$107 Cheap Flights from Tulsa (TUL) to Chicago (MDW)

View $107 flight on Thu, Dec 25, 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 $107 for one-way flights and $143 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Dec 31 - Tue, Jan 6
TUL
Tulsa
MDW
Chicago
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Tulsa to Chicago, returning Tue, Jan 6, priced at $143 found 6 days ago
Southwest Airlines
Wed, Dec 31 - Tue, Jan 6
TUL
Tulsa
MDW
Chicago
$193 Roundtrip, found 6 days ago
$193
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Tulsa to Chicago, returning Tue, Jan 6, priced at $193 found 6 days ago
Southwest Airlines
Tue, Nov 18 - Wed, Nov 19
TUL
Tulsa
MDW
Chicago
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Tulsa to Chicago, returning Wed, Nov 19, priced at $213 found 1 day ago
Southwest Airlines
Tue, Nov 18 - Wed, Nov 19
TUL
Tulsa
MDW
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Tulsa to Chicago, returning Wed, Nov 19, priced at $218 found 1 day ago
Southwest Airlines
Tue, Nov 18 - Wed, Nov 19
TUL
Tulsa
MDW
Chicago
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Tulsa to Chicago, returning Wed, Nov 19, priced at $221 found 1 day ago
Southwest Airlines
Tue, Nov 18 - Wed, Nov 19
TUL
Tulsa
MDW
Chicago
$226 Roundtrip, found 1 day ago
$226
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Tulsa to Chicago, returning Wed, Nov 19, priced at $226 found 1 day ago
Southwest Airlines
Wed, Dec 31 - Tue, Jan 6
TUL
Tulsa
MDW
Chicago
$227 Roundtrip, found 6 days ago
$227
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Tulsa to Chicago, returning Tue, Jan 6, priced at $227 found 6 days ago
Southwest Airlines
Tue, Nov 18 - Wed, Nov 19
TUL
Tulsa
MDW
Chicago
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Tulsa to Chicago, returning Wed, Nov 19, priced at $229 found 1 day ago
Delta
Thu, Nov 27 - Tue, Dec 2
TUL
Tulsa
MDW
Chicago
$244 Roundtrip, found 2 days ago
$244
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 27 from Tulsa to Chicago, returning Tue, Dec 2, priced at $244 found 2 days ago
Frontier Airlines
Sun, Oct 26 - Thu, Nov 6
TUL
Tulsa
MDW
Chicago
$284 Roundtrip, just found
$284
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Oct 26 from Tulsa to Chicago, returning Thu, Nov 6, priced at $284 just found

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

September is typically the cheapest month to fly

From $140 - $525 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $405
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $405

Frequently asked questions

How much does a flight from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $107 or cheap return flight from $143 from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW)?
Planning your trip for December is a good way to save, as it's the cheapest month for flights between TUL and MDW. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from Tulsa Intl. Airport (TUL) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from TUL to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
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.

Travel information

Travel information

Origin airport
Tulsa Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$143
Distance
583 mi
Average flight time
1 hour 47 mins

Book with confidence

Book with confidence

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 December. 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 $107 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.

 

Tulsa to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.