10 Unexpectedly Great Deals on Flights from Chicago

Want to fly somewhere new? Check out flights to these 10 destinations from Chicago that are currently on sale for shockingly low prices!

Hopper Editors - Oct. 26, 2017

Nobody really knows why Illinois’ biggest metropolis is nicknamed the Windy City. Some say it was an epithet extrapolated by eager news hacks in the late 19th century, others that it came from a poetic description of Lake Michigan’s icy Hawk Winds. But if the winds of the Windy City should be known for one thing only, perhaps it should be whisking travelers away, because the world’s onetime busiest airport has been operating from its base in the city since World War II, transporting Midwestern folk to far flung destinations and exotic climates right across the globe.

Here’s a selection of 10 flights leaving from its runways that we think makes O’Hare International worthy of its reputation, ranging from trans-Atlantic jaunts to the enthralling centers of Europe, to short hops to the sunny beaches of the south.

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Photo by Aero Icarus/Flickr.

10. Fly Swiss to Budapest, Hungary, for as low as $690 round trip


Photo by Moyan_Brenn/Flickr.

One thing’s for sure, this bargain flight to the landlocked heart of Central Europe will leave passengers with plenty more forints to dish out on those strong Magyar beers and steaming plates of galuska dumplings, not to mention on explorations through the Art Deco bath halls, ancient castles and grandiose Baroque palaces that cling to Buda and Pest alike. Unfortunately there are no direct flights into town from Chicago, but the cheapest fares on the route tend to be with the acclaimed Swiss International Air Lines, who do offer connections via Zurich for under $700!

9. Fly Spirit to San Jose, Costa Rica, for only $359 round trip


Photo by smilla4/Flickr.

Costa Rica’s bustling mountaintop capital not only offers guests a real Mesoamerican cocktail of bubbling food bazaars and lively Spanish-style cantinas, but also acts as the gateway to the country as a whole, providing access to the mouth-watering Pacific beaches of Nicoya and Guanacaste, the volcanic hiking peaks of the Central Valley, and the wealth of other cities that pop up ad hoc from the coffee terraces that dominate the land. If that’s got your attention then don’t miss this bargain indirect connection from O'Hare on Spirit for just $359!

8. Fly Spirit to Cancun, Mexico, for only $348 round trip


Photo via their official FB page.

Ah Cancun, that fabled land of vine-clad Mayan temples and postcard-perfect tropical beaches that clings to the tip of the Riviera Maya on Mexico’s Yucatan; a place of spring breaker pilgrimage, scuba diver-laden Caribbean seas and more luxury resorts than you can throw a snorkel at. This tropical paradise is now served by no fewer than three direct flights out of Chicago’s O'Hare International, while Spirit Airlines’ indirect route via Fort Lauderdale promises a budget option at around just $348.

These 10 tips from the Hopper Research team can save you up to $417 on your flights from Chicago to Cancun!

7. Fly American to Montego Bay, Jamaica, for only $323 round trip


Photo by Ian Halsey/Flickr.

Why not trade in the rough and rugged swells of Lake Michigan and the windswept dune beaches of its wild lakeshore for a dose of something a little more exotic this fall, hopping on one of these bargain $323 returns with either American Airlines, United Airlines or Frontier to the pearly-white beaches and beryl shore waters of Jamaica’s Montego Bay. The flight goes nonstop, takes just six hours and departs daily from Chicago’s O'Hare Airport to the island’s Sangster International, the gateway to the reggae bars and luxury resorts that pepper the northern coast.

6. Fly Westjet to Vancouver, Canada, for only $295 round trip


Photo by MagnusL3D/Flickr.

In its spectacular setting beneath the soaring, snow-capped peaks of the North Shore Mountains and the navy blue waters of the Straights of Georgia, Vancouver’s inner-city districts rise up in clusters of skyscrapers, docklands and leafy parks, all laden with cool art galleries, cosmopolitan eateries and plenty of cultural pursuits. What’s more, those making the most of the cheapest returns of around $295 in October and November will enjoy access to some of the most celebrated ski fields in Canada (nay, the world) with cloud-covered Grouse Mountain across the water and the sprawling Whistler resort just a little to the north!

5. Fly Spirit to San Juan, Puerto Rico, for only $280 round trip


Photo by dameetch/Flickr.

Between the painted colonial façades of San Juan’s Old Town, the soaring Spanish cliff-top fortresses that pepper its nearby coast, the rolling Caribbean surf swells, the bustling cocktail bars of the Isla Verde, and the postcard-perfect beachfronts of Condado and the western coast, there’s little question that anyone coming into Puerto Rico on one of these non-stop connections from Chicago’s O'Hare International will have plenty of things to be getting on with. What’s more, prices start at around just $280 return, with American, JetBlue and United all making the trip regularly.

4. Fly Spirit to New Orleans for as low as $154 round trip


Photo by w4nd3rl0st (InspiredinDesMoines)/Flickr.

Both American Airlines and United Airlines fly direct routes from O'Hare International Airport to New Orleans’ Louis Armstrong International, with Spirit offering passengers the best bang for their buck at only $154 return. Once in town, Chicago locals will need to jolt themselves from the trattorias of their own Little Italy and the tavernas of Greek Town, ready for a dose of Carib-Creole culture and French flamboyance amidst the iconic old quarters, European cocktail bars and Cajun cooking joints of Louisiana’s biggest party city!

3. Fly Spirit to Boston for only $154 round trip


Photo by Werner Kunz/Flickr.

If Chicago is a living, breathing example of the modern American metropolis, then Boston is a living and breathing homage to how it all began; the perfect vacationing spot for any who want to follow the Freedom Trail and wonder at the institutions that first helped forge the Declaration of Independence. The cheapest carrier currently flying the route into the town’s Logan International Airport is Spirit Airlines, with round-trip fares hovering anywhere between $148 and $187.

2. Fly Spirit to Denver for only $124 round trip


Photo by pov_steve/Flickr.

From the vast patchwork of low-lying wetlands and endless prairie that dominates the Midwest, travelers on this direct connection with Spirit Airlines can transport themselves to the quintessentially American world of snow-tipped Rocky peaks, sprawling spruce forests and hearty beer-mad locals that clusters so fiercely around Colorado’s Denver. Flights depart daily and fares can cost as little as $124 return, with the cheapest options leaving and returning mid-week in either September or October. See you in the micro-breweries!

1. Fly Frontier to Washington DC for only $104 round trip


Photo by eviltomthai/Flickr.

Why not hop across the Great Lakes and immerse yourself in the hubbub of the nation’s capital with this nonstop Frontier Airlines connection out of the O'Hare International Airport for just $104 both ways. Between D.C’s famous honorific monuments, iconic government buildings, sprawling museum complexes, huge leafy parks, thriving after dark jazz scene and cosmopolitan gastronomic offering, those arriving from the action and energy of Chicago, can rest assured there will be plenty to keep them busy.

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