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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 4 - Wed, Nov 11
Viva Logo
4:25 pm - 10:55 pmCUN  Cancun-ORD Chicago O'Hare Intl
7h 30m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
12:35 am - 4:40 pmORD  Chicago O'Hare Intl-CUN Cancun
15h 05m1 stop Monterrey Gen Mariano Escobedo
$286Viva
Fri, Nov 6 - Sun, Nov 15
Viva Logo
7:00 am - 10:55 pmCUN  Cancun-ORD Chicago O'Hare Intl
16h 55m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
12:35 am - 3:35 pmORD  Chicago O'Hare Intl-CUN Cancun
14h 00m1 stop Monterrey Gen Mariano Escobedo
$287Viva
Thu, Nov 19 - Mon, Nov 23
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
3:45 pm - 1:00 pmORD  Chicago O'Hare Intl-CUN Cancun
20h 15m1 stop Montreal Pierre Elliott Trudeau Intl
$289Air 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
1:55 pm - 12:00 pmORD  Chicago O'Hare Intl-CUN Cancun
22h 05m1 stop Montreal Pierre Elliott Trudeau Intl
$290Air Canada
Thu, Oct 22 - Mon, Oct 26
Frontier Logo
1:51 pm - 11:43 pmCUN  Cancun-MDW Chicago Midway
9h 52m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 12:41 pmMDW  Chicago Midway-CUN Cancun
6h 26m1 stop Atlanta Hartsfield-Jackson
$333Frontier
Thu, Oct 22 - Mon, Oct 26
Frontier Logo
1:51 pm - 11:43 pmCUN  Cancun-MDW Chicago Midway
9h 52m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 12:41 pmMDW  Chicago Midway-CUN Cancun
6h 26m1 stop Atlanta Hartsfield-Jackson
$334Frontier
Wed, Nov 4 - Mon, Nov 9
Delta Logo
8:00 am - 3:17 pmCUN  Cancun-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 3:06 pmMDW  Chicago Midway-CUN Cancun
8h 06m1 stop Atlanta Hartsfield-Jackson
$412Delta
Thu, Nov 12 - Tue, Nov 17
Delta Logo
11:16 am - 10:54 pmCUN  Cancun-MDW Chicago Midway
12h 38m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 8:55 pmMDW  Chicago Midway-CUN Cancun
10h 25m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$413Delta
Thu, Oct 8 - Sun, Oct 11
American Airlines Logo
1:50 pm - 8:28 pmMAD  Madrid Barajas-ORD Chicago O'Hare Intl
13h 38m1 stop Boston Logan Intl
American Airlines Logo
4:55 pm - 8:20 amORD  Chicago O'Hare Intl-MAD Madrid Barajas
8h 25mnonstop
$566American Airlines
Wed, Sep 30 - Thu, Oct 15
American Airlines Logo
3:25 pm - 9:30 pmMAD  Madrid Barajas-ORD Chicago O'Hare Intl
13h 05m1 stop Philadelphia
American Airlines Logo
4:55 pm - 8:20 amORD  Chicago O'Hare Intl-MAD Madrid Barajas
8h 25mnonstop
$570American 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

$83
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Dallas/Fort Worth Airport 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
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago