Cheap flights from OKC to MDW (Will Rogers World to Midway Intl.)

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Cheap Flights from OKC to MDW starting at $80 One Way, $161 Round Trip

Prices starting at $161 for return flights and $80 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, Apr 23 - Thu, Apr 30
OKC
Oklahoma City
MDW
Chicago
$161 Roundtrip, found 22 hours ago
$161
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Oklahoma City to Chicago, returning Thu, Apr 30, priced at $161 found 22 hours ago
Mon, Apr 27 - Mon, May 11
OKC
Oklahoma City
MDW
Chicago
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Oklahoma City to Chicago, returning Mon, May 11, priced at $170 found 1 day ago
Mon, May 4 - Mon, May 18
OKC
Oklahoma City
MDW
Chicago
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 4 from Oklahoma City to Chicago, returning Mon, May 18, priced at $172 found 1 day ago
Tue, Mar 10 - Tue, Mar 17
OKC
Oklahoma City
MDW
Chicago
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 10 from Oklahoma City to Chicago, returning Tue, Mar 17, priced at $174 found 1 day ago
Thu, Apr 16 - Mon, Apr 27
OKC
Oklahoma City
MDW
Chicago
$175 Roundtrip, found 15 hours ago
$175
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Oklahoma City to Chicago, returning Mon, Apr 27, priced at $175 found 15 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$93 nightly
The price is $109 total per night from Feb 25 to Feb 26
$109 total
Feb 25 - Feb 26
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! (9,930 reviews)
Wonderful hotel close to a lot.

Reviewed on Feb 24, 2026

Congress Plaza Hotel
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
$127 nightly
The price is $149 total per night from Mar 1 to Mar 2
$149 total
Mar 1 - Mar 2
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! (1,994 reviews)
Amazing place and staff

Reviewed on Feb 23, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$93 nightly
The price is $110 total per night from Mar 2 to Mar 3
$110 total
Mar 2 - Mar 3
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! (1,876 reviews)
The room smelled like weed and the hot tub was not working and that’s the only reason we booked it. So disappointing.

Reviewed on Feb 23, 2026

Hilton Garden Inn Chicago Downtown South Loop
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
$93 nightly
The price is $109 total per night from Feb 25 to Feb 26
$109 total
Feb 25 - Feb 26
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! (9,930 reviews)
Wonderful hotel close to a lot.

Reviewed on Feb 24, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$123 nightly
The price is $144 total per night from Mar 4 to Mar 5
$144 total
Mar 4 - Mar 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,399 reviews)
Nice and good variety breakfast. Room was nice and clean. Good shower with nice pressure. Complimentary bag storage after checking out.

Reviewed on Feb 24, 2026

Hotel Riu Plaza Chicago
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
$103 nightly
The price is $120 total per night from Mar 4 to Mar 5
$120 total
Mar 4 - Mar 5
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! (5,698 reviews)
Amazing view

Reviewed on Feb 23, 2026

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.

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
$42 nightly
The price is $48 total per night from Mar 5 to Mar 6
$48 total
Mar 5 - Mar 6
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! (1,846 reviews)
My stay was relaxing. The staff was helpful and welcoming. I'm glad I stayed here. The rooms were clean and quiet. I checked in with Tiffany. She was very kind and made me feel valued as a guest. Thank You!!

Reviewed on Feb 22, 2026

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
$91 nightly
The price is $101 total per night from Feb 25 to Feb 26
$101 total
Feb 25 - Feb 26
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! (1,283 reviews)
The entire place smelled like weed. The gym equipment (treadmill) was not working. The breakfast was not good not even the eggs or hard boiled eggs. The lobby furniture looked dirty and old.

Reviewed on Feb 23, 2026

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
$69 nightly
The price is $79 total per night from Feb 25 to Feb 26
$79 total
Feb 25 - Feb 26
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! (2,921 reviews)
The room was clean and the breakfast was hot and okay but the hotel overall disappointed me. I was expecting much better based on the reviews. There were some people that seemed intoxicated and there was smell of marijuana in the elevator and the rooms were a bit outdated. I should have stayed in ...

Reviewed on Feb 24, 2026

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
$71 nightly
The price is $84 total per night from Feb 26 to Feb 27
$84 total
Feb 26 - Feb 27
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! (2,774 reviews)
This is the best hostel I’ve ever been to and what makes it so fabulous is the staff. Anything you need they are there to make your stay comfortable and wonderful! Give it a try!

Reviewed on Feb 24, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$78 nightly
The price is $92 total per night from Feb 26 to Feb 27
$92 total
Feb 26 - Feb 27
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! (2,521 reviews)
While the hotel itself is pretty standard, the room we had been given had a few concerns. Most importantly, upon arrival inside the room, we noticed that the toilet had not been flushed since it was last used. Other than that, one of the sink handles seemed to leak water when the faucet ran and using ...

Reviewed on Feb 22, 2026

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
$42 nightly
The price is $48 total per night from Mar 5 to Mar 6
$48 total
Mar 5 - Mar 6
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! (1,846 reviews)
My stay was relaxing. The staff was helpful and welcoming. I'm glad I stayed here. The rooms were clean and quiet. I checked in with Tiffany. She was very kind and made me feel valued as a guest. Thank You!!

Reviewed on Feb 22, 2026

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
$128 nightly
The price is $151 total per night from Mar 3 to Mar 4
$151 total
Mar 3 - Mar 4
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! (2,833 reviews)
The hotel was very clean and accommodating. The complementary breakfast was very good.

Reviewed on Feb 23, 2026

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
$176 nightly
The price is $202 total per night from Mar 6 to Mar 7
$202 total
Mar 6 - Mar 7
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! (2,314 reviews)
Beautiful old hotel.

Reviewed on Feb 22, 2026

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
$103 nightly
The price is $120 total per night from Mar 4 to Mar 5
$120 total
Mar 4 - Mar 5
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! (5,698 reviews)
Amazing view

Reviewed on Feb 23, 2026

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.

OKC to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
OKC Address & GPS
Address:
7100 Terminal Drive
Oklahoma City OK, 73159-0937
United States
IATA Code:
OKC
Longitude:
-97.59609
Latitude:
35.395629
Time Zone:
America/Chicago
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

Frequently asked questions

Are there non-stop flights from Will Rogers World Airport (OKC) to MDW?
Passengers can fly from OKC to Chicago Airport with Southwest Airlines, the only airline that offers nonstop services on this route.
What is the shortest flight from Will Rogers Airport to Chicago Airport?
Getting from Will Rogers Airport to Midway Airport will take a minimum of 4 hours and 23 minutes. Enjoy a tipple and watch a show or two — here's your chance to sit back and chill out.
How many hours flight from OKC to Midway Intl. Airport (MDW)?
It typically takes about 4 hours and 27 minutes to jet from Will Rogers Airport to MDW. You'll be in your seat for quite some time, so think about bringing plenty of entertainment, like a gripping novel or your travel journal.
What airlines have the most flights from Will Rogers World Airport (OKC) to Chicago Airport?
With 58 monthly flights between OKC and Chicago Airport, Southwest Airlines will fly you to your destination comfortably and safely.

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.

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