$52 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 1/28. 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
$159
Overall average: $205
Frontier
Sat 1/17Mon 1/26
CUN - ORD • Non-stop
Cheapest one-way
$139
Typical prices: $201-$534
Spirit Airlines
Wed 1/28
CUN - ORD • 1 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

Sat, Jan 17 - Mon, Jan 26
Frontier Logo
3:25 pm - 6:40 pm
CUN
-
ORD
4h 15mnonstop
Frontier Logo
7:11 am - 12:19 pm
ORD
-
CUN
4h 08mnonstop
$159Frontier
Fri, Jan 23 - Fri, Jan 30
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
7:11 am - 12:19 pm
ORD
-
CUN
4h 08mnonstop
$166Frontier
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Multiple Airlines Logo
11:58 pm - 9:26 pm
ORD
-
CUN
20h 28m1 stop
$178Multiple Airlines
Fri, Jan 16 - Thu, Jan 22
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
7:11 am - 12:19 pm
ORD
-
CUN
4h 08mnonstop
$181Frontier
Fri, Jan 30 - Wed, Feb 4
Multiple Airlines Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Multiple Airlines Logo
6:05 am - 10:54 am
ORD
-
CUN
3h 49mnonstop
$199Multiple Airlines
Fri, Feb 6 - Mon, Feb 9
Aeromexico Logo
1:40 pm - 10:22 pm
CUN
-
MDW
9h 42m1 stop
Aeromexico Logo
10:46 am - 9:11 pm
MDW
-
CUN
9h 25m1 stop
$277Aeromexico
Thu, Jan 15 - Sun, Jan 18
Delta Logo
8:00 am - 4:29 pm
CUN
-
MDW
9h 29m1 stop
Delta Logo
6:45 am - 9:11 pm
MDW
-
CUN
13h 26m1 stop
$278Delta
Mon, Jan 12 - Sun, Jan 18
Delta Logo
12:05 pm - 10:07 pm
CUN
-
MDW
11h 02m2 stops
Delta Logo
6:45 am - 9:11 pm
MDW
-
CUN
13h 26m1 stop
$279Delta
Thu, Jan 15 - Mon, Jan 19
Finnair Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
Finnair Logo
5:40 pm - 8:50 am
ORD
-
MAD
8h 10mnonstop
$485Finnair
Wed, Apr 8 - Sun, Apr 12
Finnair Logo
4:40 pm - 6:50 pm
MAD
-
ORD
9h 10mnonstop
Finnair Logo
4:30 pm - 7:55 am
ORD
-
MAD
8h 25mnonstop
$497Finnair
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$52
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Newark Liberty Airport to Chicago Midway 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
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 $278
Business Class flights to Chicagofrom $281
Prem Econ Class flights to Chicagofrom $118
Economy Class flights to Chicagofrom $24