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, $158 Round Trip

Prices starting at $158 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.

Mon, Feb 23 - Mon, Mar 2
OKC
Oklahoma City
MDW
Chicago
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Oklahoma City to Chicago, returning Mon, Mar 2, priced at $158 found 1 day ago
Mon, Apr 20 - Mon, Apr 27
OKC
Oklahoma City
MDW
Chicago
$170 Roundtrip, found 3 days ago
$170
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Apr 20 from Oklahoma City to Chicago, returning Mon, Apr 27, priced at $170 found 3 days ago
Fri, Feb 27 - Mon, Mar 2
OKC
Oklahoma City
MDW
Chicago
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Oklahoma City to Chicago, returning Mon, Mar 2, priced at $191 found 1 day ago
Tue, Mar 10 - Tue, Mar 17
OKC
Oklahoma City
MDW
Chicago
$205 Roundtrip, found 3 days ago
$205
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Mar 10 from Oklahoma City to Chicago, returning Tue, Mar 17, priced at $205 found 3 days ago
Fri, Feb 27 - Mon, Mar 2
OKC
Oklahoma City
MDW
Chicago
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Oklahoma City to Chicago, returning Mon, Mar 2, priced at $205 found 1 day 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 Feb 6 to Feb 7
$169 total
Feb 6 - Feb 7
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! (1,178 reviews)
Great location. Clean room. Staff were kind and helpful.

Reviewed on Jan 26, 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 1 to Feb 2
$111 total
Feb 1 - Feb 2
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! (1,929 reviews)
Room was clean, could use some updates though. Staff were great. Thought it was odd the bar was closed on a Saturday at 5pm

Reviewed on Jan 25, 2026

Crowne Plaza Chicago West Loop by IHG
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 4 to Feb 5
$182 total
Feb 4 - Feb 5
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! (2,583 reviews)
My stay was truly amazing. Thank you and appreciate the hotel hospitality

Reviewed on Jan 25, 2026

Hilton 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
$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! (9,821 reviews)
Yes perfectly clean

Reviewed on Jan 24, 2026

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
$107 nightly
The price is $125 total per night from Feb 8 to Feb 9
$125 total
Feb 8 - Feb 9
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! (5,614 reviews)
Too few elevators working…

Reviewed on Jan 28, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$196 nightly
The price is $230 total per night from Feb 21 to Feb 22
$230 total
Feb 21 - Feb 22
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (2,195 reviews)
Great stay

Reviewed on Jan 23, 2026

Hilton 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.

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 Jan 31 to Feb 1
$62 total
Jan 31 - Feb 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! (1,787 reviews)
Clean room and hot coffee in the morning. Plenty of parking.

Reviewed on Jan 24, 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 30 to Jan 31
$101 total
Jan 30 - Jan 31
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! (1,258 reviews)
Breakfast

Reviewed on Jan 23, 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
$61 nightly
The price is $69 total per night from Feb 3 to Feb 4
$69 total
Feb 3 - Feb 4
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! (2,851 reviews)
Clean room, great shuttle service.

Reviewed on Jan 28, 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
$66 nightly
The price is $78 total per night from Feb 10 to Feb 11
$78 total
Feb 10 - Feb 11
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! (2,728 reviews)
Super friendly staff. Amazing location, keep it quiet, we do not want this to get out

Reviewed on Jan 28, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$72 nightly
The price is $85 total per night from Feb 23 to Feb 24
$85 total
Feb 23 - Feb 24
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! (2,506 reviews)
Room was clean everything was functional

Reviewed on Jan 24, 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
$55 nightly
The price is $62 total per night from Jan 31 to Feb 1
$62 total
Jan 31 - Feb 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! (1,787 reviews)
Clean room and hot coffee in the morning. Plenty of parking.

Reviewed on Jan 24, 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
$136 nightly
The price is $160 total per night from Feb 8 to Feb 9
$160 total
Feb 8 - Feb 9
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! (2,820 reviews)
This hotel was extremely family friendly, which was great! However, the waits for the elevators were constantly horrible. The pool was also smaller than the photo made it appear. It was too crowded with kids so we didn't use it. The sound in the rooms was overwhelming because you could hear elevators ...

Reviewed on Jan 24, 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 Feb 21 to Feb 22
$183 total
Feb 21 - Feb 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! (2,264 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
$107 nightly
The price is $125 total per night from Feb 8 to Feb 9
$125 total
Feb 8 - Feb 9
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! (5,614 reviews)
Too few elevators working…

Reviewed on Jan 28, 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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