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Cleveland → Chicago

Jan 24, 2027 · return Feb 7, 2027

CLE → MDW1 adulteconomyRound trip

3 flight options · 2 airlines

Nonstop flights

Sun, Jan 24 – Sun, Feb 7

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

Sun, Jan 24 – Sun, Feb 7

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

One-stop flights

Sun, Jan 24 – Sun, Feb 7

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

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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More dates

All dates for this routeNov 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 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)
2027-01-24 → 2027-02-07Southwest AirlinesWN1220 / WN4528$251.762026-10-29T00:57:04Z
2027-01-24 → 2027-02-07Delta Air LinesDL5359 + DL4677 / DL4688 + DL4954$323.002026-10-29T00:57:04Z
2027-01-24 → 2027-02-07Southwest AirlinesWN1218 / WN4528$251.762026-10-29T00:57:04Z

2027-01-24 → 2027-02-07 · $251.76

  • Southwest Airlines WN1220: CLE 2027-01-24 19:10:00 → MDW 2027-01-24 19:35:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN4528: MDW 2027-02-07 20:40:00 → CLE 2027-02-07 22:55:00; nonstop; 75 minutes. Local airport times.

2027-01-24 → 2027-02-07 · $323.00

  • Delta Air Lines DL5359 / DL4677: CLE 2027-01-24 14:05:00 → MDW 2027-01-24 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-01-24 14:05:00 → DTW 2027-01-24 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-01-24 17:40:00 → MDW 2027-01-24 18:01:00.
  • Delta Air Lines DL4688 / DL4954: MDW 2027-02-07 13:31:00 → CLE 2027-02-07 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-02-07 13:31:00 → DTW 2027-02-07 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-02-07 17:40:00 → CLE 2027-02-07 18:40:00.

2027-01-24 → 2027-02-07 · $251.76

  • Southwest Airlines WN1218: CLE 2027-01-24 08:45:00 → MDW 2027-01-24 09:10:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN4528: MDW 2027-02-07 20:40:00 → CLE 2027-02-07 22:55:00; nonstop; 75 minutes. Local airport times.

More dates for this route