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Midway

$129+ Cheap flights from Tulsa (TUL) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
TUL — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Tulsa to Midway

Cheapest flights from Tulsa to Midway
Explore the most affordable flight options available from Tulsa to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:15 am
TUL
-
MDW
1 stop3h 15m
Southwest
Wed 3/119:00 pm
MDW
-
TUL
Nonstop2h 00m
Southwest
Deal found 1/27$263
This Southwest deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:10 pm
TUL
-
MDW
Nonstop1h 40m
Southwest
Wed 4/1510:25 am
MDW
-
TUL
1 stop7h 45m
Southwest
Deal found 1/28$267
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/175:16 pm
TUL
-
MDW
1 stop5h 17m
Delta
Sat 2/286:00 am
MDW
-
TUL
1 stop6h 02m
Delta
Deal found 1/27$269
This Southwest deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:10 pm
TUL
-
MDW
Nonstop1h 40m
Southwest
Tue 4/142:35 pm
MDW
-
TUL
2 stops8h 10m
Southwest
Deal found 1/28$272
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:37 am
TUL
-
MDW
1 stop7h 08m
Delta
Tue 3/1010:45 am
MDW
-
TUL
1 stop5h 42m
Delta
Deal found 1/27$273
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:15 am
TUL
-
MDW
1 stop6h 50m
Southwest
Wed 2/258:10 am
MDW
-
TUL
2 stops7h 20m
Southwest
Deal found 1/27$274
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/168:50 am
TUL
-
MDW
2 stops34h 17m
Multiple Airlines
Thu 2/267:30 am
MDW
-
TUL
1 stop24h 30m
Multiple Airlines
Deal found 1/27$275
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/182:55 pm
TUL
-
MDW
1 stop6h 25m
Southwest
Wed 3/255:30 pm
MDW
-
TUL
1 stop6h 00m
Southwest
Deal found 1/27$277
This Southwest deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:00 am
TUL
-
MDW
1 stop5h 10m
Southwest
Tue 3/1011:00 am
MDW
-
TUL
2 stops7h 05m
Southwest
Deal found 1/28$278

Find flight deals from Tulsa to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Tulsa (TUL) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$263
(Southwest)

One-way from

$129
(Southwest)

Popular in

March

Cheapest in

August

Average price

$329

Good round-trip deal

$383 or less

Good one-way deal

$185 or less
Provider with most accurate pricing for Tulsa-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tulsa-Chicago Midway flights.
Search Deals
From Tulsa to Chicago Midway
Search Deals
One-way flight from Tulsa to Chicago Midway
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Tulsa to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Tulsa to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tulsa to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Tulsa to Chicago Midway Airport that are best for you.

Fly from

Tulsa

Fly to

Midway

Route

Depart

Return

Price

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 2/25

5:16 pm-10:31 pm

1 stop5h 15m

Chicago Midway

Sat 2/28

6:00 am-12:02 pm

1 stop6h 02m

$269

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 3/3

10:37 am-5:45 pm

1 stop7h 08m

Chicago Midway

Tue 3/10

10:45 am-4:27 pm

1 stop5h 42m

$273

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 4/8

3:10 pm-4:50 pm

Nonstop1h 40m

Chicago Midway

Wed 4/15

9:05 pm-11:00 pm

Nonstop1h 55m

$280

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 2/21

5:16 pm-10:31 pm

1 stop5h 15m

Chicago Midway

Mon 2/23

6:00 am-1:07 pm

1 stop7h 07m

$296

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 2/25

5:26 am-11:59 am

1 stop6h 33m

Chicago Midway

Thu 2/26

6:00 am-1:07 pm

1 stop7h 07m

$296

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 2/19

5:26 am-11:59 am

1 stop6h 33m

Chicago Midway

Wed 2/25

6:00 am-1:07 pm

1 stop7h 07m

$296

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 2/24

3:50 pm-7:05 pm

1 stop3h 15m

Chicago Midway

Thu 2/26

5:25 am-11:15 am

2 stops5h 50m

$301

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 2/21

5:35 am-10:55 am

1 stop5h 20m

Chicago Midway

Mon 2/23

12:30 pm-8:15 pm

2 stops7h 45m

$301

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 2/25

6:45 am-2:20 pm

2 stops7h 35m

Chicago Midway

Thu 2/26

1:25 pm-10:05 pm

2 stops8h 40m

$307

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 2/17

5:16 pm-10:33 pm

1 stop5h 17m

Chicago Midway

Wed 2/25

9:50 am-10:32 pm

2 stops12h 42m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 20 results
1
2

Compare providers for flights from Tulsa to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Tulsa to Midway in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Tulsa-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tulsa-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tulsa-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tulsa-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Tulsa-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Tulsa to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Tulsa with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated January 29, 2026.
See what other customers who have flown with Southwest from Tulsa to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Tulsa to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Tulsa to Chicago Midway?

    Tulsa (TUL), located 6.6 mi from the city center, is the airport you fly out of when you book flights from Tulsa to Chicago Midway. 1 airline have flights from Tulsa to Chicago Midway on a regular basis. Booking flights from Tulsa to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • How long is the flight from Tulsa to Chicago Midway Airport?

    There are many flights that can get you from Tulsa to Chicago Midway Airport in 6h 33m. Fly via Southwest or Delta to get the fastest option. Airlines will cover a distance of 582 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Tulsa to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Tulsa to Chicago Midway Airport round-trip from $167. You may be able to fly from Tulsa to Chicago Midway Airport for 50% less than the average price by searching for this airline.

  • What are the cheapest flights from Tulsa to Chicago Midway Airport?

    Looking for the cheapest flight from Tulsa to Chicago Midway Airport? While on average our users pay $306, our data indicates the cheapest price to be $144. The most popular route (Tulsa - Chicago Midway), is priced around $263.

  • Can I find deals for flights from Tulsa to Midway that include hotel bookings?

    Yes. In addition to deals on Tulsa to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Tulsa to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Tulsa to Midway.

  • Can I find deals for business class flights from Tulsa to Midway?

    Yes. Cheapflights offers flight deals from Tulsa to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Tulsa to Midway

Discover the top airline that operate flights from Tulsa to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$167Average$356FlexibilityNo cancel feeOn-time63%

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