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$99+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
TUL — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Tulsa to Chicago are usually found in August or September, booked 88 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 July 3, 2025.

Round-trip from

$197
(Southwest)

One-way from

$99
(Southwest)

Popular in

January

Cheapest in

August

Average price

$341

Good round-trip deal

$286 or less

Good one-way deal

$208 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. 19% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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 9/49:50 amTUL - MDW
Nonstop1h 45mSouthwest
Tue 9/94:50 pmMDW - TUL
Nonstop1h 50mSouthwest
Deal found 7/1$197
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Wed 8/202:41 pmTUL - ORD
Nonstop2h 04mUnited Airlines
Thu 8/2112:45 pmORD - TUL
Nonstop2h 11mUnited Airlines
Deal found 7/2$197
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/77:00 amTUL - ORD
Nonstop2h 04mAmerican Airlines
Mon 8/1110:20 pmORD - TUL
Nonstop2h 01mAmerican Airlines
Deal found 7/2$199
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 8/206:00 amTUL - MDW
1 stop5h 48mDelta
Thu 8/2110:31 amMDW - TUL
1 stop7h 23mDelta
Deal found 7/2$217
This Delta deal was found by Cheapflights users on 7/2. 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.
Thu 8/76:47 pmTUL - ORD
1 stop5h 22mDelta
Mon 8/115:45 amORD - TUL
1 stop6h 12mDelta
Deal found 7/2$217
This Southwest deal was found by Cheapflights users on 7/2. 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 9/98:25 amTUL - ORD
2 stops8h 20mSouthwest
Fri 9/123:10 pmORD - TUL
1 stop8h 05mSouthwest
Deal found 7/2$271
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/15:44 pmTUL - ORD
2 stops11h 41mMultiple Airlines
Fri 8/87:08 amORD - TUL
1 stop9h 46mMultiple Airlines
Deal found 7/2$280

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 July 3, 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

Thu 9/4

9:50 am-11:35 am

Nonstop1h 45m

Chicago Midway

Tue 9/9

4:50 pm-6:40 pm

Nonstop1h 50m

$197

TulsaChicago

TUL - ORD

TULORD

Tulsa

Wed 8/20

2:41 pm-4:45 pm

Nonstop2h 04m

Chicago O'Hare Intl

Thu 8/21

12:45 pm-2:56 pm

Nonstop2h 11m

$197

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 8/7

7:00 am-9:04 am

Nonstop2h 04m

Chicago O'Hare Intl

Mon 8/11

10:20 pm-12:21 am

Nonstop2h 01m

$199

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 8/20

6:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Thu 8/21

10:31 am-5:54 pm

1 stop7h 23m

$217

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 8/7

6:47 pm-12:09 am

1 stop5h 22m

Chicago O'Hare Intl

Mon 8/11

5:45 am-11:57 am

1 stop6h 12m

$217

TulsaChicago

TUL - ORD

TULORD

Tulsa

Tue 9/9

8:25 am-4:45 pm

2 stops8h 20m

Chicago O'Hare Intl

Fri 9/12

3:10 pm-11:15 pm

1 stop8h 05m

$271

TulsaChicago

TUL - ORD

TULORD

Tulsa

Fri 8/1

5:44 pm-5:25 am

2 stops11h 41m

Chicago O'Hare Intl

Fri 8/8

7:08 am-4:54 pm

1 stop9h 46m

$280

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 9/22

9:50 am-11:35 am

Nonstop1h 45m

$99

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 9/11

6:41 pm-8:40 pm

Nonstop1h 59m

$99

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 9/11

8:30 am-2:05 pm

1 stop5h 35m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 14 results
1
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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 June 27, 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 87 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 July 3, 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 36% 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 June 29, 2025.

Travelers seeking maximum savings on their Tulsa to Chicago flight should consider departing on Thursday mornings 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 July 3, 2025.

The most flights from TUL to CHI are scheduled on a Thursday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

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 July 3, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 19 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.

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

    Cheapflights users have booked flights from Tulsa to Chicago round-trip from $197. Other airlines that can offer you cheap pricing are United Airlines, from $197, and American Airlines, from $199. Southwest is currently priced 45% 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 $99 on Southwest. Other airlines that offer cheap prices include United Airlines from $99 and Delta from $109 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: Japan Airlines (90%), Aer Lingus (90%), Envoy Air( 87%).

  • What are the cheapest flights from Tulsa to Chicago?

    Looking at all options, your cheapest flight can be booked for $143. While the most popular route (Tulsa - Chicago O'Hare Intl) can be booked for $197 on average our data indicates $1,596 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 Tulsa?

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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$167Average$358FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$192Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$279Average$407FlexibilityNo cancel feeOn-time69%

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