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Lowest round trip fares by airline from Chicago and Cancun

Cheapest prices ($67 One Way, $149 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Cancun

GR Solaris Cancun & Spa - All Inclusive
4.0 out of 5.0
4.1 out of 5 (246 reviews)

Located in Zona Hotelera, this beachfront property is in the city center and within a 10-minute walk of El Rey Ruins and Delfines Beach. Aquaworld and Maya Cancun ...

The entertainment is really good, they have a different theme every night except sundays that’s karaoke. Fernando seems to be a main person in charge and he is excellent at it. The view from the hotel is spectacular, we got and oceanfront and there is no other way! If you can please get that. This ...
Beachscape Kin ha Villas & Suites
3.5 out of 5.0
3.9 out of 5 (42 reviews)

Nestled on the beach, this Zona Hotelera resort is within a 10-minute walk of Plaza Caracol Mall and Caracol Beach. Cancun Convention Center and Forum Beach ...

We've been coming here for 15 years straight! The place is low keyed, family friendly, super-clean with an INCREDIBLE staff!
Real Inn Cancun
3.5 out of 5.0
3.8 out of 5 (37 reviews)

Located in Zona Hotelera, this hotel is within a 15-minute walk of Langosta Beach and Tortuga Beach. Turtle Beach and Caracol Beach are also within 3 mi (5 ...

Property was amazing. Had a beautiful view. Staff were all friendly and very welcoming! The view of the beach and the ocean was very pleasing to see in the mornings & at night. The area was great.

Flights Review

Dec 9, 2019


Mar 23, 2018

Funny flight attendants.

Fly From Chicago to Cancun

Number of Daily Flights1
Earliest Flight Departure DateJun 4
Latest Flight Departure DateJun 4
Popular AirlinesAmerican Airlines

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.


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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.