Ten Tips on Finding Cheap Flights from Chicago to Cancun

Travelers can save up to $417 on their round-trip tickets from Chicago to Cancun if they follow these 10 simple tips from the team here at Hopper.

Hopper Editors - Oct. 26, 2017

Cancun, Mexico, is a major draw for those living in Chicago, especially during the winter months. In less than four hours, Chicagoans can be sitting on the sunny beaches of Cancun with a margarita in their hands. That certainly beats the below-zero temperatures of Chicago come January, and the all-inclusive offerings at several of the resorts make it an affordable vacation. Plus, while tickets are not always cheap to Mexico, O’Hare International Airport offers direct flights for under $400. Travelers may even be able to find them for less than that with these 10 tips on how to find cheap flights from Chicago to Cancun which can save up to a solid $417 on a round-trip ticket.

See the great deals travelers are finding right now on flights between Chicago and Cancun on the Hopper Flight Explorer.


Photo via their official FB page.

1. The cheapest time to book a flight from Chicago to Cancun is 20 days in advance, saving up to $160

While Chicago’s fifth snowstorm of the year might cause you to want to book a last-minute flight to Mexico, buying a ticket at least 20 days in advance can save you up to $160. Plus, it gives you time (and money) to prepare for the climate change. Buy some stylish sunglasses or an extra pair of sandals to get you excited about not having to wear a parka for a couple days.

2. The cheapest day to fly from Chicago to Cancun is on a Wednesday, saving up to $23

If you plan on escaping for a full week and your departing day doesn’t exactly matter, book your flight on a Wednesday and save up to $23. That money could better be spent on snorkeling gear or a Jetski ride in the ocean.

3. Save up to $49 by returning on a Wednesday

Same goes for booking your returning flight. If you plan to stay a week, plan to return on a Wednesday, and you can save up to $49. This also allows you time and some extra cash to plan a day excursion or two. Book a trip to visit the Mayan ruins site of Chichen Itza, which was once one of the largest Mayan cities along the Yucatan peninsula.

4. The cheapest time to fly from Chicago to Cancun is in September, saving up to $40

While traveling during the cold Chicago winter months might be the best time to visit a tropical destination, booking a flight to Cancun in September can save you up to $40. Plus, traveling in an off season means less people and therefore more options for you. No lines at the bar, no overbooked shuttles to Tulum and guaranteed hotel rooms all equal a better vacay.

5. Fly out of O’Hare for the best deals

While there are several airports in the Chicago area from which to choose, O’Hare International Airport offers the best deals to Cancun. Travelers can save up to $75 flying out of O’Hare. Plus, it offers some of the best in-and-out public transportation for locals trying to get quickly to and from the airport.

6. United has the cheapest direct flights from Chicago to Cancun, while Spirit has the best deals overall

If you’re looking for a quick getaway, booking a direct flight is the way to go. You can save by booking United, which offers direct flights for about $70 less than the other leading airlines at around $405. If you have more time and less money, check out Spirit airlines, which offers the best deals overall. A Spirit flight with stops can be as low as $344, but do check out Hopper’s Airline Fees calculator to make sure that your Spirit ticket isn’t more expensive than the United ticket once the fees are added.

Airlines offering direct flights from Chicago to Cancun:
- United makes the journey in 4 hours for $409 round trip, on average.
- American makes the journey in 4 hours for $409 round trip, on average.

Airlines offering connecting flights from Chicago to Cancun:
- Spirit makes the journey in 7.5 hours via Fort Lauderdale for $347 round trip, on average.
- Aeromexico makes the journey in 9.5 hours via Mexico City for $386 round trip, on average.

7. Frequent fliers on United can use 35,000 miles to book a round-trip ticket

United Airlines currently offer their frequent fliers a bargain deal on Travel Awards flights when it comes to routes connecting Chicago’s O’Hare International with Cancun. A one-way ticket in economy class will set customers back just 17,500 miles, with a return route coming in at 35,000 on certain departure dates. Those interested in taking first class cabin seats may be able to bag a seat for as little as 80,000 miles round trip, with business class places coming in at even less.

8. Check out Hopper’s When to Fly and Buy Reports for up-to-date information

If you’re eager to leave behind the Windy City for a jaunt on the Mexican beaches of Cancun this year, perhaps for a break from the sub-zero temperatures of Illinois mid-winter, then be sure to take a look at Hopper’s when to fly and buy reports for all flights leaving Chicago for Cancun. They provide a comprehensive breakdown of all the important statistics affecting flight prices, using crowd-sourced data from more than 6 million searches made in the last month, to provide the most up-to-date metrics on the web.

See Hopper's latest when to fly and buy report for flights from Chicago to Cancun for consistently up-to-date information

9. Take a look at Hopper’s Airline Fee Calculator to get the real cost of your ticket

Granted United Airlines offer the best fares for direct routes into Cancun, and Spirit may be the cheapest carrier overall, but add on the necessary extras — checked baggage for those party dresses and dancing shoes, carry-on luggage for that in-flight reading and a couple of drinks to set the tone — and it’s a different story all round, with Spirit soaring to a whopping $561 return and United comparable to American Airlines at $529. For the detailed breakdown, be sure to check Hopper’s Airline Fee Calculator for the route.

10. Keep in mind that a cheap flight from Chicago to Cancun is about $394 round trip

While these travel tips can help you save in multiple ways, a good deal for a direct flight from Chicago to Cancun is $394. Although some travelers have found flights for as low as $320, you can rest assured that a ticket to Cancun for under $400 is a good find that won’t break the bank.

Distribution of economy round-trip prices quoted for flights with stops from Chicago to Cancun.Search for flights from Chicago to Cancun for $394 round trip or less on Hopper, right now

Or see general tips on finding cheap flights to Cancun from any airport.

How the flight from Chicago to Cancun compares to flights to other beach destinations

Get the Hopper app to find the best deals.
You could save up to 40% on your next flight!