Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Lowest round trip fares by airline from Chicago and Cancun

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Cheap flights from Chicago to Cancun

Cheap flights from Chicago to Cancun

Chicago Midway (MDW) is located just off I-55, near Chicago’s South Side neighborhood. The airport is serviced by CTA’s Orange Line to the downtown loop, as well as the Pace Bus and RTA. Midway is accessible from Interstate 55, which connects passengers from downtown as well as State Route 50.

From Chicago Midway (MDW) to Cancun (CUN) flight duration is four to six hours, depending on stops. Once in Cancun, visitors can find public transit services outside the terminal. The airport is located about 25 minutes from Cancun, and offers many options for hotel or destination transportation.

Attractions

Most visitors come to Cancun for the beaches. It is a major Spring Break destination, with Cancun Beach and Playa Delfines being the most popular beaches. These are located in the “Hotel Zone”, and most visitors will stay in a beach hotel or resort. Visitors can take a tour to Chichen Itza to get some history, or can check out Xel-Ha Park for fun and adventure. Cancun’s Underwater Museum is a must-see, as is the Dolphin Discovery Park. For even more adventure, head to Xplor, an eco-adventure park with zip-lines, hiking trails and more.

Hints and tips

Cancun is one of the largest airports in Mexico, and is used as a midpoint for many Caribbean travelers; so getting through customs can take longer than expected.

Packages from Chicago to Cancun

Hotels in Cancun

See all 1,544 Properties in Cancun

Estimated price for 1 night/2 adults

Fiesta Americana Condesa Cancun - All Inclusive

Fiesta Americana Condesa Cancun - All Inclusive

Blvd. Kukulkan km 16.5, Zona Hotelera, Cancun, QROO
    4.0 out of 5.0
     
     
    4.3 out of 5 (119 reviews)

    Nestled on the beach, this Zona Hotelera hotel is within a 15-minute walk of Aquaworld and Maya Cancun Museum. Delfines Beach and El Rey Ruins are also within ...

    Fiesta Americana Condesa Cancun - All Inclusive$253

    May 29 - May 30

    Fiesta Americana Condesa Cancun - All Inclusive$253
    Krystal Cancun

    Krystal Cancun

    Paseo Kukulcan km 9, lotes 9 y 9A, Zona Hotelera, Cancun, QROO
      3.5 out of 5.0
       
       
      3.3 out of 5 (61 reviews)

      Set on Punta Cancún's eastern edge, this waterfront Krystal Cancun resort is near Cancún Convention Center and 1 block from nightclubs, shops, and ...

      Krystal Cancun$97

      May 28 - May 29

      Krystal Cancun$97
      Iberostar Cancun Star Prestige All Inclusive, Adults Only

      Iberostar Cancun Star Prestige All Inclusive, Adults Only

      Boulevard Kukulkán KM 17 B, Cancun, QROO
        4.0 out of 5.0
         
         
        5.0 out of 5 (4 reviews)

        Nestled on the beach, this Zona Hotelera property is within a 15-minute walk of Delfines Beach, El Rey Ruins, and Maya Cancun Museum. Aquaworld is 1.3 mi (2 ...

        Iberostar Cancun Star Prestige All Inclusive, Adults Only$440

        May 29 - May 30

        Iberostar Cancun Star Prestige All Inclusive, Adults Only$440
        The Royal Caribbean - An All Suites Resort

        The Royal Caribbean - An All Suites Resort

        Blvd. Kukulcan, Km. 17, Lote 50, Zona Hotelera, Cancun, QROO
          3.5 out of 5.0
           
           
          4.3 out of 5 (29 reviews)

          This family-friendly Cancun resort is located in Zona Hotelera, within 1 mi (2 km) of Ballenas Beach, Aquaworld, and Delfines Beach. El Rey Ruins and Maya Cancun ...

          The Royal Caribbean - An All Suites Resort$151

          Jun 8 - Jun 9

          The Royal Caribbean - An All Suites Resort$151
          Fairfield Inn & Suites by Marriott Cancun Airport

          Fairfield Inn & Suites by Marriott Cancun Airport

          Blvd Luis Donaldo Colosio SM 305 MZA 01, Cancun, QROO
            3.5 out of 5.0
             
             

            Situated in Cancun, this hotel is 2.9 mi (4.7 km) from Parish of the Risen Christ and within 6 mi (10 km) of Ventura Park Cancun and Cancun Country Club. Delfines ...

            Fairfield Inn & Suites by Marriott Cancun Airport$59

            May 31 - Jun 1

            Fairfield Inn & Suites by Marriott Cancun Airport$59
            Live Aqua Beach Resort Cancún - All Inclusive - Adults Only

            Live Aqua Beach Resort Cancún - All Inclusive - Adults Only

            Blvd. Kukulcan KM.12.5, Zona Hotelera, Cancun, QROO
              5.0 out of 5.0
               
               
              4.5 out of 5 (59 reviews)

              Nestled on the beach, this Zona Hotelera hotel is just steps from Tequila Museum and Cancun Interactive Aquarium. La Isla Shopping Mall and Aquaworld are also ...

              Live Aqua Beach Resort Cancún - All Inclusive - Adults Only$381

              May 26 - May 27

              Live Aqua Beach Resort Cancún - All Inclusive - Adults Only$381
              Grand Fiesta Americana Coral Beach Cancun

              Grand Fiesta Americana Coral Beach Cancun

              Blvd. Kukulcan km. 9.5, Zona Hotelera, Cancun, QROO
                5.0 out of 5.0
                 
                 
                4.7 out of 5 (50 reviews)

                On the beach at Punta Cancún, the resort is less than 3 km (1.5 mi) from shops and restaurants at the Plaza Forum, Plaza Flamingo, and La Isla Mall.

                Grand Fiesta Americana Coral Beach Cancun$242

                May 29 - May 30

                Grand Fiesta Americana Coral Beach Cancun$242
                Iberostar Selection Cancun All Inclusive

                Iberostar Selection Cancun All Inclusive

                Boulevard Kukulcan, Km. 17, Cancun, QROO
                  5.0 out of 5.0
                   
                   
                  4.3 out of 5 (27 reviews)

                  Nestled on the beach, this Zona Hotelera property is within a 15-minute walk of Delfines Beach, El Rey Ruins, and Maya Cancun Museum. Aquaworld is 1.2 mi (2 ...

                  Iberostar Selection Cancun All Inclusive$336

                  May 30 - May 31

                  Iberostar Selection Cancun All Inclusive$336
                  Paradisus by Meliá Cancun - All Inclusive

                  Paradisus by Meliá Cancun - All Inclusive

                  Boulevard Kukulkan Km 16.5, Cancun, QROO
                    4.5 out of 5.0
                     
                     
                    4.3 out of 5 (72 reviews)

                    Located in Zona Hotelera, this family-friendly Cancun property is within a 5-minute walk of Ballenas Beach and Aquaworld. Delfines Beach and Maya Cancun Museum ...

                    Paradisus by Meliá Cancun - All Inclusive$263

                    Jun 2 - Jun 3

                    Paradisus by Meliá Cancun - All Inclusive$263
                    ibis Cancun Centro

                    ibis Cancun Centro

                    Av Tulum Y Nichupte, Supermanzana 11 M2 L3, Cancun, QROO
                      3.0 out of 5.0
                       
                       

                      Located in Downtown Cancun, this hotel is within a 10-minute walk of Dubai Palace Casino and Plaza Las Americas. Galenia Hospital and Market 28 are also within ...

                      ibis Cancun Centro$46

                      Jun 9 - Jun 10

                      ibis Cancun Centro$46
                      Map

                      *Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

                      Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other CheapTickets users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

                      Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $75 service fee charged by CheapTickets.

                      Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.