Cheap flights from Toronto to Chicago

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Travel tip: Visit Chicago on your holidays!

Check our current prices for flights from Toronto 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 Toronto to Chicago, you will need to run a search below.

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From $218 / RT details

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Cheap Chicago airfares from $218/RT are provided by Outbound flight is leaving on 03/02/2021, 09:00 am from Toronto Toronto Is (YTZ) airport and arrives at Chicago Midway (MDW) at 09:50 am. The flight time is 0 hours and 50 minutes. The Returning flight departes on 03/16/2021, 10:30 am (other return dates are also available). Date posted: 24 Nov 2020

Price evolution for flights From Toronto To Chicago

Price overview for flights from Toronto to Chicago

Recent Deals on Flights from Toronto to Chicago:Roundtrip / Oneway

  • $218Porter Airlines flight Porter Airlines 
    Toronto, ON (YTZ)Chicago, IL (MDW)03/02/202109:00 am
    Chicago, IL (MDW)Toronto, ON (YTZ)03/16/202110:30 am check price
  • $237Porter Airlines flight Porter Airlines 
    Toronto, ON (YTZ)Chicago, IL (MDW)02/18/202106:10 pm
    Chicago, IL (MDW)Toronto, ON (YTZ)03/04/202103:25 pm check price
  • $127Porter Airlines flight Porter Airlines 
    Toronto, ON (YTZ)Chicago, IL (MDW)04/20/202109:00 am check price
  • $149Porter Airlines flight Porter Airlines 
    Toronto, ON (YTZ)Chicago, IL (MDW)02/18/202106:10 pm check price
  • $149Porter Airlines flight Porter Airlines 
    Toronto, ON (YTZ)Chicago, IL (MDW)03/04/202110:00 am check price
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Know what to do when flying to Chicago?

Chicago Travel Guide Founded in the early 1800s, Chicago is positioned between civilization and wilderness and many aspects of modern life had their start here. Chicago really does have it all, with less infrastructural problems than its coastal rivals. Though [...]
Chicago History The site where Chicago stands had long been considered as an important portage point on the water route linking the Great Lakes with the Mississippi river. Aside from this important fact, there are a lot of interesting things you need to know [...]
Chicago Sightseeing The rich cultural heritage of Chicago is depicted in its famous sights. Other tourist attractions in the city can be seen in zoos and parks as well. If you are thinking about visiting, it will help if you take a look at some of the travel [...]
Chicago Nightlife Chicago is one of the cities blessed with a variety of nightlife options. Discos, clubs, bars - name it and the place will certainly give you the pleasure you are looking for. You will surely dance the night away as you listen to the music [...]
Chicago Pictures
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