
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $124 (Kiwi.com) |
One-way from | $63 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $314 |
Good round-trip deal | $278 or less |
Good one-way deal | $184 or less |
Fly from
Fly to
Route
Depart
Return
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 6/23
6:30 am-1:09 pm
2 stops7h 39m
Chicago Midway
Tue 6/23
6:58 pm-11:59 pm
1 stop4h 01m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Tue 6/2
6:00 am-1:01 pm
2 stops8h 01m
Chicago O'Hare Intl
Wed 6/3
9:25 am-1:23 pm
1 stop2h 58m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Tue 6/23
6:00 am-1:04 pm
2 stops8h 04m
Chicago O'Hare Intl
Tue 6/23
7:17 pm-11:59 pm
1 stop3h 42m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 6/3
2:45 pm-3:05 pm
Nonstop1h 20m
Chicago Midway
Thu 6/4
7:55 am-10:10 am
Nonstop1h 15m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Sat 5/30
6:35 pm-10:35 pm
1 stop5h 00m
Chicago Midway
Tue 6/2
12:45 pm-3:00 pm
Nonstop1h 15m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Thu 5/21
6:35 am-8:43 am
1 stop3h 08m
Chicago Midway
Tue 5/26
9:22 am-1:23 pm
1 stop3h 01m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Mon 6/8
4:00 pm-8:31 pm
1 stop5h 31m
Chicago O'Hare Intl
Tue 6/9
5:30 am-1:38 pm
1 stop7h 08m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Mon 6/8
8:18 am-1:04 pm
1 stop5h 46m
Chicago O'Hare Intl
Wed 6/10
5:30 am-1:38 pm
1 stop7h 08m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 5/26
7:20 pm-10:15 pm
1 stop3h 55m
Chicago Midway
Wed 5/27
10:10 am-5:00 pm
2 stops5h 50m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Tue 5/26
1:44 pm-8:14 pm
2 stops7h 30m
Chicago O'Hare Intl
Thu 5/28
8:10 am-3:11 pm
1 stop6h 01m
The best time to book flights from Cleveland to Illinois is 87 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, June is the cheapest month in which you can book a flight from Cleveland to Illinois (average of $68). Flying from Cleveland to Illinois in February is currently the most expensive (average of $128). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s typically best to fly out from Cleveland to Illinois in the morning. Doing so could potentially save you 28% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their Cleveland to Illinois flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CLE to USIL are scheduled on a Thursday (72 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (37 on average).
Boarding
Entertainment
Crew
Food
Overall
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Entertainment
Crew
Food
Overall
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Entertainment
Crew
Food
Overall
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Entertainment
Crew
Food
Overall
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Entertainment
Crew
Food
Overall
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$127 | Average$283 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$137 | Average$261 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$143 | Average$194 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$333 | FlexibilityNo cancel fee | On-time69% |