MDW - CLE

$86 Find Cheap Flights from Chicago Midway Airport to Cleveland - Compare and Save

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Everything you should know

Cheapest round-trip
$127
Typical prices: $228-$504
Southwest
Wed 11/14Sun 11/18
MDW - CLE • Non-stop
Cheapest non-stop
$134
Typical prices: $230-$510
Southwest
Mon 9/17Wed 9/19
MDW - CLE • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 15m
Direct flights
+1
Direct flights
+1
When to travel
March
Cheapest • 31% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $243 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 3h 30m (one-way)
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Flight Deals

Cheap Flights from Midway to Cleveland (MDW-CLE)

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

Recent round-trip flight deals from Midway to Cleveland

Sat, Nov 14 - Wed, Nov 18
Southwest Logo
8:00 am - 10:20 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 20mnonstop
Southwest Logo
6:05 pm - 9:30 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
4h 25m1 stop Lambert-St Louis
$127Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
5:55 am - 12:35 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 40m1 stop Nashville Intl
Southwest Logo
5:25 pm - 5:40 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
$127Southwest
Wed, Oct 21 - Mon, Oct 26
Southwest Logo
8:00 am - 10:15 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 15mnonstop
Southwest Logo
9:00 pm - 11:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
3h 55m1 stop Nashville Intl
$127Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
5:55 am - 12:15 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 20m1 stop Baltimore/Washington
Southwest Logo
4:35 pm - 4:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 20mnonstop
$127Southwest
Mon, Oct 5 - Mon, Oct 12
Southwest Logo
5:00 am - 12:00 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
6h 00m1 stop Baltimore/Washington
Southwest Logo
8:20 pm - 8:35 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
$127Southwest
Thu, Oct 15 - Sat, Oct 17
Southwest Logo
7:45 am - 10:00 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 15mnonstop
Southwest Logo
6:40 pm - 9:40 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
4h 00m1 stop Nashville Intl
$127Southwest
Mon, Oct 19 - Mon, Oct 26
Southwest Logo
7:45 am - 10:00 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 15mnonstop
Southwest Logo
5:50 pm - 10:00 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
5h 10m1 stop Baltimore/Washington
$127Southwest
Fri, Oct 16 - Tue, Oct 20
Frontier Logo
1:12 pm - 8:26 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
6h 14m1 stop Dallas/Fort Worth
Frontier Logo
3:46 pm - 11:43 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
8h 57m1 stop Atlanta Hartsfield-Jackson
$135Frontier
Sat, Nov 14 - Sat, Nov 14
Frontier Logo
7:25 am - 1:34 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 09m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:46 pm - 11:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
9h 01m1 stop Atlanta Hartsfield-Jackson
$150Frontier
Thu, Oct 1 - Mon, Oct 5
Delta Logo
7:01 pm - 11:54 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
3h 53m1 stop Detroit Metropolitan Wayne County
Delta Logo
2:20 pm - 6:33 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
5h 13m1 stop Detroit Metropolitan Wayne County
$157Delta
Booking Insights

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

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

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

Round-trip flights from Chicago Midway Airport to Cleveland start at $127. Prices are below average for this route right now, with typical round-trip fares ranging from $228 to $504. The lowest price found in the past 5 days was $127 on Southwest.

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

Saturday is the cheapest day of the week to fly from Chicago Midway Airport to Cleveland, it is 16% cheaper than the average day. Monday is the most expensive day with flight prices 64% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • March is the cheapest month to fly from Chicago Midway Airport to Cleveland at $191 round-trip.
  • January ($553) and April ($487) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 189% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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Expert advice

Expert advice for your flight from Midway to Cleveland

 
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 Chicago Midway Airport to Cleveland flights

Low season

January

Cheapest flight

$86
Best time to beat the crowds but there is an average 99% increase in price.
Flight from Chicago Midway Airport to Cleveland

When to book flights from Midway to Cleveland

Are your dates flexible? Find out the best times to travel from Midway to Cleveland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Cleveland flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

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

    Among airlines operating Chicago Midway Airport to Cleveland flights:

    • Southwest: offers free seat selection

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

  • What airlines are available from Chicago Midway Airport to Cleveland?

    Only Southwest operates flights between Chicago Midway Airport and Cleveland.

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

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

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Cleveland 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 travelers should check the fare details before booking.

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

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

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $243 round-trip via Orlando (MCO), compared to $281 for nonstop.

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

    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 Chicago Midway Airport to Cleveland?

    The Embraer 175 (Enhanced Winglets) family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Boeing 737-800 variants.

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

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

    • Detroit Metropolitan Wayne County (DTW) - 50% of one-stop connections
    • Orlando (MCO) - 50% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

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

    On the Chicago Midway Airport to Cleveland route, being flexible with your departure day can save you up to 49%. Saturday is the cheapest day at $234 round-trip on average, while Monday is the most expensive at $457: a $223 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

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

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

  • What popular places can I visit in Cleveland?

    Some of the most popular sights in Cleveland are Progressive Field, Huntington Bank Field and Rock and Roll Hall of Fame. These are among the most viewed places in Cleveland on KAYAK.

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

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

    • Earliest: departs at 7:40 am and lands at 8:55 am
    • Latest: departs at 7:05 pm and lands at 8:20 pm.

    The flight takes about 1h 15m.

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

    A nonstop flight from Chicago Midway Airport to Cleveland takes 1h 15m, covering 305 miles.

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

    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.

  • Have flight prices from Chicago Midway Airport to Cleveland 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 $698. That means the highest observed fare was about 6x higher than the lowest one.

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

    One-way fares from Chicago Midway Airport to Cleveland are currently lower than usual. Average one-way flight prices are about $93, which is 51% below the typical average for this route.

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

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 30m, compared with 6h 16m via Orlando (MCO).

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

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

  • What car rental options are available at Cleveland Hopkins Intl Airport (CLE)?

    Cleveland Hopkins Intl Airport (CLE) hosts 5 major car rental companies, with daily rates starting from around $26 for economy cars. Top options include:
    · Hertz
    · Budget
    · Alamo
    · Dollar
    · Thrifty

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

    Round-trip flights from Chicago Midway Airport to Cleveland range from $228 to $504, with an average of $278 over the past 12 months. Anything below $228 counts as a good deal.

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

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

Your guide to booking Chicago Midway Airport to Cleveland flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Saturday departure instead of Monday. On this route, Saturday flights average $234 - about $223 less than Monday (49% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to Cleveland trip for March. Fares historically average $191 round-trip in that month - typically $362 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 Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $243 round-trip on this route - about $38 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 Cleveland Hopkins Intl Airport.
    - Hilton Garden Inn Cleveland Airport
    - Extended Stay America Select Suites - Cleveland - Airport

Prefer to fly direct from Chicago Midway Airport to Cleveland?

 
Find which airlines fly direct from Chicago Midway Airport to Cleveland Hopkins Intl Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Cleveland (CLE)