Travel with Axel,
get the best price.

Route overview: Chicago to Cleveland (CLE) flight deals

Chicago → Cleveland

May 24, 2027 · choose your return date

MDW → CLE1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

May 2027

May 24, 2027 · One waySouthwest AirlinesNonstop$125.00 May 24, 2027 · One wayDelta Air LinesUp to 1 stop each way$190.00 May 24, 2027 – May 25, 2027 · 1 nightSouthwest AirlinesNonstop$240.00 May 24, 2027 – May 25, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – May 26, 2027 · 2 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – May 26, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – May 27, 2027 · 3 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – May 27, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – May 28, 2027 · 4 nightsSouthwest AirlinesNonstop$252.00 May 24, 2027 – May 28, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$378.00 May 24, 2027 – May 29, 2027 · 5 nightsSouthwest AirlinesNonstop$252.00 May 24, 2027 – May 29, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$378.00 May 24, 2027 – May 30, 2027 · 6 nightsSouthwest AirlinesNonstop$252.00 May 24, 2027 – May 30, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$378.00 May 24, 2027 – May 31, 2027 · 7 nightsSouthwest AirlinesNonstop$252.00 May 24, 2027 – May 31, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$378.00 May 24, 2027 – Jun 1, 2027 · 8 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – Jun 1, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – Jun 2, 2027 · 9 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – Jun 2, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – Jun 3, 2027 · 10 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – Jun 3, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – Jun 4, 2027 · 11 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – Jun 4, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – Jun 5, 2027 · 12 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – Jun 5, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – Jun 6, 2027 · 13 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – Jun 6, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$360.00 May 24, 2027 – Jun 7, 2027 · 14 nightsSouthwest AirlinesNonstop$240.00 May 24, 2027 – Jun 7, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$360.00

Flights for your trip

  1. Mon, May 24 · One way

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

    One-way total · 1 adult · Taxes included

  2. Mon, May 24 · One way

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

    One-way total · 1 adult · Taxes included

  3. Mon, May 24 – Tue, May 25

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

    Round-trip total · 1 adult · Taxes included

  4. Mon, May 24 – Tue, May 25

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

    Round-trip total · 1 adult · Taxes included

  5. Mon, May 24 – Wed, May 26

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

    Round-trip total · 1 adult · Taxes included

  6. Mon, May 24 – Wed, May 26

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

    Round-trip total · 1 adult · Taxes included

  7. Mon, May 24 – Thu, May 27

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

    Round-trip total · 1 adult · Taxes included

  8. Mon, May 24 – Thu, May 27

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

    Round-trip total · 1 adult · Taxes included

  9. Mon, May 24 – Fri, May 28

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

    Round-trip total · 1 adult · Taxes included

  10. Mon, May 24 – Fri, May 28

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

    Round-trip total · 1 adult · Taxes included

  11. Mon, May 24 – Sun, May 30

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

    Round-trip total · 1 adult · Taxes included

  12. Mon, May 24 – Sun, May 30

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

    Round-trip total · 1 adult · Taxes included

  13. Mon, May 24 – Mon, May 31

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

    Round-trip total · 1 adult · Taxes included

  14. Mon, May 24 – Mon, May 31

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

    Round-trip total · 1 adult · Taxes included

  15. Mon, May 24 – Tue, Jun 1

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

    Round-trip total · 1 adult · Taxes included

  16. Mon, May 24 – Tue, Jun 1

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

    Round-trip total · 1 adult · Taxes included

  17. Mon, May 24 – Thu, Jun 3

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

    Round-trip total · 1 adult · Taxes included

  18. Mon, May 24 – Thu, Jun 3

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

    Round-trip total · 1 adult · Taxes included

  19. Mon, May 24 – Fri, Jun 4

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

    Round-trip total · 1 adult · Taxes included

  20. Mon, May 24 – Fri, Jun 4

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

    Round-trip total · 1 adult · Taxes included

  21. Mon, May 24 – Sat, Jun 5

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

    Round-trip total · 1 adult · Taxes included

  22. Mon, May 24 – Sat, Jun 5

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

    Round-trip total · 1 adult · Taxes included

  23. Mon, May 24 – Mon, Jun 7

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

    Round-trip total · 1 adult · Taxes included

  24. Mon, May 24 – Mon, Jun 7

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

    Round-trip total · 1 adult · Taxes included

Swipe to see 23 more recent deals.

1 of 24

Make this trip yours

MDW ⇄ CLE

Economy

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

No account needed to see prices.

Already have an account? Log in

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.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. 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

Explore this route

All dates for this routeMay 23, 2027 · Return optionsMay 25, 2027 · Return optionsHotels in Cleveland, Ohio with Axel
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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-05-24 · one waySouthwest AirlinesWN4528Axel-exclusive $125.002026-10-29T01:29:05Z
2027-05-24 · one wayDelta Air LinesDL4688 + DL4954Axel-exclusive $190.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-25Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-25Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-26Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-26Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-27Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-27Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-28Southwest AirlinesWN4528 / WN1220Axel-exclusive $252.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-28Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $378.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-29Southwest AirlinesWN4528 / WN1220Axel-exclusive $252.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-29Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $378.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-30Southwest AirlinesWN4528 / WN1220Axel-exclusive $252.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-30Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $378.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-31Southwest AirlinesWN4528 / WN1220Axel-exclusive $252.002026-10-29T01:29:05Z
2027-05-24 → 2027-05-31Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $378.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-01Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-01Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-02Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-02Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-03Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-03Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-04Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-04Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-05Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-05Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-06Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-06Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-07Southwest AirlinesWN4528 / WN1220Axel-exclusive $240.002026-10-29T01:29:05Z
2027-05-24 → 2027-06-07Delta Air LinesDL4688 + DL4954 / DL5359 + DL4677Axel-exclusive $360.002026-10-29T01:29:05Z

Route overview: Chicago to Cleveland (CLE) flight deals

2027-05-24 · one way · Axel-exclusive $125.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.

2027-05-24 · one way · Axel-exclusive $190.00

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

2027-05-24 → 2027-05-25 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-05-25 19:10:00 → MDW 2027-05-25 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-05-25 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-05-25 14:05:00 → MDW 2027-05-25 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-05-25 14:05:00 → DTW 2027-05-25 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-05-25 17:40:00 → MDW 2027-05-25 18:01:00.

2027-05-24 → 2027-05-26 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-05-26 19:10:00 → MDW 2027-05-26 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-05-26 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-05-26 14:05:00 → MDW 2027-05-26 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-05-26 14:05:00 → DTW 2027-05-26 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-05-26 17:40:00 → MDW 2027-05-26 18:01:00.

2027-05-24 → 2027-05-27 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-05-27 19:10:00 → MDW 2027-05-27 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-05-27 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-05-27 14:05:00 → MDW 2027-05-27 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-05-27 14:05:00 → DTW 2027-05-27 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-05-27 17:40:00 → MDW 2027-05-27 18:01:00.

2027-05-24 → 2027-05-28 · Axel-exclusive $252.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-05-28 19:10:00 → MDW 2027-05-28 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-05-28 · Axel-exclusive $378.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-05-28 14:05:00 → MDW 2027-05-28 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-05-28 14:05:00 → DTW 2027-05-28 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-05-28 17:40:00 → MDW 2027-05-28 18:01:00.

2027-05-24 → 2027-05-30 · Axel-exclusive $252.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-05-30 19:10:00 → MDW 2027-05-30 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-05-30 · Axel-exclusive $378.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-05-30 14:05:00 → MDW 2027-05-30 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-05-30 14:05:00 → DTW 2027-05-30 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-05-30 17:40:00 → MDW 2027-05-30 18:01:00.

2027-05-24 → 2027-05-31 · Axel-exclusive $252.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-05-31 19:10:00 → MDW 2027-05-31 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-05-31 · Axel-exclusive $378.00

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

2027-05-24 → 2027-06-01 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-06-01 19:10:00 → MDW 2027-06-01 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-06-01 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-06-01 14:05:00 → MDW 2027-06-01 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-06-01 14:05:00 → DTW 2027-06-01 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-06-01 17:40:00 → MDW 2027-06-01 18:01:00.

2027-05-24 → 2027-06-03 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-06-03 19:10:00 → MDW 2027-06-03 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-06-03 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-06-03 14:05:00 → MDW 2027-06-03 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-06-03 14:05:00 → DTW 2027-06-03 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-06-03 17:40:00 → MDW 2027-06-03 18:01:00.

2027-05-24 → 2027-06-04 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-06-04 19:10:00 → MDW 2027-06-04 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-06-04 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-06-04 14:05:00 → MDW 2027-06-04 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-06-04 14:05:00 → DTW 2027-06-04 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-06-04 17:40:00 → MDW 2027-06-04 18:01:00.

2027-05-24 → 2027-06-05 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-06-05 19:10:00 → MDW 2027-06-05 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-06-05 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-06-05 14:05:00 → MDW 2027-06-05 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-06-05 14:05:00 → DTW 2027-06-05 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-06-05 17:40:00 → MDW 2027-06-05 18:01:00.

2027-05-24 → 2027-06-07 · Axel-exclusive $240.00

  • Southwest Airlines WN4528: MDW 2027-05-24 20:40:00 → CLE 2027-05-24 22:55:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN1220: CLE 2027-06-07 19:10:00 → MDW 2027-06-07 19:35:00; nonstop; 85 minutes. Local airport times.

2027-05-24 → 2027-06-07 · Axel-exclusive $360.00

  • Delta Air Lines DL4688 / DL4954: MDW 2027-05-24 13:31:00 → CLE 2027-05-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
    • DL4688: MDW 2027-05-24 13:31:00 → DTW 2027-05-24 15:44:00; layover at DTW: 116 minutes.
    • DL4954: DTW 2027-05-24 17:40:00 → CLE 2027-05-24 18:40:00.
  • Delta Air Lines DL5359 / DL4677: CLE 2027-06-07 14:05:00 → MDW 2027-06-07 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
    • DL5359: CLE 2027-06-07 14:05:00 → DTW 2027-06-07 15:10:00; layover at DTW: 150 minutes.
    • DL4677: DTW 2027-06-07 17:40:00 → MDW 2027-06-07 18:01:00.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to Cleveland (CLE) · May 24, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Cleveland (CLE) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.