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

  • One way
  • Return
      • Cheapest nonstop
        DTW19:35
        1h 10m
        Direct
        MDW19:45
        Southwest Airlines|Detroit - Chicago|Wed, Jun 25
        AU$ 68AU$ 227
        70% OFF
        70% OFF
        AU$ 227AU$ 68

        Choose Southwest Airlines flights from Detroit to Chicago. The one-way direct flight with Southwest Airlines departs from Detroit Metropolitan Wayne County Airport on Wed, Jun 25, arriving at Midway International Airport. One-way Prices start from AU$ 68 including taxes and charges.

      • BOS05:25
        2h 35m
        Direct
        MDW07:00
        Southwest Airlines|Boston - Chicago|Tue, Jul 1
        AU$ 81AU$ 227
        64% OFF
        64% OFF
        AU$ 227AU$ 81

        Choose Southwest Airlines flights from Boston to Chicago. The one-way direct flight with Southwest Airlines departs from Logan International Airport on Tue, Jul 1, arriving at Midway International Airport. One-way Prices start from AU$ 81 including taxes and charges.

      • HOU16:20
        2h 25m
        Direct
        MDW18:45
        Southwest Airlines|Houston - Chicago|Sat, Aug 16
        AU$ 118AU$ 227
        48% OFF
        48% OFF
        AU$ 227AU$ 118

        Choose Southwest Airlines flights from Houston to Chicago. The one-way direct flight with Southwest Airlines departs from William P. Hobby Airport on Sat, Aug 16, arriving at Midway International Airport. One-way Prices start from AU$ 118 including taxes and charges.

      • LGA06:00
        2h 20m
        Direct
        MDW07:20
        Southwest Airlines|New York - Chicago|Tue, Sep 16
        AU$ 119
        AU$ 119

        Choose Southwest Airlines flights from New York to Chicago. The one-way direct flight with Southwest Airlines departs from LaGuardia Airport on Tue, Sep 16, arriving at Midway International Airport. One-way Prices start from AU$ 119 including taxes and charges.

      • MCO15:50
        3h 5m
        Direct
        ORD17:55
        Southwest Airlines|Orlando - Chicago|Thu, Sep 4
        AU$ 121
        AU$ 121

        Choose Southwest Airlines flights from Orlando to Chicago. The one-way direct flight with Southwest Airlines departs from Orlando International Airport on Thu, Sep 4, arriving at O'Hare International Airport. One-way Prices start from AU$ 121 including taxes and charges.

      • BWI20:40
        2h
        Direct
        MDW21:40
        Southwest Airlines|Baltimore - Chicago|Mon, Jun 30
        AU$ 122
        AU$ 122

        Choose Southwest Airlines flights from Baltimore to Chicago. The one-way direct flight with Southwest Airlines departs from Baltimore/Washington International Airport on Mon, Jun 30, arriving at Midway International Airport. One-way Prices start from AU$ 122 including taxes and charges.

      • DEN19:30
        2h 35m
        Direct
        ORD23:05
        Southwest Airlines|Denver - Chicago|Fri, Jul 4
        AU$ 138
        AU$ 138

        Choose Southwest Airlines flights from Denver to Chicago. The one-way direct flight with Southwest Airlines departs from Denver International Airport on Fri, Jul 4, arriving at O'Hare International Airport. One-way Prices start from AU$ 138 including taxes and charges.

      • SEA22:55
        4h 5m
        Direct
        MDW05:00
        Southwest Airlines|Seattle - Chicago|Tue, Jul 15
        AU$ 146
        AU$ 146

        Choose Southwest Airlines flights from Seattle to Chicago. The one-way direct flight with Southwest Airlines departs from Seattle–Tacoma International Airport on Tue, Jul 15, arriving at Midway International Airport. One-way Prices start from AU$ 146 including taxes and charges.

      • BNA21:15
        1h 35m
        Direct
        MDW22:50
        Southwest Airlines|Nashville - Chicago|Mon, Aug 18
        AU$ 154
        AU$ 154

        Choose Southwest Airlines flights from Nashville to Chicago. The one-way direct flight with Southwest Airlines departs from Nashville International Airport on Mon, Aug 18, arriving at Midway International Airport. One-way Prices start from AU$ 154 including taxes and charges.

      • TPA14:10
        2h 45m
        Direct
        MDW15:55
        Southwest Airlines|Tampa - Chicago|Fri, Jul 4
        AU$ 156
        AU$ 156

        Choose Southwest Airlines flights from Tampa to Chicago. The one-way direct flight with Southwest Airlines departs from Tampa International Airport on Fri, Jul 4, arriving at Midway International Airport. One-way Prices start from AU$ 156 including taxes and charges.

      • CMH1:00 PM
        3h 5m
        Direct
        CHI2:00 PM
        Southwest Airlines|Columbus - Chicago|Wed, Jul 2
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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 central ChicagoCheapestClosest
    Midway International Airport
    Tickets From
    AU$ 68
  • 24.74 km from central Chicago
    O'Hare International Airport
    Tickets From
    AU$ 121

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. 21 hours 18 minutes to fly from Sydney to Chicago.
    • Approx. 22 hours 58 minutes to fly from Melbourne to Chicago.
    • Approx. 4 hours 28 minutes to fly from Los Angeles to Chicago.
    • Approx. 2 hours 45 minutes to fly from New York 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.

  • 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 July. The average price of flight tickets to Chicago in July is AU$ 700.

  • When are flight tickets to Chicago the cheapest?

    Flight tickets to Chicago are the cheapest in September compared to other months, the average price is AU$ 388.

  • 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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