$88 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 8/29. 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
$276Multiple Airlines
Mon, Aug 3 - Wed, Aug 5
Frontier Logo
3:31 pm - 7:53 am
CUN
-
ORD
16h 22m
2 stops
Frontier Logo
6:05 am - 9:54 am
ORD
-
CUN
3h 49mnonstop
$279Frontier
Tue, Sep 15 - Fri, Sep 25
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
Volaris Logo
1:40 am - 2:28 pm
ORD
-
CUN
12h 48m
1 stop
$280Volaris
Fri, Sep 25 - Mon, Sep 28
JetBlue Logo
3:15 pm - 11:31 pm
CUN
-
ORD
8h 16m
1 stop
JetBlue Logo
6:00 am - 11:58 am
ORD
-
CUN
5h 58m
1 stop
$283JetBlue
Thu, Sep 17 - Mon, Sep 21
JetBlue Logo
3:15 pm - 11:31 pm
CUN
-
ORD
8h 16m
1 stop
JetBlue Logo
6:00 am - 11:58 am
ORD
-
CUN
5h 58m
1 stop
$285JetBlue
Tue, Oct 6 - Sat, Oct 10
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
Volaris Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$292Volaris
Thu, Oct 1 - Sat, Oct 3
Volaris Logo
9:50 pm - 5:52 am
CUN
-
ORD
8h 02m
1 stop
Volaris Logo
2:53 am - 12:04 pm
ORD
-
CUN
9h 11m
1 stop
$294Volaris
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
1:05 pm - 4:40 pm
CUN
-
MDW
3h 35mnonstop
Southwest Logo
8:25 am - 12:00 pm
MDW
-
CUN
3h 35mnonstop
$365Southwest
Thu, Aug 6 - Sat, Aug 8
Delta Logo
2:10 pm - 9:17 am
CUN
-
MDW
19h 07m
2 stops
Delta Logo
9:24 am - 11:25 am
MDW
-
CUN
26h 01m
2 stops
$380Delta
Tue, Oct 27 - Tue, Nov 3
Delta Logo
8:00 am - 10:10 pm
CUN
-
MDW
14h 10m
1 stop
Delta Logo
10:35 am - 9:15 pm
MDW
-
CUN
9h 40m
1 stop
$381Delta
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 seasonJanuary
Cheapest flight$88
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 4% lower on average.
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
Schererville
Munster
Chesterton
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 $323
Business Class flights to Chicagofrom $328
Premium Economy Class flights to Chicagofrom $240
Economy Class flights to Chicagofrom $56