$96 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 8/6. 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 1 - Sat, Oct 3
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
Volaris Logo
1:40 am - 2:28 pm
ORD
-
CUN
12h 48m
1 stop
$266Volaris
Thu, Sep 3 - Tue, Sep 8
Multiple Airlines Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$268Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Arajet Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Arajet Logo
5:30 am - 5:12 pm
ORD
-
CUN
11h 42m
1 stop
$270Arajet
Mon, Sep 14 - Tue, Sep 15
Volaris Logo
9:50 pm - 5:52 am
CUN
-
ORD
8h 02m
1 stop
Volaris Logo
1:40 am - 10:03 am
ORD
-
CUN
8h 23m
1 stop
$276Volaris
Tue, Aug 25 - Fri, Aug 28
Volaris Logo
12:49 pm - 12:55 am
CUN
-
ORD
12h 06m
1 stop
Volaris Logo
6:21 am - 6:14 pm
ORD
-
CUN
11h 53m
1 stop
$278Volaris
Thu, Aug 20 - Thu, Aug 27
Frontier Logo
11:10 am - 10:47 pm
CUN
-
MDW
11h 37m
2 stops
Frontier Logo
9:26 pm - 10:00 am
MDW
-
CUN
12h 34m
1 stop
$370Frontier
Fri, Sep 18 - Wed, Sep 23
Delta Logo
2:00 pm - 10:45 pm
CUN
-
MDW
8h 45m
1 stop
Delta Logo
10:48 am - 7:50 pm
MDW
-
CUN
9h 02m
1 stop
$381Delta
Tue, Oct 27 - Tue, Nov 3
Delta Logo
8:00 am - 10:25 pm
CUN
-
MDW
14h 25m
1 stop
Delta Logo
10:58 am - 9:15 pm
MDW
-
CUN
9h 17m
1 stop
$382Delta
Wed, Jul 29 - Wed, Aug 5
Frontier Logo
11:10 am - 10:03 pm
CUN
-
MDW
10h 53m
2 stops
Frontier Logo
6:05 am - 1:53 pm
MDW
-
CUN
7h 48m
1 stop
$393Frontier
Thu, Sep 3 - Wed, Sep 16
Scandinavian Airlines Logo
12:00 pm - 4:10 pm
MAD
-
ORD
35h 10m
2 stops
Scandinavian Airlines Logo
7:15 pm - 6:55 pm
ORD
-
MAD
16h 40m
1 stop
$660Scandinavian 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
Southwest
Southwest
#4 most popular
Find deals

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from New York John F Kennedy 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.

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 $323
Business Class flights to Chicagofrom $328
Premium Economy Class flights to Chicagofrom $240
Economy Class flights to Chicagofrom $56