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Detroit → Chicago

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DTW → MDW1 adulteconomy

12 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
3:45 pmDTW
1h 15m
Nonstop
4:00 pmMDW
Southwest Airlines
7:45 amMDW
1h 10m
Nonstop
9:55 amDTW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
6:15 pmDTW
1h 22m
Nonstop
6:37 pmMDW
Delta Air Lines
1:31 pmMDW
1h 13m
Nonstop
3:44 pmDTW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:45 pmDTW
1h 15m
Nonstop
4:00 pmMDW
Southwest Airlines
8:20 amMDW
1h 10m
Nonstop
10:30 amDTW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:35 pmDTW
1h 20m
Nonstop
7:55 pmMDW
Southwest Airlines
7:45 amMDW
1h 10m
Nonstop
9:55 amDTW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:35 pmDTW
1h 20m
Nonstop
7:55 pmMDW
Southwest Airlines
8:20 amMDW
1h 10m
Nonstop
10:30 amDTW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
12:44 pmDTW
1h 17m
Nonstop
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
1h 13m
Nonstop
3:44 pmDTW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
12:44 pmDTW
1h 17m
Nonstop
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
1h 13m
Nonstop
3:44 pmDTW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
6:15 pmDTW
1h 22m
Nonstop
6:37 pmMDW
Delta Air Lines
1:31 pmMDW
1h 13m
Nonstop
3:44 pmDTW

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
7:35 pmDTW
1h 20m
Nonstop
7:55 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
6:15 pmDTW
1h 22m
Nonstop
6:37 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
3:45 pmDTW
1h 15m
Nonstop
4:00 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
12:44 pmDTW
1h 17m
Nonstop
1:01 pmMDW

One-way total · 1 adult · Taxes included

Make this trip yours

DTW ⇄ MDW

Economy

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

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  • 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
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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 AirlinesWN955$120.002026-10-29T01:10:49Z
2026-11-20 · one wayDelta Air LinesDL4677$145.002026-10-29T01:10:49Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1124 / WN1076$220.002026-10-29T01:10:49Z
2026-11-20 → 2026-11-23Delta Air LinesDL4677 / DL4688$270.002026-10-29T01:10:49Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1124 / WN1076$242.002026-10-29T01:10:49Z
2026-11-20 · one waySouthwest AirlinesWN1124$120.002026-10-29T01:10:49Z
2026-11-20 · one wayDelta Air LinesDL4688$145.002026-10-29T01:10:49Z
2026-11-20 → 2026-11-23Southwest AirlinesWN955 / WN1076$220.002026-10-29T01:10:49Z
2026-11-27 → 2026-12-04Southwest AirlinesWN955 / WN1076$242.002026-10-29T01:10:49Z
2026-11-20 → 2026-11-23Delta Air LinesDL4688 / DL4688$270.002026-10-29T01:10:49Z
2026-11-27 → 2026-12-04Delta Air LinesDL4688 / DL4688$297.002026-10-29T01:10:49Z
2026-11-27 → 2026-12-04Delta Air LinesDL4677 / DL4688$297.002026-10-29T01:10:49Z

2026-11-20 · one way · $120.00

  • Southwest Airlines WN955: DTW 2026-11-20 19:35:00 → MDW 2026-11-20 19:55:00; nonstop; 80 minutes. Local airport times.

2026-11-20 · one way · $145.00

  • Delta Air Lines DL4677: DTW 2026-11-20 18:15:00 → MDW 2026-11-20 18:37:00; nonstop; 82 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $220.00

  • Southwest Airlines WN1124: DTW 2026-11-20 15:45:00 → MDW 2026-11-20 16:00:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1076: MDW 2026-11-23 07:45:00 → DTW 2026-11-23 09:55:00; nonstop; 70 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $270.00

  • Delta Air Lines DL4677: DTW 2026-11-20 18:15:00 → MDW 2026-11-20 18:37:00; nonstop; 82 minutes. Local airport times.
  • Delta Air Lines DL4688: MDW 2026-11-23 13:31:00 → DTW 2026-11-23 15:44:00; nonstop; 73 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $242.00

  • Southwest Airlines WN1124: DTW 2026-11-27 15:45:00 → MDW 2026-11-27 16:00:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1076: MDW 2026-12-04 08:20:00 → DTW 2026-12-04 10:30:00; nonstop; 70 minutes. Local airport times.

2026-11-20 · one way · $120.00

  • Southwest Airlines WN1124: DTW 2026-11-20 15:45:00 → MDW 2026-11-20 16:00:00; nonstop; 75 minutes. Local airport times.

2026-11-20 · one way · $145.00

  • Delta Air Lines DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00; nonstop; 77 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $220.00

  • Southwest Airlines WN955: DTW 2026-11-20 19:35:00 → MDW 2026-11-20 19:55:00; nonstop; 80 minutes. Local airport times.
  • Southwest Airlines WN1076: MDW 2026-11-23 07:45:00 → DTW 2026-11-23 09:55:00; nonstop; 70 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $242.00

  • Southwest Airlines WN955: DTW 2026-11-27 19:35:00 → MDW 2026-11-27 19:55:00; nonstop; 80 minutes. Local airport times.
  • Southwest Airlines WN1076: MDW 2026-12-04 08:20:00 → DTW 2026-12-04 10:30:00; nonstop; 70 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $270.00

  • Delta Air Lines DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00; nonstop; 77 minutes. Local airport times.
  • Delta Air Lines DL4688: MDW 2026-11-23 13:31:00 → DTW 2026-11-23 15:44:00; nonstop; 73 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $297.00

  • Delta Air Lines DL4688: DTW 2026-11-27 12:44:00 → MDW 2026-11-27 13:01:00; nonstop; 77 minutes. Local airport times.
  • Delta Air Lines DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; nonstop; 73 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $297.00

  • Delta Air Lines DL4677: DTW 2026-11-27 18:15:00 → MDW 2026-11-27 18:37:00; nonstop; 82 minutes. Local airport times.
  • Delta Air Lines DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; nonstop; 73 minutes. Local airport times.

More dates for this route