$94 Cheap Flights from Tulsa (TUL) to Chicago (MDW)

View $94 flight on Tue, Sep 16, 2025Opens in a new window

Popular airlines from Tulsa International Airport (TUL) to Chicago Midway Airport (MDW)

Cheap Flights from Tulsa to Chicago (TUL-MDW)

Prices were available within the past 7 days and start at $94 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Sep 16 - Wed, Sep 24
TUL
Tulsa
MDW
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 16 from Tulsa to Chicago, returning Wed, Sep 24, priced at $177 just found
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
TUL
Tulsa
MDW
Chicago
$180 Roundtrip, found 7 hours ago
$180
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Tulsa to Chicago, returning Tue, Sep 9, priced at $180 found 7 hours ago
Southwest Airlines
Tue, Sep 16 - Wed, Sep 24
TUL
Tulsa
MDW
Chicago
$187 Roundtrip, just found
$187
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 16 from Tulsa to Chicago, returning Wed, Sep 24, priced at $187 just found
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
TUL
Tulsa
MDW
Chicago
$190 Roundtrip, found 7 hours ago
$190
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Tulsa to Chicago, returning Tue, Sep 9, priced at $190 found 7 hours ago
Southwest Airlines
Thu, Aug 14 - Mon, Aug 18
TUL
Tulsa
MDW
Chicago
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Aug 14 from Tulsa to Chicago, returning Mon, Aug 18, priced at $196 found 1 day ago
Southwest Airlines
Tue, Sep 16 - Wed, Sep 24
TUL
Tulsa
MDW
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 16 from Tulsa to Chicago, returning Wed, Sep 24, priced at $197 just found
Southwest Airlines
Tue, Sep 16 - Wed, Sep 24
TUL
Tulsa
MDW
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 16 from Tulsa to Chicago, returning Wed, Sep 24, priced at $197 just found
Southwest Airlines
Thu, Oct 16 - Mon, Oct 20
TUL
Tulsa
MDW
Chicago
$200 Roundtrip, just found
$200
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 16 from Tulsa to Chicago, returning Mon, Oct 20, priced at $200 just found
Southwest Airlines
Tue, Sep 16 - Wed, Sep 24
TUL
Tulsa
MDW
Chicago
$202 Roundtrip, just found
$202
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Sep 16 from Tulsa to Chicago, returning Wed, Sep 24, priced at $202 just found
Delta
Thu, Aug 21 - Mon, Aug 25
TUL
Tulsa
MDW
Chicago
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Aug 21 from Tulsa to Chicago, returning Mon, Aug 25, priced at $208 found 2 days ago

Find the cheapest month to fly from Tulsa (TUL) to Chicago (MDW)

August is typically the cheapest month to fly

From $176 - $837 per traveler.

Graph displaying average flight prices per month

Flights from Tulsa (TUL) to Chicago (MDW)
Origin airport
Tulsa Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$177
Distance
583 mi
Average flight time
1 hour 40 mins

Tulsa to Chicago Flights

The cheapest times to fly from Tulsa to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Tulsa to Chicago are during the month of September. You can find some of the cheapest flights from Tulsa to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Tulsa to Chicago

Sunday is one of the best days to book for cheap flights from Tulsa to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Tulsa to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Tulsa to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $94 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Tulsa to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Tulsa to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW) cost?
Cheap round-trip flights from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW) start at $197. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and United flight leaving TUL on July 22 2025 and touching down at MDW. The price was last updated on June 29 2025 and has not changed since.
What is the cheapest month to fly from TUL to MDW?
The cheapest flights from TUL to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from TUL to MDW?
Journey from TUL to MDW with Southwest Airlines. This airline currently offers the cheapest one-way fare on this route, starting from $151. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from TUL on July 2 2025. Prices were last updated on June 29 2025 and have not changed since.
How many flights per day from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights departing from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from TUL to MDW?
Generally you'll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can change depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from TUL to MDW?
Southwest Airlines has the best track record for on-time direct flights from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW), with an on-time rating of 97%. Use the Expedia App to see your journey status before you go and get real-time alerts about any trip changes.
What is the best time to fly from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on time, select a flight that leaves from Tulsa Intl. Airport (TUL) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Tulsa Intl. Airport (TUL)?
Explore your flight options from Tulsa Intl. Airport (TUL) to O'Hare Intl. Airport (ORD). This is the only airport in Chicago you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from TUL to MDW shortly before your journey is usually more expensive. However, if you're flexible with your schedule, you could grab a cheap last-minute fare.
Is it cheaper to book a TUL to MDW flight and hotel package?
You'll typically save money by booking a TUL to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. Once you've selected your preferred accommodations and flights, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW)?
If you reserved your TUL to MDW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Explore a world of travel with Expedia

*Available to One Key members.