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Westjet Flights to Chicago (CHI)
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Book Westjet Flights to Chicago

  • One way
  • Round-trip
      • Cheapest nonstop
        YYC12:15
        3h 29m
        Direct
        ORD16:44
        Westjet|Calgary - Chicago|Wed, Jun 18
        S$ 503S$ 1,911
        74% OFF
        74% OFF
        S$ 1,911S$ 503

        Fly from Calgary to Chicago on Wed, Jun 18 with Westjet. One-way direct flights with Westjet depart Calgary International Airport and arrive O'Hare International Airport starting at S$ 503 including taxes and charges.

      • YXX21:20
        13h 19m
        1 stop
        ORD12:39
        Westjet|Abbotsford - Chicago|Tue, Jul 8
        S$ 139S$ 1,911
        93% OFF
        93% OFF
        S$ 1,911S$ 139

        Fly from Abbotsford to Chicago on Tue, Jul 8 with Westjet. One-way connecting flights with Westjet depart Abbotsford International Airport and arrive O'Hare International Airport starting at S$ 139 including taxes and charges.

      • YVR21:15
        13h 24m
        1 stop
        ORD12:39
        Westjet|Vancouver - Chicago|Tue, Jul 8
        S$ 155S$ 1,911
        92% OFF
        92% OFF
        S$ 1,911S$ 155

        Fly from Vancouver to Chicago on Tue, Jul 8 with Westjet. One-way connecting flights with Westjet depart Vancouver International Airport and arrive O'Hare International Airport starting at S$ 155 including taxes and charges.

      • YHZ08:30
        26h 15m
        1 stop
        MDW08:45
        Westjet|Halifax - Chicago|Fri, Jul 25
        S$ 263
        S$ 263

        Fly from Halifax to Chicago on Fri, Jul 25 with Westjet. One-way connecting flights with Westjet depart Halifax Stanfield International Airport and arrive Midway International Airport starting at S$ 263 including taxes and charges.

      • YUL07:00
        8h 48m
        1 stop
        ORD14:48
        Westjet|Montreal - Chicago|Tue, Jun 10
        S$ 335
        S$ 335

        Fly from Montreal to Chicago on Tue, Jun 10 with Westjet. One-way connecting flights with Westjet depart Montreal-Pierre Elliott Trudeau International Airport and arrive O'Hare International Airport starting at S$ 335 including taxes and charges.

      • YYZ10:11
        8h 52m
        1 stop
        ORD18:03
        Westjet|Toronto - Chicago|Thu, Jun 12
        S$ 345
        S$ 345

        Fly from Toronto to Chicago on Thu, Jun 12 with Westjet. One-way connecting flights with Westjet depart Toronto Pearson International Airport and arrive O'Hare International Airport starting at S$ 345 including taxes and charges.

      • YYJ10:20
        28h 24m
        1 stop
        ORD16:44
        Westjet|Victoria - Chicago|Sun, Jun 29
        S$ 427
        S$ 427

        Fly from Victoria to Chicago on Sun, Jun 29 with Westjet. One-way connecting flights with Westjet depart Victoria International Airport and arrive O'Hare International Airport starting at S$ 427 including taxes and charges.

      • DUB12:00
        13h 24m
        1 stop
        ORD19:24
        Westjet|Dublin - Chicago|Mon, Aug 4
        S$ 990
        S$ 990

        Fly from Dublin to Chicago on Mon, Aug 4 with Westjet. One-way connecting flights with Westjet depart Dublin Airport and arrive O'Hare International Airport starting at S$ 990 including taxes and charges.

      • ICN20:45
        33h 59m
        1 stop
        ORD16:44
        Westjet|Seoul - Chicago|Mon, Jun 30
        S$ 1,035
        S$ 1,035

        Fly from Seoul to Chicago on Mon, Jun 30 with Westjet. One-way connecting flights with Westjet depart Incheon International Airport and arrive O'Hare International Airport starting at S$ 1,035 including taxes and charges.

      • NRT18:30
        36h 14m
        1 stop
        ORD16:44
        Westjet|Tokyo - Chicago|Mon, Jun 9
        S$ 1,197
        S$ 1,197

        Fly from Tokyo to Chicago on Mon, Jun 9 with Westjet. One-way connecting flights with Westjet depart Narita International Airport and arrive O'Hare International Airport starting at S$ 1,197 including taxes and charges.

      • IST1:00 PM
        3h 5m
        Direct
        CHI2:00 PM
        Westjet|Istanbul - Chicago|Fri, Jun 13
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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 Westjet?

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

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

  • 24.74 km from central ChicagoCheapest
    O'Hare International Airport
    Tickets From
    S$ 139
  • 12.76 km from central ChicagoClosest
    Midway International Airport
    Tickets From
    S$ 189

About Westjet

Airline Name
Westjet
Airline Code
WS
Airline Type
Low-cost Carrier (LCC)
Popular Countries Westjet Flies to:
Philippines, Canada and Sweden
Popular Westjet Arrival Cities
Popular Westjet Departure Cities
Based on Trip.com Historical Data

Westjet Flights to Chicago - FAQ

  • Does Westjet have baggage allowance?

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

  • How long is the flight to Chicago?

    • Approx. 22 hours 45 minutes to fly from Singapore to Chicago.
    • Approx. 2 hours 58 minutes to fly from Boston to Chicago.
    • Approx. 3 hours 42 minutes to fly from New York to Chicago.
    • Approx. 4 hours 19 minutes to fly from San Francisco 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 June. The average price of flight tickets to Chicago in June is S$ 1,583.

  • When to buy flight tickets to Chicago the cheapest?

    Flight tickets to Chicago are the cheapest in September compared to other months, the average price is S$ 1,518.

  • 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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