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

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Cheap Flights from OKC to MDW starting at $163 One Way, $365 Round Trip

Prices starting at $365 for return flights and $163 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.

Fri, Oct 9 - Mon, Oct 12
OKC
Oklahoma City
MDW
Chicago
$365 Roundtrip, found 13 hours ago
$365
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Fri, Oct 9 from Oklahoma City to Chicago, returning Mon, Oct 12, priced at $365 found 13 hours ago
Thu, Oct 29 - Sun, Nov 1
OKC
Oklahoma City
MDW
Chicago
$374 Roundtrip, found 13 hours ago
$374
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Thu, Oct 29 from Oklahoma City to Chicago, returning Sun, Nov 1, priced at $374 found 13 hours ago
Fri, Oct 9 - Mon, Oct 12
OKC
Oklahoma City
MDW
Chicago
$380 Roundtrip, found 13 hours ago
$380
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Fri, Oct 9 from Oklahoma City to Chicago, returning Mon, Oct 12, priced at $380 found 13 hours ago
Fri, Oct 9 - Mon, Oct 12
OKC
Oklahoma City
MDW
Chicago
$384 Roundtrip, found 13 hours ago
$384
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Fri, Oct 9 from Oklahoma City to Chicago, returning Mon, Oct 12, priced at $384 found 13 hours ago
Wed, Oct 21 - Fri, Oct 23
OKC
Oklahoma City
MDW
Chicago
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Oklahoma City to Chicago, returning Fri, Oct 23, priced at $385 found 3 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
$162 nightly
The price is $188 total per night from Sep 27 to Sep 28
$188 total
Sep 27 - Sep 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 and ...
Holiday Inn Chicago – Midway Airport S by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$119 nightly
The price is $141 total per night from Sep 9 to Sep 10
$141 total
Sep 9 - Sep 10
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! (10,318 reviews)
"I loved the location. It was perfect for seeing the city sights and getting to them on public transit.. I thought the front desk was unwelcoming and acted I different to concerns. Other staff were appropriately accommodating and helpful."

Reviewed on Sep 8, 2026

Congress Plaza Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$254 nightly
The price is $302 total per night from Sep 9 to Sep 10
$302 total
Sep 9 - Sep 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,400 reviews)
"That sounds like an incredibly frustrating and chaotic stay, and it is completely unacceptable for a high-end hotel to drop the ball like that. When you pay a premium price, you expect seamless service, not a battle just to get a blanket or ride the elevator.Worse than the poor service, having a ..."

Reviewed on Sep 7, 2026

Hyatt Regency McCormick Place 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
$119 nightly
The price is $141 total per night from Sep 9 to Sep 10
$141 total
Sep 9 - Sep 10
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! (10,318 reviews)
"I loved the location. It was perfect for seeing the city sights and getting to them on public transit.. I thought the front desk was unwelcoming and acted I different to concerns. Other staff were appropriately accommodating and helpful."

Reviewed on Sep 8, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$170 nightly
The price is $202 total per night from Oct 5 to Oct 6
$202 total
Oct 5 - Oct 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,184 reviews)
"I liked the Ambassador, it was a great! location. but, no coffee in the room and no maid service, We stayed 2 nights, but didn't get our room touched up. thus the 4 stars"

Reviewed on Sep 8, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (890 reviews)
"Great spot!"

Reviewed on Sep 7, 2026

Get rates
Kasa Magnificent Mile 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.

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
$53 nightly
The price is $60 total per night from Oct 1 to Oct 2
$60 total
Oct 1 - Oct 2
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 ...
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
$100 nightly
The price is $110 total per night from Oct 4 to Oct 5
$110 total
Oct 4 - Oct 5
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 ...
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
$101 nightly
The price is $116 total per night from Sep 28 to Sep 29
$116 total
Sep 28 - Sep 29
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 ...
7.8/10 Good! (3,182 reviews)
"This hotel could definitely be in much better shape, and I have to blame management for the current condition of the property. When you first walk in, there is a sign stating that the hotel has been under renovation since April. At this point, unless you don’t mind losing money, I would strongly ..."

Reviewed on Sep 8, 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
$220 nightly
The price is $220 total per night from Sep 9 to Sep 10
$220 total
Sep 9 - Sep 10
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. ...
Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$152 nightly
The price is $181 total per night from Sep 9 to Sep 10
$181 total
Sep 9 - Sep 10
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 ...
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
$53 nightly
The price is $60 total per night from Oct 1 to Oct 2
$60 total
Oct 1 - Oct 2
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 ...
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
$231 nightly
The price is $274 total per night from Sep 10 to Sep 11
$274 total
Sep 10 - Sep 11
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 ...
8.4/10 Very Good! (3,026 reviews)
"The staff was great. Very helpful and friendly."

Reviewed on Sep 8, 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
$227 nightly
The price is $270 total per night from Sep 11 to Sep 12
$270 total
Sep 11 - Sep 12
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 ...
8.6/10 Excellent! (2,645 reviews)
"We loved the history and beauty of the property. Highly recommend."

Reviewed on Sep 8, 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
$196 nightly
The price is $233 total per night from Sep 27 to Sep 28
$233 total
Sep 27 - Sep 28
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 ...
8.6/10 Excellent! (6,015 reviews)
"Very conveniently located to Michigan Ave and the subway. Easy to get around."

Reviewed on Sep 8, 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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