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

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Cheap Flights from OKC to MDW starting at $59 One Way, $120 Round Trip

Prices starting at $120 for return flights and $59 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.

Mon, Nov 3 - Thu, Nov 13
OKC
Oklahoma City
MDW
Chicago
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Oklahoma City to Chicago, returning Thu, Nov 13, priced at $120 found 1 day ago
Mon, Nov 3 - Sun, Nov 9
OKC
Oklahoma City
MDW
Chicago
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Oklahoma City to Chicago, returning Sun, Nov 9, priced at $142 found 1 day ago
Sun, Nov 9 - Thu, Nov 13
OKC
Oklahoma City
MDW
Chicago
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Oklahoma City to Chicago, returning Thu, Nov 13, priced at $160 found 1 day ago
Mon, Oct 20 - Thu, Oct 30
OKC
Oklahoma City
MDW
Chicago
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Oklahoma City to Chicago, returning Thu, Oct 30, priced at $164 found 5 days ago
Thu, Oct 23 - Mon, Oct 27
OKC
Oklahoma City
MDW
Chicago
$176 Roundtrip, found 19 hours ago
$176
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Oklahoma City to Chicago, returning Mon, Oct 27, priced at $176 found 19 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
$149 nightly
The price is $175 total per night from Nov 9 to Nov 10
$175 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,008 reviews)
"The staff was great. He was very welcoming and helpful with the stay. The stay was very comfortable the rooms very clean as well. I recommend it. We had a great time with all of my friends."

Reviewed on Oct 10, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
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
$130 nightly
The price is $153 total per night from Nov 9 to Nov 10
$153 total
Nov 9 - Nov 10
Total with 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! (1,576 reviews)
"I was glad but surprised that my package included parking. We never left, but upon check out, the gate wouldn’t go up, and the machine told us to pay. I went to tell the front desk, and the worker came out and made the gate go up for us!"

Reviewed on Oct 6, 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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with 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 ...
8/10 Very Good! (9,320 reviews)
"Love the Congress! Very convenient location- walking distance to everything! Comfortable room and clean!"

Reviewed on Oct 6, 2025

Congress Plaza Hotel
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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with 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 ...
8/10 Very Good! (9,320 reviews)
"Love the Congress! Very convenient location- walking distance to everything! Comfortable room and clean!"

Reviewed on Oct 6, 2025

Congress Plaza 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
$152 nightly
The price is $179 total per night from Nov 9 to Nov 10
$179 total
Nov 9 - Nov 10
Total with 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! (5,056 reviews)
"We’re shops And center of the city great location close to everything what I love it"

Reviewed on Oct 7, 2025

Embassy Suites by Hilton Chicago Downtown River North
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
$95 nightly
The price is $112 total per night from Nov 11 to Nov 12
$112 total
Nov 11 - Nov 12
Total with 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! (2,432 reviews)
"Great place"

Reviewed on Oct 8, 2025

Freehand 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
$52 nightly
The price is $59 total per night from Oct 28 to Oct 29
$59 total
Oct 28 - Oct 29
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! (1,651 reviews)
"All goof"

Reviewed on Oct 7, 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
$91 nightly
The price is $101 total per night from Oct 12 to Oct 13
$101 total
Oct 12 - Oct 13
Total with 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! (1,101 reviews)
"Everything was good"

Reviewed on Oct 6, 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
$84 nightly
The price is $96 total per night from Oct 26 to Oct 27
$96 total
Oct 26 - Oct 27
Total with 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! (2,633 reviews)
"Location was very close to the airport and their shuttle service was very good. Room was clean and spacious. Breakfast was nice too."

Reviewed on Oct 5, 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
$95 nightly
The price is $112 total per night from Nov 11 to Nov 12
$112 total
Nov 11 - Nov 12
Total with 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! (2,432 reviews)
"Great place"

Reviewed on Oct 8, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
$101 nightly
The price is $119 total per night from Nov 9 to Nov 10
$119 total
Nov 9 - Nov 10
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 ...
7.2/10 Good! (2,399 reviews)
"The hotel was easy to locate using the metro coming from the airport. We attended a concert nearby and the location of the hotel was superb if you want to explore downtown Chicago. The Millennium Park, The Bean, and The Riverwalk were all walking distance. It takes longer if you want to walk to Soldier ..."

Reviewed on Oct 10, 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
$52 nightly
The price is $59 total per night from Oct 28 to Oct 29
$59 total
Oct 28 - Oct 29
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! (1,651 reviews)
"All goof"

Reviewed on Oct 7, 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
$186 nightly
The price is $218 total per night from Nov 9 to Nov 10
$218 total
Nov 9 - Nov 10
Total with 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! (2,721 reviews)
Need to improve on sofabed
"The sofa bed was caved in"

Reviewed on Oct 7, 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
$208 nightly
The price is $240 total per night from Oct 30 to Oct 31
$240 total
Oct 30 - Oct 31
Total with taxes and fees
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,001 reviews)
"Put in new carpet and update walls"

Reviewed on Oct 6, 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
$152 nightly
The price is $179 total per night from Nov 9 to Nov 10
$179 total
Nov 9 - Nov 10
Total with 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! (5,056 reviews)
"We’re shops And center of the city great location close to everything what I love it"

Reviewed on Oct 7, 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.

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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