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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
        RDU05:45
        2h 5m
        Nonstop
        MDW06:50
        Southwest Airlines|Raleigh - Chicago|Sat, Feb 15
        CAD 90CAD 142
        37% OFF
        37% OFF
        CAD 142CAD 90

        Choose Southwest Airlines flights from Raleigh to Chicago. The one-way direct flight with Southwest Airlines departs from Raleigh-Durham International Airport on Sat, Feb 15, arriving at Midway International Airport. One-way Prices start from CAD 90 including taxes and charges.

      • LGA06:30
        2h 30m
        Nonstop
        MDW08:00
        Southwest Airlines|New York - Chicago|Tue, Dec 31
        CAD 92CAD 142
        35% OFF
        35% OFF
        CAD 142CAD 92

        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, Dec 31, arriving at Midway International Airport. One-way Prices start from CAD 92 including taxes and charges.

      • DTW07:05
        1h 30m
        Nonstop
        MDW07:35
        Southwest Airlines|Detroit - Chicago|Tue, Jan 14
        CAD 97CAD 142
        32% OFF
        32% OFF
        CAD 142CAD 97

        Choose Southwest Airlines flights from Detroit to Chicago. The one-way direct flight with Southwest Airlines departs from Detroit Metropolitan Wayne County Airport on Tue, Jan 14, arriving at Midway International Airport. One-way Prices start from CAD 97 including taxes and charges.

      • DCA06:05
        2h 10m
        Nonstop
        MDW07:15
        Southwest Airlines|Washington D.C. - Chicago|Sat, Jan 11
        CAD 97
        CAD 97

        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, Jan 11, arriving at Midway International Airport. One-way Prices start from CAD 97 including taxes and charges.

      • BNA07:30
        1h 35m
        Nonstop
        MDW09:05
        Southwest Airlines|Nashville - Chicago|Wed, Jan 1
        CAD 98
        CAD 98

        Choose Southwest Airlines flights from Nashville to Chicago. The one-way direct flight with Southwest Airlines departs from Nashville International Airport on Wed, Jan 1, arriving at Midway International Airport. One-way Prices start from CAD 98 including taxes and charges.

      • MSP10:50
        1h 30m
        Nonstop
        MDW12:20
        Southwest Airlines|Minneapolis - Chicago|Wed, Jan 8
        CAD 98
        CAD 98

        Choose Southwest Airlines flights from Minneapolis to Chicago. The one-way direct flight with Southwest Airlines departs from St Paul International Airport on Wed, Jan 8, arriving at Midway International Airport. One-way Prices start from CAD 98 including taxes and charges.

      • ATL06:20
        1h 55m
        Nonstop
        MDW07:15
        Southwest Airlines|Atlanta - Chicago|Sat, Jan 4
        CAD 99
        CAD 99

        Choose Southwest Airlines flights from Atlanta to Chicago. The one-way direct flight with Southwest Airlines departs from Hartsfield-Jackson Atlanta International Airport on Sat, Jan 4, arriving at Midway International Airport. One-way Prices start from CAD 99 including taxes and charges.

      • CVG07:15
        1h 5m
        Nonstop
        MDW07:20
        Southwest Airlines|Cincinnati - Chicago|Wed, Jan 8
        CAD 101
        CAD 101

        Choose Southwest Airlines flights from Cincinnati to Chicago. The one-way direct flight with Southwest Airlines departs from Cincinnati/Northern Kentucky International Airport on Wed, Jan 8, arriving at Midway International Airport. One-way Prices start from CAD 101 including taxes and charges.

      • DEN19:05
        2h 30m
        Nonstop
        ORD22:35
        Southwest Airlines|Denver - Chicago|Tue, Jan 7
        CAD 103
        CAD 103

        Choose Southwest Airlines flights from Denver to Chicago. The one-way direct flight with Southwest Airlines departs from Denver International Airport on Tue, Jan 7, arriving at O'Hare International Airport. One-way Prices start from CAD 103 including taxes and charges.

      • PIT12:50
        1h 30m
        Nonstop
        MDW13:20
        Southwest Airlines|Pittsburgh - Chicago|Tue, Jan 7
        CAD 103
        CAD 103

        Choose Southwest Airlines flights from Pittsburgh to Chicago. The one-way direct flight with Southwest Airlines departs from Pittsburgh International Airport on Tue, Jan 7, arriving at Midway International Airport. One-way Prices start from CAD 103 including taxes and charges.

      • SHA01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Southwest Airlines|Shanghai - Chicago|Sun, Dec 29
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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 3 airports in Chicago. Find the most suitable Southwest Airlines flights to Chicago.

  • 12.76 km from central ChicagoCheapestClosest
    Midway International Airport
    Tickets From
    CAD 90
  • 24.74 km from central Chicago
    O'Hare International Airport
    Tickets From
    CAD 101
  • 139.04 km from central Chicago
    Chicago Rockford International Airport
    Tickets From
    CAD 172

About Southwest Airlines

Airline Name
Southwest Airlines
Airline Code
WN
Airline Type
Low-cost Carrier (LCC)
Popular Countries Southwest Airlines Flies to:
Canada and 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 flights to Chicago?

    • Approx. 1 hour 54 minutes to fly from Toronto to Chicago.
    • Approx. 3 hours 57 minutes to fly from Calgary to Chicago.
    • Approx. 5 hours 14 minutes to fly from Vancouver to Chicago.
    • Approx. 4 hours 35 minutes to fly from Montreal to Chicago.

  • How to get cheapest 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.

  • 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 January. The average price of flight tickets to Chicago in January is CAD 449.

  • When are flight to Chicago cheapest?

    Flight tickets to Chicago are the cheapest in March compared to other months, the average price is CAD 570.

  • What are the major 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 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

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