South America

$152+ Cheap flights from Chicago (CHI) to South America

CHI — BOG
Dec 4 — Dec 111
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Cheap flight deals from Chicago to South America

Cheapest flights from Chicago to South America

Tue 11/32:13 pm -
1 stop22h 52m
Sat 11/76:25 am -
1 stop18h 46m
Deal found 10/31$446
Sat 11/77:50 pm -
1 stop16h 45m
Tue 11/104:37 pm -
1 stop8h 19m
Deal found 11/2$459
Mon 11/165:30 am -
1 stop7h 49m
Mon 11/237:31 am -
2 stops26h 51m
Deal found 11/3$462
Tue 11/106:15 pm -
1 stop19h 04m
Sat 11/143:34 pm -
1 stop18h 07m
Deal found 11/3$467
Thu 11/127:50 pm -
1 stop18h 46m
Wed 11/184:37 pm -
1 stop16h 23m
Deal found 11/2$470
Sun 11/158:04 am -
1 stop10h 26m
Wed 11/183:55 pm -
1 stop8h 59m
Deal found 11/1$472
Mon 11/2310:35 am -
1 stop7h 55m
Tue 11/249:00 am -
1 stop11h 05m
Deal found 11/3$473
Fri 11/135:45 am -
1 stop9h 05m
Thu 12/31:05 pm -
1 stop11h 39m
Deal found 11/1$474
Sun 11/158:04 am -
1 stop29h 15m
Mon 11/233:34 pm -
1 stop26h 31m
Deal found 11/3$475
Mon 11/235:30 am -
1 stop13h 00m
Tue 12/19:00 am -
1 stop11h 09m
Deal found 10/31$475
Fri 11/135:45 am -
1 stop9h 05m
Tue 12/11:05 pm -
1 stop23h 08m
Deal found 11/2$478
Sun 11/225:30 am -
1 stop7h 55m
Sun 12/63:55 pm -
1 stop9h 01m
Deal found 11/1$479

Find flight deals from Chicago to South America

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$439
(Justfly.com)

One-way from

$152
(Expedia)

Popular in

June

Cheapest in

January

Average price

$908

Good round-trip deal

$525 or less

Good one-way deal

$456 or less
Provider with most accurate pricing for Chicago (CHI)-Sao Paulo (SAO) flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Sao Paulo (SAO) flights.
From Chicago (CHI) to South America
One-way flight from Chicago (CHI) to South America
Highest demand for flights based on searches. 13% potential increase in price ($137 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($23 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Chicago (CHI) to South America.
Price to beat on a one-way flight from Chicago (CHI) to South America.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Chicago to South America that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBogotá

ORD Chicago O'Hare Intl - BOG Bogotá El Dorado

ORDBOG

Chicago O'Hare Intl

Sun 11/15

8:04 am-7:30 pm

1 stop10h 26m

Bogotá El Dorado

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$214

ChicagoCartagena

ORD Chicago O'Hare Intl - CTG Cartagena Rafael Nunez

ORDCTG

Chicago O'Hare Intl

Sat 11/14

2:13 pm-8:35 am

1 stop17h 22m

Cartagena Rafael Nunez

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$218

ChicagoBogotá

ORD Chicago O'Hare Intl - BOG Bogotá El Dorado

ORDBOG

Chicago O'Hare Intl

Thu 12/31

11:07 am-11:05 pm

1 stop10h 58m

Bogotá El Dorado

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$218

ChicagoBogotá

ORD Chicago O'Hare Intl - BOG Bogotá El Dorado

ORDBOG

Chicago O'Hare Intl

Mon 1/25

7:00 am-7:30 pm

2 stops11h 30m

Bogotá El Dorado

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$218

ChicagoCartagena

ORD Chicago O'Hare Intl - CTG Cartagena Rafael Nunez

ORDCTG

Chicago O'Hare Intl

Mon 11/9

5:30 am-2:19 pm

1 stop7h 49m

Cartagena Rafael Nunez

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$221

ChicagoCartagena

ORD Chicago O'Hare Intl - CTG Cartagena Rafael Nunez

ORDCTG

Chicago O'Hare Intl

Sun 11/15

7:15 pm-2:19 pm

2 stops18h 04m

Cartagena Rafael Nunez

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$227

ChicagoBogotá

ORD Chicago O'Hare Intl - BOG Bogotá El Dorado

ORDBOG

Chicago O'Hare Intl

Sat 11/14

2:13 pm-11:07 am

1 stop19h 54m

Bogotá El Dorado

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$228

ChicagoBogotá

ORD Chicago O'Hare Intl - BOG Bogotá El Dorado

ORDBOG

Chicago O'Hare Intl

Tue 11/17

7:35 am-11:07 am

1 stop26h 32m

Bogotá El Dorado

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$228

ChicagoBogotá

ORD Chicago O'Hare Intl - BOG Bogotá El Dorado

ORDBOG

Chicago O'Hare Intl

Mon 11/16

2:13 pm-11:07 am

1 stop19h 54m

Bogotá El Dorado

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$228

ChicagoBogotá

ORD Chicago O'Hare Intl - BOG Bogotá El Dorado

ORDBOG

Chicago O'Hare Intl

Tue 12/1

5:30 am-7:30 pm

1 stop13h 00m

Bogotá El Dorado

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago to South America

Have a flexible travel schedule? Discover the best time to fly to South America from Chicago with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Chicago to South America

What is the cheapest month to book a flight from Chicago to South America?

Currently, February is the cheapest month in which you can book a flight from Chicago to South America (average of $541). Flying from Chicago to South America in December is currently the most expensive (average of $867). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SA?

When flying from Chicago to South America, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 45% versus a flight in the afternoon.

How often are flights from Chicago to South America delayed?

About 31% of weekly flights between Chicago and South America have experienced delays in the past year, with the average delay time being 180 minutes.

What is the most punctual flight time for Chicago to South America flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to South America flights?

Over the last year, Avianca have had the lowest number of delays on this route, with just 17% of flights being delayed.

How far ahead should I book a flight from Chicago to South America?

The price you pay for your flight from Chicago to South America may vary depending on when you book. For the best chance of a lower fare, look to book 32 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing South America

Read reviews from past customers who have flown Copa Airlines,LATAM Airlines, andUnited Airlines from Chicago to South America. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

7.8

Crew

8.1

Comfort

7.4

Entertainment

6.9

Overall

7.6

Food

7.0

Reviews

1 / 20
4.0
Okay

Marcos,Nov 2026

BOS - PTY

Not good. Boarding was delayed about 30/40min which made my making my connection very stressful. On top of that, the accommodations (seating, entertainment, and food) were subpar -- to say the least. I've traveled a lot between the US and Argentina and this may have been my worst experience yet.

Boarding

7.8

Crew

8.1

Comfort

7.4

Entertainment

6.9

Overall

7.6

Food

7.0

Reviews

1 / 20
4.0
Okay

Marcos,Nov 2026

BOS - PTY

Not good. Boarding was delayed about 30/40min which made my making my connection very stressful. On top of that, the accommodations (seating, entertainment, and food) were subpar -- to say the least. I've traveled a lot between the US and Argentina and this may have been my worst experience yet.

Boarding

7.8

Crew

8.1

Comfort

7.4

Entertainment

6.9

Overall

7.6

Food

7.0

Reviews

1 / 20
4.0
Okay

Marcos,Nov 2026

BOS - PTY

Not good. Boarding was delayed about 30/40min which made my making my connection very stressful. On top of that, the accommodations (seating, entertainment, and food) were subpar -- to say the least. I've traveled a lot between the US and Argentina and this may have been my worst experience yet.

Boarding

7.8

Crew

8.1

Comfort

7.4

Entertainment

6.9

Overall

7.6

Food

7.0

Reviews

1 / 20
4.0
Okay

Marcos,Nov 2026

BOS - PTY

Not good. Boarding was delayed about 30/40min which made my making my connection very stressful. On top of that, the accommodations (seating, entertainment, and food) were subpar -- to say the least. I've traveled a lot between the US and Argentina and this may have been my worst experience yet.

Boarding

7.8

Crew

8.1

Comfort

7.4

Entertainment

6.9

Overall

7.6

Food

7.0

Reviews

1 / 20
4.0
Okay

Marcos,Nov 2026

BOS - PTY

Not good. Boarding was delayed about 30/40min which made my making my connection very stressful. On top of that, the accommodations (seating, entertainment, and food) were subpar -- to say the least. I've traveled a lot between the US and Argentina and this may have been my worst experience yet.

Boarding

7.8

Crew

8.1

Comfort

7.4

Entertainment

6.9

Overall

7.6

Food

7.0

Reviews

1 / 20
4.0
Okay

Marcos,Nov 2026

BOS - PTY

Not good. Boarding was delayed about 30/40min which made my making my connection very stressful. On top of that, the accommodations (seating, entertainment, and food) were subpar -- to say the least. I've traveled a lot between the US and Argentina and this may have been my worst experience yet.

Related info for your journey

  • How long is the flight from Chicago to South America?

    A quick flight from Chicago to South America can take about 9h 40m. Copa Airlines provides one of the quickest options available for as low as $485. There are 2589 mi between Chicago and South America. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to South America one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $107. Users have also found prices from $115 and $126 on Avianca and American Airlines, respectively.

  • What are the most popular routes from Chicago to South America?

  • What are the cheapest flights from Chicago to South America?

    On average you can expect to pay $1,152 for a flight from Chicago to South America. The cheapest flight overall is $276 while the most popular route, (Chicago O'Hare Intl - Lima J Chavez Intl) is currently priced at $482.

  • Can I find deals for flights from Chicago to South America that include hotel bookings?

    Yes. In addition to deals on Chicago to South America flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to South America?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to South America.

  • Can I find deals for business class flights from Chicago to South America?

    Yes. Cheapflights offers flight deals from Chicago to South America by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to South America?

    Currently, February is the cheapest month in which you can book a flight from Chicago to South America (average of $541). Flying from Chicago to South America in December is currently the most expensive (average of $867). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to South America

Top 10 airlines flying from Chicago to South America

AirlineCheapestAverageFlexibilityOn-time
ArajetCheapest$137Average$613FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$153Average$797FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$161Average$661FlexibilityNo cancel feeOn-time62%
LATAM AirlinesCheapest$185Average$791FlexibilityNo cancel feeOn-time81%
VolarisCheapest$217Average$423FlexibilityNo cancel feeOn-time79%
Copa AirlinesCheapest$235Average$670FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$296Average$852FlexibilityNo cancel feeOn-time71%
AviancaCheapest$298Average$701FlexibilityNo cancel feeOn-time71%
GOLCheapest$306Average$825FlexibilityNo cancel feeOn-time74%
United AirlinesCheapest$307Average$789FlexibilityNo cancel feeOn-time69%

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