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Cheap Flights from Tulsa International to Chicago Midway

Compare Tulsa International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Tulsa International Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Tulsa International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $378. Find the lowest prices on one-way and return tickets right here.
Chicago.$378 per passenger.Departing Sat, 18 Apr, returning Tue, 21 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tulsa International on Sat, 18 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 21 Apr, arriving in Tulsa International.Price includes taxes and charges.From $378, select.
Chicago.$415 per passenger.Departing Sat, 28 Mar, returning Mon, 30 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tulsa International on Sat, 28 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 30 Mar, arriving in Tulsa International.Price includes taxes and charges.From $415, select.
Chicago.$415 per passenger.Departing Tue, 31 Mar, returning Thu, 2 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tulsa International on Tue, 31 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 2 Apr, arriving in Tulsa International.Price includes taxes and charges.From $415, select.
Chicago.$415 per passenger.Departing Thu, 4 Jun, returning Mon, 8 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tulsa International on Thu, 4 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 8 Jun, arriving in Tulsa International.Price includes taxes and charges.From $415, select.
Chicago.$513 per passenger.Departing Tue, 5 May, returning Sun, 10 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tulsa International on Tue, 5 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 10 May, arriving in Tulsa International.Price includes taxes and charges.From $513, select.
Chicago.$569 per passenger.Departing Tue, 30 Jun, returning Fri, 7 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tulsa International on Tue, 30 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 7 Aug, arriving in Tulsa International.Price includes taxes and charges.From $569, select.
Chicago.$571 per passenger.Departing Fri, 31 Jul, returning Wed, 5 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tulsa International on Fri, 31 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 5 Aug, arriving in Tulsa International.Price includes taxes and charges.From $571, select.
Chicago.$750 per passenger.Departing Fri, 4 Sep, returning Mon, 7 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Tulsa International on Fri, 4 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 7 Sep, arriving in Tulsa International.Price includes taxes and charges.From $750, select.

Find the cheapest month to fly from Tulsa International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Tulsa International to Chicago Midway flights are currently cheapest in April.
Mar
from $415
Apr
from $378
May
from $513
Jun
from $415
Jul
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Aug
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Sep
from $750
Oct
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Nov
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Dec
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Jan
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Feb
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Direct flights from Tulsa International to Chicago Midway

Tulsa International to Chicago Midway: Alternative routes

Compare routes from Tulsa International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
ClosestCheapest
from $378
Search flights

Chicago O'Hare International

25km from central Chicago
from $379
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Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Tulsa to Chicago: Flight information

The things to know before you go.
Cheapest flight found$378
Cheapest month to flyApril
Average flight time1 hr, 43 mins
Most popular airlineSouthwest Airlines
Average flights per week15

Finding cheap flights from Tulsa International to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Tulsa International to Chicago Midway is $378. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 43 minutes is the average flight time from Tulsa International to Chicago Midway.
Southwest Airlines flies direct from Tulsa International to Chicago Midway.
As of March 2026, there are 15 flights per week flying from Tulsa International to Chicago Midway.
The cheapest month to fly from Tulsa International to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Tulsa International Airport to Chicago Midway Airport on Saturday, 18 April 2026.
Yes – the average flight time is 1 hour and 43 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Tulsa International Airport (TUL) to Chicago Midway International Airport (MDW): what you need to know

  • The average duration of a direct flight from Tulsa International Airport to Chicago Midway International Airport is 1 hour 45 minutes.

  • Chicago's timezone is UTC-5, which is the same as Tulsa.

  • Choose from five weekly Tulsa International Airport to Chicago Midway International Airport flights. The 05:05 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the latest service of the day at 17:25.

  • Give yourself plenty of time to make your TUL to MDW flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • During popular months like July, it's best to get to the airport well in advance. Arrive two hours before domestic departures and four hours ahead for international flights whenever you're flying during peak periods in general.

  • Southwest Airlines is your gateway to discovering Chicago (and maybe even some other great corners of United States!). Browse the direct flights from Tulsa International Airport to Chicago Midway International Airport offered by this popular carrier.

  • Most travellers choose to fly with Southwest Airlines on this route.

  • Southwest Airlines ranks as the top on-time carrier for TUL to MDW flights, with 82.69% of services arriving on schedule.

How to find the cheapest flights from Tulsa International Airport (TUL) to Chicago Midway International Airport (MDW)

  • Currently, $207 is the cheapest price we've seen for a one-way Tulsa International Airport to Chicago Midway International Airport flight. The best price for a return ticket is $378. Keep in mind that fares may change due to availability at the time of booking.

  • To get cheap tickets from TUL to MDW, book your trip seven months ahead of your departure date.

  • The cheapest month for flights from Tulsa International Airport to Chicago Midway International Airport is June. Use the 'Whole month' tool to see the lowest prices if you have a flexible schedule.

  • Finding cheap flights from TUL to MDW is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch as soon as a new discounted fare appears.

  • Find the ideal flight for you by using the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Tulsa International Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter results by departure and arrival times, airline, and number of stops.

Handy information about Tulsa International Airport (TUL)

  • You'll find TUL at 7777 E. Apache.

  • Tulsa International Airport earns top marks for its on-time performance. 82.8% of flights that depart TUL reach their destination on time.

  • Central Tulsa to Tulsa International Airport is around 14 kilometres. Depending on traffic, it'll take you about 15 minutes to get there if you're catching a cab, ride-sharing or driving.

  • Expect a trip time of about 1 hour 35 minutes on public transport.

  • Need a handy hotel near TUL? If you're catching an early flight from Tulsa International Airport to Chicago Midway International Airport, these stays will have you sleeping moments from your departure gate:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The address for MDW is 5700 South Cicero.

  • Chicago Midway International Airport to the centre of Chicago has a drive time of around 20 minutes. It's approximately 19 kilometres away.

  • It'll take around 45 minutes if you're travelling by public transport.

When to fly to Chicago Midway International Airport (MDW)

  • July is the most popular month for flights from Tulsa International Airport to Chicago Midway International Airport. To skip the crowds, head to Chicago in May.

  • Before locking in your flight from Tulsa International Airport to Chicago Midway International Airport, consider the type of weather you like. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • If you like travelling in cooler conditions, search for a cheap ticket from TUL to MDW in January. Average temperatures are between -12ºC and 3ºC then.

Explore more of United States

  • You've visited Chicago, now it's time to discover more of United States. Travel about 451 kilometres south-east to Columbus to check off its top sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a full itinerary ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience the best of this destination with a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Tulsa to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.