$89 Find deals on international flights to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Book Cheap International Flights Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip international flight deals to Chicago

Thu, Oct 15 - Sun, Oct 18
Multiple Airlines Logo
12:35 pm - 11:40 pmCUN  Cancun-ORD Chicago O'Hare Intl
11h 05m1 stop Punta Cana
Multiple Airlines Logo
7:35 am - 9:03 pmORD  Chicago O'Hare Intl-CUN Cancun
13h 28m1 stop Mexico City Benito Juarez
$264Multiple Airlines
Wed, Sep 2 - Wed, Sep 9
Volaris Logo
9:50 pm - 5:52 amCUN  Cancun-ORD Chicago O'Hare Intl
8h 02m1 stop Mexico City Benito Juarez
Volaris Logo
7:35 am - 9:03 pmORD  Chicago O'Hare Intl-CUN Cancun
13h 28m1 stop Mexico City Benito Juarez
$278Volaris
Thu, Sep 24 - Mon, Sep 28
Volaris Logo
9:50 pm - 5:52 amCUN  Cancun-ORD Chicago O'Hare Intl
8h 02m1 stop Mexico City Benito Juarez
Volaris Logo
7:35 am - 9:03 pmORD  Chicago O'Hare Intl-CUN Cancun
13h 28m1 stop Mexico City Benito Juarez
$288Volaris
Thu, Oct 8 - Tue, Oct 13
United Airlines Logo
3:38 pm - 7:35 pmCUN  Cancun-ORD Chicago O'Hare Intl
3h 57mnonstop
United Airlines Logo
9:29 am - 1:10 pmORD  Chicago O'Hare Intl-CUN Cancun
3h 41mnonstop
$299United Airlines
Fri, Oct 9 - Mon, Oct 12
United Airlines Logo
12:11 pm - 4:04 pmCUN  Cancun-ORD Chicago O'Hare Intl
3h 53mnonstop
United Airlines Logo
9:38 pm - 10:06 amORD  Chicago O'Hare Intl-CUN Cancun
12h 28m1 stop Houston George Bush Intcntl
$300United Airlines
Wed, Feb 3 - Fri, Feb 12
Viva Logo
10:30 am - 10:50 pmCUN  Cancun-ORD Chicago O'Hare Intl
13h 20m1 stop Monterrey Gen Mariano Escobedo
Viva Logo
12:30 am - 9:40 amORD  Chicago O'Hare Intl-CUN Cancun
8h 10m1 stop Monterrey Gen Mariano Escobedo
$309Viva
Thu, Sep 24 - Sun, Sep 27
Southwest Logo
1:05 pm - 4:40 pmCUN  Cancun-MDW Chicago Midway
3h 35mnonstop
Southwest Logo
7:10 am - 1:50 pmMDW  Chicago Midway-CUN Cancun
6h 40m1 stop Baltimore/Washington
$359Southwest
Thu, Sep 24 - Sun, Sep 27
Southwest Logo
12:50 pm - 9:00 pmCUN  Cancun-MDW Chicago Midway
8h 10m1 stop Baltimore/Washington
Southwest Logo
7:10 am - 1:50 pmMDW  Chicago Midway-CUN Cancun
6h 40m1 stop Baltimore/Washington
$369Southwest
Thu, Sep 24 - Sun, Sep 27
Frontier Logo
1:51 pm - 11:44 pmCUN  Cancun-MDW Chicago Midway
9h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 12:37 pmMDW  Chicago Midway-CUN Cancun
6h 12m1 stop Atlanta Hartsfield-Jackson
$395Frontier
Thu, Sep 24 - Sun, Sep 27
Frontier Logo
1:51 pm - 11:44 pmCUN  Cancun-MDW Chicago Midway
9h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 12:37 pmMDW  Chicago Midway-CUN Cancun
6h 12m1 stop Atlanta Hartsfield-Jackson
$396Frontier
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 United Airlines, followed by American Airlines and Frontier.

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

Good to know

Low season

January

Cheapest flight

$89
Best time to beat the crowds with an average 8% drop in price.
Flight from Reagan Washington National 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
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Worldwide

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $252
Business Class flights to Chicagofrom $214
Premium Economy Class flights to Chicagofrom $181
Economy Class flights to Chicagofrom $37