10 Cheapest Flights from Chicago to South America

For a vacation to sunny beaches or charming colonial towns, check out the ten cheapest flights from Chicago to South America!

Hopper Editors - Oct. 26, 2017

Touting the soaring cloud temples of the Peruvian Andes, the shimmering surfer beaches of Brazil on the Atlantic and those of Ecuador on the Pacific, the legendary Nazca Lines, the mysterious reaches of the old Incan empire, and the colonial relics that now pepper the aging cities of the Spanish conquistadores in the hills of Colombia and the like, South America is a land of pure wonder and magic.

For travelers out of Chicago's O'Hare International Airport, the continent is accessible via a whole host of various air connections, which can vary wildly in price and often break the bank before the trip has even started! To help out, Hopper's expert flight team has crunched all the numbers using their big data research method to bring readers this list of the 10 cheapest flights on offer between Chicago and South America.

Download Hopper's new iOS app to find the best deals and you could save up to 40% on your next flight!

10. Fly from Chicago to Pisac, Peru for as low as $978 round trip

Sitting sandwiched between the ancient capital of the Incan empire at Cusco, the soaring rises of the high Andes and the legendary sites of the Sacred Valley, the town of Pisac is the stuff of bucket lists and dreams. Indirect flights into town take approximately 17 hours in the air, will set intrepid travelers out of the O'Hare International Airport back around $978 round trip, and are run by no fewer than six separate carriers — of which Avianca's are the cheapest.

9. Fly from Chicago to Campinas, Brazil for as low as $952 round trip

If you've been edged out of a bargain flight connection into the throbbing Brazilian metropolis of Sao Paulo (probably by one of the other 13,000 people searching for flights on the route from Chicago each month), then it's definitely worth checking out departures from Chicago to the city of Campinas, which sits just a short jaunt inland from the booming state capital itself. Expect to pay around $952 for round trip flights, and be sure to check out American Airlines' route via Miami for the best deals going.

8. Fly from Chicago to Sao Paulo, Brazil for as low as $919 round trip

There's no city in South America more visceral and enthralling than Sao Paulo, a 12 million strong megalopolis that sits just a stone's throw from the rolling swells of the Atlantic Ocean in southern Brazil. Expect oodles of Portuguese culinary creations next to thumping beer bars and soaring skyscrapers, not to mention a carnival season to dwarf all others. Granted, the price tag isn't tiny, but there is scope for passengers to get even cheaper tickets when flying indirect on some carriers, like Copa or AeroMéxico.

7. Fly from Chicago to Cali, Colombia for as low as $790 round trip

Touting the legendary windsurfing reaches of Lake Calima, the religious and cultural sites of Buga City and easy access to the beautiful backcountry that dominates around Pance in a medley of waterfalls and mist-clad volcanic peaks, the city of Cali is an excellent, off-the-beaten-track choice for any Illinois locals interested in exploring Colombia's rich cultures and majestic inland scenery. Expect to pay in the region of $790 for flights, going indirect on American Airlines via Miami and Bogota for the best deals overall.

6. Fly from Chicago to Guayaquil, Ecuador for as low as $719 round trip

All of four separate airlines currently run indirect connections between the Jose Joaquin de Olmedo International Airport in Guayaquil and Chicago's O'Hare, including Colombian national flag carrier Avianca, whose route via San Salvador takes around nine hours from departure to arrival and costs in the region of just $719 round trip! Once in town, Illinois locals will need to dispense of their penchant for deep-dish pizza pies, because Ecuador's largest city is famed for its super-fresh pacific seafood and hearty red meat ceviche dishes.

5. Fly from Chicago to Quito, Ecuador for as low as $713 round trip

Soaring high on the tips of the South American Andes, the city of Quito is hailed as the most altitudinous in the world — which may be why the price tag here is some $130 behind the next cheapest connection on this list! Still, that's not to say these indirect flights aren't a great deal for Midwesterners, especially those eager to case out the brooding volcanos of the Cayambe National Park, the colonial wonders of Quito's own UNESCO core, or the rainforests of Mindo just to the north.

4. Fly from Chicago to Lima, Peru for as low as $581 round trip

Sliding nicely into fourth place here with an average round trip price tag of just $581 is the city of Lima — the gateway to the legendary Peruvian coast, and the perfect South American entry point for further explorations at places like the Ballestas Islands, the Andes at Huancayo, or the vibrant carnival city of Cajamarca. (No wonder this one's the most popular destination on this list!) For the cheapest seats, be sure to check out Spirit Airlines, who go indirect via Fort Lauderdale.

3. Fly from Chicago to Cartagena, Colombia for as low as $536 round trip

Touting its long and vibrant past and fusing the fun-loving and colorful culture of the Caribbean with the earthy traditions of South American Colombia, the city of Cartagena is the perfect choice for any Midwesterners eager to explore the rich history of the continent while enjoying some of its most celebrated beaches. Flights into town will cost passengers in the region of $536 round trip, with the cheapest tickets going indirect on low-coster Spirit Airlines.

2. Fly from Chicago to Bogota, Colombia for as low as $506 round trip

Hugging the aged colonial kernel of La Candelaria, sprawling Bogota edges its way out over the rugged peaks of the high Andean plateau in a medley of cumbia beats and aromatic ajiaco soups, cooked up in the styles of the ancient, pre-Columbian hill tribes. For adventure seekers looking for a bargain air connection out of Chicago this year, this one certainly won't disappoint — and with round trip flights coming in at just $506 on budget carrier Spirit Airlines, it shouldn't break the bank either!

1. Fly from Chicago to Medellin, Colombia for as low as $453 round trip

While fliers may not have heard of the destination, they will no doubt welcome such a wallet-friendly price tag! In fact, anything shy of $500 should be seen as a mega bargain for any flight connecting Chicago with South America, but the fact that this $435 round tripper places travelers in the midst of the Colombian highlands — with the sprawling city of Bogota to the south, the vistas of the Paramillo National Park to the north, and the charming colonial towns of Jardin and Santa Fe de Antioquia all around — makes it one of the best buys on the market for sure!

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

Get the Hopper app to find the best deals.
You could save up to 40% on your next flight!