$42 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 1/26. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$159
Typical prices: $183-$297
Frontier
Thu 1/29Tue 2/3
CUN - ORD • Non-stop
Cheapest one-way
$133
Typical prices: $200-$513
Frontier
Mon 1/26
CUN - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
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 29 - Tue, Feb 3
Frontier Logo
11:40 am - 2:49 pmCUN-ORD
4h 09mnonstop
Frontier Logo
7:11 am - 12:19 pmORD-CUN
4h 08mnonstop
$159Frontier
Find Deal
Wed, Jan 14 - Sun, Jan 18
Frontier Logo
3:25 pm - 6:40 pmCUN-ORD
4h 15mnonstop
Frontier Logo
6:45 am - 11:49 amORD-CUN
4h 04mnonstop
$161Frontier
Find Deal
Tue, Dec 23 - Thu, Jan 1
Frontier Logo
6:22 pm - 9:32 pmCUN-ORD
4h 10mnonstop
Frontier Logo
10:37 am - 3:48 pmORD-CUN
4h 11mnonstop
$162Frontier
Find Deal
Thu, Dec 25 - Fri, Jan 2
Delta Logo
8:00 am - 5:26 pmCUN-MDW
10h 26m2 stops
Delta Logo
9:50 am - 4:30 pmMDW-CUN
5h 40m1 stop
$277Delta
Find Deal
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
2:51 pm - 11:25 pmCUN-MDW
9h 34m1 stop
Multiple Airlines Logo
8:56 pm - 9:18 amMDW-CUN
11h 22m1 stop
$299Multiple Airlines
Find Deal
Thu, Jan 22 - Wed, Jan 28
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
Southwest Logo
6:50 am - 3:25 pmMDW-CUN
7h 35m1 stop
$319Southwest
Find Deal
Sat, Feb 21 - Sun, Mar 1
American Airlines Logo
12:00 pm - 2:55 pmMAD-ORD
9h 55mnonstop
American Airlines Logo
11:40 am - 6:20 amORD-MAD
11h 40m1 stop
$475American Airlines
Find Deal
Fri, Feb 6 - Sun, Feb 22
American Airlines Logo
12:55 am - 9:53 amMAD-ORD
15h 58m1 stop
American Airlines Logo
5:40 pm - 8:50 amORD-MAD
8h 10mnonstop
$481American Airlines
Find Deal
Sat, Dec 13 - Thu, Feb 12
Multiple Airlines Logo
12:00 pm - 2:55 pmMAD-ORD
9h 55mnonstop
Multiple Airlines Logo
2:20 pm - 8:55 amORD-MAD
11h 35m1 stop
$487Multiple Airlines
Find Deal
Thu, Jan 15 - Thu, Jan 29
Delta Logo
6:00 am - 6:32 pmMAD-MDW
19h 32m2 stops
Delta Logo
6:35 pm - 3:20 pmMDW-MAD
13h 45m2 stops
$553Delta
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$42
Best time to beat the crowds with an average 14% 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 $210
Business Class flights to Chicagofrom $288
Prem Econ Class flights to Chicagofrom $78
Economy Class flights to Chicagofrom $24