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

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Cheap Flights from OKC to MDW starting at $164 One Way, $385 Round Trip

Prices starting at $385 for return flights and $164 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.

Wed, Oct 21 - Fri, Oct 23
OKC
Oklahoma City
MDW
Chicago
$385 Roundtrip, found 1 day ago
$385
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Oklahoma City to Chicago, returning Fri, Oct 23, priced at $385 found 1 day ago
Wed, Oct 21 - Fri, Oct 23
OKC
Oklahoma City
MDW
Chicago
$395 Roundtrip, found 1 day ago
$395
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Oklahoma City to Chicago, returning Fri, Oct 23, priced at $395 found 1 day ago
Wed, Oct 21 - Fri, Oct 23
OKC
Oklahoma City
MDW
Chicago
$400 Roundtrip, found 1 day ago
$400
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Oklahoma City to Chicago, returning Fri, Oct 23, priced at $400 found 1 day ago
Fri, Oct 2 - Sun, Oct 4
OKC
Oklahoma City
MDW
Chicago
$402 Roundtrip, found 3 days ago
$402
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Oct 2 from Oklahoma City to Chicago, returning Sun, Oct 4, priced at $402 found 3 days ago
Wed, Oct 21 - Fri, Oct 23
OKC
Oklahoma City
MDW
Chicago
$405 Roundtrip, found 1 day ago
$405
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Oklahoma City to Chicago, returning Fri, Oct 23, priced at $405 found 1 day ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
The price is $159 total per night from Sep 8 to Sep 9
$159 total
per night
Sep 8 - Sep 9
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 and ...
8/10 Very Good! (1,005 reviews)
"Room was ok no fridge thank you"

Reviewed on Sep 5, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $136 total per night from Sep 7 to Sep 8
$136 total
per night
Sep 7 - Sep 8
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! (10,282 reviews)
"This hotel is disgusting and I will never stay here again or suggest it to anyone. The lobby is well kept but once you get into the hallways the wallpaper is peeling, the carpet is dirty. the walls are crumbling and there is literal trash in the stairwells. The elevators are tiny and I had to wait ..."

Reviewed on Sep 5, 2026

Congress Plaza Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
The price is $302 total per night from Sep 6 to Sep 7
$302 total
per night
Sep 6 - Sep 7
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,386 reviews)
"They were very prepared for people staying that were attending the BTS Concert and made us feel very welcomed and safe"

Reviewed on Sep 5, 2026

Hyatt Regency McCormick Place Chicago
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
The price is $136 total per night from Sep 7 to Sep 8
$136 total
per night
Sep 7 - Sep 8
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! (10,282 reviews)
"This hotel is disgusting and I will never stay here again or suggest it to anyone. The lobby is well kept but once you get into the hallways the wallpaper is peeling, the carpet is dirty. the walls are crumbling and there is literal trash in the stairwells. The elevators are tiny and I had to wait ..."

Reviewed on Sep 5, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The price is $170 total per night from Sep 8 to Sep 9
$170 total
per night
Sep 8 - Sep 9
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"

Reviewed on Sep 4, 2026

Get rates
Kasa Magnificent Mile Chicago
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
The price is $60 total per night from Oct 1 to Oct 2
$60 total
per night
Oct 1 - Oct 2
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 ...
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
The price is $123 total per night from Sep 8 to Sep 9
$123 total
per night
Sep 8 - Sep 9
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 ...
7.6/10 Good! (1,739 reviews)
"I love the convenience to the airport with the shuttle. The hotel was clean and not overly dirty. The rooms need more maintenance but it was not a bad stay. I suggest adding a fan to the bathrooms so they can be ventilated n the steam doesn’t linger in the room making it muggy."

Reviewed on Sep 5, 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
The price is $116 total per night from Sep 27 to Sep 28
$116 total
per night
Sep 27 - Sep 28
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 ...
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
The price is $213 total per night from Sep 8 to Sep 9
$213 total
per night
Sep 8 - Sep 9
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. ...
7.8/10 Good! (3,376 reviews)
"Old building and the room had that old smell. Only complaint. Staff was great."

Reviewed on Sep 5, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
The price is $159 total per night from Sep 8 to Sep 9
$159 total
per night
Sep 8 - Sep 9
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 ...
7.6/10 Good! (2,831 reviews)
"Need better AC units"

Reviewed on Sep 5, 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
The price is $60 total per night from Oct 1 to Oct 2
$60 total
per night
Oct 1 - Oct 2
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 ...
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
The price is $247 total per night from Sep 10 to Sep 11
$247 total
per night
Sep 10 - Sep 11
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 ...
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
The price is $256 total per night from Sep 10 to Sep 11
$256 total
per night
Sep 10 - Sep 11
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 ...
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
The price is $213 total per night from Sep 7 to Sep 8
$213 total
per night
Sep 7 - Sep 8
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 ...
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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