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  1. Flights
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  3. Chicago

Flights to Chicago

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Explore the best deals

Discover the cheapest flights to Chicago
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Sun, Jun 14 - Mon, Jun 15
Frontier Airlines
Frontier AirlinesDirect
Houston, TX - Chicago
Frontier Airlines
Frontier AirlinesDirect
Chicago - Houston, TX
244$
226$
Prime price per passenger
Tue, Jun 30 - Sat, Jul 11
American Airlines
American AirlinesDirect
New York City - Chicago
American Airlines
American AirlinesDirect
Chicago - New York City
262$
241$
Prime price per passenger
Wed, Jun 24 - Thu, Jun 25
American Airlines
American AirlinesDirect
Detroit - Chicago
American Airlines
American AirlinesDirect
Chicago - Detroit
-17 %
292$
244$
Prime price per passenger
Wed, Jul 15 - Fri, Jul 17
Frontier Airlines
Frontier Airlines1 stop
Buffalo, NY - Chicago
Frontier Airlines
Frontier Airlines1 stop
Chicago - Buffalo, NY
291$
270$
Prime price per passenger
Tue, May 26 - Sat, Jun 6
Spirit Airlines
Spirit AirlinesDirect
Tampa, FL - Chicago
Frontier Airlines
Frontier Airlines1 stop
Chicago - Tampa, FL
290$
274$
Prime price per passenger
Tue, Jul 28 - Wed, Jul 29
Porter Airlines
Porter AirlinesDirect
Toronto - Chicago
Porter Airlines
Porter AirlinesDirect
Chicago - Toronto
301$
292$
Prime price per passenger
Wed, Jun 17
Frontier Airlines
Frontier AirlinesDirect
Las Vegas, NV - Chicago
-13 %
90$
79$
Prime price per passenger
Wed, Jun 17
Frontier Airlines
Frontier AirlinesDirect
Las Vegas, NV - Chicago
-13 %
90$
79$
Prime price per passenger
Fri, Jul 10
Frontier Airlines
Frontier AirlinesDirect
Dallas, TX - Chicago
-12 %
115$
102$
Prime price per passenger
Sun, Jul 12
Sun Country Airlines
Sun Country AirlinesDirect
Minneapolis - St Paul - Chicago
137$
124$
Prime price per passenger
Fri, Jul 24
Frontier Airlines
Frontier AirlinesDirect
Orlando - Chicago
155$
142$
Prime price per passenger
Sun, May 31
Alaska Airlines
Alaska AirlinesDirect
San Diego, CA - Chicago
172$
157$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Popular flight routes to Chicago

Toronto
Flights from Torontoto Chicago
181$
172$
Prime price per passenger
Calgary
Flights from Calgaryto Chicago
397$
377$
Prime price per passenger
Montreal
Flights from Montrealto Chicago
323$
312$
Prime price per passenger
Vancouver
Flights from Vancouverto Chicago
202$
190$
Prime price per passenger
Edmonton
Flights from Edmontonto Chicago
477$
437$
Prime price per passenger
Ottawa
Flights from Ottawato Chicago
405$
385$
Prime price per passenger

How long is the flight to Chicago?

If you’re planning to fly to Chicago, we at eDreams have looked at the most popular routes to help you plan your trip. From Toronto, the flight is about 1h 53m; from Montreal, around 3h 10m; and from Calgary, roughly 4h 54m.
Flight Time (in hours)
TorontoMontrealCalgaryVancouverEdmonton
0h 1h 2h 3h 4h 5h 6h
1h 53m
3h 10m
4h 54m
5h 14m
5h 27m

How much does a flight to Chicago cost?

At eDreams you can find flights from Vancouver to Chicago starting from $189, with an average price of $319. If you depart from other cities such as Windsor, you can find tickets from $310, and from Thunder Bay starting from $372, according to data from the last 72 hours.
Filter by
VancouverWindsorThunder BayOttawaSaskatoon
$189
$319
$310
$310
$372
$372
$391
$423
$412
$412
VancouverCheapest
Cheapest Price: $189
Cheapest
Average

Fly to Chicago

Chicago is a city that attracts thousands of tourists every year. In fact, Chicago even features in United States's most popular destinations. Either if you're looking for a trip to get away from it all, or a holiday to visit a new city in America, Chicago is the ideal destination to spend a few days with friends or get together with your loved ones.

Want to book a flight to Chicago? Our travel agency compares the prices of airline tickets offered by more than 660 airlines worldwide. Discover now the flights offered by eDreams Canada.

Book a cheap flight to Chicago, United States with eDreams

The online travel agency eDreams Canada offers you to go and visit the destination of your dreams and travel at the best price to Chicago. Discover all that United States has to offer and book your flight tickets to Chicago now.

Simply select your departure airport and your travel dates for Chicago, our search engine will propose you dozens of flight offers operated by different airlines. The eDreams flight comparator will default offer you the best price to facilitate your booking process. Take advantage of our flight offers and find the best price for your trip to Chicago!

Then it's up to you to adjust your flight search and filter according to your desires (price range, with or without stopover, low cost or regular airline, etc...) if the price of the flight ticket is not your only criteria. Whether it's a one-way or round-trip ticket, treat yourself! You won't be disappointed with your stay with eDreams!

FAQs about Chicago flights

What's the best way to search for low-cost flights to Chicago using eDreams?
We can help you find flights to Chicago for as little as $ 79. Our smart technology scours thousands of flight options to create great offers, ensuring you can find the ideal flight for your needs and budget. With eDreams, finding the perfect flight for your trip is simple and straightforward.
When is the ideal time to buy tickets for a trip to Chicago?
This is the period when most travelers prefer to book their tickets.
When is the ideal time of year to visit Chicago?
According to our flight data, the most popular month for traveling to Chicago is March.
Another good time to fly to Chicago is in February, which is the second most popular month for travelers.
Lastly, April is the third most-visited month for flights to Chicago.
For a more relaxed trip with fewer crowds, consider flying to Chicago in November. This is the month with the lowest demand for flights, ensuring a more tranquil atmosphere.
What are the cheapest airlines for flying to Chicago?

Our analysis of customer bookings for flights to Chicago shows that these budget airlines are among the best for finding affordable fares:

  • The average one-way ticket with Porter Airlines is $442.98. You can fly from Toronto to Chicago for about $419.46, or from Montreal for a fare of $496.68.
  • You can find great deals with Air Canada, which has an average one-way fare of $466.17. For instance, a flight from Toronto to Chicago is priced at around $334.90, while the cost from Toronto is about $390.50.
Which airlines operate flights to Chicago?

The following airlines offer non-stop flights to Chicago:

  • You can fly directly to Chicago with American Airlines from Toronto and Montreal. They also have direct service from Vancouver.
  • You can get a direct flight to Chicago with Frontier Airlines from Montreal, Toronto, and Vancouver. This airline provides easy and convenient service from these popular locations.
  • You can fly to Chicago with Air Canada from Calgary and Toronto. This airline also provides flights from Detroit.

You can also consider these airlines for flights to Chicago with one or more stops:

  • You can fly to Chicago with Etihad Airways from a number of cities, including Toronto, Toronto, and Montreal.
  • You can find flights to Chicago with Air Canada departing from Montreal, Ottawa, and Halifax.
  • Lastly, you can travel to Chicago with Turkish Airlines from a variety of departure points, such as Vancouver, Edmonton, and Winnipeg.
For a flight to Chicago, how early should I get to the airport?
For a smooth start to your journey to Chicago, plan to arrive at the airport at least two to three hours ahead of your departure time. This buffer allows for a stress-free experience as you navigate check-in, security, customs, boarding, and baggage drop-off, while also accounting for any potential delays. eDreams makes it easy to find amazing deals on flights to Chicago from over 13 cities. We also offer a range of services designed to improve your airport experience, such as priority boarding, extra baggage allowances, and lounge access. To travel with confidence, consider booking a refundable fare or purchasing travel insurance. This ensures your trip to Chicago begins with total ease!

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