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Most Popular Airlines Flying to Chicago

See which airlines fly to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.
Porter Airlines logo Porter Airlines
WestJet logo WestJet
United Airlines logo United Airlines
Air Canada logo Air Canada
American Airlines logo American Airlines
Alaska Airlines logo Alaska Airlines
Delta Air Lines logo Delta Air Lines
Air Transat logo Air Transat
EVA Air logo EVA Air
Etihad Airways logo Etihad Airways
Air India logo Air India
Emirates logo Emirates
Flair Airlines logo Flair Airlines
Frontier Airlines logo Frontier Airlines
Turkish Airlines logo Turkish Airlines
Cathay Pacific logo Cathay Pacific

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 €205. Don’t miss out!

46%
Toronto Chicago
Porter Airlines Porter Airlines
One way
Economy
Mon, Feb 9
€106
€196
72%
Calgary Chicago
WestJet WestJet
One way
Economy
Mon, Feb 2
€67
€237
59%
Vancouver Chicago
Porter Airlines Porter Airlines
One way
Economy
Sat, Mar 7
€91
€219
69%
Montreal Chicago
Porter Airlines Porter Airlines
One way
Economy
Fri, Feb 13
€72
€234
57%
Edmonton Chicago
WestJet WestJet
One way
Economy
Fri, Feb 6
€110
€256
64%
Saskatoon Chicago
WestJet WestJet
One way
Economy
Mon, Feb 9
€83
€229
57%
Regina Chicago
WestJet WestJet
One way
Economy
Fri, Feb 6
€86
€199
69%
Winnipeg Chicago
WestJet WestJet
One way
Economy
Mon, Mar 16
€92
€297
59%
Kelowna Chicago
WestJet WestJet
One way
Economy
Fri, Jan 30
€90
€217

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.

4 day trip
Fri, Feb 13- Mon, Feb 16
4 day trip
Calgary
Chicago
€117
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4 day trip
Fri, Jan 30- Mon, Feb 2
4 day trip
Kelowna
Chicago
€144
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8 day trip
Mon, Feb 2- Mon, Feb 9
8 day trip
Edmonton
Chicago
€155
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7 day trip
Sun, Jan 25- Sat, Jan 31
7 day trip
Vancouver
Chicago
€161
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8 day trip
Mon, Feb 2- Mon, Feb 9
8 day trip
Toronto
Chicago
€251
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5 day trip
Thu, Feb 5- Mon, Feb 9
5 day trip
Montreal
Chicago
€266
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Useful info for your flights to Chicago from the United Kingdom

Cheapest one-way flight price€79
Cheapest return ticket price€121
Cheapest monthApril
Peak season for travelJuly
Flight distance701.97km
Average flight time2 hours
Popular airlinePorter 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.
  • 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.
  • Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is February. The average price of flight tickets to Chicago in February is €262.
  • Flight tickets to Chicago are the cheapest in April compared to other months, the average price is €505.
  • Popular airlines with flights to Chicago: American Airlines, United Airlines, and Frontier Airlines.

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