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Southwest Airlines Flights to Chicago (CHI)
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Southwest Airlines Flights to Chicago

  • One way
  • Round-trip
      • Cheapest nonstop
        DTW19:55
        1h 10m
        Nonstop
        MDW20:05
        Southwest Airlines|Detroit - Chicago|Thu, Apr 10
        Rp 924,436Rp 2,574,745
        64% OFF
        64% OFF
        Rp 2,574,745Rp 924,436

        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, Apr 10, arriving at Midway International Airport. One-way Prices start from Rp 924,436 including taxes and charges.

      • LGA21:45
        2h 15m
        Nonstop
        MDW23:00
        Southwest Airlines|New York - Chicago|Tue, May 6
        Rp 1,391,186Rp 2,574,745
        46% OFF
        46% OFF
        Rp 2,574,745Rp 1,391,186

        Choose Southwest Airlines flights from New York to Chicago. The one-way direct flight with Southwest Airlines departs from New York LaGuardia Airport on Tue, May 6, arriving at Midway International Airport. One-way Prices start from Rp 1,391,186 including taxes and charges.

      • DEN19:30
        2h 35m
        Nonstop
        ORD23:05
        Southwest Airlines|Denver - Chicago|Fri, Apr 25
        Rp 1,468,222Rp 2,574,745
        43% OFF
        43% OFF
        Rp 2,574,745Rp 1,468,222

        Choose Southwest Airlines flights from Denver to Chicago. The one-way direct flight with Southwest Airlines departs from Denver International Airport on Fri, Apr 25, arriving at O'Hare International Airport. One-way Prices start from Rp 1,468,222 including taxes and charges.

      • LAX23:10
        4h 5m
        Nonstop
        MDW05:15
        Southwest Airlines|Los Angeles - Chicago|Tue, May 13
        Rp 1,472,754
        Rp 1,472,754

        Choose Southwest Airlines flights from Los Angeles to Chicago. The one-way direct flight with Southwest Airlines departs from Los Angeles International Airport on Tue, May 13, arriving at Midway International Airport. One-way Prices start from Rp 1,472,754 including taxes and charges.

      • ATL06:25
        1h 55m
        Nonstop
        MDW07:20
        Southwest Airlines|Atlanta - Chicago|Wed, Mar 26
        Rp 1,533,930
        Rp 1,533,930

        Choose Southwest Airlines flights from Atlanta to Chicago. The one-way direct flight with Southwest Airlines departs from Hartsfield-Jackson Atlanta International Airport on Wed, Mar 26, arriving at Midway International Airport. One-way Prices start from Rp 1,533,930 including taxes and charges.

      • DCA06:55
        2h
        Nonstop
        MDW07:55
        Southwest Airlines|Washington D.C. - Chicago|Mon, May 19
        Rp 1,783,165
        Rp 1,783,165

        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 Mon, May 19, arriving at Midway International Airport. One-way Prices start from Rp 1,783,165 including taxes and charges.

      • MSY05:15
        2h 20m
        Nonstop
        MDW07:35
        Southwest Airlines|New Orleans - Chicago|Thu, Apr 10
        Rp 1,810,355
        Rp 1,810,355

        Choose Southwest Airlines flights from New Orleans to Chicago. The one-way direct flight with Southwest Airlines departs from Louis Armstrong New Orleans International Airport on Thu, Apr 10, arriving at Midway International Airport. One-way Prices start from Rp 1,810,355 including taxes and charges.

      • BOS05:45
        2h 50m
        Nonstop
        MDW07:35
        Southwest Airlines|Boston - Chicago|Wed, Mar 19
        Rp 1,817,152
        Rp 1,817,152

        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 Wed, Mar 19, arriving at Midway International Airport. One-way Prices start from Rp 1,817,152 including taxes and charges.

      • MCO07:15
        3h
        Nonstop
        MDW09:15
        Southwest Airlines|Orlando - Chicago|Tue, Mar 25
        Rp 1,903,251
        Rp 1,903,251

        Choose Southwest Airlines flights from Orlando to Chicago. The one-way direct flight with Southwest Airlines departs from Orlando International Airport on Tue, Mar 25, arriving at Midway International Airport. One-way Prices start from Rp 1,903,251 including taxes and charges.

      • MIA07:00
        3h 10m
        Nonstop
        MDW09:10
        Southwest Airlines|Miami - Chicago|Thu, May 1
        Rp 1,982,554
        Rp 1,982,554

        Choose Southwest Airlines flights from Miami to Chicago. The one-way direct flight with Southwest Airlines departs from Miami International Airport on Thu, May 1, arriving at Midway International Airport. One-way Prices start from Rp 1,982,554 including taxes and charges.

      • SHA1:00 PM
        3h 5m
        Nonstop
        CHI2:00 PM
        Southwest Airlines|Shanghai - Chicago|Tue, Mar 25
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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.

  • 12.76 km from downtown ChicagoCheapestClosest
    Midway International Airport
    Tickets From
    Rp 924,436
  • 24.74 km from downtown Chicago
    O'Hare International Airport
    Tickets From
    Rp 1,468,222

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

  • Does Southwest Airlines have 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. 32 hours 43 minutes to fly from Jakarta to Chicago.
    • Approx. 2 hours 44 minutes to fly from New York to Chicago.
    • Approx. 3 hours 5 minutes to fly from Orlando to Chicago.
    • Approx. 41 hours 5 minutes to fly from Bali to Chicago.

  • How to get cheap flights to Chicago?

    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.

  • How many airports in Chicago?

  • 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

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