Cheap flights from CLE to MDW (Hopkins Intl. to Midway Intl.)

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Cheap Flights from CLE to MDW starting at $46 One Way, $85 Round Trip

Prices starting at $85 for return flights and $46 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 28 - Wed, Sep 3
CLE
Cleveland
MDW
Chicago
$85 Roundtrip, found 6 days ago
$85
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Cleveland to Chicago, returning Wed, Sep 3, priced at $85 found 6 days ago
Thu, Aug 28 - Mon, Sep 1
CLE
Cleveland
MDW
Chicago
$93 Roundtrip, found 6 days ago
$93
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Cleveland to Chicago, returning Mon, Sep 1, priced at $93 found 6 days ago
Thu, Aug 28 - Wed, Sep 3
CLE
Cleveland
MDW
Chicago
$95 Roundtrip, found 6 days ago
$95
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Cleveland to Chicago, returning Wed, Sep 3, priced at $95 found 6 days ago
Thu, Aug 28 - Wed, Sep 3
CLE
Cleveland
MDW
Chicago
$100 Roundtrip, found 6 days ago
$100
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Cleveland to Chicago, returning Wed, Sep 3, priced at $100 found 6 days ago
Mon, Aug 4 - Wed, Aug 6
CLE
Cleveland
MDW
Chicago
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Aug 4 from Cleveland to Chicago, returning Wed, Aug 6, priced at $102 found 5 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
$147 nightly
The price is $173 total per night from Aug 10 to Aug 11
$173 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,251 reviews)
"Good place to stay"

Reviewed on Jul 13, 2025

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$169 nightly
The price is $199 total per night from Aug 10 to Aug 11
$199 total
Aug 10 - Aug 11
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,958 reviews)
"Best place to stay in Chicago! Accessible to all CTA stations, phenomenal view, and nearby to so many great places"

Reviewed on Jul 13, 2025

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
$161 nightly
The price is $189 total per night from Aug 10 to Aug 11
$189 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,011 reviews)
"Its was very nice and pleasant stay"

Reviewed on Jul 15, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$169 nightly
The price is $199 total per night from Aug 10 to Aug 11
$199 total
Aug 10 - Aug 11
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,958 reviews)
"Best place to stay in Chicago! Accessible to all CTA stations, phenomenal view, and nearby to so many great places"

Reviewed on Jul 13, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
$251 nightly
The price is $289 total per night from Aug 7 to Aug 8
$289 total
Aug 7 - Aug 8
Total includes taxes and fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,047 reviews)
"Great. Just hard to get parked to get into hotel due to busy location."

Reviewed on Jul 15, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
$147 nightly
The price is $172 total per night from Aug 10 to Aug 11
$172 total
Aug 10 - Aug 11
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,449 reviews)
"Great location, downtown Chicago! Room had everything that was needed"

Reviewed on Jul 14, 2025

Hilton Chicago/Magnificent Mile Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
$57 nightly
The price is $64 total per night from Jul 28 to Jul 29
$64 total
Jul 28 - Jul 29
Total includes taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,536 reviews)
"Like: Nothing in particular Didn't like: parking lot looked unsafe but was okay; bathroom door was not lockable;"

Reviewed on Jul 10, 2025

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue, Bensenville, IL
$95 nightly
The price is $106 total per night from Jul 20 to Jul 21
$106 total
Jul 20 - Jul 21
Total includes taxes and fees
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
7/10 Good! (1,022 reviews)
"Good hotel if you are stranded near O’Hare. Convenient shuttle, property is a little dated but rooms are clean and spacious."

Reviewed on Jul 13, 2025

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road, Schiller Park, IL
$96 nightly
The price is $109 total per night from Jul 21 to Jul 22
$109 total
Jul 21 - Jul 22
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,549 reviews)
"The staff was amazing, the rooms were clean and spacious. It’s close to so much in the area. The beds, especially the mattress on the pullout, could stand to be replaced. They were a little rough."

Reviewed on Jul 13, 2025

Comfort Suites Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Chicago Hotels

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
$127 nightly
The price is $149 total per night from Aug 6 to Aug 7
$149 total
Aug 6 - Aug 7
Total includes taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,075 reviews)
Great Place
"Great place, been coming here often."

Reviewed on Jul 14, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
$122 nightly
The price is $143 total per night from Aug 4 to Aug 5
$143 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7/10 Good! (2,235 reviews)
"Great value for the cost. Pleasant room and facilities, and very friendly and helpful staff. Will stay there again."

Reviewed on Jul 12, 2025

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
$57 nightly
The price is $64 total per night from Jul 28 to Jul 29
$64 total
Jul 28 - Jul 29
Total includes taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,536 reviews)
"Like: Nothing in particular Didn't like: parking lot looked unsafe but was okay; bathroom door was not lockable;"

Reviewed on Jul 10, 2025

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive, Chicago, IL
$233 nightly
The price is $273 total per night from Aug 10 to Aug 11
$273 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,744 reviews)
"Nice"

Reviewed on Jul 13, 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
$198 nightly
The price is $229 total per night from Aug 5 to Aug 6
$229 total
Aug 5 - Aug 6
Total includes taxes and fees
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,787 reviews)
"Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite! Personnel at the hotel were kind and helpful. Have a cocktail and a brownie in the lobby- you won't regret ..."

Reviewed on Jul 15, 2025

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
$220 nightly
The price is $258 total per night from Aug 4 to Aug 5
$258 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,453 reviews)
"The location was great for our museum tour of Chicago. The staff is very friendly, accommodating and the service was excellent. The atrium on the mezzanine level is beautiful and the fountain adds a pleasant, serene ambiance when you enter the lobby. I have always had top notch stays at Embassy Suites ..."

Reviewed on Jul 14, 2025

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

CLE to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from Hopkins Intl. Airport (CLE) to Chicago Airport?
Before you climb aboard your flight at Hopkins Intl. Airport (CLE), you should pack loads of tasty snacks in your carry-on bag. Southwest Airlines flies directly to Chicago Airport, so you won't get the chance to top up your supplies en route.
What is the shortest flight from Hopkins Intl. Airport (CLE) to Chicago Airport?
From Cleveland, the distinctive sights and sounds of Chicago are around 5 hours and 8 minutes away. Secure your favorite seat, or perhaps even one with more legroom, and jet to your destination in pure comfort.
How many hours flight from Cleveland Hopkins Intl. Airport to Midway Intl. Airport (MDW)?
It takes an easy 5 hours and 14 minutes on average to fly from CLE to MDW. Whip out that travel book and circle all the spots you'd like to visit. It won't be long before you'll be seeing them for yourself.
What airlines have the most flights from Cleveland Hopkins Intl. Airport to Chicago Airport?
One of the most well-known airlines operating on the Cleveland to Chicago route, Southwest Airlines is the start of your next amazing adventure. You can select from 67 flights per month with this carrier.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.