Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline American Airlines

The cheapest airline(s) flying from Cleveland to Chicago is American Airlines.

  • American Airlines American Airlines
  • Frontier Airlines Frontier Airlines
  • Delta Air Lines Delta Air Lines
  • United Airlines United Airlines
  • Southwest Airlines Southwest Airlines
  • Spirit Airlines Spirit Airlines
  • JetBlue Airways JetBlue Airways
  • Alaska Airlines Alaska Airlines
Cheapest Month January

Travel Period: November 2024 - October 2025

The cheapest month(s) to fly from Cleveland to Chicago is January.

  • Nov 2024
  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
Cheapest Day of the Week Friday

The cheapest day(s) of the week to fly from Cleveland to Chicago is Friday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Wed, 2 Oct, 2024

  • Time Earliest
    • Earliest
    • Latest
  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • Duration
    • Shortest
    • Longest
  • Stopover
    All
    • Airline Filter by Airline
      View All Airline
      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 21:35 CLE
        21:50 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 21:35 - MDW 21:50 1h 15m Direct
      • CLECleveland Hopkins International Airport 21:35
      • MDWChicago Midway Airport 21:50
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 3025)Boeing 737 800
      • Southwest Airlines (WN 3025)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 06:00 CLE
        06:29 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 06:00 - ORD 06:29 1h 29m Direct
      • CLECleveland Hopkins International Airport 06:00
      • ORDChicago O'Hare International Airport 06:29
      • 1h 29m
      • Direct
      • United Airlines (UA 1421)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1421)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 Max 9 Passenger
      • 06:45 CLE
        07:00 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 06:45 - MDW 07:00 1h 15m Direct
      • CLECleveland Hopkins International Airport 06:45
      • MDWChicago Midway Airport 07:00
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 1772)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1772)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 06:45 CLE
        07:11 ORD
        1Hrs, 26m Direct
      • CLECleveland Hopkins International Airport 06:45 - ORD 07:11 1h 26m Direct
      • CLECleveland Hopkins International Airport 06:45
      • ORDChicago O'Hare International Airport 07:11
      • 1h 26m
      • Direct
      • American Airlines (AA 769)Boeing 737 Max 8 Passenger
      • American Airlines (AA 769)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 06:50 CLE
        07:16 ORD
        1Hrs, 26m Direct
      • CLECleveland Hopkins International Airport 06:50 - ORD 07:16 1h 26m Direct
      • CLECleveland Hopkins International Airport 06:50
      • ORDChicago O'Hare International Airport 07:16
      • 1h 26m
      • Direct
      • American Airlines (AA 769)Boeing 737 Max 8 Passenger
      • American Airlines (AA 769)
        • -
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 07:00 CLE
        07:29 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 07:00 - ORD 07:29 1h 29m Direct
      • CLECleveland Hopkins International Airport 07:00
      • ORDChicago O'Hare International Airport 07:29
      • 1h 29m
      • Direct
      • United Airlines (UA 398)Boeing 737 800
      • United Airlines (UA 398)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 07:00 CLE
        07:15 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 07:00 - MDW 07:15 1h 15m Direct
      • CLECleveland Hopkins International Airport 07:00
      • MDWChicago Midway Airport 07:15
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 655)Boeing 737 700
      • Southwest Airlines (WN 655)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 07:00 CLE
        07:20 MDW
        1Hrs, 20m Direct
      • CLECleveland Hopkins International Airport 07:00 - MDW 07:20 1h 20m Direct
      • CLECleveland Hopkins International Airport 07:00
      • MDWChicago Midway Airport 07:20
      • 1h 20m
      • Direct
      • Southwest Airlines (WN 1772)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1772)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 07:05 CLE
        07:20 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 07:05 - MDW 07:20 1h 15m Direct
      • CLECleveland Hopkins International Airport 07:05
      • MDWChicago Midway Airport 07:20
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 1772)Boeing 737 800
      • Southwest Airlines (WN 1772)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 08:25 CLE
        08:40 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 08:25 - MDW 08:40 1h 15m Direct
      • CLECleveland Hopkins International Airport 08:25
      • MDWChicago Midway Airport 08:40
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 1270)Boeing 737 700
      • Southwest Airlines (WN 1270)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 08:25 CLE
        08:40 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 08:25 - MDW 08:40 1h 15m Direct
      • CLECleveland Hopkins International Airport 08:25
      • MDWChicago Midway Airport 08:40
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 1270)Boeing 737 800
      • Southwest Airlines (WN 1270)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 08:29 CLE
        09:04 ORD
        1Hrs, 35m Direct
      • CLECleveland Hopkins International Airport 08:29 - ORD 09:04 1h 35m Direct
      • CLECleveland Hopkins International Airport 08:29
      • ORDChicago O'Hare International Airport 09:04
      • 1h 35m
      • Direct
      • American Airlines (AA 3568)Embraer Emb 175
      • American Airlines (AA 3568)
        • -
        • -
        • W
        • T
        • -
        • -
        • S
      • Embraer Emb 175
      • 08:29 CLE
        09:04 ORD
        1Hrs, 35m Direct
      • CLECleveland Hopkins International Airport 08:29 - ORD 09:04 1h 35m Direct
      • CLECleveland Hopkins International Airport 08:29
      • ORDChicago O'Hare International Airport 09:04
      • 1h 35m
      • Direct
      • American Airlines (AA 3568)Embraer 170
      • American Airlines (AA 3568)
        • M
        • T
        • -
        • -
        • F
        • S
        • -
      • Embraer 170
      • 09:00 CLE
        09:29 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 09:00 - ORD 09:29 1h 29m Direct
      • CLECleveland Hopkins International Airport 09:00
      • ORDChicago O'Hare International Airport 09:29
      • 1h 29m
      • Direct
      • United Airlines (UA 2465)Boeing 737 700
      • United Airlines (UA 2465)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 700
      • 09:15 CLE
        09:44 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 09:15 - ORD 09:44 1h 29m Direct
      • CLECleveland Hopkins International Airport 09:15
      • ORDChicago O'Hare International Airport 09:44
      • 1h 29m
      • Direct
      • United Airlines (UA 2465)Boeing 737 800
      • United Airlines (UA 2465)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 09:49 CLE
        10:23 ORD
        1Hrs, 34m Direct
      • CLECleveland Hopkins International Airport 09:49 - ORD 10:23 1h 34m Direct
      • CLECleveland Hopkins International Airport 09:49
      • ORDChicago O'Hare International Airport 10:23
      • 1h 34m
      • Direct
      • American Airlines (AA 6121)Crj Canadair Regional
      • American Airlines (AA 6121)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Crj Canadair Regional
      • 10:57 CLE
        11:26 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 10:57 - ORD 11:26 1h 29m Direct
      • CLECleveland Hopkins International Airport 10:57
      • ORDChicago O'Hare International Airport 11:26
      • 1h 29m
      • Direct
      • United Airlines (UA 609)Boeing 737 900
      • United Airlines (UA 609)
        • M
        • -
        • W
        • -
        • F
        • S
        • S
      • Boeing 737 900
      • 10:57 CLE
        11:26 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 10:57 - ORD 11:26 1h 29m Direct
      • CLECleveland Hopkins International Airport 10:57
      • ORDChicago O'Hare International Airport 11:26
      • 1h 29m
      • Direct
      • United Airlines (UA 609)Boeing 737 800
      • United Airlines (UA 609)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 11:00 CLE
        11:29 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 11:00 - ORD 11:29 1h 29m Direct
      • CLECleveland Hopkins International Airport 11:00
      • ORDChicago O'Hare International Airport 11:29
      • 1h 29m
      • Direct
      • United Airlines (UA 609)Boeing 737 900
      • United Airlines (UA 609)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 11:10 CLE
        11:25 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 11:10 - MDW 11:25 1h 15m Direct
      • CLECleveland Hopkins International Airport 11:10
      • MDWChicago Midway Airport 11:25
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 1177)Boeing 737 800
      • Southwest Airlines (WN 1177)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 11:13 CLE
        11:48 ORD
        1Hrs, 35m Direct
      • CLECleveland Hopkins International Airport 11:13 - ORD 11:48 1h 35m Direct
      • CLECleveland Hopkins International Airport 11:13
      • ORDChicago O'Hare International Airport 11:48
      • 1h 35m
      • Direct
      • American Airlines (AA 4089)Embraer Emb 175
      • American Airlines (AA 4089)
        • -
        • T
        • W
        • T
        • -
        • S
        • S
      • Embraer Emb 175
      • 11:13 CLE
        11:48 ORD
        1Hrs, 35m Direct
      • CLECleveland Hopkins International Airport 11:13 - ORD 11:48 1h 35m Direct
      • CLECleveland Hopkins International Airport 11:13
      • ORDChicago O'Hare International Airport 11:48
      • 1h 35m
      • Direct
      • American Airlines (AA 4089)Embraer 170
      • American Airlines (AA 4089)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Embraer 170
      • 12:15 CLE
        12:30 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 12:15 - MDW 12:30 1h 15m Direct
      • CLECleveland Hopkins International Airport 12:15
      • MDWChicago Midway Airport 12:30
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 3767)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3767)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 13:40 CLE
        13:55 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 13:40 - MDW 13:55 1h 15m Direct
      • CLECleveland Hopkins International Airport 13:40
      • MDWChicago Midway Airport 13:55
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 1177)Boeing 737 700
      • Southwest Airlines (WN 1177)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 13:45 CLE
        14:00 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 13:45 - MDW 14:00 1h 15m Direct
      • CLECleveland Hopkins International Airport 13:45
      • MDWChicago Midway Airport 14:00
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 1449)Boeing 737 700
      • Southwest Airlines (WN 1449)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 14:00 CLE
        14:29 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 14:00 - ORD 14:29 1h 29m Direct
      • CLECleveland Hopkins International Airport 14:00
      • ORDChicago O'Hare International Airport 14:29
      • 1h 29m
      • Direct
      • United Airlines (UA 1124)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1124)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 14:02 CLE
        14:31 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 14:02 - ORD 14:31 1h 29m Direct
      • CLECleveland Hopkins International Airport 14:02
      • ORDChicago O'Hare International Airport 14:31
      • 1h 29m
      • Direct
      • United Airlines (UA 1124)Boeing 737 900
      • United Airlines (UA 1124)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 900
      • 14:10 CLE
        14:25 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 14:10 - MDW 14:25 1h 15m Direct
      • CLECleveland Hopkins International Airport 14:10
      • MDWChicago Midway Airport 14:25
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 2926)Boeing 737 800
      • Southwest Airlines (WN 2926)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 15:25 CLE
        15:40 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 15:25 - MDW 15:40 1h 15m Direct
      • CLECleveland Hopkins International Airport 15:25
      • MDWChicago Midway Airport 15:40
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 2926)Boeing 737 800
      • Southwest Airlines (WN 2926)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 15:30 CLE
        15:59 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 15:30 - ORD 15:59 1h 29m Direct
      • CLECleveland Hopkins International Airport 15:30
      • ORDChicago O'Hare International Airport 15:59
      • 1h 29m
      • Direct
      • American Airlines (AA 2160)Boeing 737 800
      • American Airlines (AA 2160)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 16:11 CLE
        16:40 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 16:11 - ORD 16:40 1h 29m Direct
      • CLECleveland Hopkins International Airport 16:11
      • ORDChicago O'Hare International Airport 16:40
      • 1h 29m
      • Direct
      • American Airlines (AA 2160)Boeing 737 800
      • American Airlines (AA 2160)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 16:15 CLE
        16:43 ORD
        1Hrs, 28m Direct
      • CLECleveland Hopkins International Airport 16:15 - ORD 16:43 1h 28m Direct
      • CLECleveland Hopkins International Airport 16:15
      • ORDChicago O'Hare International Airport 16:43
      • 1h 28m
      • Direct
      • United Airlines (UA 457)Boeing 737 900
      • United Airlines (UA 457)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 900
      • 17:00 CLE
        17:29 ORD
        1Hrs, 29m Direct
      • CLECleveland Hopkins International Airport 17:00 - ORD 17:29 1h 29m Direct
      • CLECleveland Hopkins International Airport 17:00
      • ORDChicago O'Hare International Airport 17:29
      • 1h 29m
      • Direct
      • American Airlines (AA 2160)Boeing 737 800
      • American Airlines (AA 2160)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 17:53 CLE
        18:25 ORD
        1Hrs, 32m Direct
      • CLECleveland Hopkins International Airport 17:53 - ORD 18:25 1h 32m Direct
      • CLECleveland Hopkins International Airport 17:53
      • ORDChicago O'Hare International Airport 18:25
      • 1h 32m
      • Direct
      • United Airlines (UA 1673)Boeing 737 900
      • United Airlines (UA 1673)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • Boeing 737 900
      • 18:03 CLE
        18:35 ORD
        1Hrs, 32m Direct
      • CLECleveland Hopkins International Airport 18:03 - ORD 18:35 1h 32m Direct
      • CLECleveland Hopkins International Airport 18:03
      • ORDChicago O'Hare International Airport 18:35
      • 1h 32m
      • Direct
      • United Airlines (UA 1673)Boeing 737 900
      • United Airlines (UA 1673)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 900
      • 18:30 CLE
        18:45 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 18:30 - MDW 18:45 1h 15m Direct
      • CLECleveland Hopkins International Airport 18:30
      • MDWChicago Midway Airport 18:45
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 920)Boeing 737 700
      • Southwest Airlines (WN 920)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 18:40 CLE
        19:00 MDW
        1Hrs, 20m Direct
      • CLECleveland Hopkins International Airport 18:40 - MDW 19:00 1h 20m Direct
      • CLECleveland Hopkins International Airport 18:40
      • MDWChicago Midway Airport 19:00
      • 1h 20m
      • Direct
      • Southwest Airlines (WN 3025)Boeing 737 800
      • Southwest Airlines (WN 3025)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 18:45 CLE
        19:05 MDW
        1Hrs, 20m Direct
      • CLECleveland Hopkins International Airport 18:45 - MDW 19:05 1h 20m Direct
      • CLECleveland Hopkins International Airport 18:45
      • MDWChicago Midway Airport 19:05
      • 1h 20m
      • Direct
      • Southwest Airlines (WN 3025)Boeing 737 800
      • Southwest Airlines (WN 3025)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 18:45 CLE
        19:00 MDW
        1Hrs, 15m Direct
      • CLECleveland Hopkins International Airport 18:45 - MDW 19:00 1h 15m Direct
      • CLECleveland Hopkins International Airport 18:45
      • MDWChicago Midway Airport 19:00
      • 1h 15m
      • Direct
      • Southwest Airlines (WN 920)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 920)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 19:06 CLE
        19:34 ORD
        1Hrs, 28m Direct
      • CLECleveland Hopkins International Airport 19:06 - ORD 19:34 1h 28m Direct
      • CLECleveland Hopkins International Airport 19:06
      • ORDChicago O'Hare International Airport 19:34
      • 1h 28m
      • Direct
      • American Airlines (AA 62)Boeing 737 800
      • American Airlines (AA 62)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Cleveland to Chicago?

      The fastest flight time for direct flights from Cleveland to Chicago is 1 hour 15 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Cleveland to Chicago?

      The most popular airline flying from Cleveland to Chicago is American Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Cleveland?

      The flight distance between Cleveland and Chicago is 495km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 06:00. The last flight of the day departs at 21:35. See the full list of flight times on Wego.

      How many airlines offer direct flights from Cleveland to Chicago?

      There are 3 airlines that offer direct flights from Cleveland to Chicago. Find out the list of airlines on Wego.

      Popular Airlines flying from Cleveland to Chicago

      American Airlines ‏()
      United Airlines ‏()

      Popular Destinations from Chicago

      Popular Destinations from Cleveland

      Popular Hotels in Chicago

      Hotels In Popular Destinations