ORD - CUN

Find cheap flights from Chicago to Cancun

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KAYAK searches hundreds of travel sites at once for deals on flights to Cancún

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cancún, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cancún, as well as popular online travel agencies
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Cheap Flight Deals from Chicago to Cancún (ORD-CUN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Cancún 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.

Recent round-trip flight deals from Chicago to Cancún

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Cancún.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
American Airlines Logo
ORD-CUN
3h 40mdirect
American Airlines Logo
CUN-ORD
4h 00mdirect
American Airlines
Find Deal
Frontier Logo
ORD-CUN
4h 02mdirect
Frontier Logo
CUN-ORD
4h 03mdirect
Frontier
Find Deal
Emirates Logo
ORD-CUN
3h 53mdirect
Emirates Logo
CUN-ORD
3h 58mdirect
Emirates
Find Deal
Southwest Logo
ORD-CUN
3h 45mdirect
Southwest Logo
CUN-ORD
4h 00mdirect
Southwest
Find Deal
United Airlines Logo
ORD-CUN
3h 53mdirect
United Airlines Logo
CUN-ORD
3h 58mdirect
United Airlines
Find Deal
Spirit Airlines Logo
ORD-CUN
3h 41mdirect
Spirit Airlines Logo
CUN-ORD
4h 03mdirect
Spirit Airlines
Find Deal

Expert advice for your flight from Chicago to Cancún

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are specific to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
ORD

Security lines at O'Hare can exceed 30 minutes during peak times. Arrive early to ensure a smooth departure.

Read more about ORDby Stefanie Waldek
CUN

Immigration at Cancun Airport is typically quick, often taking just 5–15 minutes thanks to recent renovations.

Read more about CUNby Brandon Schultz
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Brandon Schultz

Brandon Schultz

Expert on CUN

Brandon Schultz

Brandon Schultz

Brandon travels every week and makes friends with stray cats wherever he goes. Dogs, too... he once brought one home to the US from the Amalfi Coast. He’s written 6 books, visited 6 continents (still waiting on Antarctica), and would eat ice cream 6 times a day if he could. He lives in Brooklyn, New York, with his partner and three cats.

Read more

KAYAK's insights & trends for Chicago to Cancún flights

Get data-powered insights and trends into flights from Chicago to Cancún to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Cancún?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Cancún, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago O'Hare Intl Airport to Cancún is September, where tickets cost C$ 442 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is C$ 704 and C$ 683 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Cancún?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Cancún, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago O'Hare Intl Airport to Cancún, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low season

September

High season

March
Best time to beat the crowds (22% less expensive on average)
Most popular time to fly (25% more expensive on average)

When to book flights from Chicago to Cancún

Are your dates flexible? Find out the best times to travel from Chicago to Cancún based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Cancun flights

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Cancun?

    American Airlines, British Airways, Delta, and Aeromexico offer inflight Wi-Fi service on the Chicago to Cancun flight route.

  • Which aircraft models fly most regularly from Chicago to Cancun?

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago to Cancun flight route.

  • Which airline alliances offer flights from Chicago to Cancun?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Cancun, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Cancun?

    There are direct flights from Chicago to Cancun on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago to Cancun?

    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 Chicago to Cancun.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Cancun?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cancun from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Cancun?

    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 Cancun with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Cancun?

    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 Cancun from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Cancún

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 402 or less one-way.

Prefer to fly direct from Chicago to Cancun?

Find which airlines fly direct from Chicago O'Hare Intl Airport to Cancun Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Cancun

Monday

American Airlines,Emirates,Frontier, +2 more

American Airlines,Emirates, +3 more

Tuesday

American Airlines,Emirates,Frontier, +1 more

American Airlines,Emirates, +2 more

Wednesday

American Airlines,Emirates,Frontier, +1 more

American Airlines,Emirates, +2 more

Thursday

American Airlines,Emirates,Frontier, +2 more

American Airlines,Emirates, +3 more

Friday

American Airlines,Emirates,Frontier, +2 more

American Airlines,Emirates, +3 more

Saturday

American Airlines,Emirates,Frontier, +3 more

American Airlines,Emirates, +4 more

Sunday

American Airlines,Emirates,Frontier, +2 more

American Airlines,Emirates, +3 more

See more nonstop flights

Direct returns

Cancun to Chicago O'Hare Intl

Monday

American Airlines,Emirates,Frontier, +3 more

American Airlines,Emirates, +4 more

Tuesday

American Airlines,Emirates,Frontier, +2 more

American Airlines,Emirates, +3 more

Wednesday

American Airlines,Emirates,Frontier, +2 more

American Airlines,Emirates, +3 more

Thursday

American Airlines,Emirates,Frontier, +3 more

American Airlines,Emirates, +4 more

Friday

American Airlines,Emirates,Frontier, +3 more

American Airlines,Emirates, +4 more

Saturday

American Airlines,Emirates,Frontier, +4 more

American Airlines,Emirates, +5 more

Sunday

American Airlines,Emirates,Frontier, +3 more

American Airlines,Emirates, +4 more

See more nonstop flights
See more nonstop flights

Everything you need to know for your flight from Chicago to Cancún

Information on your arrival and departure airports

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