Cheap Flights from Cancun to Chicago Starting at $124

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.

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.

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