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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
        BOS07:40
        2h 35m
        Nonstop
        MDW09:15
        Southwest Airlines|Boston - Chicago|Sun, Apr 27
        AED 202AED 357
        43% OFF
        43% OFF
        AED 357AED 202

        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 Sun, Apr 27, arriving at Midway International Airport. One-way Prices start from AED 202 including taxes and charges.

      • STL12:30
        1h 10m
        Nonstop
        MDW13:40
        Southwest Airlines|St. Louis - Chicago|Tue, May 6
        AED 206AED 357
        42% OFF
        42% OFF
        AED 357AED 206

        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 Tue, May 6, arriving at Midway International Airport. One-way Prices start from AED 206 including taxes and charges.

      • DTW06:30
        1h 10m
        Nonstop
        MDW06:40
        Southwest Airlines|Detroit - Chicago|Thu, May 1
        AED 206AED 357
        42% OFF
        42% OFF
        AED 357AED 206

        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, May 1, arriving at Midway International Airport. One-way Prices start from AED 206 including taxes and charges.

      • LGA06:10
        2h 20m
        Nonstop
        MDW07:30
        Southwest Airlines|New York - Chicago|Sun, Apr 27
        AED 282
        AED 282

        Choose Southwest Airlines flights from New York to Chicago. The one-way direct flight with Southwest Airlines departs from New York LaGuardia Airport on Sun, Apr 27, arriving at Midway International Airport. One-way Prices start from AED 282 including taxes and charges.

      • DAL20:15
        2h 10m
        Nonstop
        MDW22:25
        Southwest Airlines|Dallas - Chicago|Fri, Apr 11
        AED 290
        AED 290

        Choose Southwest Airlines flights from Dallas to Chicago. The one-way direct flight with Southwest Airlines departs from Dallas Love Field on Fri, Apr 11, arriving at Midway International Airport. One-way Prices start from AED 290 including taxes and charges.

      • ATL16:10
        1h 55m
        Nonstop
        MDW17:05
        Southwest Airlines|Atlanta - Chicago|Tue, Apr 29
        AED 299
        AED 299

        Choose Southwest Airlines flights from Atlanta to Chicago. The one-way direct flight with Southwest Airlines departs from Hartsfield-Jackson Atlanta International Airport on Tue, Apr 29, arriving at Midway International Airport. One-way Prices start from AED 299 including taxes and charges.

      • DEN21:05
        2h 25m
        Nonstop
        MDW00:30
        Southwest Airlines|Denver - Chicago|Mon, May 19
        AED 303
        AED 303

        Choose Southwest Airlines flights from Denver to Chicago. The one-way direct flight with Southwest Airlines departs from Denver International Airport on Mon, May 19, arriving at Midway International Airport. One-way Prices start from AED 303 including taxes and charges.

      • MSP05:15
        1h 30m
        Nonstop
        MDW06:45
        Southwest Airlines|Minneapolis - Chicago|Thu, Apr 24
        AED 307
        AED 307

        Choose Southwest Airlines flights from Minneapolis to Chicago. The one-way direct flight with Southwest Airlines departs from St Paul International Airport on Thu, Apr 24, arriving at Midway International Airport. One-way Prices start from AED 307 including taxes and charges.

      • BNA10:50
        1h 55m
        Nonstop
        ORD12:45
        Southwest Airlines|Nashville - Chicago|Fri, Apr 11
        AED 307
        AED 307

        Choose Southwest Airlines flights from Nashville to Chicago. The one-way direct flight with Southwest Airlines departs from Nashville International Airport on Fri, Apr 11, arriving at O'Hare International Airport. One-way Prices start from AED 307 including taxes and charges.

      • LAS23:45
        3h 35m
        Nonstop
        MDW05:20
        Southwest Airlines|Las Vegas - Chicago|Wed, Apr 9
        AED 316
        AED 316

        Choose Southwest Airlines flights from Las Vegas to Chicago. The one-way direct flight with Southwest Airlines departs from Harry Reid International Airport on Wed, Apr 9, arriving at Midway International Airport. One-way Prices start from AED 316 including taxes and charges.

      • SHA1:00 PM
        3h 5m
        Nonstop
        CHI2:00 PM
        Southwest Airlines|Shanghai - Chicago|Tue, Apr 15
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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
    AED 202
  • 24.74 km from downtown Chicago
    O'Hare International Airport
    Tickets From
    AED 290

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. 21 hours 57 minutes to fly from Dubai to Chicago.
    • Approx. 18 hours to fly from Addis Ababa to Chicago.
    • Approx. 1 hour 28 minutes to fly from Detroit to Chicago.
    • Approx. 3 hours 29 minutes to fly from Miami 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 3,726.

  • 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 3,726.

  • 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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