Cheap Flights to Chicago from CAD 175
Find today's best flight deals, with flights to Chicago from as low as CAD 175!
Most Popular Airlines Flying to Chicago
Porter Airlines 
Air Canada 
United Airlines 
WestJet 
American Airlines 
Delta Air Lines 
Air Transat 
Etihad Airways 
Frontier Airlines 
Japan Airlines 
Alaska Airlines 
Spirit Airlines 
Aer Lingus 
Volaris 
Philippine Airlines 
Cathay Pacific 
Asiana Airlines Latest Flight Deals to Chicago
These are the best offers on flights to Chicago you’ll find over the next 60 days, with savings of up to CAD 898. Don’t miss out!
Air Canada
WestJet Air Canada Air Canada United Airlines Air Canada WestJet WestJet Etihad AirwaysWhen is the cheapest time to book flights to Chicago?
What is the cheapest month for one-way flights from Toronto to Chicago?
Based on Trip.com data, the cheapest month to fly from Toronto to Chicago is June, with an average price of CAD 226. The most expensive month is usually October, with average prices reaching CAD 333.
What is the cheapest month for return flights from Toronto to Chicago?
Based on Trip.com's historical data, September is often the cheapest month for fly from Toronto to Chicago, with an average price of CAD 322. October is usually the most expensive period, with prices averaging as high as CAD 452.
Which day of the week is cheapest to fly from Toronto to Chicago?
Based on Trip.com data from the past 12 months, the cheapest day to fly from Toronto to Chicago is Saturday. The average fare on this day is usually lower than on other days. Try to avoid flying on Sunday as fares are usually the highest.
Round-trip fights to Chicago
Whether it's a quick getaway or a business trip to remember, our 3–7 day round trips are perfect for experiencing Chicago affordably.
Useful info for your flights to Chicago from the United Kingdom
| Cheapest one-way flight price | CAD 159 |
|---|---|
| Cheapest return ticket price | CAD 255 |
| Cheapest month | September |
| Peak season for travel | July |
| Flight distance | 701.97km |
| Average flight time | 2 hours 4 minutes |
| Popular airline | Porter Airlines |
Frequently asked questions: Booking Chicago flights
How long is the flights to Chicago?
- Approx. 1 hour 54 minutes to fly from Toronto to Chicago.
- Approx. 3 hours 39 minutes to fly from Calgary to Chicago.
- Approx. 4 hours 20 minutes to fly from Vancouver to Chicago.
- Approx. 5 hours 21 minutes to fly from Edmonton to Chicago.
How to get cheapest flights to Chicago?
You can book cheaper flights in the following ways:- Search for tickets to a city or airport near Chicago.
- Look up different airlines that have flights to Chicago.
- Browse different departure dates from the same month.
- Filter for different departure times from the same day.
- Check for discount information on various social media sites.
- Explore deals and discounts on airline websites.
What is the most popular month to visit Chicago?
Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is July. The average price of flight tickets to Chicago in July is CAD 361.When are flight to Chicago cheapest?
Flight tickets to Chicago are the cheapest in September compared to other months, the average price is CAD 255.What are the major airports in Chicago?
Which popular airlines have flights to Chicago?
Popular airlines with flights to Chicago: American Airlines, United Airlines, and Frontier Airlines.
Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.