CLE - MDW

$59 Find Cheap Flights from Cleveland to Chicago Midway Airport - Compare and Save

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 9/11. 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

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Everything you should know

Cheapest round-trip
$137
Typical prices: $186-$339
Southwest
Sat 9/5Sun 9/6
CLE - MDW • 1 stop
Cheapest non-stop
$142
Typical prices: $186-$339
Southwest
Fri 9/11Mon 9/14
CLE - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 14m
Direct flights
Direct flights
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Direct flights
Direct flights
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When to travel
April
Cheapest • 25% price drop
August
Most popular
Good to know
Good to know
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Good to know
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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

Sat, Sep 5 - Sun, Sep 6
Southwest Logo
3:15 pm - 8:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
6h 20m1 stop Baltimore/Washington
Southwest Logo
8:55 am - 2:25 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
4h 30m1 stop Nashville Intl
$137Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
10:35 am - 2:10 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
4h 35m1 stop Nashville Intl
Southwest Logo
6:35 am - 1:15 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 40m1 stop Lambert-St Louis
$137Southwest
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
5:25 pm - 5:40 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
8:05 am - 10:25 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 20mnonstop
$142Southwest
Tue, Sep 15 - Wed, Sep 16
Southwest Logo
1:15 pm - 9:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
9h 40m2 stops Nashville Intl Lambert-St Louis
Southwest Logo
3:05 pm - 9:05 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 00m1 stop Baltimore/Washington
$142Southwest
Sat, Sep 5 - Mon, Sep 7
Southwest Logo
4:35 pm - 4:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
8:05 am - 10:25 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 20mnonstop
$142Southwest
Wed, Oct 28 - Fri, Oct 30
Southwest Logo
8:35 am - 8:55 amCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
7:45 am - 10:00 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 15mnonstop
$142Southwest
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
5:25 pm - 5:40 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
8:05 am - 10:25 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 20mnonstop
$142Southwest
Wed, Sep 9 - Fri, Sep 11
Southwest Logo
7:15 pm - 7:30 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
4:25 pm - 6:40 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 15mnonstop
$142Southwest
Thu, Oct 15 - Thu, Oct 22
Frontier Logo
3:40 pm - 9:58 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
7h 18m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:03 pm - 8:37 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
7h 34m1 stop Atlanta Hartsfield-Jackson
$154Frontier
Wed, Sep 2 - Fri, Sep 4
Frontier Logo
5:15 pm - 10:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
6h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:50 am - 10:31 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
9h 41m1 stop Atlanta Hartsfield-Jackson
$154Frontier
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.

How much is a round-trip flight from Cleveland to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Cleveland to Chicago Midway Airport departing in September.

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from Cleveland usually cost between $156 and $437 in September.
The lowest price found in the past 5 days was $137 on Southwest (Sep 5-Sep 6).

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 Saturday and avoid Mondays if you are looking for the best rates. For your return to Cleveland, you’ll find the best rates on Saturdays 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 April, where tickets cost $234 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $591 and $411 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.

No, with an average price for the route of $236, prices are generally cheapest when you fly direct.

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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 season

January

Cheapest flight

$59
Best time to beat the crowds but there is an average 88% increase in price.
Most popular time to fly and prices are also 18% 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 5 days, the lowest price for a flight from Cleveland to Chicago Midway Airport was $59 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, JetBlue, and Alaska Airlines 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 $167 or less one-way and $256 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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Cleveland Hopkins Intl

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

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

Information on your arrival and departure airports

Cleveland (CLE)
Midway (MDW)