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$59+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
TUL — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Tulsa to Chicago are usually found in August or May, booked 55 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap 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 September 15, 2025.

Round-trip from

$133
(Southwest)

One-way from

$59
(American Airlines)

Popular in

January

Cheapest in

August

Average price

$323

Good round-trip deal

$303 or less

Good one-way deal

$194 or less
From Tulsa to Chicago (CHI)
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One-way flight from Tulsa to Chicago (CHI)
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Highest demand for flights based on searches. 20% potential increase in price ($92 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Tulsa to Chicago (CHI).
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Price to beat on a one-way flight from Tulsa to Chicago (CHI).
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Find 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/2912:05 pmTUL - MDW
Nonstop1h 45mSouthwest
Fri 10/318:25 amMDW - TUL
Nonstop1h 55mSouthwest
Deal found 9/13$133
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/76:16 pmTUL - ORD
Nonstop2h 08mAmerican Airlines
Thu 10/910:20 pmORD - TUL
Nonstop2h 02mAmerican Airlines
Deal found 9/13$133
This Southwest deal was found by Cheapflights users on 9/13. 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 10/305:30 pmTUL - MDW
1 stop7h 15mSouthwest
Tue 11/41:55 pmMDW - TUL
Nonstop1h 50mSouthwest
Deal found 9/13$143
This Southwest deal was found by Cheapflights users on 9/13. 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 11/134:45 pmTUL - MDW
Nonstop1h 45mSouthwest
Sat 11/1510:10 amMDW - TUL
2 stops9h 30mSouthwest
Deal found 9/13$154
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/295:35 amTUL - ORD
1 stop5h 10mSouthwest
Fri 10/311:30 pmORD - TUL
1 stop6h 35mSouthwest
Deal found 9/13$182
This Delta deal was found by Cheapflights users on 9/13. 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 11/16:00 amTUL - ORD
1 stop6h 16mDelta
Tue 11/46:45 amORD - TUL
1 stop5h 17mDelta
Deal found 9/13$197
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:47 amTUL - ORD
Nonstop2h 10mUnited Airlines
Sun 10/58:19 pmORD - TUL
Nonstop2h 11mUnited Airlines
Deal found 9/12$219
This Southwest deal was found by Cheapflights users on 9/13. 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 10/306:15 amTUL - ORD
1 stop7h 45mSouthwest
Tue 11/42:15 pmORD - TUL
1 stop7h 20mSouthwest
Deal found 9/13$223
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Sun 10/196:16 pmTUL - ORD
Nonstop2h 08mAmerican Airlines
Sun 10/2610:20 pmORD - TUL
Nonstop2h 02mAmerican Airlines
Deal found 9/13$238
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/16:00 amTUL - ORD
1 stop7h 46mAmerican Airlines
Tue 11/411:46 amORD - TUL
1 stop10h 43mAmerican Airlines
Deal found 9/14$243
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sun 10/194:00 pmTUL - MDW
Nonstop1h 40mSouthwest
Sun 10/266:35 pmMDW - TUL
Nonstop1h 50mSouthwest
Deal found 9/13$248
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/23:02 pmTUL - ORD
Nonstop2h 09mAmerican Airlines
Sun 10/55:00 amORD - TUL
1 stop8h 13mAmerican Airlines
Deal found 9/12$248

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 September 15, 2025.
Use the filters below to find and compare flights from Tulsa to Chicago that are best for you.

Fly from

Tulsa

Fly to

Chicago

Route

Depart

Return

Price

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 10/29

12:05 pm-1:50 pm

Nonstop1h 45m

Chicago Midway

Fri 10/31

8:25 am-10:20 am

Nonstop1h 55m

$133

TulsaChicago

TUL - ORD

TULORD

Tulsa

Tue 10/7

6:16 pm-8:24 pm

Nonstop2h 08m

Chicago O'Hare Intl

Thu 10/9

10:20 pm-12:22 am

Nonstop2h 02m

$133

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 10/30

9:35 am-11:25 am

Nonstop1h 50m

Chicago Midway

Tue 11/4

3:20 pm-9:35 pm

2 stops6h 15m

$177

TulsaChicago

TUL - ORD

TULORD

Tulsa

Wed 10/29

5:35 am-10:45 am

1 stop5h 10m

Chicago O'Hare Intl

Fri 10/31

1:30 pm-8:05 pm

1 stop6h 35m

$182

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 12/11

12:57 pm-6:47 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 12/15

4:21 pm-11:59 pm

1 stop7h 38m

$197

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 11/13

3:05 pm-12:20 am

1 stop9h 15m

Chicago Midway

Sat 11/15

10:10 am-7:40 pm

2 stops9h 30m

$220

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 10/30

6:15 am-2:00 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 11/4

2:15 pm-9:35 pm

1 stop7h 20m

$223

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 12/11

6:46 pm-11:32 pm

1 stop4h 46m

Chicago Midway

Mon 12/15

5:32 pm-11:59 pm

1 stop6h 27m

$248

TulsaChicago

TUL - ORD

TULORD

Tulsa

Mon 10/27

6:47 pm-11:58 pm

1 stop5h 11m

Chicago O'Hare Intl

Thu 10/30

5:20 am-12:02 pm

1 stop6h 42m

$248

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sun 10/19

4:00 pm-5:40 pm

Nonstop1h 40m

Chicago Midway

Sun 10/26

6:35 pm-8:25 pm

Nonstop1h 50m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 37 results
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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?

Use this chart to determine the optimal time to book a round-trip flight from Tulsa to Chicago. Price data was last updated on September 12, 2025.

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 55 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, August is the cheapest month in which you can book a flight from Tulsa to Chicago (average of $245). Flying from Tulsa to Chicago in March is currently the most expensive (average of $321). 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 September 15, 2025.

One of the essential ways to save on airfare from Tulsa to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 34% 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 September 14, 2025.

Travelers seeking maximum savings on their Tulsa to Chicago flight should consider departing on Friday evenings 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 September 15, 2025.

The most flights from TUL to CHI are scheduled on a Monday (37 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (26 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 September 15, 2025.
See what other customers who have flown with Southwest, United Airlines, and American 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
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $167. Other airlines that can offer you cheap pricing are American Airlines, from $189, and United Airlines, from $282. Southwest is currently priced 54% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Tulsa to Chicago one-way?

    One-way options have recently been found by users for as low as $69 on Southwest. Other airlines that offer cheap prices include Delta from $99 and United Airlines from $126 one-way.

  • 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: Qatar Airways (82%), SkyWest Airlines (79%), Japan Airlines( 77%).

  • What are the cheapest flights from Tulsa to Chicago?

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Tulsa - Chicago O'Hare Intl) can be booked for $197 on average, our data indicates $852 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, August is the cheapest month in which you can book a flight from Tulsa to Chicago (average of $245). Flying from Tulsa to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Tulsa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$167Average$355FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$189Average$344FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$282Average$416FlexibilityNo cancel feeOn-time69%

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