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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
$135
Typical prices: $215-$487
Frontier
Wed 11/7Sat 11/10
MDW - CLE • 1 stop
Cheapest non-stop
$171
Typical prices: $213-$489
Southwest
Wed 11/21Thu 11/22
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

Fri, Nov 27 - Thu, Dec 3
Frontier Logo
9:07 am - 8:09 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
10h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:00 am - 2:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
9h 55m1 stop Atlanta Hartsfield-Jackson
$135Frontier
Tue, Nov 24 - Thu, Dec 3
Frontier Logo
8:42 pm - 8:41 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
10h 59m1 stop Orlando
Frontier Logo
6:00 am - 2:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
9h 55m1 stop Atlanta Hartsfield-Jackson
$135Frontier
Sat, Nov 7 - Tue, Nov 10
Frontier Logo
7:15 am - 1:34 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
5h 19m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:35 am - 5:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
12h 12m1 stop Atlanta Hartsfield-Jackson
$135Frontier
Thu, Dec 3 - Sun, Dec 6
Frontier Logo
3:50 pm - 12:55 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
8h 05m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:00 am - 2:55 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
9h 55m1 stop Atlanta Hartsfield-Jackson
$151Frontier
Sat, Oct 31 - Sun, Nov 1
Frontier Logo
7:25 am - 8:54 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
12h 29m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:35 am - 5:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
12h 12m1 stop Atlanta Hartsfield-Jackson
$157Frontier
Wed, Oct 28 - Mon, Nov 2
Frontier Logo
6:16 am - 8:54 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
13h 38m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:35 am - 5:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
12h 12m1 stop Atlanta Hartsfield-Jackson
$166Frontier
Sat, Nov 21 - Sun, Nov 22
Southwest Logo
7:45 am - 10:05 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 20mnonstop
Southwest Logo
12:35 pm - 12:50 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 15mnonstop
$171Southwest
Sat, Nov 21 - Sun, Nov 22
Southwest Logo
7:45 am - 10:05 amMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 20mnonstop
Southwest Logo
7:55 pm - 8:30 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 35mnonstop
$171Southwest
Tue, Nov 3 - Tue, Nov 10
Frontier Logo
6:16 am - 8:20 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
13h 04m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:35 am - 5:47 pmCLE  Cleveland Hopkins Intl-MDW Chicago Midway
12h 12m1 stop Atlanta Hartsfield-Jackson
$171Frontier
Fri, Dec 18 - Fri, Dec 25
Southwest Logo
7:35 pm - 9:45 pmMDW  Chicago Midway-CLE Cleveland Hopkins Intl
1h 10mnonstop
Southwest Logo
8:45 am - 9:10 amCLE  Cleveland Hopkins Intl-MDW Chicago Midway
1h 25mnonstop
$171Southwest
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 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 typically range from $215 to $487. The lowest price found in the past 5 days was $135, on Frontier.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Chicago Midway Airport to Cleveland. It’s 16% cheaper than the average day, while Monday is the most expensive, with prices 81% higher.

What’s 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
Beat the crowds with an average 62% drop in travelers.
The most popular month to fly with an average 62% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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 7:35 am and lands at 8:50 am
    • Latest: departs at 8:40 pm and lands at 9:55 pm.

    The flight takes about 1h 15m.

  • 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 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.

  • 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 $215 to $487, with an average of $277 over the past 12 months. Anything below $215 counts as a good deal.

  • 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 $277 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 Boeing 737-800 family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Embraer 175 (Enhanced Winglets) variants.

  • 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%.

  • 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 $135 to $733. That means the highest observed fare was about 5x 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 $88, which is 61% below the typical average for this route.

  • 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

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

    One-stop flights from Chicago Midway Airport to Cleveland most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 67% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 17% of one-stop connections
    • Orlando (MCO) - 17% of one-stop connections

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

    Yes. Flexible dates can save you up to 54% on flights from Chicago Midway Airport to Cleveland. Saturday is the cheapest departure day at $234 round-trip on average, while Monday is the most expensive at $503, a difference of $269.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Chicago Midway Airport to Cleveland?

    Only Southwest operates flights between Chicago Midway Airport and Cleveland.

  • 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) and 6h 49m via Atlanta Hartsfield-Jackson (ATL).

  • 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 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.

  • 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.

  • 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 always check the fare details before booking.

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 are flexible, aim for a Saturday departure and avoid flying on Monday. On this route, Saturday flights average $234, about $269 less than Monday fares (53% 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 $34 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.

    • Extended Stay America Select Suites - Cleveland - Airport
    • Hilton Garden Inn 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

Southwest

Southwest

Tuesday

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Southwest

Wednesday

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Thursday

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Friday

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Southwest

Saturday

Southwest

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Sunday

Southwest

Southwest

See more direct flights

Direct returns

Cleveland Hopkins Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

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Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Midway to Cleveland

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

Car rentals in Cleveland
Hotels in Cleveland
Vacations in Cleveland