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

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Cheap Flights from OKC to MDW starting at $130 One Way, $259 Round Trip

Prices starting at $259 for return flights and $130 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, Nov 16 - Wed, Nov 18
OKC
Oklahoma City
MDW
Chicago
$259 Roundtrip, found 2 hours ago
$259
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Nov 16 from Oklahoma City to Chicago, returning Wed, Nov 18, priced at $259 found 2 hours ago
Mon, Nov 16 - Wed, Nov 18
OKC
Oklahoma City
MDW
Chicago
$269 Roundtrip, found 2 hours ago
$269
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Nov 16 from Oklahoma City to Chicago, returning Wed, Nov 18, priced at $269 found 2 hours ago
Mon, Nov 16 - Wed, Nov 18
OKC
Oklahoma City
MDW
Chicago
$274 Roundtrip, found 2 hours ago
$274
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Nov 16 from Oklahoma City to Chicago, returning Wed, Nov 18, priced at $274 found 2 hours ago
Mon, Nov 16 - Wed, Nov 18
OKC
Oklahoma City
MDW
Chicago
$279 Roundtrip, found 2 hours ago
$279
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Nov 16 from Oklahoma City to Chicago, returning Wed, Nov 18, priced at $279 found 2 hours ago
Mon, Nov 9 - Mon, Nov 16
OKC
Oklahoma City
MDW
Chicago
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Oklahoma City to Chicago, returning Mon, Nov 16, priced at $279 found 3 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$104 nightly
The price is $124 total per night from Nov 22 to Nov 23
$124 total
Nov 22 - Nov 23
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 ...
Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$108 nightly
The price is $129 total per night from Nov 24 to Nov 25
$129 total
Nov 24 - Nov 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Chicago - Downtown by IHG
Chicago Parthenon Hostel

Chicago Parthenon Hostel

2 out of 5
310 S. Halsted Street Chicago IL
$130 nightly
The price is $153 total per night from Nov 2 to Nov 3
$153 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this hostel in Chicago. Enjoy free WiFi, concierge services, and rainfall showerheads. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.2/10 Very Good! (603 reviews)
"The absence of an elevator was a major drawback, as guests are expected to carry their own heavy luggage up the stairs. This is quite unacceptable and difficult to comprehend in this day and age. The Wi-Fi was adequate, and the room cleanliness and staff cooperation were satisfactory. Overall, while ..."

Reviewed on Oct 25, 2026

Chicago Parthenon Hostel
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
$104 nightly
The price is $124 total per night from Nov 22 to Nov 23
$124 total
Nov 22 - Nov 23
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 ...
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
$122 nightly
The price is $145 total per night from Nov 22 to Nov 23
$145 total
Nov 22 - Nov 23
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$107 nightly
The price is $127 total per night from Nov 26 to Nov 27
$127 total
Nov 26 - Nov 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River 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
$62 nightly
The price is $70 total per night from Nov 4 to Nov 5
$70 total
Nov 4 - Nov 5
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
$101 nightly
The price is $112 total per night from Nov 9 to Nov 10
$112 total
Nov 9 - Nov 10
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 ...
7.6/10 Good! (1,894 reviews)
"The airport shuttle was the best part of the stay. We stayed for 3 days. During our stay, there was construction going on to the building. It was ridiculously noisy. We knew about the construction when we booked the room but had no idea it would sound like a wrecking ball crashing thru the ceiling ..."

Reviewed on Oct 27, 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
$92 nightly
The price is $106 total per night from Nov 22 to Nov 23
$106 total
Nov 22 - Nov 23
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 ...
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
$154 nightly
The price is $183 total per night from Nov 3 to Nov 4
$183 total
Nov 3 - Nov 4
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! (3,391 reviews)
"Location was convenient, staff was very helpful. I had a great experience, would stay here again."

Reviewed on Oct 26, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$106 nightly
The price is $124 total per night from Nov 11 to Nov 12
$124 total
Nov 11 - Nov 12
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 ...
7.8/10 Good! (2,949 reviews)
"There was no parking, no amenities offered such as free continental breakfast, work space, workout facility. Air conditioning was a box in a window too small for the entire area."

Reviewed on Oct 26, 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
$62 nightly
The price is $70 total per night from Nov 4 to Nov 5
$70 total
Nov 4 - Nov 5
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
$143 nightly
The price is $170 total per night from Nov 24 to Nov 25
$170 total
Nov 24 - Nov 25
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! (3,032 reviews)
"We enjoyed our stay, the hotel was clean and staff was helpful. The location is great but there not being a lobby at ground level felt annoying at times. It was such an ordeal to get down to the sky lobby and then catch a second elevator to get to ground level, especially because at times the elevators ..."

Reviewed on Oct 26, 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
$152 nightly
The price is $180 total per night from Nov 24 to Nov 25
$180 total
Nov 24 - Nov 25
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! (2,734 reviews)
"Destination Fee: Understanding a $25 fee was very misleading resulting in greater charges which I discussed with the manager that had to adjust my bill. The manager explained it was confusing to their own employees hotel staff, which is why they provided signage explaining the fee, which was also ..."

Reviewed on Oct 26, 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
$127 nightly
The price is $151 total per night from Nov 22 to Nov 23
$151 total
Nov 22 - Nov 23
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 ...
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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