Flights from Cleveland to Chicago from $104

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Flights Chicago → Cleveland
Flights Schedule   Cheap Tickets   Airlines   Airports

Airfare Deals Cleveland to Chicago

On HolidayPrice.com you will find 4 direct and 0 connecting flights from Cleveland to Chicago at a price of from $104. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out CLE - CHI flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Cleveland to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

You might be interested in this:

Cheap flights from Cleveland
Cheap flights to Chicago
Airline tickets to United States

One way flight from Cleveland to Chicago

Below are the prices of tickets for direct one-way flights from Cleveland to Chicago. The cheapest flight from Cleveland to Chicago starts from $104 – the departure date for this flight is 13 November 2025.

*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Cleveland to Chicago

You can buy a round-trip ticket from Cleveland to Chicago (United States) and back using the table below. The best offer starts from $243, the flight dates are: there on 15 November 2025 year and back on 15 November 2025 year.

*Prices include: baggage, hand luggage, airline fees and charges.
Not found promotions and sales.

Flight Schedule Cleveland to Chicago 2025

The current flight schedule for the route from Cleveland to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 11 flights every day, from 1hours 15min. Local departure and arrival times are indicated.
06:00 → 06:30
United Airlines UA593 United Airlines UA593
CLE → ORD
- - - - Fr - -
Check price
06:00 → 06:30
United Airlines UA729 United Airlines UA729
CLE → ORD
Mo Tu We Th Fr - Su
Check price
06:39 → 07:20
American Airlines AA1080 American Airlines AA1080
CLE → ORD
Mo - - Th Fr - Su
Check price
06:45 → 07:00
Southwest Airlines WN349 Southwest Airlines WN349
CLE → MDW
Mo - - Th Fr - -
Check price
07:00 → 07:15
Southwest Airlines WN349 Southwest Airlines WN349
CLE → MDW
- - - - - - Su
Check price
07:00 → 07:34
United Airlines UA398 United Airlines UA398
CLE → ORD
Mo Tu We Th Fr Sa Su
Check price
07:05 → 07:20
Southwest Airlines WN2019 Southwest Airlines WN2019
CLE → MDW
- Tu We - - - -
Check price
07:15 → 07:30
Southwest Airlines WN349 Southwest Airlines WN349
CLE → MDW
- - - - - Sa -
Check price
08:40 → 09:14
United Airlines UA567 United Airlines UA567
CLE → ORD
Mo Tu We Th Fr - -
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08:40 → 09:14
United Airlines UA2465 United Airlines UA2465
CLE → ORD
Mo - We Th Fr Sa Su
Check price
09:00 → 09:39
American Airlines AA1080 American Airlines AA1080
CLE → ORD
- Tu We - - Sa -
Check price
09:05 → 09:39
United Airlines UA567 United Airlines UA567
CLE → ORD
- - - - - - Su
Check price
Show all

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from Cleveland takes 01:10 minutes (excluding transfers). The distance between Cleveland and Chicago is 307 miles (494 kilometers). Planes depart from Cleveland between 00:05 and 23:50. The fastest flight from the company United Airlines with flight number UA 1704. Flies for just 01:08 minutes with departure from Cleveland Hopkins and arrival in O'Hare.

time

Average flight time

01:10 min

distance

Distance

307 mi

The earliest flight

The earliest flight

00:05

The latest flight

The latest flight

23:50

Airplane

The fastest flight

01:08

Airlines

Direct flight

There are 4 airlines that fly directly from Cleveland to Chicago. The most popular company carrying out non-stop flights is American Airlines.

*Flight number

Flights with Transfers

Flights with transfers from Cleveland to Chicago can be bought from 0 airlines:

*Transit cities

Airports

Airports serving the air communication between Cleveland and Chicago. You can fly to Chicago from 1 Cleveland airports. Planes arrive at 2 airport in Chicago.

Cleveland airports:

Cleveland Hopkins  ~ 16 km* from $ 37

Chicago airports:

O'Hare  ~ 25 km* from $ 69Chicago Midway  ~ 14 km* from $ 80

*Distance from the airport to the city center

Aircraft

You can fly from Cleveland to Chicago on board of 4 airlines that utilize 12 aircraft models.

  • Airbus A319
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Canadair reg jet 700
  • Canadair regional jet
  • Embraer 170
  • Embraer 175
  • Embraer EMB 175
  • Embraer ERJ-135/140/145 Regional Jet
  • Embraer RJ145

Connecting cities

The list of cities on transfer flights to Chicago from Cleveland. The best options are to fly through: .

Cheap airline tickets from Cleveland to United States

Here is a list of flights from Cleveland to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Cleveland - New York DL 5094 Delta Air Lines Canadair Regional Jet 900
21:45 Cleveland Hopkins
in a way 1 hours 15 min Direct
23:00 LaGuardia
Flights
from $43 18 November 2025
Cleveland - Los Angeles UA 580 United Airlines Boeing 737-900
15:29 Cleveland Hopkins
in a way 4 hours 31 min Direct
20:00 Los Angeles
Flights
from $125 03 March 2026
Cleveland - Miami NK 1625 Spirit Airlines Airbus A320
23:30 Cleveland Hopkins
in a way 2 hours 45 min Direct
02:15 Fort Lauderdale Executive Airport
Flights
from $66 10 November 2025
Cleveland - Chicago UA 1704 United Airlines Boeing 737-900
00:52 Cleveland Hopkins
in a way 1 hours 8 min Direct
02:00 O'Hare
Flights
from $104 13 November 2025
Cleveland - San Francisco UA 413 United Airlines Boeing 737-900
02:32 Cleveland Hopkins
in a way 5 hours 7 min Direct
07:39 San Francisco
Flights
from $78 21 November 2025

All flights from Cleveland

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Chicago UA 761 United Airlines Boeing 737-800
13:00 LaGuardia
in a way 2 hours 0 min Direct
15:00 O'Hare
Flights
from $27 15 November 2025
Los Angeles - Chicago UA 910 United Airlines Boeing 737-800
10:23 Los Angeles
in a way 3 hours 37 min Direct
14:00 O'Hare
Flights
from $50 15 November 2025
Miami - Chicago AA 2796 American Airlines Boeing 767-300
17:05 Miami
in a way 2 hours 55 min Direct
20:00 O'Hare
Flights
from $46 26 November 2025
Miami - Chicago WN 1626 Southwest Airlines Boeing 737
13:35 Fort Lauderdale Executive Airport
in a way 3 hours 0 min Direct
16:35 Chicago Midway
Flights
from $46 26 November 2025
San Francisco - Chicago UA 1800 United Airlines Airbus A319
04:15 San Francisco
in a way 3 hours 45 min Direct
08:00 O'Hare
Flights
from $64 12 January 2026

All flights to Chicago

Tips for buying a ticket

Cleveland – Chicago – Cleveland round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Cleveland to Chicago
Chicago city

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