One Way

Popular Filters

+ 1 more

One Way Price

CAD 270 CAD 900

Duration

4 h 30 m 14 h 30 m

Stops From Chicago

Departure From Chicago

Before 6 AM

CAD 270

6 AM - 12 PM

CAD 270

12 PM - 6 PM

CAD 307

After 6 PM

CAD 288

Arrival at Cancun

6 AM - 12 PM

CAD 288

12 PM - 6 PM

CAD 270

After 6 PM

CAD 270

Alliances & Airlines

Oneworld

(3)

SkyTeam

(6)

Star Alliance

(5)

+ 1 more

Layover Airports

Layover Duration

45 m 7 h 30 m

Chicago To Cancun Flights

Book Chicago to Cancun flight tickets at lowest price. Get best deals on your upcoming Chicago to Cancun flights only on MakeMyTrip. Also Book Cancun to Chicago Flights. Currently 19 flights flying from Chicago to Cancun. To save maximum on flight booking click on below Fare Calendar button and choose your dates.Avail Zero Cancellation for flight bookings.


Sorted By:
Departure
Duration
Arrival
Price
Volaris

CAD 270

Chicago to Cancun , 2 Jun

Volaris Y4 | 703

01:40

Tue, 2 Jun 26

Terminal T5

Chicago, United States

04 h 10 m

04:50

Tue, 2 Jun 26

Terminal T1

Mexico City, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Volaris Y4 | 102

11:10

Tue, 2 Jun 26

Terminal T1

Mexico City, Mexico

02 h 18 m

14:28

Tue, 2 Jun 26

Terminal T2

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

CAD 288

Transit Visa may be required

Chicago to Cancun , 2 Jun

Air Canada AC | 5138 | Operated By United Airlines

21:20

Tue, 2 Jun 26

Terminal T1

Chicago, United States

01 h 39 m

23:59

Tue, 2 Jun 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 1810

06:50

Wed, 3 Jun 26

Terminal T1

Toronto, Canada

04 h

09:50

Wed, 3 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Volaris

CAD 302

Chicago to Cancun , 2 Jun

Volaris Y4 | 7731

01:59

Tue, 2 Jun 26

Terminal T5

Chicago, United States

03 h 51 m

04:50

Tue, 2 Jun 26

Leon/Guanajuato, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Volaris Y4 | 3501

07:00

Tue, 2 Jun 26

Leon/Guanajuato, Mexico

02 h 31 m

10:31

Tue, 2 Jun 26

Terminal T2

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

CAD 317

CAD 307

Transit Visa may be required

Chicago to Cancun , 2 Jun

Air Canada AC | 4899 | Operated By United Airlines

12:55

Tue, 2 Jun 26

Terminal T1

Chicago, United States

01 h 51 m

15:46

Tue, 2 Jun 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 1812

17:10

Tue, 2 Jun 26

Terminal T1

Toronto, Canada

04 h

20:10

Tue, 2 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

More Timing Options

CAD 347

CAD 335

Chicago to Cancun , 2 Jun

Delta Air Lines DL | 1247

07:07

Tue, 2 Jun 26

Terminal T5

Chicago, United States

02 h 10 m

10:17

Tue, 2 Jun 26

Terminal S

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 598

11:02

Tue, 2 Jun 26

Terminal I

Atlanta, United States

02 h 38 m

12:40

Tue, 2 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Aeromexico

CAD 401

Chicago to Cancun , 2 Jun

Aeromexico AM | 4237 | Operated By Delta Air Lines

08:10

Tue, 2 Jun 26

Terminal T5

Chicago, United States

01 h 57 m

11:07

Tue, 2 Jun 26

Terminal S

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Aeromexico AM | 5533 | Operated By Delta Air Lines

12:27

Tue, 2 Jun 26

Terminal I

Atlanta, United States

02 h 35 m

14:02

Tue, 2 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

CAD 501

CAD 484

Chicago to Cancun , 2 Jun

American Airlines AA | 1503

08:20

Tue, 2 Jun 26

Terminal T3

Chicago, United States

03 h 48 m

12:08

Tue, 2 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

United Airlines

CAD 516

CAD 499

Chicago to Cancun , 2 Jun

United Airlines UA | 1198

09:17

Tue, 2 Jun 26

Terminal T1

Chicago, United States

03 h 53 m

13:10

Tue, 2 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Aeromexico

CAD 499

Chicago to Cancun , 2 Jun

Aeromexico AM | 4011 | Operated By Delta Air Lines

07:07

Tue, 2 Jun 26

Terminal T5

Chicago, United States

02 h 10 m

10:17

Tue, 2 Jun 26

Terminal S

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Aeromexico AM | 5319 | Operated By Delta Air Lines

11:02

Tue, 2 Jun 26

Terminal I

Atlanta, United States

02 h 38 m

12:40

Tue, 2 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

CAD 532

Chicago-Midway to Cancun , 2 Jun

Southwest Airlines WN | 218

10:30

Tue, 2 Jun 26

Chicago-Midway, United States

03 h 30 m

14:00

Tue, 2 Jun 26

Terminal T4

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Cancun Address

Chicago Address

Chicago to Cancun Flights Information:-

Looking for Chicago to Cancun Flight? Hereโ€™s all you need to know! For convenience and to save time, pick the airport that is closest to your destination. The nearest airport to Cancun is Cancun Intl and the IATA code for the same is CUN.
Currently, there are 7 airlines operating flights between the two destinations and approximately 19 flights take off from Chicago to Cancun every week.

Need information on Chicago to Cancun airfare?

The minimum airfare for a Chicago to Cancun flight would be 270, which may go up to 814 depending on the route, booking time and availability.
It is recommended that you book a round-trip, since it always works out to be more economical.

Flight Details for Chicago to Cancun

If you are looking for Chicago to Cancun flights, there is no dearth of options to choose from. Several reputed airlines currently offer both direct and indirect flights between the two destinations. Some of these are Aeromexico, Air Canada, American Airlines, Delta Air Lines, Southwest Airlines, United Airlines, Volaris. Out of these, only 5 airlines operate direct flights. Indirect flights may involve more travel time, but they usually cost lesser than direct flights.

The number of flights operated by each airline is as follows:Aeromexico : 2, Air Canada : 2, American Airlines : 2, Delta Air Lines : 2, Southwest Airlines : 2, United Airlines : 2, Volaris : 2

To board the first Chicago to Cancun flight, choose Volaris, which departs at 01:40 The last flight for this route is Air Canada, departing at 21:20

Cancun Airport Information

Cancun Intl

About Chicago (CHI)

Chicago is a dazzling city that captivates visitors with its vibrant atmosphere and stunning architecture. For travelers from Canada, Chicago offers an array of experiences, from world-class museums to picturesque waterfront parks. The city's rich cultural heritage and dynamic arts scene make it a must-visit destination.

Best Time to Visit

The ideal time to visit Chicago is during the spring (April to June) and fall (September to November) when the weather is pleasant, and the city is alive with festivals. Summers can be warm and bustling, while winters are cold and snowy, perfect for those who enjoy winter sports.

Getting There

Chicago is served by two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). There are numerous flights to Chicago from Canada, including direct flights from Toronto, Vancouver, and Montreal. Ensure you have a valid passport and check visa requirements before booking your flight. Airlines such as Air Canada and United Airlines offer cheap flights to Chicago, making it accessible for Canadian travelers.

Where to Stay

Chicago boasts a wide range of accommodation options to suit all budgets. For luxury, consider staying in the Magnificent Mile area, home to upscale hotels and designer boutiques. Budget travelers can find affordable options in neighborhoods like Lincoln Park and Wicker Park. The Loop, Chicago's downtown area, is ideal for tourists wanting to be close to major attractions.

Must-See Places & Experiences

Chicago is renowned for its iconic landmarks and cultural institutions. Don't miss:
โ€ข The Art Institute of Chicago
โ€ข Millennium Park and the famous Cloud Gate sculpture
โ€ข Navy Pier, offering entertainment and stunning lake views
โ€ข Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium
โ€ข The Magnificent Mile for shopping
โ€ข Willis Tower Skydeck for breathtaking city views

Local Transportation

Chicago's public transportation system is efficient and easy to navigate. The Chicago Transit Authority (CTA) operates buses and trains that connect the city and suburbs. Taxis and ride-sharing services like Uber and Lyft are readily available. For a scenic option, consider renting a bike and exploring the city's extensive bike paths.

Food & Dining

Chicago's culinary scene is diverse and delicious. Be sure to try local specialties such as deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. The city offers a variety of dining options, from Michelin-starred restaurants to casual eateries. Recommended spots include:
โ€ข Lou Malnati's Pizzeria for deep-dish pizza
โ€ข Portillo's for Chicago-style hot dogs
โ€ข Alinea for an upscale dining experience

Practical Travel Tips

โ€ข Currency: The US Dollar (USD)
โ€ข Language: English
โ€ข Safety: Chicago is generally safe, but be aware of your surroundings and avoid less populated areas at night
โ€ข Useful Apps: Download the CTA Transit app for public transport information and OpenTable for restaurant reservations

Start planning your trip and book your Chicago flight today. With so much to offer, Chicago is a city that promises unforgettable experiences for Canadian travelers.

About Cancun (CUN)

Cancun

Frequently Asked Questions - Chicago to Cancun Flights

Which airlines offer cheapest airfare from Chicago to Cancun?

There is no set pricing for airlines to offer cheap flight fare from Chicago to Cancun. These fares are mostly decided on the basis of algorithms followed by air carriers to final the prizing based on demand. However, some multiple route flights with stop-overs offer cheap flights as compared to direct flight departing from Chicago to Cancun.

How do MakeMyTrip finds the lowest available dare for flights from Chicago to Cancun?

MakeMyTrip is a popular travel portal that also works as a travel search engine that allows you to see best available results for your flight search. Every time you make search for flights to any destination, the MMT algorithm picks all the available air carriers for the route and filter rates basis on the cheapest fare available in their system. At MMT, you can not only search flights on the basis of the fare, but you can also see which flight offers direct route, which has multiple stop-overs, baggage allowance, in-flight meal options, cancellation policy, etc. You can also check available discounts offered by payments partners and air carriers when booking the flight.

What is the best time to book cheap flight tickets from Chicago to Cancun?

To get cheap flight tickets from Chicago to Cancun, the best time would be to plan your trip during the off season. At that time the flight tickets are usually cheaper than the peak season and the accommodation booking is also available at the affordable price. The other way of booking cheap flight tickets from Chicago (CHI) to Cancun (CUN) is to book atleast 4 weeks in advance before your departure date to get competitive pricing on your tickets even during the peak season.

Can I find cheap accommodation near to airport when travelling from Chicago to Cancun?

There are several accommodation options available near the Cancun Intl. You can check for both budget friendly and well as five star accommodation near the airport depending on your requirement and budget. These hotels are mostly suitable for business travellers.

Is there a way to make flexible departure date bookings for your Chicago to Cancun flight tickets?

Some travel portals like MakeMyTrip offer flexible departure and arrival booking option with certain air carrier when booking from Chicago to Cancun. You can check the flexible booking flight options once you get the results filters based on your search and make the booking accordingly. Please note, some airlines make charge extra for flexible travel dates.

Can I cancel my ticket from Chicago to Cancun without cancellation charges?

To avoid cancellation charges on your air tickets, you need to make a selection at the time of booking for ZERO cancellation. Please note, the zero cancellation facility is chargeable with minimum amount and can help you save a lot at the time sudden cancellations.

Is passport mandatory to travel from Chicago to Cancun?

When making an international trip, passport is mandatory as it defines your identity to the other nation officials. The VISA norms may differ from country to country, which means some would allow Visa on arrival and others may require you to obtain visa in advance. But the availability of passport is mandatory at the time of departure and arrival as well.