$72 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 6/9. 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, Jul 23 - Wed, Jul 29
Frontier Logo
11:00 am - 3:09 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
6:05 am - 9:54 am
ORD
-
CUN
3h 49mnonstop
$266Frontier
Mon, Aug 31 - Wed, Sep 9
Volaris Logo
3:20 pm - 11:47 pm
CUN
-
ORD
8h 27m
1 stop
Volaris Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$282Volaris
Thu, Jun 11 - Mon, Jun 15
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
Volaris Logo
1:59 am - 10:31 am
ORD
-
CUN
8h 32m
1 stop
$298Volaris
Fri, Jul 24 - Fri, Jul 31
Delta Logo
8:00 am - 10:15 pm
CUN
-
MDW
14h 15m
1 stop
Delta Logo
12:41 pm - 8:23 pm
MDW
-
CUN
7h 42m
1 stop
$332Delta
Tue, Jul 21 - Tue, Jul 28
Delta Logo
8:00 am - 6:25 pm
CUN
-
MDW
10h 25m
2 stops
Delta Logo
6:00 am - 2:36 pm
MDW
-
CUN
8h 36m
1 stop
$351Delta
Wed, Jun 10 - Sun, Jun 28
Multiple Airlines Logo
10:40 am - 7:04 pm
CUN
-
MDW
8h 24m
1 stop
Multiple Airlines Logo
6:00 am - 1:51 pm
MDW
-
CUN
7h 51m
1 stop
$370Multiple Airlines
Sat, Jun 13 - Wed, Jul 8
British Airways Logo
10:25 am - 3:44 pm
MAD
-
ORD
12h 19m
1 stop
British Airways Logo
3:29 pm - 9:35 am
ORD
-
MAD
11h 06m
1 stop
$663British Airways
Sat, Sep 5 - Sun, Sep 20
British Airways Logo
1:35 pm - 4:00 pm
MAD
-
ORD
9h 25mnonstop
British Airways Logo
9:00 pm - 3:50 pm
ORD
-
MAD
11h 50m
1 stop
$664British Airways
Tue, Jun 16 - Tue, Jun 30
ITA Airways Logo
5:55 am - 1:10 pm
MAD
-
ORD
14h 15m
1 stop
ITA Airways Logo
3:00 pm - 5:10 pm
ORD
-
MAD
19h 10m
1 stop
$665ITA Airways
Fri, Oct 30 - Sat, Nov 7
Multiple Airlines Logo
1:00 pm - 4:10 pm
MAD
-
ORD
9h 10mnonstop
Multiple Airlines Logo
9:45 pm - 4:50 pm
ORD
-
MAD
12h 05m
1 stop
$666Multiple Airlines
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$72
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Dallas/Fort Worth 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
Schererville
Chesterton
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 $361
Business Class flights to Chicagofrom $312
Premium Economy Class flights to Chicagofrom $303
Economy Class flights to Chicagofrom $56