Cheap Flights from Chicago to Cancun Starting at $92
Helping travelers to find the best flight offers
Cheapest flights from Chicago to Cancun
Fly from Chicago to sunny Cancún with confidence—our search scans over 700 airlines, more than 50 agencies and 5+ top booking systems to uncover the best prices, schedules and conditions for your trip. Compare options in seconds and lock in the perfect flight for beach days, quick getaways, or family adventures.
Remember that on average the ideal time to book flights is 2 months before departure!
Fly nonstop from Chicago to Cancún for the quickest, most convenient way to swap city streets for Caribbean beaches — fewer hassles, no layovers, and more time to relax. While connecting flights can sometimes be cheaper, a direct flight saves hours and offers a far more comfortable start to your vacation, so book now to make the most of your getaway.
Schedule of direct flights from Chicago to Cancun
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Cancun:
Chicago airports overview
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Cancun airports overview
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Frequently asked questions (FAQ)
Answers to questions about the route that travelers are most interested in.
Special offers and sales on air tickets from Chicago to Cancun
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Alternative routes
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Cheapest one way flight
$92
Frontier Airlines
Direct flight
4h 1m
01/08/2026
The cheapest one-way flight from Chicago to Cancun departs on 01/08/2026, is operated by Frontier Airlines and costs $92
Cheapest round trip flight
$148
Southwest Airlines
Direct flight
7h 35m
11/08/2025
The cheapest roundtrip flight from Chicago to Cancun departs on 11/08/2025, is operated by Southwest Airlines and costs $148
The fastest flight
3h 50m
Fastest flight from Chicago to Cancun takes 3h 50m
Direct flights
Several times a week
There are direct flights on this route 3 days a week: Th, Fr, and Sa
Earliest flight
7:34 AM
Latest flight
10:05 AM
Average flight duration
3h 41m
Direct flights count
12
Distance
2318km
Timezone difference
1h
The distance between Chicago and Cancun is 2318km (1437 miles). The average flight duration is 3h 41m. There are 12 direct flights from Chicago to Cancun. The time difference between Chicago and Cancun is 1h. Flights from Chicago begin at 7:34 AM. The latest flight from Chicago departs at 10:05 AM
The route Chicago — Cancun is served by many carriers — 7 in total, including Southwest Airlines, Frontier Airlines, American Airlines, United Airlines, VivaAerobus, Volaris, and Spirit Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $92) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
Chicago is served by two main airports with distinct roles. O'Hare International (ORD) is the city’s primary international hub and a major United Airlines and American Airlines gateway, typically offering the widest range of long-haul and connecting flights; fares can be competitive for transcontinental and international travel. It lies about 17 miles northwest of downtown, with transit options including the CTA Blue Line (around 45–60 minutes) and airport shuttles or taxis (35–60 minutes, fares vary widely). O’Hare’s size brings many amenities but can mean longer security and transfer times during peak hours.
Midway International (MDW) often functions more as a domestic and low-cost carrier base, historically favored by Southwest Airlines and other value carriers for short- and medium-haul routes. Located roughly 10 miles southwest of the Loop, Midway is generally quicker to reach — the Orange Line takes about 25–35 minutes to downtown, and rideshares or taxis typically take 20–40 minutes depending on traffic; fares are usually lower for shorter trips. Travelers may appreciate Midway’s smaller, easier-to-navigate terminals, though it offers fewer international connections and amenities compared with O’Hare.
Cancún International Airport (CUN) is the main gateway to Mexico’s Caribbean coast, acting as a major international hub with a mix of full-service carriers and many low-cost airlines serving North American and European routes. Fares can range from budget-friendly to premium depending on season and carrier. The airport lies about 16 km (roughly 25–35 minutes) from downtown Cancún and 20–60 minutes to popular hotel zones; shared shuttles, private transfers and taxis are common, and public buses offer very economical service for around a few dollars. Pros: plentiful international connections and dedicated tourist services; cons: can be busy during high season and may involve longer lines for immigration and baggage.
How much is the cheapest flight ticket from Chicago to Cancun?
The cheapest flight ticket from Chicago to Cancun according to data for the last 48 hours costs $92
When is the best time to buy air tickets on the route Chicago — Cancun?
Often the best time to buy tickets from Chicago to Cancun is 2 months before departure.
When is the cheapest time of year to fly from Chicago to Cancun?
Based on statistics over the past years, the lowest prices for flights from Chicago to Cancun can be found flying in these months: November.
How long does it take to fly from Chicago to Cancun?
The fastest flights from Chicago to Cancun start from 3 hours 50 minutes in the air.
Which airline can fly direct from Chicago to Cancun?
The following airlines operate direct flights on the route Chicago — Cancun: Southwest Airlines, Frontier Airlines, American Airlines
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Cancun
We couldn't find any special offers for flights from Chicago to Cancun
