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Cheap flights from Cleveland to Chicago from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Chicago departing on 5/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Cleveland to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Cleveland to Chicago.
Frontier Logo
5:30 am - 12:24 pmCLE-MDW
7h 54m1 stop
Frontier Logo
1:19 pm - 12:36 amMDW-CLE
10h 17m1 stop
$170Frontier
Find Deal
Thu, May 15 - Mon, May 19
Frontier Logo
3:05 pm - 11:32 pmCLE-ORD
9h 27m1 stop
Frontier Logo
5:45 am - 2:18 pmORD-CLE
7h 33m1 stop
$170Frontier
Find Deal
Sat, May 17 - Sun, May 18
American Airlines Logo
5:30 am - 6:09 amCLE-ORD
1h 39mnonstop
American Airlines Logo
9:42 am - 12:04 pmORD-CLE
1h 22mnonstop
$197American Airlines
Find Deal
Sat, May 24 - Sun, May 25
American Airlines Logo
12:41 pm - 1:20 pmCLE-ORD
1h 39mnonstop
American Airlines Logo
9:42 am - 12:04 pmORD-CLE
1h 22mnonstop
$198American Airlines
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
6:50 am - 7:05 amCLE-MDW
1h 15mnonstop
Southwest Logo
7:50 pm - 10:05 pmMDW-CLE
1h 15mnonstop
$207Southwest
Find Deal
Sat, May 24 - Sun, May 25
United Airlines Logo
6:00 am - 6:29 amCLE-ORD
1h 29mnonstop
United Airlines Logo
9:20 pm - 11:46 pmORD-CLE
1h 26mnonstop
$217United Airlines
Find Deal
Wed, Jun 11 - Wed, Jun 11
Delta Logo
2:10 pm - 6:45 pmCLE-MDW
5h 35m1 stop
Delta Logo
6:25 pm - 10:05 pmMDW-CLE
2h 40m1 stop
$217Delta
Find Deal
Sat, May 24 - Sun, May 25
Delta Logo
10:30 am - 5:14 pmCLE-MDW
7h 44m2 stops
Delta Logo
6:00 am - 1:15 pmMDW-CLE
6h 15m1 stop
$222Delta
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
6:45 am - 7:00 amCLE-MDW
1h 15mnonstop
Southwest Logo
8:25 pm - 10:40 pmMDW-CLE
1h 15mnonstop
$224Southwest
Find Deal
Tue, Jul 22 - Sat, Jul 26
United Airlines Logo
8:50 am - 9:23 amCLE-ORD
1h 33mnonstop
United Airlines Logo
7:34 am - 10:00 amORD-CLE
1h 26mnonstop
$284United Airlines
Find Deal
Wed, Jun 18 - Sat, Jun 21

United Airlines flights from Cleveland to Chicago

Our best United Airlines deals on Cleveland to Chicago flight tickets
United Airlines
Jun 11
CLE6:00 amCleveland Hopkins Intl
1h 29m
ORD6:29 amChicago O'Hare Intl
Jun 11
ORD9:20 pmChicago O'Hare Intl
1h 26m
CLE11:46 pmCleveland Hopkins Intl
United Airlines
Jun 18
CLE8:50 amCleveland Hopkins Intl
1h 33m
ORD9:23 amChicago O'Hare Intl
Jun 21
ORD7:34 amChicago O'Hare Intl
1h 26m
CLE10:00 amCleveland Hopkins Intl
United Airlines
Jun 12
CLE8:50 amCleveland Hopkins Intl
1h 33m
ORD9:23 amChicago O'Hare Intl
Jun 14
ORD2:25 pmChicago O'Hare Intl
1h 27m
CLE4:52 pmCleveland Hopkins Intl

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets
Frontier
May 17
CLE3:05 pmCleveland Hopkins Intl
9h 27m
1 stop
ORD11:32 pmChicago O'Hare Intl
May 18
ORD5:45 amChicago O'Hare Intl
7h 33m
1 stop
CLE2:18 pmCleveland Hopkins Intl
Frontier
May 21
CLE8:30 amCleveland Hopkins Intl
11h 20m
1 stop
ORD6:50 pmChicago O'Hare Intl
May 24
ORD1:02 pmChicago O'Hare Intl
8h 38m
1 stop
CLE10:40 pmCleveland Hopkins Intl
Frontier
May 12
CLE6:25 amCleveland Hopkins Intl
10h 44m
1 stop
ORD4:09 pmChicago O'Hare Intl
May 15
ORD4:15 pmChicago O'Hare Intl
7h 21m
1 stop
CLE12:36 amCleveland Hopkins Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Cleveland to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Cleveland, with most prices found around $237. If you’re not able to fly to Chicago in September, then April is your next best option. Flight prices from Cleveland to Chicago during April average around $250.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $496. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Cleveland to Chicago for around $675.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cleveland to Chicago during this time can be as low as $495. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,030.

What is the cheapest Cleveland Hopkins Intl to Chicago flight route?

Fly from Cleveland Hopkins Intl to Chicago Midway for the best Cleveland Hopkins Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Cleveland when booking 18 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $298 when searching 18 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Cleveland for as low as $185 on momondo.

What cabin class options are available on Cleveland Hopkins Intl to Chicago flights?

There are 4 cabin classes available to choose from on Cleveland Hopkins Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Cleveland to Chicago flight prices changed over time?

As of April 2025, prices for Cleveland to Chicago flights are approximately 10% more expensive when compared to flights at the same time last year.

When to book flights from Cleveland to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cleveland to Chicago (CLE to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Chicago

Best Price Found

$90

Fastest flight time

1h 15m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Cleveland in the past 72 hours is $90. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $170.
The fastest flight from Cleveland to Chicago takes 1h 15m
Direct flights go from Cleveland to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • Is flying the fastest way to get from Cleveland to Chicago?

    The quickest way to travel this route is to take a flight from Cleveland to Chicago, doing so can potentially save up to 6h 20m of travel time. While these options may take longer, booking a train from Cleveland to Chicago or a bus from Cleveland to Chicago may suit your needs if travel time is less of a factor in your decision making.

  • Is flying the cheapest way to get from Cleveland to Chicago?

    Expect a bus to be one of the cheapest options available to you for travel. Currently, a bus has deals available from $90. While they may not be the most cost-effective options currently available a flight from Cleveland to Chicago or a train from Cleveland to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

  • How far is Cleveland Hopkins Intl to Chicago by plane?

    Cleveland Hopkins Intl and Chicago are 307.0 mi apart from one another. A reasonable flight in good conditions will take 1h 15m.

  • When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Chicago?

    Prices for flights from Cleveland Hopkins Intl Airport to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Chicago?

  • How old do you have to be to fly from Cleveland Hopkins Intl Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cleveland Hopkins Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Cleveland to Chicago?

  • What is the most popular airline from Cleveland to Chicago?


Best airlines flying from Cleveland to Chicago

Compare and see reviews for airlines that fly from Cleveland to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $100Free CancellationRating
5.9
3,285 reviews
Search Frontier flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
8,694 reviews
Search United Airlines flights
American AirlinesPriceFrom $161Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $172Free CancellationRating
8.0
4,292 reviews
Search Southwest flights
  • Southwest Flights From Cleveland to Chicago

    Southwest flight deals from Cleveland to Chicago start from $172 round-trip. Over the 20 Southwest flights for this route in a normal week, average airfare is usually $281 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Cleveland to Chicago

    United Airlines (7.4/10 from 8,694 reviews) operates around 44 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $324, with deals from around $157 rare but found on momondo. Referenced prices are for round-trip Cleveland to Chicago flight searches in the last 72 hours.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Cleveland to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Cleveland to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Cleveland to Chicago with flexible booking policies on momondo?

All flight searches from Cleveland to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Cleveland to Chicago?

Once you have performed a search for Cleveland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Cleveland to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Cleveland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


Choose the best way to get from Cleveland to Chicago

Buses

7h 35m
$43 one-way$90 round-trip
Nonstop · from $901 stop · from $90

Distance to downtown

F990.8 mi

Find Buses

Cleveland to Chicago Buses

Trains

6h 46m
$59 one-way$150 round-trip
Nonstop · from $150

Distance to downtown

ZUN0.7 mi

Flights

1h 15m
$90 one-way$170 round-trip
Nonstop · from $197

Distance to downtown

ORD15.9 mi
MDW8.6 mi

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1 adult
From?
To?
Sat 5/3
Sat 5/10

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago