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Southwest Airlines Flights to Chicago (CHI)
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WN

Southwest Airlines Flights to Chicago

  • One way
  • Round-trip
      • Cheapest nonstop
        BNA14:55
        1h 50m
        Nonstop
        ORD16:45
        Southwest Airlines|Nashville - Chicago|Wed, Mar 5
        AED 291AED 556
        48% OFF
        48% OFF
        AED 556AED 291

        Choose Southwest Airlines flights from Nashville to Chicago. The one-way direct flight with Southwest Airlines departs from Nashville International Airport on Wed, Mar 5, arriving at O'Hare International Airport. One-way Prices start from AED 291 including taxes and charges.

      • DTW13:00
        1h 10m
        Nonstop
        MDW13:10
        Southwest Airlines|Detroit - Chicago|Thu, Mar 6
        AED 312AED 556
        44% OFF
        44% OFF
        AED 556AED 312

        Choose Southwest Airlines flights from Detroit to Chicago. The one-way direct flight with Southwest Airlines departs from Detroit Metropolitan Wayne County Airport on Thu, Mar 6, arriving at Midway International Airport. One-way Prices start from AED 312 including taxes and charges.

      • STL08:45
        1h 10m
        Nonstop
        MDW09:55
        Southwest Airlines|St. Louis - Chicago|Mon, Apr 7
        AED 335AED 556
        40% OFF
        40% OFF
        AED 556AED 335

        Choose Southwest Airlines flights from St. Louis to Chicago. The one-way direct flight with Southwest Airlines departs from St. Louis Lambert International Airport on Mon, Apr 7, arriving at Midway International Airport. One-way Prices start from AED 335 including taxes and charges.

      • LGA06:30
        2h 30m
        Nonstop
        MDW08:00
        Southwest Airlines|New York - Chicago|Thu, Feb 27
        AED 347
        AED 347

        Choose Southwest Airlines flights from New York to Chicago. The one-way direct flight with Southwest Airlines departs from New York LaGuardia Airport on Thu, Feb 27, arriving at Midway International Airport. One-way Prices start from AED 347 including taxes and charges.

      • DEN19:30
        2h 35m
        Nonstop
        ORD23:05
        Southwest Airlines|Denver - Chicago|Wed, Apr 16
        AED 371
        AED 371

        Choose Southwest Airlines flights from Denver to Chicago. The one-way direct flight with Southwest Airlines departs from Denver International Airport on Wed, Apr 16, arriving at O'Hare International Airport. One-way Prices start from AED 371 including taxes and charges.

      • DAL19:10
        2h 20m
        Nonstop
        ORD21:30
        Southwest Airlines|Dallas - Chicago|Wed, Feb 26
        AED 404
        AED 404

        Choose Southwest Airlines flights from Dallas to Chicago. The one-way direct flight with Southwest Airlines departs from Dallas Love Field Airport on Wed, Feb 26, arriving at O'Hare International Airport. One-way Prices start from AED 404 including taxes and charges.

      • BOS06:30
        2h 45m
        Nonstop
        MDW08:15
        Southwest Airlines|Boston - Chicago|Fri, Mar 28
        AED 405
        AED 405

        Choose Southwest Airlines flights from Boston to Chicago. The one-way direct flight with Southwest Airlines departs from General Edward Lawrence Logan International Airport on Fri, Mar 28, arriving at Midway International Airport. One-way Prices start from AED 405 including taxes and charges.

      • ATL11:00
        2h
        Nonstop
        MDW12:00
        Southwest Airlines|Atlanta - Chicago|Thu, Feb 27
        AED 406
        AED 406

        Choose Southwest Airlines flights from Atlanta to Chicago. The one-way direct flight with Southwest Airlines departs from Hartsfield-Jackson Atlanta International Airport on Thu, Feb 27, arriving at Midway International Airport. One-way Prices start from AED 406 including taxes and charges.

      • MSP10:25
        1h 35m
        Nonstop
        MDW12:00
        Southwest Airlines|Minneapolis - Chicago|Sat, Mar 1
        AED 407
        AED 407

        Choose Southwest Airlines flights from Minneapolis to Chicago. The one-way direct flight with Southwest Airlines departs from St Paul International Airport on Sat, Mar 1, arriving at Midway International Airport. One-way Prices start from AED 407 including taxes and charges.

      • DCA06:00
        2h
        Nonstop
        MDW07:00
        Southwest Airlines|Washington D.C. - Chicago|Sat, May 10
        AED 411
        AED 411

        Choose Southwest Airlines flights from Washington D.C. to Chicago. The one-way direct flight with Southwest Airlines departs from Ronald Reagan Washington National Airport on Sat, May 10, arriving at Midway International Airport. One-way Prices start from AED 411 including taxes and charges.

      • SHA01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Southwest Airlines|Shanghai - Chicago|Fri, Feb 28
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly to Chicago with Southwest Airlines?

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

There are 2 airports in Chicago. Find the most suitable Southwest Airlines flights to Chicago.

  • 24.74 km from downtown ChicagoCheapest
    O'Hare International Airport
    Tickets From
    AED 291
  • 12.76 km from downtown ChicagoClosest
    Midway International Airport
    Tickets From
    AED 293

About Southwest Airlines

Airline Name
Southwest Airlines
Airline Code
WN
Airline Type
Low-cost Carrier (LCC)
Popular Countries Southwest Airlines Flies to:
United States
Popular Southwest Airlines Arrival Cities
Popular Southwest Airlines Departure Cities
Based on Trip.com Historical Data

Southwest Airlines Flights to Chicago - FAQ

  • Is there a baggage allowance?

    0-1 pieces of luggage are usually permitted for each economy class passenger traveling with Southwest Airlines (WN). This information can vary depending on your flight, so be sure to check your itinerary.

  • How long is the flight to Chicago?

    • Approx. 1 hour 24 minutes to fly from Cedar Rapids to Chicago.
    • Approx. 1 hour 31 minutes to fly from Rochester to Chicago.
    • Approx. 24 hours 18 minutes to fly from Medellin to Chicago.
    • Approx. 7 hours 55 minutes to fly from Calgary to Chicago.

  • How can I book cheaper tickets?

    You can book cheaper flights in the following ways:
    • Search for tickets to a city or airport near Chicago.
    • Look up different airlines that have flights to Chicago.
    • Browse different departure dates from the same month.
    • Filter for different departure times from the same day.
    • Check for discount information on various social media sites.
    • Explore deals and discounts on airline websites.

  • What is the most popular month to visit Chicago?

    Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is May. The average price of flight tickets to Chicago in May is AED 3,760.

  • When are flight tickets to Chicago the cheapest?

    Flight tickets to Chicago are the cheapest in May compared to other months, the average price is AED 3,760.

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

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