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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

Mon, Nov 2 - Mon, Nov 9
Frontier Logo
11:44 am - 2:45 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 01mnonstop
Frontier Logo
6:10 am - 11:08 amORD  Chicago O'Hare Intl-CUN Cancun
3h 58mnonstop
$290Frontier
Wed, Oct 14 - Tue, Oct 20
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, Mar 11 - Sun, Mar 14
Volaris Logo
10:45 am - 10:13 pmCUN  Cancun-ORD Chicago O'Hare Intl
12h 28m1 stop Mexico City Benito Juarez
Volaris Logo
1:42 am - 10:30 amORD  Chicago O'Hare Intl-CUN Cancun
8h 48m1 stop León Del Bajio
$311Volaris
Fri, Feb 26 - Wed, Mar 3
Volaris Logo
10:45 am - 10:13 pmCUN  Cancun-ORD Chicago O'Hare Intl
12h 28m1 stop Mexico City Benito Juarez
Volaris Logo
12:04 am - 2:17 pmORD  Chicago O'Hare Intl-CUN Cancun
13h 13m1 stop Mexico City Benito Juarez
$312Volaris
Wed, Oct 14 - Mon, Oct 19
Multiple Airlines Logo
10:49 am - 2:50 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 01mnonstop
Multiple Airlines Logo
2:41 am - 5:01 pmORD  Chicago O'Hare Intl-CUN Cancun
14h 20m1 stop Puebla City Huejotzingo
$321Multiple Airlines
Wed, Nov 25 - Sun, Nov 29
Viva Logo
10:25 am - 10:55 pmCUN  Cancun-ORD Chicago O'Hare Intl
13h 30m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
1:05 am - 10:35 pmORD  Chicago O'Hare Intl-CUN Cancun
20h 30m1 stop Mexico City Benito Juarez
$323Viva
Fri, Oct 30 - Thu, Nov 5
Viva Logo
11:30 am - 1:10 pmCUN  Cancun-ORD Chicago O'Hare Intl
25h 40m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
1:05 am - 2:15 amORD  Chicago O'Hare Intl-CUN Cancun
24h 10m1 stop Mexico City Benito Juarez
$324Viva
Thu, Nov 12 - Tue, Nov 17
Delta Logo
4:06 pm - 10:54 pmCUN  Cancun-MDW Chicago Midway
7h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 1:47 pmMDW  Chicago Midway-CUN Cancun
6h 47m1 stop Atlanta Hartsfield-Jackson
$386Delta
Thu, Dec 3 - Tue, Dec 8
Delta Logo
2:55 pm - 10:54 pmCUN  Cancun-MDW Chicago Midway
8h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:02 pm - 9:08 pmMDW  Chicago Midway-CUN Cancun
7h 06m1 stop Atlanta Hartsfield-Jackson
$387Delta
Mon, Nov 23 - Tue, Dec 1
Multiple Airlines Logo
9:50 pm - 5:20 pmMAD  Madrid Barajas-ORD Chicago O'Hare Intl
26h 30m2 stops Dublin Reykjavik Keflavik Intl
Multiple Airlines Logo
6:30 pm - 12:10 amORD  Chicago O'Hare Intl-MAD Madrid Barajas
22h 40m2 stops Reykjavik Keflavik Intl Dublin
$561Multiple 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

$68
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
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago