
Keep the following information in mind while searching for Cleveland to Illinois flight deals. Data was last updated November 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Trip.com) |
One-way from | $59 (Southwest) |
Popular in | January |
Cheapest in | May |
Average price | $260 |
Good round-trip deal | $245 or less |
Good one-way deal | $209 or less |
Fly from
Fly to
Route
Depart
Return
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 12/12
4:35 pm-5:00 pm
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Fri 1/1
8:45 am-9:10 am
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Tue 12/1
5:10 am-5:50 am
Nonstop1h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 12/1
7:10 pm-7:35 pm
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 11/24
6:40 am-2:45 pm
1 stop9h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 12/15
2:05 pm-6:01 pm
1 stop4h 56m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 12/12
6:10 am-9:37 am
1 stop4h 27m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Wed 12/9
2:05 pm-6:01 pm
1 stop4h 56m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Thu 12/10
10:45 am-1:01 pm
1 stop3h 16m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Fri 12/11
2:05 pm-4:17 pm
1 stop3h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
Everything you need to know about your flight from Cleveland to Illinois
Boarding
Crew
Comfort
Entertainment
Overall
Food
Reviews
Reza,Jun 2026
TPA - MDW
Boarding
Crew
Comfort
Entertainment
Overall
Food
Reviews
Reza,Jun 2026
TPA - MDW
Boarding
Crew
Comfort
Entertainment
Overall
Food
Reviews
Reza,Jun 2026
TPA - MDW
Boarding
Crew
Comfort
Entertainment
Overall
Food
Reviews
Reza,Jun 2026
TPA - MDW
Boarding
Crew
Comfort
Entertainment
Overall
Food
Reviews
Reza,Jun 2026
TPA - MDW
Find useful and relevant information for your journey from Cleveland to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$283 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$134 | Average$269 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$139 | Average$337 | FlexibilityNo cancel fee | On-time69% |