CLE - MDW

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

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$127
Typical prices: $196-$312
Southwest
Sun 10/21Sun 10/28
CLE - MDW • Non-stop
Cheapest non-stop
$144
Typical prices: $198-$313
Southwest
Sun 10/14Tue 10/16
CLE - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 22m
Direct flights
+1
Direct flights
+1
When to book
23 weeks
in advance
Our data shows that travelers who book at least 23 weeks in advance save around 77% compared to booking last minute.
Insights
Insights
When to travel
April
Cheapest • 16% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $176 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 3h 14m (one-way)
Insights
Insights
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 Chicago Midway Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Cleveland to Midway (CLE-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cleveland to Midway

Sat, Oct 24 - Mon, Oct 26
Southwest Logo
9:10 am - 9:30 amCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
5:50 pm - 10:30 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
3h 40m1 stop Lambert-St Louis
$127Southwest
Wed, Oct 21 - Wed, Oct 28
Southwest Logo
7:25 pm - 7:40 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
2:45 pm - 9:15 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 30m1 stop Lambert-St Louis
$127Southwest
Mon, Oct 19 - Tue, Oct 20
Southwest Logo
9:00 pm - 11:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
3h 55m1 stop Nashville Intl
Southwest Logo
8:00 am - 10:15 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 15mnonstop
$127Southwest
Sat, Oct 17 - Tue, Oct 20
Southwest Logo
5:25 pm - 5:45 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
2:10 pm - 9:05 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 55m1 stop Nashville Intl
$127Southwest
Tue, Oct 27 - Sat, Oct 31
Southwest Logo
2:20 pm - 2:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
6:45 am - 1:45 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
6h 00m1 stop Baltimore/Washington
$127Southwest
Mon, Oct 19 - Thu, Oct 22
Southwest Logo
8:20 pm - 8:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
6:25 pm - 11:50 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
4h 25m1 stop Baltimore/Washington
$127Southwest
Tue, Nov 10 - Thu, Nov 12
Southwest Logo
6:05 pm - 9:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
4h 30m1 stop Lambert-St Louis
Southwest Logo
7:50 am - 10:10 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 20mnonstop
$127Southwest
Tue, Nov 10 - Wed, Nov 11
Southwest Logo
7:10 pm - 7:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
6:00 am - 12:00 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 00m1 stop Baltimore/Washington
$127Southwest
Sat, Oct 24 - Tue, Oct 27
Frontier Logo
3:46 pm - 11:43 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
8h 57m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:53 am - 8:54 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
10h 01m1 stop Atlanta Hartsfield-Jackson
$134Frontier
Fri, Nov 13 - Sat, Nov 14
Frontier Logo
7:00 am - 5:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
11h 47m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:25 am - 1:34 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 09m1 stop Atlanta Hartsfield-Jackson
$135Frontier
Booking Insights

Price, demand and travel trends for Cleveland to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Cleveland to Chicago Midway Airport typically range from $196 to $312. The lowest price found in the past 5 days was $127, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Cleveland to Chicago Midway Airport. It’s 16% cheaper than the average day, while Monday is the most expensive, with prices 9% higher.

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

•April and May are the cheapest months to fly from Cleveland to Chicago Midway Airport at $214 round-trip.
•January ($379) and March ($281) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 77% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Cleveland to Chicago Midway Airport the cheapest?

Flights from Cleveland to Chicago Midway Airport are cheapest 23 weeks before departure. Booking in this window typically costs about 77% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals
Expert advice

Expert advice for your flight from Cleveland to Midway

 
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

Key details for Cleveland to Chicago Midway Airport flights

Low season

January

Cheapest flight

$59
Beat the crowds with an average 61% drop in travelers.
The most popular month to fly with an average 26% increase in travelers.
One-way 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

Your Cleveland to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Cleveland to Chicago Midway Airport?

    These are the earliest and latest flight times available from Cleveland to Chicago Midway Airport:

    • Earliest: departs at 7:30 am and lands at 8:52 am
    • Latest: departs at 9:35 pm and lands at 10:57 pm.

    The flight takes about 1h 22m.

  • What cabin classes can I book on flights from Cleveland to Chicago Midway Airport?

    Only Economy Class is available on flights from Cleveland to Chicago Midway Airport.

  • How long is a flight from Cleveland to Chicago Midway Airport?

    A nonstop flight from Cleveland to Chicago Midway Airport takes 1h 22m, covering 305 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Cleveland to Chicago Midway Airport flight?

    Round-trip flights from Cleveland to Chicago Midway Airport range from $196 to $312, with an average of $254 over the past 12 months. Anything below $196 counts as a good deal.

  • How expensive are last-minute Cleveland to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 135% above the $254 route average. Book 23 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Cleveland to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $176 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $255 for nonstop.

  • What is the standard checked-bag allowance on flights from Cleveland to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Cleveland to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest. Other aircraft seen on the route include Boeing 737-800 Passenger/BBJ2 (winglets) variants.

  • How are flight departures from Cleveland to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Cleveland to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

  • Have flight prices from Cleveland to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $127 to $849. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on Cleveland to Chicago Midway Airport flights?

    JetBlue is the only airline on the Cleveland to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Cleveland to Chicago Midway Airport looking right now?

    One-way fares from Cleveland to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $60, which is 65% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Cleveland to Chicago Midway Airport?

    Flights from Cleveland to Chicago Midway Airport usually depart from Cleveland Hopkins Intl (CLE) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Cleveland to Chicago Midway Airport pass through?

    Connecting flights from Cleveland to Chicago Midway Airport most commonly pass through:

    • Atlanta Hartsfield-Jackson (ATL) - 75% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 25% of one-stop connections

  • Can I save money by using flexible dates for flights from Cleveland to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 23% on flights from Cleveland to Chicago Midway Airport. Wednesday is the cheapest departure day at $214 round-trip on average, while Monday is the most expensive at $277, a difference of $63.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Cleveland to Chicago Midway Airport?

    Only Southwest operates flights between Cleveland and Chicago Midway Airport.

  • How much time can I save by choosing a different layover airport from Cleveland to Chicago Midway Airport?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 14m, compared with 8h 58m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Cleveland and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Cleveland (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Cleveland to Chicago Midway Airport flights?

    Among airlines operating Cleveland to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Cleveland to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Cleveland to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Monday. On this route, Wednesday flights average $214, about $63 less than Monday fares (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 23 weeks before you fly. On this route, that window historically saves about 77% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Cleveland to Chicago Midway Airport trip for April. Fares historically average $214 round-trip in that month - typically $165 less than the most expensive month, which is January (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $176 round-trip on this route - about $78 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

Prefer to fly direct from Cleveland to Chicago Midway Airport?

 
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

More options for your flight from Cleveland to Midway

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago