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

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Cheap Flights from OKC to MDW starting at $81 One Way, $160 Round Trip

Prices starting at $160 for return flights and $81 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, Feb 23 - Mon, Mar 2
OKC
Oklahoma City
MDW
Chicago
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Oklahoma City to Chicago, returning Mon, Mar 2, priced at $160 found 2 hours ago
Tue, Mar 24 - Thu, Apr 9
OKC
Oklahoma City
MDW
Chicago
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 24 from Oklahoma City to Chicago, returning Thu, Apr 9, priced at $185 found 1 day ago
Mon, Mar 2 - Tue, Mar 17
OKC
Oklahoma City
MDW
Chicago
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Mar 2 from Oklahoma City to Chicago, returning Tue, Mar 17, priced at $189 found 1 day ago
Mon, Feb 23 - Thu, Mar 12
OKC
Oklahoma City
MDW
Chicago
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Oklahoma City to Chicago, returning Thu, Mar 12, priced at $199 found 1 day ago
Tue, Mar 10 - Tue, Mar 17
OKC
Oklahoma City
MDW
Chicago
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Mar 10 from Oklahoma City to Chicago, returning Tue, Mar 17, priced at $205 found 4 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
105 N MAY STREET Chicago IL
$144 nightly
The price is $169 total per night from Jan 29 to Jan 30
$169 total
Jan 29 - Jan 30
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 ...
8.8/10 Excellent! (1,170 reviews)
We loved our stay at the Hyatt House! Within walking distance to multiple restaurants, close to the United Center. Uber/Lyft was easily accessible as well as the L. Comfortable, clean rooms and reasonably priced!

Reviewed on Jan 21, 2026

Hyatt House Chicago West Loop
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
$95 nightly
The price is $111 total per night from Feb 8 to Feb 9
$111 total
Feb 8 - Feb 9
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! (1,907 reviews)
Room clean Staff excellent Everything was excellent , no complaints!!!

Reviewed on Jan 19, 2026

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$89 nightly
The price is $104 total per night from Jan 31 to Feb 1
$104 total
Jan 31 - Feb 1
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! (9,804 reviews)
Just a lovely visit all around. Highly recommend

Reviewed on Jan 21, 2026

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
$89 nightly
The price is $104 total per night from Jan 31 to Feb 1
$104 total
Jan 31 - Feb 1
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! (9,804 reviews)
Just a lovely visit all around. Highly recommend

Reviewed on Jan 21, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$155 nightly
The price is $182 total per night from Feb 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,556 reviews)
Did not have breakfast

Reviewed on Jan 19, 2026

Hilton 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
$106 nightly
The price is $124 total per night from Feb 5 to Feb 6
$124 total
Feb 5 - Feb 6
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! (5,583 reviews)
Always a great stay, clean, great breakfast, great pool.

Reviewed on Jan 22, 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 Jan 25 to Jan 26
$48 total
Jan 25 - Jan 26
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! (1,774 reviews)
Everyone has gone above and beyond to accommodate my stay.. when in the area I would stay here again.

Reviewed on Jan 15, 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 Jan 23 to Jan 24
$101 total
Jan 23 - Jan 24
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! (1,252 reviews)
Great value for the price! Front desk staff vey nice and welcoming! Would stay again.

Reviewed on Jan 19, 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
$59 nightly
The price is $67 total per night from Feb 5 to Feb 6
$67 total
Feb 5 - Feb 6
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! (2,804 reviews)
Good room and great staff.

Reviewed on Jan 15, 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
$67 nightly
The price is $79 total per night from Feb 1 to Feb 2
$79 total
Feb 1 - Feb 2
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! (2,699 reviews)
would definitely stay again, good price point

Reviewed on Jan 16, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$73 nightly
The price is $86 total per night from Feb 22 to Feb 23
$86 total
Feb 22 - Feb 23
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! (2,503 reviews)
Only thing I would change is add mini fridges to the rooms.

Reviewed on Jan 10, 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 Jan 25 to Jan 26
$48 total
Jan 25 - Jan 26
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! (1,774 reviews)
Everyone has gone above and beyond to accommodate my stay.. when in the area I would stay here again.

Reviewed on Jan 15, 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
$134 nightly
The price is $158 total per night from Jan 25 to Jan 26
$158 total
Jan 25 - Jan 26
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! (2,799 reviews)
We like the hotel, staff and accommodations were great, and it was exactly what we needed.

Reviewed on Jan 20, 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
$159 nightly
The price is $183 total per night from Jan 29 to Jan 30
$183 total
Jan 29 - Jan 30
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! (2,254 reviews)
.

Reviewed on Jan 18, 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
$106 nightly
The price is $124 total per night from Feb 5 to Feb 6
$124 total
Feb 5 - Feb 6
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! (5,583 reviews)
Always a great stay, clean, great breakfast, great pool.

Reviewed on Jan 22, 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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