$69 Find deals on international flights to Chicago - Compare and Save

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Book Cheap International Flights Deals to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip international flight deals to Chicago

Wed, Nov 18 - Tue, Nov 24
Air Canada Logo
10:30 am - 7:52 pmCUN  Cancun-ORD Chicago O'Hare Intl
10h 22m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
7:05 am - 10:45 pmORD  Chicago O'Hare Intl-CUN Cancun
14h 40m1 stop Montreal Pierre Elliott Trudeau Intl
$275Air Canada
Thu, Oct 22 - Mon, Oct 26
Air Canada Logo
10:00 am - 8:12 pmCUN  Cancun-ORD Chicago O'Hare Intl
10h 12m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:40 pm - 9:40 amORD  Chicago O'Hare Intl-CUN Cancun
13h 00m1 stop Toronto Pearson Intl
$279Air Canada
Tue, Dec 22 - Tue, Jan 5
Frontier Logo
11:38 am - 2:38 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 00mnonstop
Frontier Logo
7:29 am - 12:52 pmORD  Chicago O'Hare Intl-CUN Cancun
4h 23mnonstop
$290Frontier
Thu, Oct 15 - Mon, Oct 19
Frontier Logo
10:49 am - 2:50 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 01mnonstop
Frontier Logo
6:10 am - 9:58 amORD  Chicago O'Hare Intl-CUN Cancun
3h 48mnonstop
$291Frontier
Thu, Nov 12 - Tue, Nov 17
Delta Logo
8:15 am - 6:04 pmCUN  Cancun-MDW Chicago Midway
10h 49m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 12:30 pmMDW  Chicago Midway-CUN Cancun
5h 30m1 stop Atlanta Hartsfield-Jackson
$432Delta
Thu, Nov 12 - Tue, Nov 17
Delta Logo
9:24 am - 10:54 pmCUN  Cancun-MDW Chicago Midway
14h 30m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 3:06 pmMDW  Chicago Midway-CUN Cancun
8h 06m1 stop Atlanta Hartsfield-Jackson
$433Delta
Fri, Dec 4 - Sat, Dec 12
Multiple Airlines Logo
12:00 pm - 2:55 pmMAD  Madrid Barajas-ORD Chicago O'Hare Intl
9h 55mnonstop
Multiple Airlines Logo
9:50 pm - 4:50 pmORD  Chicago O'Hare Intl-MAD Madrid Barajas
12h 00m1 stop London Heathrow
$560Multiple Airlines
Sat, Oct 10 - Mon, Oct 26
Iberia Logo
9:00 pm - 12:30 pmMAD  Madrid Barajas-ORD Chicago O'Hare Intl
22h 30m1 stop London Heathrow
Iberia Logo
6:40 pm - 8:50 amORD  Chicago O'Hare Intl-MAD Madrid Barajas
8h 10mnonstop
$563Iberia
Thu, Jan 21 - Mon, Jan 25
Iberia Logo
12:00 pm - 2:55 pmMAD  Madrid Barajas-ORD Chicago O'Hare Intl
9h 55mnonstop
Iberia Logo
5:10 pm - 11:55 amORD  Chicago O'Hare Intl-MAD Madrid Barajas
11h 45m1 stop London Heathrow
$565Iberia
Wed, Nov 4 - Tue, Jan 19
Multiple Airlines Logo
3:45 am - 2:30 pmDEL  New Delhi Indira Gandhi Intl-ORD Chicago O'Hare Intl
22h 15m1 stop Doha Hamad Intl
Multiple Airlines Logo
6:50 pm - 8:20 amORD  Chicago O'Hare Intl-DEL New Delhi Indira Gandhi Intl
26h 00m1 stop Doha Hamad Intl
$830Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What are the most popular airlines flying to Chicago?

The most popular airline among KAYAK users flying to Chicago is American Airlines, followed by United Airlines and Frontier.

American Airlines
American Airlines
#1 most popular
United Airlines
United Airlines
#2 most popular
Frontier
Frontier
#3 most popular
Delta
Delta
#4 most popular
Find deals

Good to know

Low season

January

Cheapest flight

$69
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Fort Lauderdale to Chicago O'Hare Airport

FAQs for booking Worldwide to Chicago flights

  • How does KAYAK find such low prices on flights from Worldwide to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Worldwide to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Worldwide to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Worldwide is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Worldwide to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Worldwide with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Worldwide to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Worldwide up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Chesterton
Munster
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago