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.

$89 International Flights to Chicago

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Flight Deals

Book Cheap International Flights Deals to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip international flight deals to Chicago

Thu, Sep 24 - Mon, Sep 28

12:35 pm - 11:40 pmCUN Cancun-ORD Chicago O'Hare Intl

11h 05m1 stop Punta Cana

7:35 am - 9:03 pmORD Chicago O'Hare Intl-CUN Cancun

13h 28m1 stop Mexico City Benito Juarez

$289Multiple Airlines

Thu, Sep 24 - Mon, Sep 28

12:35 pm - 11:40 pmCUN Cancun-ORD Chicago O'Hare Intl

11h 05m1 stop Punta Cana

7:35 am - 9:03 pmORD Chicago O'Hare Intl-CUN Cancun

13h 28m1 stop Mexico City Benito Juarez

$291Multiple Airlines

Thu, Sep 24 - Mon, Sep 28

12:35 pm - 11:40 pmCUN Cancun-ORD Chicago O'Hare Intl

11h 05m1 stop Punta Cana

7:35 am - 9:03 pmORD Chicago O'Hare Intl-CUN Cancun

13h 28m1 stop Mexico City Benito Juarez

$301Multiple Airlines

Sun, Feb 7 - Fri, Feb 19

12:30 pm - 10:50 pmCUN Cancun-ORD Chicago O'Hare Intl

11h 20m1 stop Monterrey Gen Mariano Escobedo

12:30 am - 10:50 pmORD Chicago O'Hare Intl-CUN Cancun

21h 20m1 stop Monterrey Gen Mariano Escobedo

$303Viva

Thu, Oct 1 - Mon, Oct 5

9:50 pm - 5:52 amCUN Cancun-ORD Chicago O'Hare Intl

8h 02m1 stop Mexico City Benito Juarez

7:35 am - 9:03 pmORD Chicago O'Hare Intl-CUN Cancun

13h 28m1 stop Mexico City Benito Juarez

$307Volaris

Thu, Sep 3 - Mon, Sep 7

12:35 pm - 11:40 pmCUN Cancun-ORD Chicago O'Hare Intl

11h 05m1 stop Punta Cana

5:30 am - 5:12 pmORD Chicago O'Hare Intl-CUN Cancun

11h 42m1 stop Punta Cana

$309Arajet

Thu, Sep 24 - Mon, Sep 28

1:51 pm - 11:44 pmCUN Cancun-MDW Chicago Midway

9h 53m1 stop Atlanta Hartsfield-Jackson

6:25 am - 12:37 pmMDW Chicago Midway-CUN Cancun

6h 12m1 stop Atlanta Hartsfield-Jackson

$310Frontier

Thu, Sep 3 - Tue, Sep 8

12:35 pm - 11:40 pmCUN Cancun-ORD Chicago O'Hare Intl

11h 05m1 stop Punta Cana

1:40 am - 10:03 amORD Chicago O'Hare Intl-CUN Cancun

8h 23m1 stop Mexico City Benito Juarez

$310Multiple Airlines

Fri, Oct 30 - Sun, Nov 8

10:29 am - 2:30 pmCUN Cancun-ORD Chicago O'Hare Intl

4h 01mnonstop

7:30 am - 12:25 pmORD Chicago O'Hare Intl-CUN Cancun

3h 55mnonstop

$313Frontier

Fri, Sep 4 - Mon, Sep 7

9:50 pm - 5:52 amCUN Cancun-ORD Chicago O'Hare Intl

8h 02m1 stop Mexico City Benito Juarez

7:35 am - 9:03 pmORD Chicago O'Hare Intl-CUN Cancun

13h 28m1 stop Mexico City Benito Juarez

$315Volaris

Recent last minute international flight deals to Chicago

Thu, Aug 20 - Fri, Aug 21

11:10 am - 8:15 pmCUN Cancun-ORD Chicago O'Hare Intl

9h 05m1 stop Dallas/Fort Worth

1:59 am - 1:36 pmORD Chicago O'Hare Intl-CUN Cancun

11h 37m1 stop León Del Bajio

$420Volaris

Fri, Aug 21 - Fri, Aug 28

11:10 am - 8:31 pmCUN Cancun-MDW Chicago Midway

9h 21m1 stop Dallas/Fort Worth

8:23 pm - 9:55 amMDW Chicago Midway-CUN Cancun

13h 32m1 stop Guadalajara Miguel Hidal

$447Multiple Airlines

Fri, Aug 21 - Mon, Aug 24

5:22 pm - 10:15 amCUN Cancun-ORD Chicago O'Hare Intl

16h 53m1 stop Houston George Bush Intcntl

9:29 am - 1:10 pmORD Chicago O'Hare Intl-CUN Cancun

3h 41mnonstop

$535United Airlines

Fri, Aug 21 - Fri, Aug 28

1:00 pm - 9:30 pmCUN Cancun-MDW Chicago Midway

8h 30m1 stop Orlando

8:25 am - 12:00 pmMDW Chicago Midway-CUN Cancun

3h 35mnonstop

$571Southwest

Fri, Aug 21 - Fri, Aug 28

7:51 am - 12:59 amCUN Cancun-ORD Chicago O'Hare Intl

17h 08m1 stop Houston George Bush Intcntl

10:46 am - 2:26 pmORD Chicago O'Hare Intl-CUN Cancun

3h 40mnonstop

$605United Airlines

Fri, Aug 21 - Fri, Aug 28

1:00 pm - 10:40 pmCUN Cancun-MDW Chicago Midway

9h 40m1 stop Orlando

5:30 am - 3:00 pmMDW Chicago Midway-CUN Cancun

9h 30m2 stops Dallas Love Field Houston Hobby

$660Southwest

Sun, Aug 23 - Wed, Aug 26

8:05 am - 10:36 pmCUN Cancun-MDW Chicago Midway

14h 31m1 stop Atlanta Hartsfield-Jackson

9:24 am - 8:05 pmMDW Chicago Midway-CUN Cancun

10h 41m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$846Delta

Mon, Aug 24 - Mon, Sep 28

12:50 pm - 4:10 pmMAD Madrid Barajas-ORD Chicago O'Hare Intl

34h 20m1 stop Kastrup Copenhagen

7:15 pm - 6:55 pmORD Chicago O'Hare Intl-MAD Madrid Barajas

16h 40m1 stop Kastrup Copenhagen

$858Scandinavian Airlines

Sun, Aug 23 - Wed, Sep 9

12:50 pm - 4:10 pmMAD Madrid Barajas-ORD Chicago O'Hare Intl

34h 20m2 stops Stockholm Arlanda Kastrup Copenhagen

7:15 pm - 6:55 pmORD Chicago O'Hare Intl-MAD Madrid Barajas

16h 40m1 stop Kastrup Copenhagen

$872Scandinavian Airlines

Mon, Aug 24 - Mon, Aug 31

6:00 am - 2:30 pmMAD Madrid Barajas-ORD Chicago O'Hare Intl

15h 30m1 stop Amsterdam Schiphol

5:20 pm - 4:45 pmORD Chicago O'Hare Intl-MAD Madrid Barajas

16h 25m2 stops Detroit Metropolitan Wayne County Paris Charles de Gaulle

$930Delta

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 United Airlines, followed by American Airlines and Frontier.

Low season	January
High season	October
Cheapest flight	$89

Best time to beat the crowds with an average 8% drop in price.

Flight from Reagan Washington National Airport to Chicago O'Hare Airport

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.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

Direct Flights

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Return flight deals

Cabin class types available on flights to Worldwide

First Class flights to Chicagofrom $252

Business Class flights to Chicagofrom $214

Premium Economy Class flights to Chicagofrom $181

Economy Class flights to Chicagofrom $37

$89 Find deals on international flights to Chicago - Compare and Save

Book Cheap International Flights Deals to Chicago

Recent round-trip international flight deals to Chicago

Recent one-way international flight deals to Chicago

Recent last minute international flight deals to Chicago

Recent direct international flight deals to Chicago

KAYAK's insights & trends for flights to Chicago

What are the most popular airlines flying to Chicago?

Good to know

Low season

High season

Cheapest flight

FAQs for booking Worldwide to Chicago flights

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Worldwide

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Worldwide

Choose which airport to fly into in Chicago

Find deals for your return flight