Flights to Chicago (ORD)
Flying from Canada to Chicago? See fares from Toronto, Montreal, Vancouver into ORD and compare airlines on BookingTrolley.
Cheap flights from airports near you to Chicago
Popular international departures to Chicago
- from TorontoYYZ · Canada · 701 kmView →
- from MontrealYUL · Canada · 1,201 kmfromC$ 971.33
- from MonterreyMTY · Mexico · 2,119 kmView →
- from CancunCUN · Mexico · 2,330 kmfromC$ 858.99
- from Mexico CityMEX · Mexico · 2,718 kmView →
- from GuadalajaraGDL · Mexico · 2,789 kmView →
- from VancouverYVR · Canada · 2,831 kmView →
- from San SalvadorSAL · El Salvador · 3,175 kmView →
- from Panama CityPTY · Panama · 3,753 kmfromC$ 1,948.14
- from BogotaBOG · Colombia · 4,363 kmfromC$ 1,306.98
- from DublinDUB · Ireland · 5,897 kmView →
- from LimaLIM · Peru · 6,105 kmView →
- from ManchesterMAN · United Kingdom · 6,140 kmView →
- from LondonLHR · United Kingdom · 6,345 kmView →
- from NantesNTE · France · 6,501 kmView →
- from AmsterdamAMS · Netherlands · 6,613 kmView →
- from ParisCDG · France · 6,665 kmView →
- from ParisORY · France · 6,670 kmView →
Popular airlines to Chicago
- Delta Air Lines
- American Airlines
- United Airlines
- Air Canada
- WestJet
- Porter Airlines
About flights to Chicago
Canada travellers commonly reach Chicago via Toronto, Montreal, Vancouver. BookingTrolley also lists other international gateways into Chicago such as Toronto, Montreal, Monterrey.
Airlines serving Chicago include Delta Air Lines, American Airlines, United Airlines and Air Canada. Compare published fares from Canada origins into ORD before you book.
Frequently asked questions about flights to Chicago
- How do I fly from Canada to Chicago?
- Travellers in Canada reach Chicago (ORD) via gateways such as Toronto, Montreal, Vancouver. BookingTrolley compares fares from these Canada airports into Chicago so you can pick the best origin for price and travel time.
- Which Canada airports offer flights to Chicago?
- Common Canada airports with routes toward Chicago include Toronto, Montreal, Vancouver. Availability varies by season and carrier — search live on BookingTrolley to confirm which gateway is cheapest for your dates.
- Which airlines fly to Chicago?
- Airlines serving Chicago (ORD) include Delta Air Lines, American Airlines, United Airlines and Air Canada, among others. BookingTrolley compares their fares on routes from Canada and other origins into Chicago.
- How do I find cheap flights from Canada to Chicago?
- Compare fares from several Canada airports (for example Toronto), stay flexible on mid-week dates, and check both nonstop and one-stop options. BookingTrolley shows recent starting fares for each origin into Chicago.
- When is the cheapest time to fly to Chicago from Canada?
- Shoulder seasons and mid-week departures from Canada into Chicago usually cost less than peak holidays. BookingTrolley tracks fares into ORD so you can book when prices dip.