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$109+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
TUL — MDW
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
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 May 6, 2026.

This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 6/25:05 am
TUL
-
MDW
Nonstop1h 45m
Southwest
Tue 6/99:05 pm
MDW
-
TUL
Nonstop1h 50m
Southwest
Deal found 5/3$217
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sat 5/305:10 am
TUL
-
MDW
Nonstop1h 45m
Southwest
Wed 6/39:05 pm
MDW
-
TUL
Nonstop1h 55m
Southwest
Deal found 4/30$230
This Southwest deal was found by Cheapflights users on 5/4. 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 7/85:00 am
TUL
-
MDW
Nonstop1h 45m
Southwest
Wed 7/1511:45 am
MDW
-
TUL
Nonstop1h 45m
Southwest
Deal found 5/4$237
This Southwest deal was found by Cheapflights users on 5/4. 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.
Thu 5/283:55 pm
TUL
-
MDW
Nonstop1h 45m
Southwest
Mon 6/19:50 pm
MDW
-
TUL
Nonstop1h 55m
Southwest
Deal found 5/4$243
This Southwest deal was found by Cheapflights users on 5/2. 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.
Sat 6/63:10 pm
TUL
-
MDW
Nonstop1h 45m
Southwest
Tue 6/93:10 pm
MDW
-
TUL
2 stops7h 40m
Southwest
Deal found 5/2$245
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 6/64:28 pm
TUL
-
MDW
1 stop4h 41m
Delta
Wed 6/106:00 am
MDW
-
TUL
1 stop6h 04m
Delta
Deal found 4/30$250
This Southwest deal was found by Cheapflights users on 5/4. 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.
Tue 7/143:10 pm
TUL
-
MDW
Nonstop1h 45m
Southwest
Tue 7/2110:15 am
MDW
-
TUL
2 stops6h 00m
Southwest
Deal found 5/4$252

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 May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Southwest)

One-way from

$109
(Southwest)

Popular in

March

Cheapest in

August

Average price

$315

Good round-trip deal

$377 or less

Good one-way deal

$190 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.
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From Tulsa to Chicago Midway
Search Deals
One-way flight from Tulsa to Chicago Midway
Search Deals
High demand for flights, 4% potential price rise
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 May 2026
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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.
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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 May 6, 2026.
Use the filters below to find and compare flights from Tulsa to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 6/1

5:10 am-6:55 am

Nonstop1h 45m

Chicago Midway

Tue 6/16

9:05 pm-10:55 pm

Nonstop1h 50m

$240

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 5/28

3:55 pm-5:40 pm

Nonstop1h 45m

Chicago Midway

Mon 6/1

9:50 pm-11:45 pm

Nonstop1h 55m

$243
Quickest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 6/1

5:10 am-6:55 am

Nonstop1h 45m

Chicago Midway

Mon 6/8

9:30 pm-11:15 pm

Nonstop1h 45m

$243

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 6/27

5:05 am-6:50 am

Nonstop1h 45m

Chicago Midway

Wed 7/1

11:45 am-1:30 pm

Nonstop1h 45m

$293

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 5/21

5:10 am-6:55 am

Nonstop1h 45m

Chicago Midway

Sat 5/23

4:20 pm-10:35 pm

1 stop6h 15m

$293

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/8

2:20 pm-7:10 pm

1 stop4h 50m

Chicago Midway

Wed 8/12

8:45 pm-10:35 pm

Nonstop1h 50m

$293

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sun 6/21

4:45 pm-10:17 pm

1 stop5h 32m

Chicago Midway

Wed 6/24

6:00 am-12:04 pm

1 stop6h 04m

$319

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Fri 6/5

7:40 am-1:35 pm

2 stops5h 55m

Chicago Midway

Tue 6/9

5:20 pm-11:20 pm

1 stop6h 00m

$324

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 6/13

5:05 am-6:50 am

Nonstop1h 45m

Chicago Midway

Sat 6/13

10:15 am-12:00 pm

Nonstop1h 45m

$349
Cheapest one-way
Quickest one-way

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 5/27

3:10 pm-4:50 pm

Nonstop1h 40m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 20 resultsSorted by cheapest first
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 May.
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.

Cheapflights Insights

Everything you need to know about your flight from Tulsa to Chicago Midway Airport

What is the cheapest time of day to fly from TUL to MDW?

Find hourly flight availability from Tulsa to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Tulsa to Chicago Midway Airport as you normally would.

How much does it cost to fly round-trip from Tulsa to Chicago Midway Airport?

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 May 6, 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
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,305 reviews
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 1 outbound flight 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 1h 45m. Fly via Southwest to get the fastest option. Airlines will cover a distance of 582 mi. All flights are typically nonstop.

  • 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 $197. You may be able to fly from Tulsa to Chicago Midway Airport for 41% 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 $325, our data indicates the cheapest price to be $134. The most popular route (Tulsa - Chicago Midway), is priced around $237.

  • 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$356FlexibilityNo cancel feeOn-time63%

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