TUL - CHI

$105 Find Cheap Flights from Tulsa to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tulsa to Chicago departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tulsa to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tulsa to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$167
Typical prices: $352-$267
Delta
Tue 5/19Wed 5/27
TUL - MDW • 1 stop
Cheapest non-stop
$209
Typical prices: $364-$348
Southwest
Wed 5/20Tue 5/26
TUL - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest allows two free checked bags, saving costs.
United's Wi-Fi offers free messaging for passengers.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $167 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 04m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 14% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $216 (round-trip)
Shortest trip • 3h 50m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 58% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Tulsa to Chicago (TUL-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tulsa to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tulsa to Chicago

Tue, May 19 - Wed, May 27
Delta Logo
4:28 pm - 9:09 pm
TUL
-
MDW
4h 41m
1 stop
Delta Logo
5:12 pm - 11:20 pm
MDW
-
TUL
6h 08m
1 stop
$167Delta
Thu, May 7 - Mon, May 11
Delta Logo
6:51 pm - 11:59 pm
TUL
-
ORD
5h 08m
1 stop
Delta Logo
6:06 pm - 11:20 pm
ORD
-
TUL
5h 14m
1 stop
$167Delta
Tue, May 19 - Wed, May 27
American Airlines Logo
7:32 pm - 9:41 pm
TUL
-
ORD
2h 09mnonstop
American Airlines Logo
4:59 pm - 7:10 pm
ORD
-
TUL
2h 11mnonstop
$209American Airlines
Wed, May 20 - Tue, May 26
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
9:05 pm - 11:00 pm
MDW
-
TUL
1h 55mnonstop
$209Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
3:10 pm - 4:50 pm
TUL
-
MDW
1h 40mnonstop
Southwest Logo
9:05 pm - 11:00 pm
MDW
-
TUL
1h 55mnonstop
$211Southwest
Tue, May 19 - Wed, May 27
United Airlines Logo
6:30 pm - 8:38 pm
TUL
-
ORD
2h 08mnonstop
United Airlines Logo
8:45 am - 11:03 am
ORD
-
TUL
2h 18mnonstop
$217United Airlines
Tue, May 19 - Wed, May 27
Southwest Logo
3:10 pm - 4:50 pm
TUL
-
MDW
1h 40mnonstop
Southwest Logo
9:05 pm - 11:00 pm
MDW
-
TUL
1h 55mnonstop
$217Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
10:20 am - 4:35 pm
TUL
-
MDW
6h 15m
1 stop
Southwest Logo
9:05 pm - 11:00 pm
MDW
-
TUL
1h 55mnonstop
$221Southwest
Wed, May 20 - Tue, May 26
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
5:30 am - 10:05 am
MDW
-
TUL
4h 35m
1 stop
$225Southwest
Sat, Jun 6 - Tue, Jun 9
American Airlines Logo
12:19 pm - 2:25 pm
TUL
-
ORD
2h 06mnonstop
American Airlines Logo
9:53 pm - 11:58 pm
ORD
-
TUL
2h 05mnonstop
$239American Airlines
Booking Insights

KAYAK's insights & trends for Tulsa to Chicago flights

Get data-powered insights and trends into flights from Tulsa to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Tulsa to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Tulsa to Chicago departing in May.

What is the cheapest Tulsa to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Tulsa to Chicago costs $231 on the route between Tulsa (TUL) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 14% cheaper than other Tulsa-Chicago routes. The most popular route is between Tulsa (TUL) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Tulsa to Chicago?

The average price of all round-trip flights from Tulsa to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Tulsa to Chicago, you should consider leaving on a Thursday and avoid Tuesdays if you are looking for the best rates. For your return to Tulsa, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Tulsa to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tulsa to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Tulsa to Chicago is May, where tickets cost $296 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $397 and $392 respectively.

Can I save money by flying with a layover from Tulsa to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $344 on average.

How far in advance should I book a flight from Tulsa to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Tulsa to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Tulsa to Chicago, you should book around 4 weeks before departure, which saves you about 58% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Expert advice

Expert advice for your flight from Tulsa to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Duncan Madden

Duncan Madden

Expert on British Airways

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonOctober
Cheapest flight$84
Most popular time to fly and prices are also 2% lower on average.
Flight from Tulsa to Chicago Midway Airport

When to book flights from Tulsa to Chicago

Are your dates flexible? Find out the best times to travel from Tulsa to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Tulsa to Chicago

  • Where can I park my car at the Tulsa Airport?

    Your most affordable option for parking at TUL is in the Uncovered Economy Parking Lot. You can catch a free shuttle from this lot to the TUL terminal. If you want to be closer to the terminal, you can park in the Covered Garage, just opposite the terminal. However, this will cost a little bit more.

  • Are there any therapy dogs at TUL?

    Yes. As you wait for your flight to Chicago, you might encounter a therapy dog from the Welcome Waggin’ Program at TUL. Therapy dogs and their trained handlers roam Departures in order to offer delight, distraction, and solace to passengers who are waiting for a flight.

  • Which of the Chicago airports has private facilities for nursing moms?

    Both Chicago airports provide private areas where traveling moms can nurse or pump. Midway has a Mamava lactation pod on Concourse A near Gate A5 and a Mother's Room next to the Yoga Room on Concourse C. At ORD, you can find Mother's Rooms in Terminals 1, 2, 3, and 5, and Mamava pods in 1, 2, and 3.

  • Can I find a USO military lounge at either Chicago Airport?

    Yes. Both ORD and MDW have USO lounges. In fact, ORD has two. These private military lounges welcome US military personnel and their families free of charge. The USO at MDW is located airside on Concourse C and open every day from 8 am to 8 pm. One USO at ORD is in T2 on the Mezzanine level and the other is in T3 in the Rotunda of the G Concourse. The USO military lounges at ORD are open every day from 9 am to 5 pm.

  • What is the cheapest flight from Tulsa to Chicago?

    In the last 3 days, the lowest price for a flight from Tulsa to Chicago was $84 for a one-way ticket and $167 for a round-trip.

  • Do I need a passport to fly between Tulsa and Chicago?

    No

  • Which airports will I be using when flying from Tulsa to Chicago?

    On your way to Chicago, you’ll fly out from Tulsa. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Tulsa to Chicago?

    American Airlines, Delta, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Tulsa to Chicago flight route.

  • Which aircraft models fly most regularly from Tulsa to Chicago?

    The Embraer 170 is the aircraft model that flies most regularly on the Tulsa to Chicago flight route.

  • Which airline alliances offer flights from Tulsa to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between Tulsa and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Tulsa to Chicago?

    There are nonstop flights from Tulsa to Chicago on a daily basis.

  • Which is the best airline for flights from Tulsa to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Tulsa to Chicago are Southwest and United Airlines. With an average price for the route of $329 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $362 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Tulsa to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tulsa to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tulsa to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Tulsa is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tulsa to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Tulsa with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tulsa to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Tulsa up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Tulsa to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $216 or less one-way and $398 or less round-trip.
  • A hub for Omni Air International, the Tulsa International Airport (TUL) is located in northeastern Oklahoma. Flights to Chicago land at either Midway International Airport (MDW) or the larger Chicago O'Hare International Airport (ORD). Midway is a hub for Southwest and O'Hare is a hub for United and American Airlines.
  • If you are a flying from TUL into MDW, you can catch a flight on Southwest or Delta with one stop in either Dallas, St. Louis, or Atlanta. Delta also offers flights from TUL to MDW with two stops, either in Atlanta and then Dallas or in Atlanta and then Minneapolis.
  • TUL makes several accommodations in order to make travel as efficient as possible for differently-abled travelers. Passengers can find at least one accessible stall in every restroom, wheelchair availability, and a sunflower lanyard program designed to assist passengers who have challenges that may not be immediately noticeable, such as hearing loss, Crohn's disease, or PTSD.
  • Southwest, American, Delta, and United offer flights from TUL to ORD with one stop in cities such as Houston, Washington DC, New York, Denver, or Charlotte, among others. Delta, United, and American also offer flights from TUL to ORD with two stops.
  • If you have time to indulge yourself before your flight to Chicago, you can visit one of the many Massage Chairs located throughout TUL. These massage stations can be found both landside and airside.

Prefer to fly direct from Tulsa to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Tulsa to Chicago.
Find which airlines fly direct from Tulsa Airport to Chicago, which days they fly and book direct flights.

Direct departures

Tulsa to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Tulsa

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top 3 airlines serving from Tulsa to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Tulsa to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Tulsa to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4327 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Everything you need to know for your flight from Tulsa to Chicago

Information on your arrival and departure airports