CLE offers complimentary Wi-Fi throughout the terminal, with charging stations and work stations available in each concourse.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $165 (Kiwi.com) |
One-way from | $100 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $279 |
Good round-trip deal | $312 or less |
Good one-way deal | $205 or less |
Fly from
Fly to
Route
Depart
Return
Price
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 12/3
5:22 am-8:54 am
1 stop4h 32m
Chicago Midway
Wed 12/3
1:14 pm-12:37 am
2 stops10h 23m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Wed 12/10
9:07 am-9:39 am
Nonstop1h 32m
Chicago O'Hare Intl
Fri 12/12
6:15 pm-8:36 pm
Nonstop1h 21m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Wed 12/24
2:14 pm-2:52 pm
Nonstop1h 38m
Chicago O'Hare Intl
Sun 12/28
7:35 pm-10:04 pm
Nonstop1h 29m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Sun 12/14
7:05 pm-11:30 pm
1 stop5h 25m
Chicago Midway
Tue 12/16
10:05 am-12:30 pm
Nonstop1h 25m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Sat 1/17
3:52 pm-9:04 pm
1 stop6h 12m
Chicago O'Hare Intl
Tue 1/20
5:54 pm-12:39 am
1 stop5h 45m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 1/20
6:30 am-1:09 pm
1 stop7h 39m
Chicago Midway
Tue 1/27
9:34 am-1:49 pm
1 stop3h 15m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Wed 12/17
4:02 pm-8:35 pm
1 stop5h 33m
Chicago O'Hare Intl
Wed 12/24
1:22 pm-7:52 pm
1 stop5h 30m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 1/21
10:20 am-12:48 pm
1 stop3h 28m
Chicago Midway
Wed 1/28
6:17 pm-12:39 am
1 stop5h 22m
ClevelandChicago
CLE - ORD
CLEORD
Cleveland Hopkins Intl
Wed 12/31
2:14 pm-2:52 pm
Nonstop1h 38m
Chicago O'Hare Intl
Sun 1/4
7:35 pm-10:04 pm
Nonstop1h 29m
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Thu 12/4
4:35 pm-4:55 pm
Nonstop1h 20m
Chicago Midway
Sat 12/6
9:50 am-12:10 pm
Nonstop1h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Cleveland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, November is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $71). Flying from Cleveland to Chicago in January is currently the most expensive (average of $137). 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.
A simple way to save on the total cost of your ticket is to fly from Cleveland to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 28% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Cleveland to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CLE to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 on average).
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$166 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$297 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$141 | Average$283 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$302 | FlexibilityNo cancel fee | On-time69% |