$39 Cheap Flights from Cleveland (CLE) to Chicago (MDW)

View $39 flight on Wed, Jun 25, 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.

Cheap Flights from Cleveland to Chicago (CLE-MDW)

Prices were available within the past 7 days and start at $39 for one-way flights and $77 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Jun 25 - Mon, Jun 30
CLE
Cleveland
MDW
Chicago
$77 Roundtrip, found 1 hour ago
$77
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Cleveland to Chicago, returning Mon, Jun 30, priced at $77 found 1 hour ago
Southwest Airlines
Wed, Jun 25 - Mon, Jun 30
CLE
Cleveland
MDW
Chicago
$87 Roundtrip, found 1 hour ago
$87
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Cleveland to Chicago, returning Mon, Jun 30, priced at $87 found 1 hour ago
Southwest Airlines
Mon, Aug 11 - Wed, Aug 27
CLE
Cleveland
MDW
Chicago
$92 Roundtrip, found 1 hour ago
$92
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Mon, Aug 11 from Cleveland to Chicago, returning Wed, Aug 27, priced at $92 found 1 hour ago
Southwest Airlines
Wed, Jun 25 - Mon, Jun 30
CLE
Cleveland
MDW
Chicago
$97 Roundtrip, found 1 hour ago
$97
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Cleveland to Chicago, returning Mon, Jun 30, priced at $97 found 1 hour ago
Southwest Airlines
Mon, Aug 11 - Wed, Aug 27
CLE
Cleveland
MDW
Chicago
$102 Roundtrip, found 1 hour ago
$102
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Mon, Aug 11 from Cleveland to Chicago, returning Wed, Aug 27, priced at $102 found 1 hour ago
Southwest Airlines
Mon, Aug 11 - Wed, Aug 27
CLE
Cleveland
MDW
Chicago
$107 Roundtrip, found 1 hour ago
$107
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Mon, Aug 11 from Cleveland to Chicago, returning Wed, Aug 27, priced at $107 found 1 hour ago
Southwest Airlines
Wed, Jun 25 - Mon, Jun 30
CLE
Cleveland
MDW
Chicago
$114 Roundtrip, found 1 hour ago
$114
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Cleveland to Chicago, returning Mon, Jun 30, priced at $114 found 1 hour ago
Southwest Airlines
Wed, Jun 25 - Mon, Jun 30
CLE
Cleveland
MDW
Chicago
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Cleveland to Chicago, returning Mon, Jun 30, priced at $117 found 1 hour ago
Delta
Wed, Jun 25 - Mon, Jun 30
CLE
Cleveland
MDW
Chicago
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Jun 25 from Cleveland to Chicago, returning Mon, Jun 30, priced at $127 found 1 hour ago
Frontier Airlines
Thu, May 15 - Fri, May 16
CLE
Cleveland
MDW
Chicago
$170 Roundtrip, found 2 hours ago
$170
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, May 15 from Cleveland to Chicago, returning Fri, May 16, priced at $170 found 2 hours ago

Frequently asked questions

How much does a flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) cost?
You can pick up cheap return fares starting at $197 from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and United flight leaving CLE on May 20 2025 and touching down at MDW. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from CLE to MDW?
The cheapest flights from CLE to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Catch a nonstop flight with Southwest Airlines and journey straight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from CLE to MDW?
Currently, the cheapest airline offering one-way flights from CLE to MDW is Southwest Airlines. You can jet off on this route from $99. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from CLE on July 5 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
With an average of 2 direct flights that operate from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) daily, you’ll be on your way in no time.
What are the most popular departure times for flights from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
The 7 AM departures from CLE to MDW are the top choice for many travelers. These flights can come with a higher price due to their popularity. If you’re looking to save, book during off-peak hours.
What day of the week has the most flights from CLE to MDW?
If you jet off on a Friday, you’ll get the widest range of options for flights from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW).
What is the earliest flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Hopkins Intl. Airport (CLE)’s earliest flight to Midway Intl. Airport (MDW) takes off at approximately 6:55AM UTC-5. With a travel time of 1h 30m, you’ll arrive at around 7:25AM UTC-6.
How long does it take to fly from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
The average flight duration from CLE to MDW is 1 hour and 25 minutes, covering a total distance of 310 mi.
What is the best time to fly from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Opt for a flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Hopkins Intl. Airport (CLE)?
Take a direct flight from Hopkins Intl. Airport (CLE) to Chicago and arrive at O’Hare Intl. Airport (ORD). Another gateway to the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from CLE to MDW right before your getaway is typically more expensive. But if you’re flexible with your departure times and dates, you could snag a cheap last-minute fare.
Is it cheaper to book a CLE to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a CLE to MDW flight and hotel package with Expedia could result in significant savings. What’s more, having everything in one convenient place will take the stress out of planning your trip. Simply secure your flights and choose from our wide range of hotels, then tailor your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Hopkins Intl. Airport (CLE) to Midway Intl. Airport (MDW)?
Generally, it’s possible to cancel or reschedule your CLE to MDW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline’s policies in your itinerary to see what changes are allowed and whether any costs are involved. You’ll also find more information on our Customer Service portal.
*Available to One Key members.