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Find Chicago to Cancun flights starting at CAD 95.

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

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD06:38
        4h 4m
        Nonstop
        CUN11:42
        Tue, Jan 7|Chicago - Cancun|Frontier Airlines
        CAD 95CAD 306
        69% OFF
        69% OFF
        CAD 306CAD 95

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Tue, Jan 7, arriving at Cancún International Airport. One-way Prices start from CAD 95 including taxes and charges.

      • ORD06:00
        4h 19m
        Nonstop
        CUN11:19
        Tue, Feb 4|Chicago - Cancun|Frontier Airlines
        CAD 102CAD 306
        67% OFF
        67% OFF
        CAD 306CAD 102

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Tue, Feb 4, arriving at Cancún International Airport. One-way Prices start from CAD 102 including taxes and charges.

      • ORD06:00
        4h 19m
        Nonstop
        CUN11:19
        Mon, Jan 20|Chicago - Cancun|Frontier Airlines
        CAD 103CAD 306
        66% OFF
        66% OFF
        CAD 306CAD 103

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Mon, Jan 20, arriving at Cancún International Airport. One-way Prices start from CAD 103 including taxes and charges.

      • ORD06:30
        4h 19m
        Nonstop
        CUN11:49
        Mon, Feb 24|Chicago - Cancun|Frontier Airlines
        CAD 103
        CAD 103

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Mon, Feb 24, arriving at Cancún International Airport. One-way Prices start from CAD 103 including taxes and charges.

      • ORD06:00
        4h 4m
        Nonstop
        CUN11:04
        Tue, Jan 14|Chicago - Cancun|Frontier Airlines
        CAD 103
        CAD 103

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Tue, Jan 14, arriving at Cancún International Airport. One-way Prices start from CAD 103 including taxes and charges.

      • ORD06:00
        4h 19m
        Nonstop
        CUN11:19
        Tue, Jan 21|Chicago - Cancun|Frontier Airlines
        CAD 103
        CAD 103

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Tue, Jan 21, arriving at Cancún International Airport. One-way Prices start from CAD 103 including taxes and charges.

      • ORD06:00
        4h 4m
        Nonstop
        CUN11:04
        Mon, Jan 13|Chicago - Cancun|Frontier Airlines
        CAD 103
        CAD 103

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Mon, Jan 13, arriving at Cancún International Airport. One-way Prices start from CAD 103 including taxes and charges.

      • ORD06:30
        4h 19m
        Nonstop
        CUN11:49
        Tue, Feb 25|Chicago - Cancun|Frontier Airlines
        CAD 104
        CAD 104

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Tue, Feb 25, arriving at Cancún International Airport. One-way Prices start from CAD 104 including taxes and charges.

      • ORD06:00
        4h 19m
        Nonstop
        CUN11:19
        Sun, Jan 26|Chicago - Cancun|Frontier Airlines
        CAD 105
        CAD 105

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Sun, Jan 26, arriving at Cancún International Airport. One-way Prices start from CAD 105 including taxes and charges.

      • ORD06:00
        4h 19m
        Nonstop
        CUN11:19
        Mon, Jan 27|Chicago - Cancun|Frontier Airlines
        CAD 105
        CAD 105

        Choose Frontier Airlines flights from Chicago to Cancun. The one-way direct flight with Frontier Airlines departs from O'Hare International Airport on Mon, Jan 27, arriving at Cancún International Airport. One-way Prices start from CAD 105 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        CUN02:00 pm
        Tue, Jan 14|Chicago - Cancun|Frontier Airlines
        Find More Flights
        Find More Flights

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

When is the 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 cheapest average weekly prices of the corresponding route on Trip.com.

Find 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 CAD 95
Volaris
From CAD 151
American Airlines
From CAD 161
Southwest Airlines
From CAD 178
Spirit Airlines
From CAD 207
Aeromexico
From CAD 208
Delta Air Lines
From CAD 224
United Airlines
From CAD 229
Viva
From CAD 276
Jetblue Airways
From CAD 426

Find more flights and airlines

Alternative Routes for Chicago to Cancun Flights

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

  • Cheapest
    Frontier Airlines
    ORD
    06:38
    4h 4m
    Nonstop
    CUN
    11:42
    O'Hare International Airport - Cancún International Airport
    Tue, Jan 7Frontier Airlines
    CAD 95
  • Frontier Airlines
    MDW
    05:10
    28h 11m
    1 transfer
    CUN
    10:21
    Midway International Airport - Cancún International Airport
    Sat, Mar 1Frontier Airlines
    CAD 158
  • Frontier Airlines
    MDW
    05:10
    28h 11m
    1 transfer
    CUN
    10:21
    Midway International Airport - Cancún International Airport
    Sat, Mar 1Frontier Airlines
    CAD 158
    Find More Flights

FAQ

  • When are 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 are flights from Chicago (CHI) to Cancun (CUN) cost?

    According to Trip.com's data, the lowest price is around CAD 619.

  • How long is the flight from Chicago (CHI) to Cancun (CUN)?

    It takes about 4 hours 1 minute 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 are the most popular airlines that fly from Chicago (CHI) to Cancun (CUN)?

    Airlines with flights from Chicago (CHI) to Cancun (CUN): American Airlines, United Airlines, Volaris, Emirates, Southwest 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 (CUN)?

    There are 1 airport(s) in Cancun (CUN): 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.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information for Chicago to Cancun Flights

Cheapest direct flight priceCAD 95
Cheapest return ticket priceCAD 228
Off-season travel monthJanuary
Peak season for travelApril
Flight distance2,318.16km
Average flight time4 hours 1 minute
Popular airlineAeromexico

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