Helping travelers to find the best flight offers
Find the best flights from Cancun to Chicago quickly and confidently — our search scans over 700 airlines, 50+ agencies, and more than 5 top booking systems to uncover the most competitive prices, convenient schedules, and flexible conditions. Whether you need nonstop options or budget-friendly connections, we make it easy to compare choices and book the itinerary that suits your trip.
Fly nonstop from sunny Cancún to bustling Chicago for the fastest, most convenient way to bridge beach time and city adventures—no layovers, no extra hassle. While connecting itineraries can sometimes cost less, a direct flight saves hours and offers a more relaxed, reliable trip so you can get straight to exploring Windy City sights and neighborhoods.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Cancun to Chicago:
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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.
The cheapest one-way flight from Cancun to Chicago departs on 12/25/2025, is operated by Spirit Airlines and costs $124
There is no information about the cheapest roundtrip flight from Cancun to Chicago
Fastest flight from Cancun to Chicago takes 4h 2m
There are direct flights on this route 3 days a week: Tu, Th, and Fr
The distance between Cancun and Chicago is 2318km (1437 miles). There are 11 direct flights from Cancun to Chicago. The time difference between Cancun and Chicago is 1h. Flights from Cancun begin at 12:27 PM. The latest flight from Cancun departs at 3:20 PM
More than 4 airlines operate flights from Cancun to Chicago, including United Airlines, Southwest Airlines, American Airlines, and Spirit Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $124, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
Starting at $197
Starting at $204
Starting at $160
Starting at $124
Cancun — Chicago
12/09/2025
Departure
Direct flight
UA1423
Starting at $255
Cancun — Chicago
12/25/2025
Departure
Direct flight
WN221
Starting at $204
Cancun — Chicago
01/08/2026
Departure
Direct flight
UA1423
Starting at $270
Cancun — Chicago
05/15/2026
Departure
Direct flight
AA752
Starting at $277
Unable to find information about the schedule of direct flights from
Cancún International Airport (CUN) is Mexico’s primary Caribbean gateway and typically functions as a major international hub for leisure travel rather than a domestic low-cost base. You’ll commonly find full-service carriers and seasonal charter flights alongside low-cost airlines serving North American, European and regional routes. The airport sits about 16 km (10 miles) northwest of the Hotel Zone and downtown Cancún; transfer times are usually 20–40 minutes by taxi or shuttle, with fares often ranging from modest to mid-range depending on service level. Public buses and shared shuttles can be cheaper but slower. Pros: direct international connections and plentiful ground-transport options. Cons: busy peak-season crowds and variable wait times for immigration and baggage.
O'Hare International Airport (ORD) is Chicago's primary global hub, serving many international and long-haul carriers as well as United and American hub operations; it typically handles a mix of premium and connecting traffic. Located about 17 miles northwest of downtown, travel to the Loop can take 30–50 minutes by CTA Blue Line (fare around $2.50) or 30–60 minutes by taxi or rideshare (fares usually varying widely depending on traffic). Metra and airport shuttle options are also available. Pros: extensive route network and frequent flights; cons: sizable terminals and possible long walks or waits during peak periods. Midway International Airport (MDW) is Chicago's smaller, more budget-leaning facility that often hosts low-cost and domestic carriers, notably Southwest, making it popular for short-haul travel around the US. Situated roughly 10 miles southwest of downtown, transit times are typically 20–35 minutes via CTA Orange Line (fare about $2.50) or 25–40 minutes by taxi/rideshare with generally lower fares than from O'Hare. Parking and curbside access can be more compact and quicker to navigate. Pros: easier check-ins and shorter transfers for domestic trips; cons: fewer international connections and limited long-haul service.
We couldn't find any special offers for flights from Cancun to Chicago
The cheapest flight ticket from Cancun to Chicago according to data for the last 48 hours costs $124
Often the best time to buy tickets from Cancun to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Cancun to Chicago can be found flying in these months: January.
The fastest flights from Cancun to Chicago start from 4 hours 2 minutes in the air.
The following airlines operate direct flights on the route Cancun — Chicago: United Airlines, Southwest 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 Cancun to Chicago