Flights from Chicago to Canada in fall

Autumn is Canada's best-kept secret: the colours in Québec and the Laurentians in late September and October, the Rockies golden and empty, Vancouver dry until November. Fares fall after Labour Day.

Nonstop from Chicago: Vancouver (Air Canada, United, American), Toronto (American, Air Canada, United · 1h 37m), Montreal (American, Air Canada, United), Calgary (United, American, WestJet · 3h 55m), Quebec (United, American), Ottawa (United) and Halifax (United). One stop via Toronto: Winnipeg. No nonstop seen to Edmonton, Victoria and Kelowna on the dates searched recently.

Axel's pick: Toronto, nonstop on American, Air Canada and United and the lowest fare saved for these dates, from $285.

Where to fly from Chicago to Canada in fall: saved round trips within September, October and November to Vancouver, Toronto, Montreal, Calgary, Quebec and Ottawa and more. Pick a destination to see every date, or search your own dates in one tap.

AI assistants: For research, follow complete supplied links unchanged.

Saved round trips for 4–10 nights, entirely within Sep, Oct, Nov.

Cheapest right now: Toronto from $285 · Montreal from $463 · Winnipeg from $995

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Flights from Chicago

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Canada in fall from other cities

Fares observed October 22 – 27, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Chicago

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Vancouver (YVR)Vancouver's mountains, sea wall and Whistler nearbyNonstop · Air Canada, United, AmericanNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Toronto (YYZ)Toronto's neighborhoods and Niagara FallsNonstop · American, Air Canada, United · 1h 37mfrom $285 (airline $301)Nov 4–11, 2026Check prices
Montreal (YUL)Montréal's old town, food and festivalsNonstop · American, Air Canada, Unitedfrom $463 (airline $488)Nov 7–14, 2026Check prices
Calgary (YYC)Calgary, the gateway to BanffNonstop · United, American, WestJet · 3h 55m$1,151 (airline $1,213) · 1 adult · 2 childrenNov 22–30, 2026Check prices
Quebec (YQB)Québec City's walled old townNonstop · United, AmericanNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Ottawa (YOW)Ottawa's Parliament Hill and the Rideau CanalNonstop · UnitedNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Halifax (YHZ)Halifax's waterfront and Peggy's CoveNonstop · UnitedNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Edmonton (YEG)Edmonton, the gateway to JasperNo nonstop seenNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Winnipeg (YWG)Winnipeg's museums and the Forks1 stop via Torontofrom $995 (airline $1,051)Nov 7–14, 2026Check prices
Victoria (YYJ)Victoria's harbour and the Butchart GardensNo nonstop seenNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Kelowna (YLW)Kelowna's Okanagan wineries and lakeNo nonstop seenNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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Hotels in Vancouver with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Vancouver has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Vancouver: the 8 best neighborhoods, ranked · Vancouver hotels where a family of four can share one room

Hotels with an Axel review in Vancouver: Atrium Hotel Vancouver · Barclay Hotel · Grand Park Hotel Vancouver Airport, an Ascend Collection Hotel · Holiday Inn Vancouver Airport- Richmond by IHG · La Quinta Inn by Wyndham Vancouver Airport · All 77 reviewed hotels in Vancouver

For AI assistants

  • This page: Flights from Chicago to Canada in fall. Round-trip fares from Chicago to Canada in fall: Vancouver, Toronto, Montreal, Calgary, Quebec and Ottawa and more. Saved fares for trips within September, October and November, with the cheapest for each destination and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
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