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Cheap flights from Tulsa to Chicago from $89

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 8/22. 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

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 - 6:45 am
TUL
-
MDW
1h 40mnonstop
Southwest Logo
10:30 am - 12:15 pm
MDW
-
TUL
1h 45mnonstop
$177Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
5:05 am - 6:45 am
TUL
-
MDW
1h 40mnonstop
Southwest Logo
5:20 pm - 10:30 pm
MDW
-
TUL
5h 10m
1 stop
$187Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
1:30 pm - 3:10 pm
TUL
-
MDW
1h 40mnonstop
Southwest Logo
9:30 pm - 11:20 pm
MDW
-
TUL
1h 50mnonstop
$190Southwest
Sat, Oct 3 - Mon, Oct 5
Southwest Logo
5:05 am - 6:45 am
TUL
-
MDW
1h 40mnonstop
Southwest Logo
3:50 pm - 10:30 pm
MDW
-
TUL
6h 40m
2 stops
$192Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
4:05 pm - 5:50 pm
TUL
-
MDW
1h 45mnonstop
Southwest Logo
7:05 am - 11:20 am
MDW
-
TUL
4h 15m
1 stop
$196Southwest
Thu, Oct 29 - Tue, Nov 3
Delta Logo
10:01 am - 4:15 pm
TUL
-
MDW
6h 14m
1 stop
Delta Logo
6:05 am - 11:56 am
MDW
-
TUL
5h 51m
1 stop
$197Delta
Wed, Aug 5 - Wed, Aug 12
Southwest Logo
5:05 am - 6:50 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
5:20 pm - 10:30 pm
MDW
-
TUL
5h 10m
1 stop
$200Southwest
Sat, Aug 1 - Tue, Aug 4
Southwest Logo
3:25 pm - 11:20 pm
TUL
-
MDW
7h 55m
1 stop
Southwest Logo
7:00 am - 1:00 pm
MDW
-
TUL
6h 00m
1 stop
$202Southwest
Sat, Jul 25 - Tue, Jul 28
Southwest Logo
5:15 am - 7:00 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
10:10 am - 12:00 pm
MDW
-
TUL
1h 50mnonstop
$203Southwest
Mon, Oct 26 - Wed, Oct 28
Southwest Logo
7:35 am - 2:45 pm
TUL
-
MDW
7h 10m
2 stops
Southwest Logo
9:30 pm - 11:20 pm
MDW
-
TUL
1h 50mnonstop
$205Southwest
Sat, Oct 3 - Mon, Oct 5

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Southwest flights from Tulsa to Chicago Midway Airport

Our best Southwest deals on Tulsa to Chicago Midway Airport flight tickets
Southwest
Aug 8
TUL5:05 amTulsa
1h 40m
MDW6:45 amChicago Midway
Aug 11
MDW10:30 amChicago Midway
1h 45m
TUL12:15 pmTulsa
$177
Southwest
Aug 8
TUL5:05 amTulsa
1h 40m
MDW6:45 amChicago Midway
Aug 11
MDW5:20 pmChicago Midway
5h 10m
1 stop
TUL10:30 pmTulsa
$187
Southwest
Oct 3
TUL1:30 pmTulsa
1h 40m
MDW3:10 pmChicago Midway
Oct 5
MDW9:30 pmChicago Midway
1h 50m
TUL11:20 pmTulsa
$190

Delta flights from Tulsa to Chicago Midway Airport

Our best Delta deals on Tulsa to Chicago Midway Airport flight tickets
Delta
Aug 5
TUL10:01 amTulsa
6h 14m
1 stop
MDW4:15 pmChicago Midway
Aug 12
MDW6:05 amChicago Midway
5h 51m
1 stop
TUL11:56 amTulsa
$197
Delta
Aug 17
TUL6:00 amTulsa
5h 51m
1 stop
MDW11:51 amChicago Midway
Aug 18
MDW5:10 pmChicago Midway
5h 08m
1 stop
TUL10:18 pmTulsa
$210
Delta
Aug 24
TUL4:44 pmTulsa
5h 52m
1 stop
MDW10:36 pmChicago Midway
Aug 29
MDW6:11 amChicago Midway
5h 45m
1 stop
TUL11:56 amTulsa
$223

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 July 7, 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

Sat 8/8

5:05 am-6:45 am

Nonstop1h 40m

Chicago Midway

Tue 8/11

10:30 am-12:15 pm

Nonstop1h 45m

$177

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/8

5:05 am-6:45 am

Nonstop1h 40m

Chicago Midway

Tue 8/11

5:20 pm-10:30 pm

1 stop5h 10m

$187

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 10/3

1:30 pm-3:10 pm

Nonstop1h 40m

Chicago Midway

Mon 10/5

9:30 pm-11:20 pm

Nonstop1h 50m

$190

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/8

5:05 am-6:45 am

Nonstop1h 40m

Chicago Midway

Tue 8/11

3:50 pm-10:30 pm

2 stops6h 40m

$192

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 10/29

4:05 pm-5:50 pm

Nonstop1h 45m

Chicago Midway

Tue 11/3

7:05 am-11:20 am

1 stop4h 15m

$196

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 8/5

10:01 am-4:15 pm

1 stop6h 14m

Chicago Midway

Wed 8/12

6:05 am-11:56 am

1 stop5h 51m

$197

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/1

5:05 am-6:50 am

Nonstop1h 45m

Chicago Midway

Tue 8/4

5:20 pm-10:30 pm

1 stop5h 10m

$200

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 7/25

3:25 pm-11:20 pm

1 stop7h 55m

Chicago Midway

Tue 7/28

7:00 am-1:00 pm

1 stop6h 00m

$202

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 10/26

5:15 am-7:00 am

Nonstop1h 45m

Chicago Midway

Wed 10/28

10:10 am-12:00 pm

Nonstop1h 50m

$203

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 10/3

7:35 am-2:45 pm

2 stops7h 10m

Chicago Midway

Mon 10/5

9:30 pm-11:20 pm

Nonstop1h 50m

$205

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 month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Tulsa, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Tulsa during the month August is also very affordable. Most momondo users find prices during this month for around $253.

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 $380. 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, Friday 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 $449.

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

Flying to Chicago Midway Airport from Tulsa in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $405 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $425. 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 Airport flights?

There is only 1 cabin class available to choose from on Tulsa to Chicago Midway Airport 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

$250

Fastest flight time

1h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Tulsa in the past 72 hours is $250. The best round-trip flight deal from Tulsa to Chicago Midway Airport found on momondo in the last 72 hours is $380.
The fastest flight from Tulsa to Chicago Midway Airport takes 1h 40m
Direct flights go from Tulsa to Chicago Midway Airport every day.
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 $237Free CancellationRating
7.9
4,251 reviews
Search Southwest flights

  • Southwest Flights From Tulsa to Chicago Midway Airport

    Southwest operates around 10 flights from Tulsa to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $378, but momondo users have found Southwest deals from Tulsa to Chicago Midway Airport from as low as $237 round-trip. Southwest has been scored 7.9/10 in 4,251 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
Benton Harbor
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Schererville
Munster
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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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