$50 Find deals on international flights to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 4/23. 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
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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, Apr 23 - Mon, Apr 27
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
6:30 am - 10:38 am
ORD
-
CUN
4h 08mnonstop
$144Frontier
Wed, Apr 22 - Sun, Apr 26
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
6:30 am - 10:38 am
ORD
-
CUN
4h 08mnonstop
$145Frontier
Thu, Apr 16 - Fri, Apr 24
Frontier Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Frontier Logo
6:30 am - 10:38 am
ORD
-
CUN
4h 08mnonstop
$161Frontier
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
10:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$201Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Delta Logo
12:40 pm - 10:28 pm
CUN
-
MDW
9h 48m
1 stop
Delta Logo
10:41 am - 8:15 pm
MDW
-
CUN
9h 34m
1 stop
$276Delta
Thu, Apr 23 - Mon, Apr 27
Delta Logo
1:50 pm - 10:28 pm
CUN
-
MDW
8h 38m
1 stop
Delta Logo
10:41 am - 8:15 pm
MDW
-
CUN
9h 34m
1 stop
$279Delta
Thu, Apr 16 - Wed, Apr 29
TAP AIR PORTUGAL Logo
10:25 pm - 4:00 pm
MAD
-
ORD
24h 35m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 7:10 pm
ORD
-
MAD
18h 10m
1 stop
$483TAP AIR PORTUGAL
Wed, Apr 15 - Wed, Apr 22
TAP AIR PORTUGAL Logo
7:40 am - 4:00 pm
MAD
-
ORD
15h 20m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 5:00 pm
ORD
-
MAD
16h 00m
1 stop
$484TAP AIR PORTUGAL
Thu, Apr 16 - Wed, Apr 29
Virgin Atlantic Logo
12:45 pm - 10:28 pm
MAD
-
MDW
16h 43m
1 stop
Virgin Atlantic Logo
10:41 am - 9:56 am
MDW
-
MAD
16h 15m
2 stops
$588Virgin Atlantic
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
3:11 pm - 11:00 am
CUN
-
RFD
43h 49m
2 stops
Multiple Airlines Logo
10:37 am - 12:38 pm
RFD
-
CUN
26h 01m
1 stop
$605Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$50
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 9% 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 $155
Business Class flights to Chicagofrom $271
Premium Economy Class flights to Chicagofrom $156
Economy Class flights to Chicagofrom $48