The Five Cheapest Flights from Chicago to Mexico

Want a sunny vacation that won't break the bank? Read on for a list of the 5 cheapest flights from Chicago to Mexico!

Hopper Editors - Oct. 26, 2017

Whether you're pining for a stay amid the colonial palaces and crumbling Aztec sites of Mexico City, a luxurious jaunt along the shimmering Caribbean beaches of Tulum, Quintana Roo and the Yucatan Peninsula, or an adventurous incursion through the jungled wilds of Montes Azules and across the steaming ridges of the Puebla volcanoes, let this rundown of the five cheapest air connections between Chicago's O'Hare International Airport and Mexico be your guide!

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It's been devised by Hopper's expert flight team, who've used millions of pieces of data to identify the aggregate average prices for seats on connections out of Chicago, helping Midwesterners get the best bang for their buck as they make their way down to the sun-kissed swathes of Mesoamerica.

5. Fly from Chicago to Guadalajara, Mexico for as low as $425 round trip

It's good news for Illinois locals desperate to leave behind the blustery chills of the Windy City for the sultry climbs of central Mexico this year, because these flights to Guadalajara run nonstop on flag carrier AeroMéxico and offer a super-cheap return trip price tag of just $425. Once in town, travelers can choose to wallow between the exquisite rises of the Guadalajara Cathedral and the wealth of colonial wonders that surround it, or make a beeline for the resort town of Puerto Vallarta and its concomitant beaches on the Pacific to the east.

4. Fly from Chicago to Leon, Mexico for as low as $425 round trip

For Chicagoans who've been ousted out of bagging a bargain flight into one of Mexico's other major inland cities, these flights from Chicago to the Del Bajio International Airport in Guanajuato are the perfect alternative. Not only do they attract just a fraction of the competition for the cheapest seats, but they also boast an attractive average round trip price tag of just $425 and drop passengers within easy reach of Guadalajara in the east and Mexico City to the south.

3. Fly from Chicago to Cabo San Lucas, Mexico for as low as $394 round trip

Strewn out between the historic heart of San Jose del Cabo and the so-called Main Town of Cabo San Lucas itself, this celebrated destination on the Pacific does well to show both sides of the Mexican coin: the laid-back Spanish side with its sleepy plazas laden with tanned hombres, and the hedonistic high-life side, with all the ubiquitous resort strips, spring breaker clubs and jet setter beaches! Expect to pay in the region of $394 for nonstop flights into town, with the cheapest options on United Airlines, US Airways or American.

2. Fly from Chicago to Mexico City, Mexico for as low as $380 round trip

For all those proud Chicagoan city lovers — the ones who prefer heady metropolitan streets, curious cultural monuments, sprawling museums and smoky subterranean clubs to open beaches and the like — these bargain air connections offer transportation into the bubbling, bustling heart of Mexico's capital. What's more, nonstop connections on the route are actually cheaper than ones with stopovers, and carriers United Airlines, American Airlines and US Airways all offer bargain seats at around just $380 return.

1. Fly from Chicago to Cancun, Mexico for as low as $373 round trip

Studious members of the University of Illinois are sure to love this one, but then so are most all of Chicago's sun lovers and spring break party goers, because Cancun is the veritable kingpin of Mexican nightlife on the Caribbean, bursting at the seams with Senor Frogs, beachside cocktail bars, and thumping mega clubs touting some of the biggest DJ names on the planet. With that in mind, it's probably worth trying to save as much cash as possible for the ride, which means these super-cheap, nonstop, $373 round trip flights with American Airlines are a real gift!

Learn more ways to find the best deals on airfare by taking a look at our when to fly and buy reports at

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