S$ 105 Cheap Flights from Chicago to Cancun (CHI-CUN)

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Cheap Flights from Chicago to Cancun starting at S$ 105

We've found these cheap flights for you. You can book one-way or return flight tickets.

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from Chicago to Cancun

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Cheapest Airlines flying from Chicago to Cancun

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines

From S$ 106

Spirit Airlines

From S$ 107

American Airlines

From S$ 155

United Airlines

From S$ 205

Aeromexico

From S$ 216

Avianca

From S$ 218

Sun Country Airlines

From S$ 232

Southwest Airlines

From S$ 234

Volaris

From S$ 240

Jetblue Airways

From S$ 282

ANA airlines

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Alternative Routes from Chicago to Cancun

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Cancun.

Cheapest
ORD
08:12
4h 8m
Direct
CUN
12:20
O'Hare International Airport - Cancún International Airport
Sat, Apr 27Frontier Airlines
S$ 106
MDW
07:00
9h 6m
1 transfer
CUN
16:06
Midway International Airport - Cancún International Airport
Tue, May 7Frontier Airlines
S$ 117
MDW
07:00
9h 6m
1 transfer
CUN
16:06
Midway International Airport - Cancún International Airport
Tue, May 7Frontier Airlines
S$ 117
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Frequently Asked Questions

When to buy flight tickets from Chicago (CHI) to Cancun (CUN) the cheapest?
Airlines adjust prices for flights from Chicago to Cancun based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from Chicago (CHI) to Cancun (CUN) cost?
According to Trip.com's data, the lowest price is around S$ 624.
How long is a flight from Chicago (CHI) to Cancun (CUN)?
It takes about 3 hours 44 minutes to fly from Chicago (CHI) to Cancun (CUN).
What is the transportation method from the main airport to downtown in Cancun?
- The distance from Cancún International Airport to downtown is about 13km, by taxi about 30 minutes.
What time does the earliest flight from Chicago to Cancun depart?
The earliest flight departs from Chicago (ORD) at 07:09 and arrives in Cancun (CUN) at 11:03.
What are the most popular airlines that fly from Chicago (CHI) to Cancun (CUN)?
Airlines with flights from Chicago (CHI) to Cancun (CUN): American Airlines, Southwest Airlines, Volaris, Emirates, United Airlines, Spirit Airlines and Frontier Airlines.
What's the most popular airline for direct flights from Chicago (CHI) to Cancun (CUN)?
Frontier Airlines operates 3 direct flights from Chicago (CHI) to Cancun (CUN).
How many airports in Cancun?
There are 1 airports near Cancun: Cancún International Airport.

How to find a cheap flight from Chicago to Cancun

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Cancun. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

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Look Out for Deals

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Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

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Find cheapest flight ticket from Chicago to Cancun

Cheapest direct flight price	S$ 105
Cheapest return ticket price	S$ 233
Cheapest month	January
Peak season for travel	July
Flight distance	2,318.16km
Average flight time	3 hours 44 minutes
Popular airline	American Airlines