TUL - CHI

$109 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 5/5. 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
$217
Typical prices: $352-$267
Southwest
Tue 5/5Tue 5/12
TUL - MDW • Non-stop
Cheapest one-way
$109
Southwest
Tue 5/5
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 $217 (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 00m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 8% 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 • 14% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Chicago!
Flight Deals
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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 5 - Tue, May 12
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
9:05 pm - 11:00 pm
MDW
-
TUL
1h 55mnonstop
$217Southwest
Tue, May 19 - Wed, May 27
American Airlines Logo
9:25 am - 11:34 am
TUL
-
ORD
2h 09mnonstop
American Airlines Logo
9:50 pm - 11:56 pm
ORD
-
TUL
2h 06mnonstop
$217American Airlines
Tue, May 5 - Tue, May 12
Southwest Logo
3:10 pm - 4:50 pm
TUL
-
MDW
1h 40mnonstop
Southwest Logo
12:35 pm - 8:50 pm
MDW
-
TUL
8h 15m
1 stop
$227Southwest
Thu, May 7 - Tue, May 12
American Airlines Logo
7:32 pm - 9:41 pm
TUL
-
ORD
2h 09mnonstop
American Airlines Logo
6:40 am - 8:50 am
ORD
-
TUL
2h 10mnonstop
$230American Airlines
Mon, Apr 27 - Tue, Apr 28
Southwest Logo
5:10 am - 6:55 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
9:40 am - 11:35 am
MDW
-
TUL
1h 55mnonstop
$230Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
7:20 am - 4:35 pm
TUL
-
MDW
9h 15m
2 stops
Southwest Logo
9:40 am - 11:35 am
MDW
-
TUL
1h 55mnonstop
$232Southwest
Tue, May 19 - Wed, May 27
Delta Logo
4:28 pm - 9:09 pm
TUL
-
MDW
4h 41m
1 stop
Delta Logo
12:53 pm - 6:06 pm
MDW
-
TUL
5h 13m
1 stop
$237Delta
Tue, May 19 - Wed, May 27
Delta Logo
4:28 pm - 10:27 pm
TUL
-
ORD
5h 59m
1 stop
Delta Logo
6:06 pm - 11:20 pm
ORD
-
TUL
5h 14m
1 stop
$237Delta
Thu, May 7 - Tue, May 12
American Airlines Logo
6:33 pm - 11:48 pm
TUL
-
ORD
5h 15m
1 stop
American Airlines Logo
4:52 pm - 7:02 pm
ORD
-
TUL
2h 10mnonstop
$240American Airlines
Thu, May 7 - Tue, May 12
Delta Logo
6:51 pm - 11:59 pm
TUL
-
ORD
5h 08m
1 stop
Delta Logo
5:30 am - 12:07 pm
ORD
-
TUL
6h 37m
1 stop
$250Delta
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 $237 on the route between Tulsa (TUL) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 8% 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 August, where tickets cost $299 (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$109
Most popular time to fly and prices are also 15% 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

  • 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 $109 for a one-way ticket and $217 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 175 (Enhanced Winglets) 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 $339 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 $357 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 $198 or less one-way and $400 or less round-trip.

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 4337 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

6.0 GoodKenley, Apr 2026
AUS - LAS
Read more Southwest reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

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.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

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

Information on your arrival and departure airports