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

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Cheap Flights from OKC to MDW starting at $136 One Way, $270 Round Trip

Prices starting at $270 for return flights and $136 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.

Thu, Jun 25 - Tue, Jun 30
OKC
Oklahoma City
MDW
Chicago
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jun 25 from Oklahoma City to Chicago, returning Tue, Jun 30, priced at $270 found 3 days ago
Wed, Jul 15 - Tue, Jul 21
OKC
Oklahoma City
MDW
Chicago
$327 Roundtrip, found 6 days ago
$327
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Oklahoma City to Chicago, returning Tue, Jul 21, priced at $327 found 6 days ago
Wed, Jul 15 - Tue, Jul 21
OKC
Oklahoma City
MDW
Chicago
$337 Roundtrip, found 6 days ago
$337
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Oklahoma City to Chicago, returning Tue, Jul 21, priced at $337 found 6 days ago
Wed, Jul 15 - Tue, Jul 21
OKC
Oklahoma City
MDW
Chicago
$342 Roundtrip, found 6 days ago
$342
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Oklahoma City to Chicago, returning Tue, Jul 21, priced at $342 found 6 days ago
Tue, Oct 20 - Thu, Oct 22
OKC
Oklahoma City
MDW
Chicago
$346 Roundtrip, found 7 hours ago
$346
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Tue, Oct 20 from Oklahoma City to Chicago, returning Thu, Oct 22, priced at $346 found 7 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$208 nightly
The price is $247 total per night from Jul 2 to Jul 3
$247 total
Jul 2 - Jul 3
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! (1,095 reviews)
"Still-attractive hotel despite being the older of the two hotels next to McCormick Place with excellent beds, adequate space, good facilities. It is a very good choice next to the convention centre given its location and cleanliness. The staff were very helpful."

Reviewed on Jun 2, 2026

Hyatt Regency McCormick Place Chicago
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
$174 nightly
The price is $207 total per night from Jun 28 to Jun 29
$207 total
Jun 28 - Jun 29
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 ...
9/10 Wonderful! (2,232 reviews)
"ok"

Reviewed on Jun 1, 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
$154 nightly
The price is $183 total per night from Jul 1 to Jul 2
$183 total
Jul 1 - Jul 2
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! (10,158 reviews)
"Older hotel but well maintained. Rooms took a bit to cool off during the summer but the view was great!"

Reviewed on Jun 2, 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
$154 nightly
The price is $183 total per night from Jul 1 to Jul 2
$183 total
Jul 1 - Jul 2
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! (10,158 reviews)
"Older hotel but well maintained. Rooms took a bit to cool off during the summer but the view was great!"

Reviewed on Jun 2, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$154 nightly
The price is $183 total per night from Jun 28 to Jun 29
$183 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,505 reviews)
"I did not stay because my medical reason for booking this was canceled. They would not work with me to change the dates."

Reviewed on Jun 2, 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$203 nightly
The price is $242 total per night from Jun 30 to Jul 1
$242 total
Jun 30 - Jul 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,322 reviews)
"Excellent location and good selection of breakfast"

Reviewed on Jun 2, 2026

Hotel Riu Plaza 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
$65 nightly
The price is $73 total per night from Jun 25 to Jun 26
$73 total
Jun 25 - Jun 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! (1,942 reviews)
"The floor felt like I was going to fall through. My feet turned black from dirty floor. Doors looked like they had been water damage. The top bed blanket was dirty. For the price I paid, should of had a mIcrowave and refrigerator included."

Reviewed on Jun 1, 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
$107 nightly
The price is $119 total per night from Jun 30 to Jul 1
$119 total
Jun 30 - Jul 1
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! (1,465 reviews)
"Good location great shuttle service"

Reviewed on Jun 3, 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
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! (3,022 reviews)
"Staff was friendly. Breakfast area did not look clean. Part of parking area was poorly lit and full construction equipment. Catalyst stolen from our car the last night."

Reviewed on Jun 3, 2026

Get rates
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
$134 nightly
The price is $159 total per night from Jun 29 to Jun 30
$159 total
Jun 29 - Jun 30
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. ...
8/10 Very Good! (3,049 reviews)
"No toilet paper. Stained curtains. But bed was ok."

Reviewed on Jun 2, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$134 nightly
The price is $159 total per night from Jun 28 to Jun 29
$159 total
Jun 28 - Jun 29
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! (2,595 reviews)
"The room was clean although pretty outdated. The staff was helpful and polite."

Reviewed on May 31, 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
$65 nightly
The price is $73 total per night from Jun 25 to Jun 26
$73 total
Jun 25 - Jun 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! (1,942 reviews)
"The floor felt like I was going to fall through. My feet turned black from dirty floor. Doors looked like they had been water damage. The top bed blanket was dirty. For the price I paid, should of had a mIcrowave and refrigerator included."

Reviewed on Jun 1, 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
$253 nightly
The price is $300 total per night from Jun 30 to Jul 1
$300 total
Jun 30 - Jul 1
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! (2,864 reviews)
"Excelent stay in Chicago with a great breakfast that is include. Awesome location and staff was very helpful."

Reviewed on May 31, 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
$209 nightly
The price is $248 total per night from Jul 2 to Jul 3
$248 total
Jul 2 - Jul 3
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! (2,472 reviews)
"in room coffee service was a bit of a disappointment. it was hard to get pods for the coffee maker."

Reviewed on Jun 2, 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
$219 nightly
The price is $261 total per night from Jun 14 to Jun 15
$261 total
Jun 14 - Jun 15
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! (5,947 reviews)
"The location of this property was perfect for walking to Navy Pier, the Field Museum and Millennium Park."

Reviewed on Jun 2, 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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