Cheap Flights from Chicago to Cancun — $87

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.

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.

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.

The route Chicago — Cancun is served by many carriers — 8 in total, including Southwest Airlines, Spirit Airlines, American Airlines, United Airlines, Frontier Airlines, Volaris, VivaAerobus, and Air Canada. This gives passengers wide opportunities: from finding the lowest fare (from $87) 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.