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, $157 Round Trip

Prices starting at $157 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.

Tue, Mar 24 - Thu, Apr 9
OKC
Oklahoma City
MDW
Chicago
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Mar 24 from Oklahoma City to Chicago, returning Thu, Apr 9, priced at $157 found 6 days ago
Tue, Mar 17 - Tue, Mar 24
OKC
Oklahoma City
MDW
Chicago
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Mar 17 from Oklahoma City to Chicago, returning Tue, Mar 24, priced at $160 found 3 days ago
Tue, Mar 17 - Wed, Mar 18
OKC
Oklahoma City
MDW
Chicago
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Mar 17 from Oklahoma City to Chicago, returning Wed, Mar 18, priced at $164 found 3 days ago
Mon, Feb 23 - Fri, Feb 27
OKC
Oklahoma City
MDW
Chicago
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Oklahoma City to Chicago, returning Fri, Feb 27, priced at $170 found 1 day ago
Fri, Feb 27 - Mon, Mar 2
OKC
Oklahoma City
MDW
Chicago
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Oklahoma City to Chicago, returning Mon, Mar 2, priced at $171 found 1 day 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
$91 nightly
The price is $107 total per night from Jan 25 to Jan 26
$107 total
Jan 25 - Jan 26
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! (1,851 reviews)
Everything was good. Staff was very friendly.

Reviewed on Jan 6, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$164 nightly
The price is $192 total per night from Jan 19 to Jan 20
$192 total
Jan 19 - Jan 20
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! (2,507 reviews)
Clean, good breakfast, quiet. Easy acces

Reviewed on Jan 9, 2026

Hilton Chicago
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$75 nightly
The price is $89 total per night from Feb 8 to Feb 9
$89 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 room service. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,812 reviews)
We love staying here! Thank you for a great stay, AGAIN!

Reviewed on Jan 12, 2026

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

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$164 nightly
The price is $192 total per night from Jan 19 to Jan 20
$192 total
Jan 19 - Jan 20
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! (2,507 reviews)
Clean, good breakfast, quiet. Easy acces

Reviewed on Jan 9, 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$168 nightly
The price is $193 total per night from Jan 19 to Jan 20
$193 total
Jan 19 - Jan 20
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! (2,240 reviews)
Best hotel in Chicago

Reviewed on Jan 13, 2026

Palmer House a Hilton Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$89 nightly
The price is $105 total per night from Jan 25 to Jan 26
$105 total
Jan 25 - Jan 26
Total with 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! (3,688 reviews)
Very satisfying

Reviewed on Jan 11, 2026

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
$37 nightly
The price is $41 total per night from Jan 28 to Jan 29
$41 total
Jan 28 - Jan 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! (1,758 reviews)
Room was perfect

Reviewed on Jan 6, 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 14 to Jan 15
$101 total
Jan 14 - Jan 15
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! (1,247 reviews)
The room was okay. It needs updates, but it works for an overnight stay. The shuttle was on time and courteous.

Reviewed on Jan 5, 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 Jan 18 to Jan 19
$69 total
Jan 18 - Jan 19
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! (2,799 reviews)
I felt very good there!

Reviewed on Jan 11, 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
$63 nightly
The price is $75 total per night from Feb 8 to Feb 9
$75 total
Feb 8 - Feb 9
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! (2,698 reviews)
Clean. Everyone very accommodating. Great location. Safe

Reviewed on Jan 7, 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 Jan 19 to Jan 20
$85 total
Jan 19 - Jan 20
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)
Check in person was great. View of train tracks was not great and was noisy Location very convenient location to university

Reviewed on Jan 5, 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
$37 nightly
The price is $41 total per night from Jan 28 to Jan 29
$41 total
Jan 28 - Jan 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! (1,758 reviews)
Room was perfect

Reviewed on Jan 6, 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
$120 nightly
The price is $141 total per night from Jan 21 to Jan 22
$141 total
Jan 21 - Jan 22
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! (2,772 reviews)
Just very crowded. 15 minute wait for a drink. Even longer line in the morning for a fresh omelette. We did stay over a holiday.

Reviewed on Jan 7, 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
$168 nightly
The price is $193 total per night from Jan 19 to Jan 20
$193 total
Jan 19 - Jan 20
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! (2,240 reviews)
Best hotel in Chicago

Reviewed on Jan 13, 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
$93 nightly
The price is $110 total per night from Jan 19 to Jan 20
$110 total
Jan 19 - Jan 20
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! (5,531 reviews)
All good

Reviewed on Jan 9, 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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