$87 Cheap Flights from Tulsa (TUL) to Chicago (MDW)

View $87 flight on Wed, Sep 17, 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 $87 for one-way flights and $169 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Sep 24 - Thu, Sep 25
TUL
Tulsa
MDW
Chicago
$169 Roundtrip, found 4 days ago
$169
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Sep 24 from Tulsa to Chicago, returning Thu, Sep 25, priced at $169 found 4 days ago
Southwest Airlines
Thu, Nov 6 - Tue, Nov 11
TUL
Tulsa
MDW
Chicago
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Nov 6 from Tulsa to Chicago, returning Tue, Nov 11, priced at $174 found 6 days ago
Southwest Airlines
Thu, Nov 27 - Tue, Dec 2
TUL
Tulsa
MDW
Chicago
$176 Roundtrip, found 3 days ago
$176
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 27 from Tulsa to Chicago, returning Tue, Dec 2, priced at $176 found 3 days ago
Southwest Airlines
Thu, Nov 27 - Tue, Dec 2
TUL
Tulsa
MDW
Chicago
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 27 from Tulsa to Chicago, returning Tue, Dec 2, priced at $181 found 3 days ago
Southwest Airlines
Mon, Oct 27 - Fri, Oct 31
TUL
Tulsa
MDW
Chicago
$187 Roundtrip, found 6 days ago
$187
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Tulsa to Chicago, returning Fri, Oct 31, priced at $187 found 6 days ago
Southwest Airlines
Tue, Sep 16 - Wed, Sep 24
TUL
Tulsa
MDW
Chicago
$190 Roundtrip, found 14 hours ago
$190
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Tulsa to Chicago, returning Wed, Sep 24, priced at $190 found 14 hours ago
Southwest Airlines
Tue, Sep 2 - Wed, Sep 3
TUL
Tulsa
MDW
Chicago
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Tulsa to Chicago, returning Wed, Sep 3, priced at $195 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Mon, Oct 27
TUL
Tulsa
MDW
Chicago
$197 Roundtrip, found 16 hours ago
$197
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Tulsa to Chicago, returning Mon, Oct 27, priced at $197 found 16 hours ago
Delta
Tue, Nov 11 - Tue, Nov 18
TUL
Tulsa
MDW
Chicago
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Nov 11 from Tulsa to Chicago, returning Tue, Nov 18, priced at $209 found 3 days ago
Frontier Airlines
Sun, Oct 19 - Sun, Nov 2
TUL
Tulsa
MDW
Chicago
$666 Roundtrip, found 1 day ago
$666
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Oct 19 from Tulsa to Chicago, returning Sun, Nov 2, priced at $666 found 1 day ago

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

September is typically the cheapest month to fly

From $148 - $776 per traveler.

Graph displaying average flight prices per month

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. Average driving time to city center is 23 minutes. Flights from $397
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $397
Flights from Tulsa (TUL) to Chicago (MDW)
Origin airport
Tulsa Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$169
Distance
583 mi
Average flight time
3 hours 46 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 $87 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?
Get a cheap one-way flight from $87 or cheap return flight from $169 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 September 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.

Explore a world of travel with Expedia

*Available to One Key members.