$54 Find deals on international flights to Chicago

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 2/26. 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

KAYAK searches hundreds of travel sites at once for cheap international flights to Chicago

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Everything you should know

Cheapest round-trip
$195
Overall average: $324
Frontier
Fri 3/6Mon 3/9
CUN - ORD • Non-stop
Cheapest non-stop
$191
Typical prices: $155-$230
Frontier
Thu 2/19Mon 2/23
CUN - ORD • Non-stop
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We hope you love your trip to Chicago!
Flight Deals
Useful Info
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

Fri, Mar 6 - Mon, Mar 9
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
6:30 am - 10:34 am
ORD
-
CUN
4h 04mnonstop
$195Frontier
Wed, May 6 - Sun, May 17
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
6:30 am - 10:33 am
ORD
-
CUN
4h 03mnonstop
$201Frontier
Wed, May 6 - Sun, May 17
Multiple Airlines Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$215Multiple Airlines
Wed, May 6 - Sun, May 17
Multiple Airlines Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$225Multiple Airlines
Thu, Apr 16 - Tue, Apr 21
United Airlines Logo
12:55 pm - 5:00 pm
CUN
-
ORD
4h 05mnonstop
United Airlines Logo
8:51 am - 7:19 pm
ORD
-
CUN
10h 28m
1 stop
$234United Airlines
Fri, Feb 27 - Mon, Mar 2
Aeromexico Logo
8:00 am - 5:45 pm
CUN
-
MDW
10h 45m
1 stop
Aeromexico Logo
10:49 am - 9:11 pm
MDW
-
CUN
9h 22m
1 stop
$280Aeromexico
Thu, Apr 16 - Tue, Apr 21
Delta Logo
10:00 am - 10:28 pm
CUN
-
MDW
12h 28m
1 stop
Delta Logo
9:27 am - 8:14 pm
MDW
-
CUN
10h 47m
2 stops
$281Delta
Thu, Feb 26 - Wed, Mar 4
Delta Logo
1:40 pm - 10:31 pm
CUN
-
MDW
9h 51m
1 stop
Delta Logo
9:34 am - 9:11 pm
MDW
-
CUN
10h 37m
2 stops
$291Delta
Fri, Mar 6 - Sun, Mar 8
Aeromexico Logo
8:00 am - 5:45 pm
CUN
-
MDW
10h 45m
1 stop
Aeromexico Logo
6:00 am - 8:20 pm
MDW
-
CUN
14h 20m
1 stop
$343Aeromexico
Fri, Feb 27 - Mon, Mar 9
United Airlines Logo
11:15 am - 7:53 pm
MAD
-
ORD
15h 38m
1 stop
United Airlines Logo
2:35 pm - 9:15 am
ORD
-
MAD
12h 40m
1 stop
$498United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$54
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 10% increase in price.
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.

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
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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 $359
Business Class flights to Chicagofrom $249
Premium Economy Class flights to Chicagofrom $157
Economy Class flights to Chicagofrom $49