$38 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 1/8. 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
$155
Typical prices: $163-$289
Frontier
Thu 1/15Fri 1/30
CUN - ORD • Non-stop
Cheapest one-way
$136
Typical prices: $200-$523
Spirit Airlines
Thu 1/8
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

Thu, Jan 15 - 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
$155Frontier
Fri, Jan 23 - Mon, Jan 26
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
5:40 am - 1:47 pm
ORD
-
CUN
7h 07m1 stop
$156Frontier
Fri, Jan 23 - Mon, Jan 26
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
5:40 am - 1:47 pm
ORD
-
CUN
7h 07m1 stop
$157Frontier
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
3:25 pm - 6:40 pm
CUN
-
ORD
4h 15mnonstop
Frontier Logo
7:11 am - 12:19 pm
ORD
-
CUN
4h 08mnonstop
$158Frontier
Mon, Jan 26 - Sun, Feb 1
Multiple Airlines Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Multiple Airlines Logo
6:54 pm - 9:48 am
MDW
-
CUN
13h 54m1 stop
$267Multiple Airlines
Thu, Apr 2 - Sat, Apr 11
TAP AIR PORTUGAL Logo
10:25 pm - 4:00 pm
MAD
-
ORD
24h 35m1 stop
TAP AIR PORTUGAL Logo
6:15 pm - 3:20 pm
ORD
-
MAD
14h 05m1 stop
$495TAP AIR PORTUGAL
Thu, Jan 15 - Thu, Jan 29
Iberia Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
Iberia Logo
6:45 pm - 2:15 pm
ORD
-
MAD
12h 30m1 stop
$509Iberia
Thu, Jan 15 - Mon, Jan 19
British Airways Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
British Airways Logo
6:25 pm - 1:35 pm
ORD
-
MAD
12h 10m1 stop
$510British Airways
Thu, Jan 22 - Thu, Feb 5
British Airways Logo
12:40 pm - 11:27 pm
MAD
-
ORD
17h 47m1 stop
British Airways Logo
5:10 pm - 1:35 pm
ORD
-
MAD
13h 25m1 stop
$515British Airways
Thu, Jan 15 - Thu, Jan 29
Multiple Airlines Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
Multiple Airlines Logo
11:44 am - 6:20 am
ORD
-
MAD
11h 36m1 stop
$523Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$38
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 Dallas/Fort Worth 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
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 $193
Business Class flights to Chicagofrom $334
Prem Econ Class flights to Chicagofrom $128
Economy Class flights to Chicagofrom $24