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Cheap flights from Tulsa to Chicago from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Tulsa to Chicago departing on 6/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Tulsa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
9:40 am - 11:35 am
MDW
-
TUL
1h 55mnonstop
$217Southwest
Tue, May 19 - Wed, May 27
Southwest Logo
10:45 am - 5:00 pm
TUL
-
MDW
6h 15m
1 stop
Southwest Logo
9:05 pm - 11:00 pm
MDW
-
TUL
1h 55mnonstop
$227Southwest
Tue, May 19 - Wed, May 27
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
6:15 pm - 8:10 pm
MDW
-
TUL
1h 55mnonstop
$230Southwest
Wed, Apr 29 - Sat, May 2
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
3:00 pm - 9:50 pm
MDW
-
TUL
6h 50m
2 stops
$232Southwest
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
$237Delta
Tue, May 19 - Wed, May 27
Southwest Logo
10:45 am - 5:00 pm
TUL
-
MDW
6h 15m
1 stop
Southwest Logo
6:15 pm - 8:10 pm
MDW
-
TUL
1h 55mnonstop
$240Southwest
Wed, Apr 29 - Sat, May 2
Southwest Logo
10:45 am - 3:25 pm
TUL
-
MDW
4h 40m
1 stop
Southwest Logo
3:00 pm - 9:50 pm
MDW
-
TUL
6h 50m
2 stops
$242Southwest
Tue, May 19 - Wed, May 27
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
9:05 pm - 11:00 pm
MDW
-
TUL
1h 55mnonstop
$243Southwest
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
10:45 am - 5:05 pm
TUL
-
MDW
6h 20m
2 stops
Southwest Logo
6:15 pm - 8:10 pm
MDW
-
TUL
1h 55mnonstop
$245Southwest
Wed, Apr 29 - Sat, May 2
Southwest Logo
10:45 am - 4:55 pm
TUL
-
MDW
6h 10m
2 stops
Southwest Logo
4:40 pm - 10:45 pm
MDW
-
TUL
6h 05m
2 stops
$247Southwest
Tue, May 19 - Wed, May 27

Delta flights from Tulsa to Chicago Midway Airport

Our best Delta deals on Tulsa to Chicago Midway Airport flight tickets
Delta
May 19
TUL4:28 pmTulsa
4h 41m
1 stop
MDW9:09 pmChicago Midway
May 27
MDW5:12 pmChicago Midway
6h 08m
1 stop
TUL11:20 pmTulsa
$237
Delta
Apr 22
TUL4:49 pmTulsa
5h 39m
1 stop
MDW10:28 pmChicago Midway
Apr 23
MDW6:00 amChicago Midway
7h 09m
1 stop
TUL1:09 pmTulsa
$250
Delta
May 23
TUL4:28 pmTulsa
4h 41m
1 stop
MDW9:09 pmChicago Midway
May 27
MDW5:12 pmChicago Midway
6h 08m
1 stop
TUL11:20 pmTulsa
$278

Southwest flights from Tulsa to Chicago Midway Airport

Our best Southwest deals on Tulsa to Chicago Midway Airport flight tickets
Southwest
May 19
TUL5:05 amTulsa
1h 45m
MDW6:50 amChicago Midway
May 27
MDW9:40 amChicago Midway
1h 55m
TUL11:35 amTulsa
$217
Southwest
May 19
TUL10:45 amTulsa
6h 15m
1 stop
MDW5:00 pmChicago Midway
May 27
MDW9:05 pmChicago Midway
1h 55m
TUL11:00 pmTulsa
$227
Southwest
Apr 29
TUL5:05 amTulsa
1h 45m
MDW6:50 amChicago Midway
May 2
MDW6:15 pmChicago Midway
1h 55m
TUL8:10 pmTulsa
$230

momondo Fare Finder

 
Customize your flight search to find flights from Tulsa to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated April 3, 2026.
Use the filters below to find and compare flights from Tulsa to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 5/19

5:05 am-6:50 am

Nonstop1h 45m

Chicago Midway

Wed 5/27

9:40 am-11:35 am

Nonstop1h 55m

$217

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 5/19

10:45 am-5:00 pm

1 stop6h 15m

Chicago Midway

Wed 5/27

9:05 pm-11:00 pm

Nonstop1h 55m

$227

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 4/29

5:05 am-6:50 am

Nonstop1h 45m

Chicago Midway

Sat 5/2

6:15 pm-8:10 pm

Nonstop1h 55m

$230

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 5/19

5:05 am-6:50 am

Nonstop1h 45m

Chicago Midway

Wed 5/27

3:00 pm-9:50 pm

2 stops6h 50m

$232

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 5/19

4:28 pm-9:09 pm

1 stop4h 41m

Chicago Midway

Wed 5/27

5:12 pm-11:20 pm

1 stop6h 08m

$237

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 4/29

10:45 am-5:00 pm

1 stop6h 15m

Chicago Midway

Sat 5/2

6:15 pm-8:10 pm

Nonstop1h 55m

$240

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 5/19

10:45 am-3:25 pm

1 stop4h 40m

Chicago Midway

Wed 5/27

3:00 pm-9:50 pm

2 stops6h 50m

$242

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 4/22

5:05 am-6:50 am

Nonstop1h 45m

Chicago Midway

Wed 4/29

9:05 pm-11:00 pm

Nonstop1h 55m

$243

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 4/29

10:45 am-5:05 pm

2 stops6h 20m

Chicago Midway

Sat 5/2

6:15 pm-8:10 pm

Nonstop1h 55m

$245

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 5/19

10:45 am-4:55 pm

2 stops6h 10m

Chicago Midway

Wed 5/27

4:40 pm-10:45 pm

2 stops6h 05m

$247

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Tulsa to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Tulsa and Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Tulsa. The lowest ticket price found for a Wednesday departure recently was $353. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Tulsa because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $467.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Tulsa at noon is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $417. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Tulsa to Chicago Midway flight route?

Fly from Tulsa to Chicago Midway for the best Tulsa - Chicago Midway flight prices

What cabin class options are available on Tulsa to Chicago Midway flights?

There is only 1 cabin class available to choose from on Tulsa to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Tulsa to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Tulsa to Chicago Midway Airport.

When to book flights from Tulsa to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Tulsa to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Tulsa to Chicago Midway Airport (TUL to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Tulsa to Chicago Midway Airport

Best Price Found

$193

Fastest flight time

1h 40m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Tulsa in the past 72 hours is $193. The best round-trip flight deal from Tulsa to Chicago Midway Airport found on momondo in the last 72 hours is $336.
The fastest flight from Tulsa to Chicago Midway Airport takes 1h 40m
Direct flights go from Tulsa to Chicago Midway Airport on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Tulsa to Chicago Midway Airport

  • How far is Tulsa to Chicago Midway by plane?

    The straight-line distance from Tulsa to Chicago Midway is 588.8 mi. By plane, this route typically takes 1h 40m.

  • When did momondo last update prices for flights from Tulsa Airport to Chicago Midway Airport?

    Prices for flights from Tulsa Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Tulsa Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Tulsa Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Tulsa Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Tulsa to Chicago Midway Airport?

  • What is the most popular airline from Tulsa to Chicago Midway Airport?

Best airlines flying from Tulsa to Chicago Midway Airport

Compare and see reviews for airlines that fly from Tulsa to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $197Free CancellationRating
8.0
4,344 reviews
Search Southwest flights

  • Southwest Flights From Tulsa to Chicago Midway Airport

    Southwest operates around 6 flights from Tulsa to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $356, but momondo users have found Southwest deals from Tulsa to Chicago Midway Airport from as low as $197 round-trip. Southwest has been scored 8.0/10 in 4,344 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Tulsa to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Tulsa to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Tulsa to Chicago with flexible booking policies on momondo?

All flight searches from Tulsa to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Tulsa to Chicago?

Once all potential Tulsa to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Tulsa to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Tulsa are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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