$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 11/2. 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, Sep 24 - Mon, Sep 28
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
$295Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
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
$297Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
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
$298Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
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
$301Arajet
Fri, Oct 9 - Sat, Oct 17
Viva Logo
11:30 am - 1:10 pm
CUN
-
ORD
25h 40m
1 stop
Viva Logo
2:40 pm - 10:15 pm
ORD
-
CUN
7h 35m
1 stop
$310Viva
Thu, Oct 22 - Mon, Oct 26
Arajet Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Arajet Logo
4:30 am - 4:57 pm
ORD
-
CUN
12h 27m
1 stop
$311Arajet
Sun, Sep 13 - Sun, Sep 20
Frontier Logo
1:51 pm - 11:44 pm
CUN
-
MDW
9h 53m
1 stop
Frontier Logo
6:25 am - 12:37 pm
MDW
-
CUN
6h 12m
1 stop
$393Frontier
Thu, Nov 5 - Sun, Nov 8
Frontier Logo
3:24 pm - 9:53 pm
CUN
-
MDW
7h 29m
1 stop
Frontier Logo
7:25 am - 2:14 pm
MDW
-
CUN
5h 49m
1 stop
$394Frontier
Fri, Oct 2 - Mon, Oct 5
Delta Logo
7:01 am - 10:44 pm
CUN
-
MDW
15h 43m
2 stops
Delta Logo
1:00 pm - 7:50 pm
MDW
-
CUN
6h 50m
1 stop
$401Delta
Wed, Oct 14 - Wed, Oct 28
Delta Logo
9:16 am - 10:33 pm
CUN
-
MDW
13h 17m
2 stops
Delta Logo
9:29 am - 7:55 pm
MDW
-
CUN
10h 26m
2 stops
$413Delta
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 season

January

Cheapest flight

$89
Best time to beat the crowds with an average 7% 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.

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