Cheap flights from MCO to MDW (Orlando Intl. to Midway Intl.)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
Cheap Flights from MCO to MDW starting at $35 One Way, $68 Round Trip
Prices starting at $68 for return flights and $35 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.
MCO
Orlando
MDW
Chicago
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
MCO
Orlando
MDW
Chicago
$69 Roundtrip, found 1 day ago
$69
Roundtrip
found 1 day ago
MCO
Orlando
MDW
Chicago
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
MCO
Orlando
MDW
Chicago
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
MCO
Orlando
MDW
Chicago
$106 Roundtrip, found 21 hours ago
$106
Roundtrip
found 21 hours ago
Hotel Ideas near Midway Intl.
Airport Hotels near Midway Intl.
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
$128 nightly
The price is $151 total per night from Apr 26 to Apr 27
$151 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,001 reviews)
Yes
Reviewed on Apr 7, 2026
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
$135 nightly
The price is $158 total per night from Apr 26 to Apr 27
$158 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,075 reviews)
Very nice and clean reccomend high floor good view
Reviewed on Apr 8, 2026
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
$122 nightly
The price is $143 total per night from Apr 28 to Apr 29
$143 total
Apr 28 - Apr 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,947 reviews)
Clean and comfortable room.
Reviewed on Apr 9, 2026
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
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,073 reviews)
Room was clean, but cheaply remodeled and nothing really special.
Reviewed on Apr 9, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with 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 ...
9/10 Wonderful! (4,087 reviews)
Clean room, quiet safe area, nice walking distance to the lake or shopping. Lovely staff.
Reviewed on Apr 9, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$139 nightly
The price is $163 total per night from Apr 19 to Apr 20
$163 total
Apr 19 - Apr 20
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,828 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...
Reviewed on Apr 9, 2026
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
$55 nightly
The price is $62 total per night from Apr 13 to Apr 14
$62 total
Apr 13 - Apr 14
Total with 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! (1,912 reviews)
No pool, never use the WI Fi, They do Not enforced that None Smoking Policy, Smoke stinking Hallways and rooms and not regular smoking. Room Mattress old and not very comfortable
Reviewed on Apr 8, 2026
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
777 E Grand Avenue Bensenville IL
$95 nightly
The price is $105 total per night from Apr 30 to May 1
$105 total
Apr 30 - May 1
Total with taxes and fees
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.4/10 Good! (1,341 reviews)
Breakfast just ok, did not use the pool
Reviewed on Apr 9, 2026
Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
$76 nightly
The price is $87 total per night from Apr 29 to Apr 30
$87 total
Apr 29 - Apr 30
Total with taxes and fees
Book a stay at this 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! (2,949 reviews)
Really great value. Enjoyed my stay and the Unos on site. Room needs to be updated. Couch is a great touch but you sink through it. Staff is overall great. Jennifer at the front desk is an all star. Lee not so much but maybe just having a bad day. Would come back.
Reviewed on Apr 9, 2026
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
$75 nightly
The price is $88 total per night from Apr 14 to Apr 15
$88 total
Apr 14 - Apr 15
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (2,857 reviews)
I asked to fix my outlet on my room to fix it to give me extension cord but seems they don't have time to do it .
Reviewed on Apr 9, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
$110 nightly
The price is $129 total per night from Apr 12 to Apr 13
$129 total
Apr 12 - Apr 13
Total with 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 ...
7.4/10 Good! (2,554 reviews)
Under construction, so I give them Grace, but stiff beds, loud heaters, and old shower
Reviewed on Apr 9, 2026
Motel 6 Elk Grove Village, IL - O'Hare
2881 Touhy Ave Elk Grove Village IL
$55 nightly
The price is $62 total per night from Apr 13 to Apr 14
$62 total
Apr 13 - Apr 14
Total with 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! (1,912 reviews)
No pool, never use the WI Fi, They do Not enforced that None Smoking Policy, Smoke stinking Hallways and rooms and not regular smoking. Room Mattress old and not very comfortable
Reviewed on Apr 8, 2026
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
$162 nightly
The price is $190 total per night from May 10 to May 11
$190 total
May 10 - May 11
Total with taxes and fees
Book a stay at this 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! (2,816 reviews)
The breakfast was good. For the hot bar everyday was the same thing, would have been nice for a little more variety with that. One set of elevators were not working and during busy times such as checkout it was hard to get on an elevator. The staff was amazing! Two free drinks from the bar each night ...
Reviewed on Apr 8, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
$184 nightly
The price is $212 total per night from May 8 to May 9
$212 total
May 8 - May 9
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,371 reviews)
We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff.
Reviewed on Apr 8, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$139 nightly
The price is $163 total per night from Apr 19 to Apr 20
$163 total
Apr 19 - Apr 20
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,828 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...
Reviewed on Apr 9, 2026
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.
MCO to MDW Route Info
Origin Airport | |
|---|---|
Destination Airport | |
Number Of Airlines Serving | |
Distance | |
Shortest Flight Departure Time | |
Shortest Flight Departure Date |
- Airport Locations
- More Popular Flights
- Top Trending
- Flights from Other Cities
- Flights From Other Airports
MCO Address & GPS
Address:
One Airport Boulevard
Orlando FL, 32827-4399
United States
IATA Code:
MCO
Longitude:
-81.308301
Latitude:
28.432177
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 Orlando Intl. Airport (MCO)
Other Flights to Midway Intl. Airport (MDW)
- Kissimmee Gateway Airport (ISM)
- Orlando Sanford Intl. Airport (SFB)
- Leesburg Intl. Airport (LEE)
- Orlando Melbourne Intl. Airport (MLB)
- Lakeland Intl. Airport Airport (LAL)
- Daytona Beach Intl. Airport (DAB)
- Avon Park Executive Airport (AVO)
- Sebring Regional Airport (SEF)
- Vero Beach Municipal Airport (VRB)
- Peter O. Knight Airport (TPF)
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.