CLE - MDW

$75 Find Cheap Flights from Cleveland to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Midway departing on 4/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cleveland to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cleveland to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$139
Overall average: $247
Frontier
Wed 4/29Wed 5/6
CLE - MDW • 1 stop
Cheapest non-stop
$154
Typical prices: $157-$347
Southwest
Thu 6/4Tue 6/9
CLE - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Arrive 90 minutes early at CLE for smooth security.
Use the CTA Orange Line from MDW to reach downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $137 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 21m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Atlanta (ATL)
Cheapest • Avg $186 (round-trip)
Detroit (DTW)
Shortest trip • 3h 18m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 30% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Cleveland to Midway (CLE-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cleveland to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cleveland to Midway

Wed, Apr 29 - Wed, May 6
Frontier Logo
11:46 am - 10:14 pm
CLE
-
MDW
11h 28m
1 stop
Frontier Logo
6:00 am - 6:27 pm
MDW
-
CLE
11h 27m
1 stop
$139Frontier
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:50 am - 2:05 pm
CLE
-
MDW
9h 15m
2 stops
Southwest Logo
7:00 am - 12:10 pm
MDW
-
CLE
4h 10m
1 stop
$142Southwest
Tue, Apr 7 - Sat, Apr 11
Southwest Logo
4:20 pm - 7:30 pm
CLE
-
MDW
4h 10m
1 stop
Southwest Logo
7:40 am - 9:50 am
MDW
-
CLE
1h 10mnonstop
$144Southwest
Mon, May 4 - Wed, May 6
Frontier Logo
4:22 pm - 11:12 am
CLE
-
MDW
19h 50m
1 stop
Frontier Logo
12:04 pm - 6:27 pm
MDW
-
CLE
5h 23m
1 stop
$145Frontier
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:50 am - 2:05 pm
CLE
-
MDW
9h 15m
2 stops
Southwest Logo
10:10 am - 5:00 pm
MDW
-
CLE
5h 50m
2 stops
$147Southwest
Tue, May 5 - Thu, May 7
Southwest Logo
1:30 pm - 9:50 pm
CLE
-
MDW
9h 20m
2 stops
Southwest Logo
12:50 pm - 3:05 pm
MDW
-
CLE
1h 15mnonstop
$149Southwest
Wed, Apr 15 - Sat, Apr 18
Frontier Logo
3:33 pm - 10:14 pm
CLE
-
MDW
7h 41m
1 stop
Frontier Logo
7:30 am - 12:43 am
MDW
-
CLE
16h 13m
1 stop
$151Frontier
Mon, Apr 27 - Mon, May 4
Frontier Logo
4:22 pm - 10:19 pm
CLE
-
MDW
6h 57m
1 stop
Frontier Logo
2:15 pm - 9:40 pm
MDW
-
CLE
6h 25m
1 stop
$152Frontier
Mon, Apr 27 - Mon, May 4
Frontier Logo
4:22 pm - 10:19 pm
CLE
-
MDW
6h 57m
1 stop
Frontier Logo
2:15 pm - 9:40 pm
MDW
-
CLE
6h 25m
1 stop
$153Frontier
Wed, Apr 15 - Thu, Apr 16
Southwest Logo
7:20 pm - 10:15 pm
CLE
-
MDW
3h 55m
1 stop
Southwest Logo
5:30 am - 12:15 pm
MDW
-
CLE
5h 45m
1 stop
$154Southwest
Booking Insights

KAYAK's insights & trends for Cleveland to Midway flights

Get data-powered insights and trends into flights from Cleveland to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Cleveland to Chicago Midway Airport?

The average price of all round-trip flights from Cleveland to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

When flying from Cleveland to Chicago Midway Airport, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Cleveland, you’ll find the best rates on Wednesdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Cleveland to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Cleveland to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Cleveland to Chicago Midway Airport is September, where tickets cost $214 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $591 and $361 respectively.

Can I save money by flying with a layover from Cleveland to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $244 on average.

Find deals
Expert advice

Expert advice for your flight from Cleveland to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Brandon Schultz

Brandon Schultz

Expert on CLE

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Good to know

Low seasonJanuary
Cheapest flight$75
Best time to beat the crowds but there is an average 94% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Cleveland to Chicago Midway Airport

When to book flights from Cleveland to Midway

Are your dates flexible? Find out the best times to travel from Cleveland to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Cleveland to Chicago Midway Airport flights

  • What is the cheapest flight from Cleveland to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Cleveland to Chicago Midway Airport was $75 for a one-way ticket and $137 for a round-trip.

  • Do I need a passport to fly between Cleveland and Chicago Midway Airport?

    No

  • Which airports will I be using when flying from Cleveland to Chicago Midway Airport?

    Cleveland and Chicago Midway Airport are both served by 1 main airport. You will leave Cleveland from Cleveland Hopkins Intl and will be arriving at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Cleveland to Chicago Midway Airport?

    American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the Cleveland to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Cleveland to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Cleveland to Chicago Midway Airport flight route.

  • On which days can I fly direct from Cleveland to Chicago Midway Airport?

    There are nonstop flights from Cleveland to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Cleveland to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cleveland to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cleveland to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Cleveland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cleveland to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Cleveland with another airline. Booking your flights between Cleveland and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cleveland to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Cleveland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Cleveland to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $218 or less one-way and $334 or less round-trip.

Prefer to fly direct from Cleveland to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Cleveland Hopkins Intl to Chicago Midway.
Find which airlines fly direct from Cleveland Hopkins Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Cleveland Hopkins Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Cleveland Hopkins Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Cleveland to Midway

 
See real verified KAYAK customer reviews for airlines flying from Cleveland to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Cleveland to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4320 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Everything you need to know for your flight from Cleveland to Midway

Information on your arrival and departure airports

Cleveland (CLE)
Midway (MDW)