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

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Cheap Flights from OKC to MDW starting at $75 One Way, $141 Round Trip

Prices starting at $141 for return flights and $75 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, Jan 15 - Thu, Jan 22
OKC
Oklahoma City
MDW
Chicago
$141 Roundtrip, found 6 days ago
$141
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jan 15 from Oklahoma City to Chicago, returning Thu, Jan 22, priced at $141 found 6 days ago
Fri, Dec 5 - Sun, Dec 14
OKC
Oklahoma City
MDW
Chicago
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Oklahoma City to Chicago, returning Sun, Dec 14, priced at $152 found 5 days ago
Sun, Dec 7 - Sun, Dec 14
OKC
Oklahoma City
MDW
Chicago
$154 Roundtrip, found 5 days ago
$154
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Dec 7 from Oklahoma City to Chicago, returning Sun, Dec 14, priced at $154 found 5 days ago
Thu, Dec 4 - Thu, Jan 1
OKC
Oklahoma City
MDW
Chicago
$154 Roundtrip, found 5 days ago
$154
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Oklahoma City to Chicago, returning Thu, Jan 1, priced at $154 found 5 days ago
Fri, Dec 5 - Sun, Dec 7
OKC
Oklahoma City
MDW
Chicago
$156 Roundtrip, found 5 days ago
$156
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Oklahoma City to Chicago, returning Sun, Dec 7, priced at $156 found 5 days ago

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
$119 nightly
The price is $140 total per night from Nov 27 to Nov 28
$140 total
Nov 27 - Nov 28
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 ...
8.8/10 Excellent! (1,685 reviews)
Nice

Reviewed on Nov 20, 2025

Crowne Plaza Chicago West Loop by IHG
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
$83 nightly
The price is $98 total per night from Dec 8 to Dec 9
$98 total
Dec 8 - Dec 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.6/10 Excellent! (2,130 reviews)
Everything is good.

Reviewed on Nov 21, 2025

Homewood Suites by Hilton Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$79 nightly
The price is $93 total per night from Dec 21 to Dec 22
$93 total
Dec 21 - Dec 22
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 ...
8.6/10 Excellent! (1,712 reviews)
The room was fabulous: comfortable and clean. The staff were friendly and helpful. The only annoyance was dropping the car off for the valet service, but the valet staff were friendly and helpful.

Reviewed on Nov 17, 2025

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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$128 nightly
The price is $146 total per night from Dec 21 to Dec 22
$146 total
Dec 21 - Dec 22
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 ...
8.4/10 Very Good! (2,089 reviews)
This was my first time in this historic hotel, and I enjoyed every minute!

Reviewed on Nov 24, 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
$87 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
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 ...
8.4/10 Very Good! (5,274 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.

Reviewed on Nov 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$116 nightly
The price is $136 total per night from Nov 26 to Nov 27
$136 total
Nov 26 - Nov 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! (9,616 reviews)
Lovely room, walkable or bus / drive to attractions.

Reviewed on Nov 20, 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.

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
$35 nightly
The price is $40 total per night from Nov 30 to Dec 1
$40 total
Nov 30 - Dec 1
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! (1,693 reviews)
The hotel was clean and the staff was nice. Not much around the hotel though. Although there is a cool “airport” bar/grill just a couple minutes walk away. For the money and our needs, it worked perfect.

Reviewed on Nov 23, 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
$71 nightly
The price is $79 total per night from Nov 26 to Nov 27
$79 total
Nov 26 - Nov 27
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 ...
7.2/10 Good! (1,181 reviews)
Excellent customer service. This is my second stay stay at country inn but the location is different. I am never disappointed staying here. The rooms are nice and clean. The only thing is I wish they had steaming services. I don't like the cable channels. I wish they had apps like the DoubleTree ...

Reviewed on Nov 19, 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
$76 nightly
The price is $86 total per night from Dec 17 to Dec 18
$86 total
Dec 17 - Dec 18
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! (2,742 reviews)
All great

Reviewed on Nov 23, 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
$85 nightly
The price is $100 total per night from Dec 25 to Dec 26
$100 total
Dec 25 - Dec 26
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. ...
7.8/10 Good! (2,600 reviews)
Clean, close to everything.

Reviewed on Nov 23, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$87 nightly
The price is $102 total per night from Dec 7 to Dec 8
$102 total
Dec 7 - Dec 8
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! (2,463 reviews)
Nice and handy to downtown

Reviewed on Nov 19, 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
$35 nightly
The price is $40 total per night from Nov 30 to Dec 1
$40 total
Nov 30 - Dec 1
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! (1,693 reviews)
The hotel was clean and the staff was nice. Not much around the hotel though. Although there is a cool “airport” bar/grill just a couple minutes walk away. For the money and our needs, it worked perfect.

Reviewed on Nov 23, 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
$105 nightly
The price is $123 total per night from Dec 7 to Dec 8
$123 total
Dec 7 - Dec 8
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! (2,751 reviews)
Clean

Reviewed on Nov 23, 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
$128 nightly
The price is $146 total per night from Dec 21 to Dec 22
$146 total
Dec 21 - Dec 22
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 ...
8.4/10 Very Good! (2,089 reviews)
This was my first time in this historic hotel, and I enjoyed every minute!

Reviewed on Nov 24, 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
$87 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
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 ...
8.4/10 Very Good! (5,274 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.

Reviewed on Nov 19, 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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