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$95+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
TUL — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$203
(Southwest)

One-way from

$95
(Southwest)

Popular in

November

Cheapest in

August

Average price

$253

Good round-trip deal

$242 or less

Good one-way deal

$203 or less
From Tulsa to Chicago Midway
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One-way flight from Tulsa to Chicago Midway
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Highest demand for flights based on searches. 19% potential increase in price ($103 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Tulsa to Chicago Midway.
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Price to beat on a one-way flight from Tulsa to Chicago Midway.
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Find 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/14. 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 10/46:35 amTUL - MDW
Nonstop1h 45mSouthwest
Tue 10/75:30 pmMDW - TUL
Nonstop1h 50mSouthwest
Deal found 8/14$203
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 9/36:00 amTUL - MDW
1 stop7h 36mDelta
Tue 9/96:00 amMDW - TUL
1 stop7h 10mDelta
Deal found 8/13$209
This Southwest deal was found by Cheapflights users on 8/12. 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 10/167:05 pmTUL - MDW
1 stop5h 00mSouthwest
Mon 10/273:45 pmMDW - TUL
Nonstop1h 45mSouthwest
Deal found 8/12$227
This Southwest deal was found by Cheapflights users on 8/13. 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 10/29:35 amTUL - MDW
Nonstop1h 50mSouthwest
Sun 10/56:35 pmMDW - TUL
Nonstop1h 50mSouthwest
Deal found 8/13$232
This Southwest deal was found by Cheapflights users on 8/14. 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 9/45:55 amTUL - MDW
1 stop10h 30mSouthwest
Mon 9/83:20 pmMDW - TUL
1 stop6h 50mSouthwest
Deal found 8/14$237

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 August 14, 2025.
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

Sat 10/4

6:35 am-8:20 am

Nonstop1h 45m

Chicago Midway

Tue 10/7

5:30 pm-7:20 pm

Nonstop1h 50m

$203

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 9/3

6:00 am-1:36 pm

1 stop7h 36m

Chicago Midway

Tue 9/9

6:00 am-1:10 pm

1 stop7h 10m

$209

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 9/23

9:57 am-5:35 pm

1 stop7h 38m

Chicago Midway

Tue 9/30

6:00 am-11:56 am

1 stop5h 56m

$209

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 10/16

7:05 pm-12:05 am

1 stop5h 00m

Chicago Midway

Mon 10/27

3:45 pm-5:30 pm

Nonstop1h 45m

$227

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 10/2

9:35 am-11:25 am

Nonstop1h 50m

Chicago Midway

Sun 10/5

6:35 pm-8:25 pm

Nonstop1h 50m

$232

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 9/4

5:55 am-4:25 pm

1 stop10h 30m

Chicago Midway

Mon 9/8

3:20 pm-10:10 pm

1 stop6h 50m

$237

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 9/23

9:05 am-10:50 am

Nonstop1h 45m

$95

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 11/12

3:15 pm-5:00 pm

Nonstop1h 45m

$95

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 9/16

9:05 am-10:50 am

Nonstop1h 45m

$95

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 9/17

9:05 am-10:50 am

Nonstop1h 45m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 15 results
1
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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 August 14, 2025.

One of the essential ways to save on airfare from Tulsa to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 8% on airfare.

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 August 14, 2025.
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
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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 53% 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 $308, our data indicates the cheapest price to be $108. The most popular route (Tulsa - Chicago Midway), is priced around $209.

  • 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.

  • What is the cheapest month to book a flight from Tulsa to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Tulsa to Chicago Midway Airport (average of $160). Flying from Tulsa to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$358FlexibilityNo cancel feeOn-time63%

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