Cheap flights from CLE to MDW (Hopkins Intl. to Midway Intl.)
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Cheap Flights from CLE to MDW starting at $64 One Way, $102 Round Trip
Prices starting at $102 for return flights and $64 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.
CLE
Cleveland
MDW
Chicago
$102 Roundtrip, found 6 days ago
$102
Roundtrip
found 6 days ago
CLE
Cleveland
MDW
Chicago
$123 Roundtrip, found 6 days ago
$123
Roundtrip
found 6 days ago
CLE
Cleveland
MDW
Chicago
$127 Roundtrip, found 17 hours ago
$127
Roundtrip
found 17 hours ago
CLE
Cleveland
MDW
Chicago
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
CLE
Cleveland
MDW
Chicago
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Hotel Ideas near Midway Intl.
Airport Hotels near Midway Intl.
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
$155 nightly
The price is $182 total per night from Jul 27 to Jul 28
$182 total
Jul 27 - Jul 28
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! (1,265 reviews)
"Excellent stay"
Reviewed on Jul 15, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
$178 nightly
The price is $209 total per night from Aug 17 to Aug 18
$209 total
Aug 17 - Aug 18
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! (8,985 reviews)
"Historic hotel!"
Reviewed on Jul 16, 2025
Holiday Inn & Suites Chicago - Downtown by IHG
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
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
520 South Michigan Avenue, Chicago, IL
$178 nightly
The price is $209 total per night from Aug 17 to Aug 18
$209 total
Aug 17 - Aug 18
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! (8,985 reviews)
"Historic hotel!"
Reviewed on Jul 16, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
$253 nightly
The price is $291 total per night from Aug 10 to Aug 11
$291 total
Aug 10 - Aug 11
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, 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
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
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
2881 Touhy Ave, Elk Grove Village, IL
$60 nightly
The price is $68 total per night from Jul 23 to Jul 24
$68 total
Jul 23 - Jul 24
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! (1,535 reviews)
"I'm going through a difficult time right now and it gives me and my children a safe place."
Reviewed on Jul 15, 2025
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
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
Comfort Suites Chicago O'Hare Airport
4200 North River Road, Schiller Park, IL
$96 nightly
The price is $109 total per night from Aug 10 to Aug 11
$109 total
Aug 10 - Aug 11
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! (2,557 reviews)
"It was good …the carpet in the rooms could be much clean ..but was acceptable"
Reviewed on Jul 16, 2025
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
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! (2,079 reviews)
"This was my first time staying at this hostel and in Chicago. Staff was super friendly and welcoming. Room was clean and comfortable. Location was great! About a 20 minute walk to Navy Pier."
Reviewed on Jul 16, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
$123 nightly
The price is $145 total per night from Aug 4 to Aug 5
$145 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! (2,223 reviews)
"Perfect hotel if you just need a quick place to crash after long and busy days in the city. The room was nice and cold, the bed was comfy and the room was clean. Our room was directly in front of the elevator but wasn’t loud at all. About a 10 minute walk to the bean, but just two streets away from ..."
Reviewed on Jul 16, 2025
Motel 6 Elk Grove Village, IL - O'Hare
2881 Touhy Ave, Elk Grove Village, IL
$60 nightly
The price is $68 total per night from Jul 23 to Jul 24
$68 total
Jul 23 - Jul 24
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! (1,535 reviews)
"I'm going through a difficult time right now and it gives me and my children a safe place."
Reviewed on Jul 15, 2025
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
511 North Columbus Drive, Chicago, IL
$209 nightly
The price is $246 total per night from Aug 17 to Aug 18
$246 total
Aug 17 - Aug 18
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! (2,756 reviews)
"My only issue was hearing the front desk talk about reprimanding the house keeping staff for giving a guest an extra towel. Seriously made me think that the management was putting in a position to be extremely cheap. It reflected on how the employees felt about their job and I really do think that ..."
Reviewed on Jul 16, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
$206 nightly
The price is $238 total per night from Aug 6 to Aug 7
$238 total
Aug 6 - Aug 7
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$192 nightly
The price is $226 total per night from Aug 17 to Aug 18
$226 total
Aug 17 - Aug 18
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
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 | Cleveland |
|---|---|
Destination Airport | Chicago |
Number Of Airlines Serving | 1 |
Distance | 306 mi |
Shortest Flight Departure Time | 6:30AM CDT |
Shortest Flight Departure Date | Jul 24 |
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CLE Address & GPS
Address:
5300 Riverside Drive
Cleveland OH, 44135-3193
United States
IATA Code:
CLE
Longitude:
-81.83821
Latitude:
41.410856
Time Zone:
America/New_York
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
Other Flights from Hopkins Intl. Airport (CLE)
Other Flights to Midway Intl. Airport (MDW)
- Burke Lakefront Airport (BKL)
- Cuyahoga County Airport (CGF)
- Akron-Canton Airport (CAK)
- Youngstown - Warren Regional Airport (YNG)
- Marion Municipal Airport (MNN)
- Coleman A. Young Municipal Airport (DET)
- Detroit Metropolitan Wayne County Airport (DTW)
- Erie Intl. Airport (ERI)
- Toledo Express Airport (TOL)
- Venango Regional Airport (FKL)
Frequently asked questions
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.