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

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Cheap Flights from OKC to MDW starting at $76 One Way, $200 Round Trip

Prices starting at $200 for return flights and $76 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.

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

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
$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
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! (1,238 reviews)
"Great location and hotel"

Reviewed on Jul 10, 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
$179 nightly
The price is $210 total per night from Jul 27 to Jul 28
$210 total
Jul 27 - Jul 28
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! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
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! (1,001 reviews)
"ALL WAS GOOD"

Reviewed on Jul 7, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
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
$179 nightly
The price is $210 total per night from Jul 27 to Jul 28
$210 total
Jul 27 - Jul 28
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! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
$235 nightly
The price is $271 total per night from Aug 10 to Aug 11
$271 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! (2,001 reviews)
"Excellent hotel, walk distance from best spots at Chicago"

Reviewed on Jul 8, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
$162 nightly
The price is $191 total per night from Aug 10 to Aug 11
$191 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! (2,428 reviews)
"Staff is very friendly. Great location, reasonably priced. Only complaint was that the pool is not open due to renovation."

Reviewed on Jul 12, 2025

Hilton Chicago/Magnificent Mile Suites
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
$55 nightly
The price is $62 total per night from Jul 28 to Jul 29
$62 total
Jul 28 - Jul 29
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! (1,531 reviews)
"Good"

Reviewed on Jul 9, 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 Jul 13 to Jul 14
$101 total
Jul 13 - Jul 14
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! (1,011 reviews)
"..."

Reviewed on Jul 9, 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
$96 nightly
The price is $109 total per night from Jul 20 to Jul 21
$109 total
Jul 20 - Jul 21
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! (2,543 reviews)
"I Iiked Cleanliness, staff & service, property"

Reviewed on Jul 6, 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
$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! (2,041 reviews)
"really great place to stay for the price. I had a private room, and I loved the lounge and bar area in the hotel -- very cool looking for what is a hostel -- it looks more like an Ace Hotel "lite""

Reviewed on Jul 9, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
$127 nightly
The price is $149 total per night from Aug 5 to Aug 6
$149 total
Aug 5 - Aug 6
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! (2,227 reviews)
"This hotel is old and needs updated. The ac is a window unit and the heater was a standalone in the room. It felt almost like and old New York City apartment. It was fairly clean however. The price was very affordable and it was only a block from the subway. The staff was excellent. The woman who ..."

Reviewed on Jul 9, 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
$55 nightly
The price is $62 total per night from Jul 28 to Jul 29
$62 total
Jul 28 - Jul 29
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! (1,531 reviews)
"Good"

Reviewed on Jul 9, 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
$212 nightly
The price is $248 total per night from Aug 10 to Aug 11
$248 total
Aug 10 - Aug 11
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! (2,730 reviews)
"Hotel and breakfast was very good"

Reviewed on Jul 10, 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
$207 nightly
The price is $239 total per night from Aug 4 to Aug 5
$239 total
Aug 4 - Aug 5
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! (1,779 reviews)
"The reception area and ceilings. I’ve been going to the Palmer since 1965. This time with wife celebrating our 54th wedding anniversary. Just a wonderful place to stay. Only complaint is the price of cocktails. Two house old fashions with tax and tip costs about $50 dollars. That’s just too much ..."

Reviewed on Jul 11, 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
$211 nightly
The price is $247 total per night from Aug 10 to Aug 11
$247 total
Aug 10 - Aug 11
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! (4,419 reviews)
"We had a wonderful stay in Chicago."

Reviewed on Jul 11, 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
Oklahoma City
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
690 mi
Shortest Flight Departure Time
6:25AM CDT
Shortest Flight Departure Date
Jul 19
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.