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Cleveland → Chicago

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CLE → MDW1 adulteconomy

9 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:40 pmMDW
1h 15m
Nonstop
10:55 pmCLE

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:40 pmMDW
1h 15m
Nonstop
10:55 pmCLE

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:10 pmCLE
1h 25m
Nonstop
7:35 pmMDW
Southwest Airlines
8:40 pmMDW
1h 15m
Nonstop
10:55 pmCLE

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:10 pmCLE
1h 25m
Nonstop
7:35 pmMDW
Southwest Airlines
8:40 pmMDW
1h 15m
Nonstop
10:55 pmCLE

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:10 pmCLE
1h 25m
Nonstop
7:35 pmMDW

One-way total · 1 adult · Taxes included

Make this trip yours

CLE ⇄ 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 AirlinesWN1218$140.002026-10-29T00:57:04Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1218 / WN4528$265.002026-10-29T00:57:04Z
2026-11-20 · one wayDelta Air LinesDL5359 + DL4677$195.002026-10-29T00:57:04Z
2026-11-20 → 2026-11-23Delta Air LinesDL5359 + DL4677 / DL4688 + DL4954$340.002026-10-29T00:57:04Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1218 / WN4528$304.752026-10-29T00:57:04Z
2026-11-20 · one waySouthwest AirlinesWN1220$140.002026-10-29T00:57:04Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1220 / WN4528$265.002026-10-29T00:57:04Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1220 / WN4528$304.752026-10-29T00:57:04Z
2026-11-27 → 2026-12-04Delta Air LinesDL5359 + DL4677 / DL4688 + DL4954$391.002026-10-29T00:57:04Z

2026-11-20 · one way · $140.00

  • Southwest Airlines WN1218: CLE 2026-11-20 08:45:00 → MDW 2026-11-20 09:10:00; nonstop; 85 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $265.00

  • Southwest Airlines WN1218: CLE 2026-11-20 08:45:00 → MDW 2026-11-20 09:10:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN4528: MDW 2026-11-23 20:40:00 → CLE 2026-11-23 22:55:00; nonstop; 75 minutes. Local airport times.

2026-11-20 · one way · $195.00

  • Delta Air Lines DL5359 / DL4677: CLE 2026-11-20 14:05:00 → MDW 2026-11-20 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2026-11-20 14:05:00 → DTW 2026-11-20 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2026-11-20 17:40:00 → MDW 2026-11-20 18:01:00.

2026-11-20 → 2026-11-23 · $340.00

  • Delta Air Lines DL5359 / DL4677: CLE 2026-11-20 14:05:00 → MDW 2026-11-20 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2026-11-20 14:05:00 → DTW 2026-11-20 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2026-11-20 17:40:00 → MDW 2026-11-20 18:01:00.
  • Delta Air Lines DL4688 / DL4954: MDW 2026-11-23 13:31:00 → CLE 2026-11-23 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2026-11-23 13:31:00 → DTW 2026-11-23 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2026-11-23 17:40:00 → CLE 2026-11-23 18:40:00.

2026-11-27 → 2026-12-04 · $304.75

  • Southwest Airlines WN1218: CLE 2026-11-27 08:45:00 → MDW 2026-11-27 09:10:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN4528: MDW 2026-12-04 20:40:00 → CLE 2026-12-04 22:55:00; nonstop; 75 minutes. Local airport times.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN1220: CLE 2026-11-20 19:10:00 → MDW 2026-11-20 19:35:00; nonstop; 85 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $265.00

  • Southwest Airlines WN1220: CLE 2026-11-20 19:10:00 → MDW 2026-11-20 19:35:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN4528: MDW 2026-11-23 20:40:00 → CLE 2026-11-23 22:55:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $304.75

  • Southwest Airlines WN1220: CLE 2026-11-27 19:10:00 → MDW 2026-11-27 19:35:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN4528: MDW 2026-12-04 20:40:00 → CLE 2026-12-04 22:55:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $391.00

  • Delta Air Lines DL5359 / DL4677: CLE 2026-11-27 14:05:00 → MDW 2026-11-27 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2026-11-27 14:05:00 → DTW 2026-11-27 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2026-11-27 17:40:00 → MDW 2026-11-27 18:01:00.
  • Delta Air Lines DL4688 / DL4954: MDW 2026-12-04 13:31:00 → CLE 2026-12-04 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2026-12-04 17:40:00 → CLE 2026-12-04 18:40:00.

More dates for this route