One Way

Popular Filters

+ 1 more

One Way Price

SGD 250 SGD 800

Duration

4 h 30 m 25 h 0 m

Stops From Chicago

Departure From Chicago

Before 6 AM

SGD 250

6 AM - 12 PM

SGD 250

12 PM - 6 PM

SGD 291

After 6 PM

SGD 266

Arrival at Cancun

6 AM - 12 PM

SGD 266

12 PM - 6 PM

SGD 250

After 6 PM

SGD 250

Alliances & Airlines

Oneworld

(3)

SkyTeam

(5)

Star Alliance

(7)

+ 1 more

Layover Airports

+ 1 more

Layover Duration

45 m 18 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 20 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

SGD 250

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

SGD 266

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

SGD 279

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

SGD 287

Transit Visa may be required

Chicago to Cancun , 2 Jun

Air Canada AC | 510

20:20

Tue, 2 Jun 26

Terminal T2

Chicago, United States

01 h 43 m

23:03

Tue, 2 Jun 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 1812

17:10

Wed, 3 Jun 26

Terminal T1

Toronto, Canada

04 h

20:10

Wed, 3 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

SGD 291

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

SGD 314

Chicago to Cancun , 2 Jun

Delta Air Lines DL | 2543

20:20

Tue, 2 Jun 26

Terminal T5

Chicago, United States

02 h 24 m

23:44

Tue, 2 Jun 26

Terminal C

New York-LaGuardia Apt, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 621

08:23

Wed, 3 Jun 26

Terminal T4

New York, United States

04 h 17 m

11:40

Wed, 3 Jun 26

Terminal T3

Cancun, Mexico

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

SGD 318

Transit Visa may be required

Chicago to Cancun , 2 Jun

Air Canada AC | 8550

14:00

Tue, 2 Jun 26

Terminal T2

Chicago, United States

01 h 41 m

16:41

Tue, 2 Jun 26

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

Delta Air Lines

SGD 321

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

SGD 371

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

Aeromexico

SGD 461

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

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 20 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 250, which may go up to 780 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 dynamic city that offers a blend of modernity and rich cultural heritage, making it an exciting destination for travelers from Singapore. Known for its stunning skyline, vibrant arts scene, and diverse neighborhoods, Chicago promises a variety of experiences that cater to all interests. Whether you're exploring world-class museums, indulging in deep-dish pizza, or strolling along the scenic Lake Michigan, Chicago has something for everyone.

Best Time to Visit

For Singapore travelers, the best time to visit Chicago is during the spring (April to June) and fall (September to October) when the weather is pleasant and the city is bustling with activities. Summers are warm and ideal for outdoor festivals, while winters can be quite cold and snowy, offering a magical winter wonderland experience.

Getting There

Chicago is well-connected to Singapore with direct flights from Changi Airport (SIN) to O'Hare International Airport (ORD). Major airlines such as Singapore Airlines and United Airlines offer flights to Chicago, making it convenient for travelers. Ensure you have a valid visa for entry into the United States, and check for any travel advisories before booking your trip.

Where to Stay

Chicago offers a range of accommodations to suit different budgets. For luxury stays, consider hotels in the Magnificent Mile area, such as the Peninsula Chicago or the Four Seasons Hotel. Budget travelers can find affordable options in neighborhoods like River North and Lincoln Park.

Must-See Places & Experiences

โ€ข Millennium Park: Home to the iconic Cloud Gate sculpture (The Bean) and beautiful gardens.
โ€ข Art Institute of Chicago: Renowned for its impressive collection of art from around the world.
โ€ข Navy Pier: A lively entertainment hub with rides, restaurants, and stunning lake views.
โ€ข Willis Tower Skydeck: Offers breathtaking views of the city from its observation deck.
โ€ข Museum Campus: Includes the Field Museum, Shedd Aquarium, and Adler Planetarium.

Local Transportation

Getting around Chicago is easy with its extensive public transportation system. The 'L' trains and buses operated by the Chicago Transit Authority (CTA) connect various parts of the city. Taxis and rideshare services like Uber and Lyft are also widely available.

Food & Dining

Chicago is a culinary paradise with a diverse food scene. Don't miss trying the famous deep-dish pizza at Giordano's or Lou Malnati's. For fine dining, Alinea offers an unforgettable experience. Explore the ethnic neighborhoods for authentic cuisines, such as Chinatown for dim sum and Pilsen for Mexican delicacies.

Practical Travel Tips

โ€ข Currency: The US Dollar (USD) is used in Chicago.
โ€ข Language: English is the primary language.
โ€ข Safety: Chicago is generally safe for tourists, but stay vigilant in crowded areas.
โ€ข Apps: Download the CTA app for public transport info and Yelp for restaurant reviews.

Start planning your trip and get your tickets booked from MakeMyTrip.com. The website offers you a host of services such as hotel deals, flight deals, and holiday packages. You have the freedom to book cheap flight tickets to Chicago and hotels to any destination in the world according to your budget and need.

Important Information about Chicago to Cancun Flight

Lowest Fare to Travel with Date SGD null- 02 Jun
Total flights from Chicago to Cancun in a week 20 Flights
First Flight Volaris, departs at 01:40
Last FlightAir Canada, departs at 21:20
Non-Stop Flights from Chicago to Cancun5
Airport Name & codes of Chicago & Cancun Chicago Midway Intl, Chicago-CHI, Cancun Intl,Cancun-CUN

Chicago Address

About Cancun (CUN)

Cancun

Cancun Address

Frequently Asked Questions - Chicago to Cancun Flights

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.

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.

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.

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.

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.

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.