-11-20 17:40:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN3158: SEA 2026-11-20 07:55:00 → SAN 2026-11-20 10:40:00; layover at SAN: 65 minutes.
    • WN1156: SAN 2026-11-20 11:45:00 → MDW 2026-11-20 17:40:00.
  • Southwest Airlines WN3032: MDW 2026-11-23 22:30:00 → SEA 2026-11-24 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN424 / WN1932: SEA 2026-11-20 14:05:00 → MDW 2026-11-21 00:15:00; 1 stop(s) via LAS; 490 minutes. Local airport times.
    • WN424: SEA 2026-11-20 14:05:00 → LAS 2026-11-20 16:30:00; layover at LAS: 140 minutes.
    • WN1932: LAS 2026-11-20 18:50:00 → MDW 2026-11-21 00:15:00.
  • Southwest Airlines WN3032: MDW 2026-11-23 22:30:00 → SEA 2026-11-24 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN3823 / WN776: SEA 2026-11-20 13:35:00 → MDW 2026-11-20 21:30:00; 1 stop(s) via DEN; 355 minutes. Local airport times.
    • WN3823: SEA 2026-11-20 13:35:00 → DEN 2026-11-20 17:05:00; layover at DEN: 60 minutes.
    • WN776: DEN 2026-11-20 18:05:00 → MDW 2026-11-20 21:30:00.
  • Southwest Airlines WN3032: MDW 2026-11-23 22:30:00 → SEA 2026-11-24 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN698 / WN1769: SEA 2026-11-20 15:45:00 → MDW 2026-11-21 00:45:00; 1 stop(s) via DAL; 420 minutes. Local airport times.
    • WN698: SEA 2026-11-20 15:45:00 → DAL 2026-11-20 21:30:00; layover at DAL: 60 minutes.
    • WN1769: DAL 2026-11-20 22:30:00 → MDW 2026-11-21 00:45:00.
  • Southwest Airlines WN3032: MDW 2026-11-23 22:30:00 → SEA 2026-11-24 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN3823 / WN776: SEA 2026-11-27 13:35:00 → MDW 2026-11-27 21:30:00; 1 stop(s) via DEN; 355 minutes. Local airport times.
    • WN3823: SEA 2026-11-27 13:35:00 → DEN 2026-11-27 17:05:00; layover at DEN: 60 minutes.
    • WN776: DEN 2026-11-27 18:05:00 → MDW 2026-11-27 21:30:00.
  • Southwest Airlines WN3032: MDW 2026-12-04 22:30:00 → SEA 2026-12-05 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN3158 / WN1156: SEA 2026-11-27 07:55:00 → MDW 2026-11-27 17:40:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN3158: SEA 2026-11-27 07:55:00 → SAN 2026-11-27 10:40:00; layover at SAN: 65 minutes.
    • WN1156: SAN 2026-11-27 11:45:00 → MDW 2026-11-27 17:40:00.
  • Southwest Airlines WN3032: MDW 2026-12-04 22:30:00 → SEA 2026-12-05 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN698 / WN1769: SEA 2026-11-27 15:45:00 → MDW 2026-11-28 00:45:00; 1 stop(s) via DAL; 420 minutes. Local airport times.
    • WN698: SEA 2026-11-27 15:45:00 → DAL 2026-11-27 21:30:00; layover at DAL: 60 minutes.
    • WN1769: DAL 2026-11-27 22:30:00 → MDW 2026-11-28 00:45:00.
  • Southwest Airlines WN3032: MDW 2026-12-04 22:30:00 → SEA 2026-12-05 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN424 / WN1932: SEA 2026-11-27 14:05:00 → MDW 2026-11-28 00:15:00; 1 stop(s) via LAS; 490 minutes. Local airport times.
    • WN424: SEA 2026-11-27 14:05:00 → LAS 2026-11-27 16:30:00; layover at LAS: 140 minutes.
    • WN1932: LAS 2026-11-27 18:50:00 → MDW 2026-11-28 00:15:00.
  • Southwest Airlines WN3032: MDW 2026-12-04 22:30:00 → SEA 2026-12-05 01:20:00; nonstop; 290 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $410.00

  • Delta Air Lines DL810 / DL4684: SEA 2026-11-20 23:14:00 → MDW 2026-11-21 09:46:00; 1 stop(s) via DTW; 512 minutes. Local airport times.
    • DL810: SEA 2026-11-20 23:14:00 → DTW 2026-11-21 06:29:00; layover at DTW: 161 minutes.
    • DL4684: DTW 2026-11-21 09:10:00 → MDW 2026-11-21 09:46:00.
  • Delta Air Lines DL4711 / DL728: MDW 2026-11-23 09:30:00 → SEA 2026-11-23 14:55:00; 1 stop(s) via DTW; 445 minutes. Local airport times.
    • DL4711: MDW 2026-11-23 09:30:00 → DTW 2026-11-23 11:45:00; layover at DTW: 68 minutes.
    • DL728: DTW 2026-11-23 12:53:00 → SEA 2026-11-23 14:55:00.

2026-11-27 → 2026-12-04 · $481.75

  • Delta Air Lines DL536 / DL4714: SEA 2026-11-27 08:30:00 → MDW 2026-11-27 16:39:00; 1 stop(s) via MSP; 369 minutes. Local airport times.
    • DL536: SEA 2026-11-27 08:30:00 → MSP 2026-11-27 13:48:00; layover at MSP: 72 minutes.
    • DL4714: MSP 2026-11-27 15:00:00 → MDW 2026-11-27 16:39:00.
  • Delta Air Lines DL4711 / DL728: MDW 2026-12-04 09:30:00 → SEA 2026-12-04 14:55:00; 1 stop(s) via DTW; 445 minutes. Local airport times.
    • DL4711: MDW 2026-12-04 09:30:00 → DTW 2026-12-04 11:45:00; layover at DTW: 68 minutes.
    • DL728: DTW 2026-12-04 12:53:00 → SEA 2026-12-04 14:55:00.

2026-11-27 → 2026-12-04 · $481.75

  • Delta Air Lines DL810 / DL4684: SEA 2026-11-27 23:14:00 → MDW 2026-11-28 09:46:00; 1 stop(s) via DTW; 512 minutes. Local airport times.
    • DL810: SEA 2026-11-27 23:14:00 → DTW 2026-11-28 06:29:00; layover at DTW: 161 minutes.
    • DL4684: DTW 2026-11-28 09:10:00 → MDW 2026-11-28 09:46:00.
  • Delta Air Lines DL4711 / DL728: MDW 2026-12-04 09:30:00 → SEA 2026-12-04 14:55:00; 1 stop(s) via DTW; 445 minutes. Local airport times.
    • DL4711: MDW 2026-12-04 09:30:00 → DTW 2026-12-04 11:45:00; layover at DTW: 68 minutes.
    • DL728: DTW 2026-12-04 12:53:00 → SEA 2026-12-04 14:55:00.

More dates for this route