HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Santa Cruz de la Sierra

$495+ Cheap flights from Chicago (CHI) to Santa Cruz de la Sierra (VVI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VVI
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Santa Cruz de la Sierra with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Santa Cruz de la Sierra

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Santa Cruz de la Sierra (VVI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated agosto 20, 2025.

Round-trip from

$559
(Avianca Connect)

One-way from

$495
(Kiwi.com)

Popular in

July

Cheapest in

March

Average price

$566
From Chicago (CHI) to Santa Cruz de la Sierra Viru Viru Intl
Search Deals
One-way flight from Chicago (CHI) to Santa Cruz de la Sierra Viru Viru Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Chicago to Santa Cruz de la Sierra

Cheapest flights from Chicago to Santa Cruz de la Sierra
Explore the most affordable flight options available from Chicago to Santa Cruz de la Sierra. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 20, 2025.

This Avianca Connect deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca Connect is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/205:05 amORD - VVI
2 stops19h 45mMultiple Airlines
mié. 10/222:50 amVVI - ORD
2 stops16h 34mMultiple Airlines
Deal found 8/18$559
This Copa Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/33:07 pmORD - VVI
1 stop11h 29mCopa Airlines
vie. 11/71:09 amVVI - ORD
1 stop13h 37mCopa Airlines
Deal found 8/19$587
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/219:10 pmORD - VVI
2 stops47h 36mUnited Airlines
sáb. 11/291:09 amVVI - ORD
2 stops24h 46mUnited Airlines
Deal found 8/18$594
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/49:31 pmORD - VVI
2 stops23h 54mUnited Airlines
sáb. 9/131:09 amVVI - ORD
2 stops24h 06mUnited Airlines
Deal found 8/18$603
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/1310:45 amORD - VVI
2 stops34h 32mUnited Airlines
vie. 10/241:09 amVVI - ORD
2 stops21h 35mUnited Airlines
Deal found 8/18$617
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/229:25 pmORD - VVI
2 stops23h 21mUnited Airlines
sáb. 11/291:09 amVVI - ORD
2 stops27h 18mUnited Airlines
Deal found 8/20$669
This Avianca deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/410:54 amORD - VVI
2 stops13h 56mAvianca
sáb. 9/132:50 amVVI - ORD
1 stop11h 25mAvianca
Deal found 8/18$703
This Avianca deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/38:50 amORD - VVI
2 stops16h 00mAvianca
vie. 11/73:40 amVVI - ORD
1 stop18h 40mAvianca
Deal found 8/19$706
This Mytrip deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/136:26 pmORD - VVI
3 stops30h 24mMultiple Airlines
vie. 10/242:50 amVVI - ORD
2 stops16h 34mMultiple Airlines
Deal found 8/18$786

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Santa Cruz de la Sierra that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 20, 2025.
Use the filters below to find and compare flights from Chicago to Santa Cruz de la Sierra that are best for you.

Fly from

Chicago

Fly to

Santa Cruz de la Sierra

Route

Depart

Return

Price

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

lun. 10/20

5:05 am-1:50 am

2 stops19h 45m

Santa Cruz de la Sierra Viru Viru Intl

mié. 10/22

2:50 am-6:24 pm

2 stops16h 34m

$559

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

vie. 10/3

3:07 pm-3:36 am

1 stop11h 29m

Santa Cruz de la Sierra Viru Viru Intl

vie. 11/7

1:09 am-12:46 pm

1 stop13h 37m

$587

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

lun. 10/20

3:07 pm-3:36 am

1 stop11h 29m

Santa Cruz de la Sierra Viru Viru Intl

jue. 10/23

11:59 am-12:21 am

1 stop13h 22m

$587

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

sáb. 11/22

9:30 pm-10:46 pm

2 stops47h 16m

Santa Cruz de la Sierra Viru Viru Intl

sáb. 11/29

1:09 am-11:55 pm

2 stops24h 46m

$594

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

vie. 11/21

9:10 pm-10:46 pm

2 stops47h 36m

Santa Cruz de la Sierra Viru Viru Intl

sáb. 11/29

1:09 am-11:55 pm

2 stops24h 46m

$594

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

vie. 10/3

12:55 pm-10:17 pm

2 stops32h 22m

Santa Cruz de la Sierra Viru Viru Intl

vie. 11/7

1:09 am-11:59 pm

2 stops24h 50m

$603

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

jue. 9/4

9:31 pm-10:25 pm

2 stops23h 54m

Santa Cruz de la Sierra Viru Viru Intl

sáb. 9/13

1:09 am-12:15 am

2 stops24h 06m

$603

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

lun. 10/13

10:45 am-10:17 pm

2 stops34h 32m

Santa Cruz de la Sierra Viru Viru Intl

vie. 10/24

1:09 am-9:44 pm

2 stops21h 35m

$617

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

sáb. 12/13

1:35 pm-4:50 am

1 stop13h 15m

$495

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

sáb. 12/13

5:55 pm-10:46 pm

2 stops26h 51m

$699

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Best time to book a flight from Chicago to Santa Cruz de la Sierra

Have a flexible travel schedule? Discover the best time to fly to Santa Cruz de la Sierra from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Santa Cruz de la Sierra

What is the cheapest month to book a flight from Chicago to Santa Cruz de la Sierra?

Currently, October is the cheapest month in which you can book a flight from Chicago to Santa Cruz de la Sierra (average of $597). Flying from Chicago to Santa Cruz de la Sierra in December is currently the most expensive (average of $822). 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 VVI?

Find hourly flight availability from Chicago to Santa Cruz de la Sierra. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 15% on flights from Chicago to Santa Cruz de la Sierra by exploring options for tickets in the morning.

How much does it cost to fly round-trip from Chicago to Santa Cruz de la Sierra?

Reviews of airlines servicing Santa Cruz de la Sierra

Get insights into the airlines that provide service to Santa Cruz de la Sierra. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Santa Cruz de la Sierra. Reviews last updated agosto 20, 2025.
Peruse reviews from past customers who have flown with Copa Airlines and United Airlines from Chicago to Santa Cruz de la Sierra to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,511 reviews

Crew

8.1

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,511 reviews
Copa Airlines
7.5
Good
1,511 reviews

Crew

8.1

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,928 reviews
Copa Airlines
7.5
Good
1,511 reviews

Crew

8.1

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Santa Cruz de la Sierra. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Santa Cruz de la Sierra from Chicago?

    For a flight from Chicago to Santa Cruz de la Sierra, you will be flying into Viru Viru Intl. Santa Cruz de la Sierra Viru Viru Intl (VVI) is just 11.5 mi from the center of the city. Viru Viru Intl is the only Santa Cruz de la Sierra airport and it handles 0 inbound flights from Chicago per day. 2 airlines have flights to Santa Cruz de la Sierra Viru Viru Intl from Chicago on a regular basis.

  • How long is the flight from Chicago to Santa Cruz de la Sierra?

    There are many flights that can get you from Chicago to Santa Cruz de la Sierra in 11h 29m. Fly via Copa Airlines or United Airlines to get the fastest option. Airlines will cover a distance of 4410 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Santa Cruz de la Sierra round-trip?

    Currently priced at $566, Copa Airlines will fly you from Chicago to Santa Cruz de la Sierra and back. In addition to Copa Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $581. Users have found that Copa Airlines is 15% cheaper than the other options available to this destination.

  • Can I find deals for flights from Chicago to Santa Cruz de la Sierra that include hotel bookings?

    Yes. In addition to deals on Chicago to Santa Cruz de la Sierra flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Santa Cruz de la Sierra?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Santa Cruz de la Sierra.

  • Can I find deals for business class flights from Chicago to Santa Cruz de la Sierra?

    Yes. Cheapflights offers flight deals from Chicago to Santa Cruz de la Sierra 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 Santa Cruz de la Sierra?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Santa Cruz de la Sierra (average of $597). Flying from Chicago to Santa Cruz de la Sierra in December is currently the most expensive (average of $822). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 2 airlines flying from Chicago to Santa Cruz de la Sierra

Discover the top 2 airlines that operate flights from Chicago to Santa Cruz de la Sierra. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$566Average$779FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$581Average$649FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.