Cheap flights from Montreal to Chicago
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Travel tip: Don't miss to visit The Renaissance Society in Hyde Park.Check our current prices for flights from Montreal to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Montreal to Chicago, you will need to run a search below.
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Cheap Chicago airfares from $270/RT are provided by Cheapoair.com. Outbound flight is leaving on 05/20/2025, 10:45 am from Montreal Dorval (YUL) airport and arrives at Chicago Midway (MDW) at 04:24 pm. The flight time is 5 hours and 39 minutes. The Returning flight departes on 05/27/2025, 09:15 am (other return dates are also available). Date posted: 01 Feb 2025
Price evolution for flights From Montreal To Chicago
Recent Deals on Flights from Montreal to Chicago:Roundtrip / Oneway
- $270
Porter Airlines
cheapoair.com check priceFrom To Departure Time Montreal, QC (YUL) Chicago, IL (MDW) 05/20/2025 10:45 am Chicago, IL (MDW) Montreal, QC (YUL) 05/27/2025 09:15 am - $346
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Montreal, QC (YUL) Chicago, IL (MDW) 05/20/2025 10:45 am Chicago, IL (MDW) Montreal, QC (YUL) 05/27/2025 09:20 am - $521 Porter Airlines
cheapoair.com check priceFrom To Departure Time Montreal, QC (YUL) Chicago, IL (MDW) 12/29/2025 10:45 am Chicago, IL (MDW) Montreal, QC (YUL) 01/02/2026 11:15 am - $161 Porter Airlines
cheapoair.com check priceFrom To Departure Time Montreal, QC (YUL) Chicago, IL (MDW) 06/03/2025 01:10 pm - $198
Westjet
cheapoair.com check priceFrom To Departure Time Montreal, QC (YUL) Chicago, IL (MDW) 06/03/2025 12:45 pm
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Know what to do when flying to Chicago?
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