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$109+ Cheap flights from Tulsa (TUL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
TUL — CHI
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
1 adult, Economy
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Cheapflights Tip: The best prices from Tulsa to Chicago are usually found in August or May, booked 44 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Tulsa to Chicago

Cheapest flights from Tulsa to Chicago
Explore the most affordable flight options available from Tulsa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 9, 2026.

This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:00 am
TUL
-
MDW
Nonstop1h 45m
Southwest
Wed 6/1711:45 am
MDW
-
TUL
Nonstop1h 45m
Southwest
Deal found 5/7$237
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:35 am
TUL
-
ORD
Nonstop2h 13m
American Airlines
Wed 7/159:40 am
ORD
-
TUL
Nonstop2h 04m
American Airlines
Deal found 5/6$237
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:10 am
TUL
-
MDW
Nonstop1h 45m
Southwest
Wed 6/39:40 am
MDW
-
TUL
Nonstop1h 55m
Southwest
Deal found 5/7$240
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:35 pm
TUL
-
ORD
Nonstop2h 09m
American Airlines
Wed 6/1011:15 am
ORD
-
TUL
Nonstop2h 05m
American Airlines
Deal found 5/5$240
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:10 am
TUL
-
MDW
Nonstop1h 45m
Southwest
Mon 6/19:50 pm
MDW
-
TUL
Nonstop1h 55m
Southwest
Deal found 5/6$243
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:26 pm
TUL
-
ORD
Nonstop2h 04m
American Airlines
Mon 9/1410:15 pm
ORD
-
TUL
Nonstop1h 59m
American Airlines
Deal found 5/6$243
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:43 pm
TUL
-
ORD
Nonstop2h 22m
American Airlines
Mon 6/111:14 am
ORD
-
TUL
Nonstop2h 07m
American Airlines
Deal found 5/4$244
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/84:05 pm
TUL
-
MDW
Nonstop1h 45m
Southwest
Tue 6/169:05 pm
MDW
-
TUL
Nonstop1h 50m
Southwest
Deal found 5/9$251
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:43 pm
TUL
-
ORD
Nonstop2h 22m
American Airlines
Mon 6/15:00 am
ORD
-
TUL
1 stop5h 11m
American Airlines
Deal found 5/4$253
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:43 pm
TUL
-
MDW
1 stop5h 32m
Delta
Wed 7/156:00 am
MDW
-
TUL
1 stop5h 56m
Delta
Deal found 5/6$257
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:04 am
TUL
-
ORD
1 stop7h 08m
Delta
Wed 7/155:30 am
ORD
-
TUL
1 stop6h 26m
Delta
Deal found 5/6$257
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/64:28 pm
TUL
-
MDW
1 stop4h 41m
Delta
Wed 6/106:00 am
MDW
-
TUL
1 stop6h 04m
Delta
Deal found 5/5$260

Find flight deals from Tulsa to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Tulsa (TUL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Southwest)

One-way from

$109
(American Airlines)

Popular in

January

Cheapest in

August

Average price

$307

Good round-trip deal

$377 or less

Good one-way deal

$190 or less
Provider with most accurate pricing for Tulsa-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tulsa-Chicago (CHI) flights.
Search Deals
From Tulsa to Chicago (CHI)
Search Deals
One-way flight from Tulsa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Tulsa to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Tulsa to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tulsa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 9, 2026.
Use the filters below to find and compare flights from Tulsa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 6/9

4:50 pm-10:00 pm

1 stop5h 10m

Chicago Midway

Wed 6/17

9:05 pm-10:55 pm

Nonstop1h 50m

$247

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 6/1

8:00 pm-5:25 am

1 stop9h 25m

Chicago Midway

Tue 6/16

9:05 pm-10:55 pm

Nonstop1h 50m

$250

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 5/28

3:55 pm-5:40 pm

Nonstop1h 45m

Chicago Midway

Mon 6/1

6:15 pm-11:40 pm

1 stop5h 25m

$253

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 7/14

4:43 pm-10:15 pm

1 stop5h 32m

Chicago Midway

Wed 7/15

6:00 am-11:56 am

1 stop5h 56m

$257

TulsaChicago

TUL - ORD

TULORD

Tulsa

Tue 7/14

10:04 am-5:12 pm

1 stop7h 08m

Chicago O'Hare Intl

Wed 7/15

5:30 am-11:56 am

1 stop6h 26m

$257

TulsaChicago

TUL - ORD

TULORD

Tulsa

Sat 6/6

4:28 pm-12:08 am

1 stop7h 40m

Chicago O'Hare Intl

Wed 6/10

5:30 am-12:04 pm

1 stop6h 34m

$260

TulsaChicago

TUL - ORD

TULORD

Tulsa

Mon 6/1

4:28 pm-9:53 pm

1 stop5h 25m

Chicago O'Hare Intl

Mon 6/8

5:30 am-12:04 pm

1 stop6h 34m

$263

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 8/11

6:00 am-11:51 am

1 stop5h 51m

Chicago Midway

Tue 8/11

5:10 pm-10:18 pm

1 stop5h 08m

$267

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 7/29

7:35 am-1:35 pm

2 stops6h 00m

Chicago Midway

Tue 8/4

3:50 pm-10:30 pm

2 stops6h 40m

$307
Quickest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 7/22

3:10 pm-4:55 pm

Nonstop1h 45m

Chicago Midway

Sun 7/26

9:25 pm-11:15 pm

Nonstop1h 50m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 42 resultsSorted by cheapest first
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Compare providers for flights from Tulsa to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Tulsa to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Tulsa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tulsa-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tulsa-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tulsa-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Tulsa-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Tulsa to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Tulsa with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

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

The price you pay for your flight from Tulsa to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 26 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Tulsa to Chicago?

Currently, September is the cheapest month in which you can book a flight from Tulsa to Chicago (average of $93). Flying from Tulsa to Chicago in July is currently the most expensive (average of $239). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from TUL to CHI?

Find hourly flight availability from Tulsa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 9, 2026.

One of the essential ways to save on airfare from Tulsa to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 18% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Tulsa to Chicago. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Tulsa to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Tulsa to Chicago

Explore weekly flight availability from Tulsa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 9, 2026.

The most flights from TUL to CHI are scheduled on a Monday (35 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (24 on average).

How much does it cost to fly round-trip from Tulsa to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 9, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Tulsa to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,302 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,302 reviews
Southwest
8.0
Very good
4,302 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,692 reviews
Southwest
8.0
Very good
4,302 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,669 reviews
Southwest
8.0
Very good
4,302 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Tulsa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Tulsa to Chicago?

    Tulsa (TUL) is the airport you will fly out of if you book a flight from Tulsa to Chicago. You should not have trouble finding flights to Chicago from Tulsa; the airport handles an average of 32 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Tulsa airport to Chicago. It is only a 6.6 mi journey to Tulsa (TUL) from Tulsa’s city center.

  • How long is the flight from Tulsa to Chicago?

    Departing from Tulsa to Chicago will take you 1h 45m. There are 582 mi between Tulsa and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Tulsa to Chicago round-trip?

    Cheapflights users have booked flights from Tulsa to Chicago round-trip from $189. Other airlines that can offer you cheap pricing are Southwest, from $197, and United Airlines, from $230. American Airlines is currently priced 46% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Tulsa to Chicago?

    Before booking your flight to Chicago from Tulsa, check out the most reliable airlines to get you to your destination on time: American Airlines (80%), Qatar Airways (79%), SkyWest Airlines( 79%).

  • What are the cheapest flights from Tulsa to Chicago?

    Looking at all options, your cheapest flight can be booked for $161. While the most popular route (Tulsa - Chicago O'Hare Intl) can be booked for $237 on average, our data indicates $863 when flying from Tulsa to Chicago.

  • Can I find deals for flights from Tulsa to Chicago that include hotel bookings?

    Yes. In addition to deals on Tulsa to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Tulsa to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Tulsa to Chicago.

  • Can I find deals for business class flights from Tulsa to Chicago?

    Yes. Cheapflights offers flight deals from Tulsa to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Tulsa to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Tulsa to Chicago (average of $93). Flying from Tulsa to Chicago in July is currently the most expensive (average of $239). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 3 airlines flying from Tulsa to Chicago

Discover the top 3 airlines that operate flights from Tulsa to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$361FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$356FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$230Average$373FlexibilityNo cancel feeOn-time69%

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