
Flights to Chicago with American Airlines from 261CAD*
Popular flights to Chicago
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CAD
*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. Additional bag and optional fees for products and services may apply.
Find deals on flights to Chicago
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*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

Chicago routes with American Airlines
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Please use the search function at the top of the page to find our best flight deals
Fly to Chicago with American Airlines
Arriving in Chicago
Chicago is one of the United States’ premiere destinations. Book your flights to Chicago and get ready to wander through its innovative parks, diverse museums, plethora of stores and boutiques, and fantastic restaurants. Visit American Airlines.com to find flight deals to Chicago.
First Time in Chicago
No trip to Chicago is complete without a visit to Millennium Park. A mix of cutting-edge art and landscape design, the park provides the backdrop for hundreds of live performances, tours, and family fun all year long. Within the park, the Lurie Garden encompasses five acres of gorgeous greenery and is a focal point of the city.
Your Chicago
Travelers young and old will love the Peggy Notebaert Nature Museum. A recreated prairie, rooftop gardens, and the Judy Istock Butterfly Haven make this one of the most interactive and unique museums in the world. Reserve your tickets to Chicago and immerse yourself in this city of traditional delights and modern amenities.
Making the Most of Your Chicago Holiday
Chicago has four distinct seasons each year. To avoid excessive crowds, visitors may want to travel to Chicago during the winter. Temperatures can be very cold and snowy, but attractions will be more accessible, and cheap hotels in Chicago much easier to find.
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From | To | Fare type | Travel dates | Price |
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Vancouver (YVR) | Chicago (ORD) | Round trip I Economy | 06/18/2025 - 06/25/2025 | from 433CADFare subject to changes Updated: 21 hours ago |
Toronto (YYZ) | Chicago (ORD) | Round trip I Economy | 04/29/2025 - 05/06/2025 | from 361CADFare subject to changes Updated: 4 hours ago |
Montreal (YUL) | Chicago (ORD) | Round trip I Economy | 05/03/2025 - 05/10/2025 | from 385CADFare subject to changes Updated: 21 hours ago |
Calgary (YYC) | Chicago (ORD) | Round trip I Economy | 06/03/2025 - 06/10/2025 | from 261CADFare subject to changes Updated: 10 hours ago |
Québec (YQB) | Chicago (ORD) | Round trip I Economy | 07/01/2025 - 07/08/2025 | from 567CADFare subject to changes Updated: 4 hours ago |
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One way | Guatemala City (GUA) | Orlando (ORL) |
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One way | Dallas (DFW) | Guatemala City (GUA) |
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One way | Chicago (CHI) | Guatemala City (GUA) |
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One way | Guatemala City (GUA) | Washington, D.C. (WAS) |
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One way | Boston (BOS) | Guatemala City (GUA) |
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One way | Guatemala City (GUA) | San Francisco (SFO) |
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One way | Guatemala City (GUA) | Las Vegas (LAS) |
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One way | Denver (DEN) | Guatemala City (GUA) |
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