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Santa Cruz de la Sierra

$261+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VVI
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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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 septiembre 16, 2025.

Round-trip from

$556
(Avianca)

One-way from

$261
(Avianca Connect)

Popular in

July

Cheapest in

March

Average price

$602
From Chicago (CHI) to Santa Cruz de la Sierra Viru Viru Intl
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One-way flight from Chicago (CHI) to Santa Cruz de la Sierra Viru Viru Intl
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Highest demand for flights based on searches. 7% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septiembre 16, 2025.

This Avianca deal was found by Cheapflights users on 9/15. 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. 11/148:50 amORD - VVI
2 stops15h 45mAvianca
mié. 1/143:40 amVVI - ORD
1 stop18h 40mAvianca
Deal found 9/15$556
This United Airlines deal was found by Cheapflights users on 9/14. 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. 11/249:10 pmORD - VVI
2 stops23h 36mUnited Airlines
sáb. 11/291:09 amVVI - ORD
2 stops48h 34mUnited Airlines
Deal found 9/14$611
This United Airlines deal was found by Cheapflights users on 9/15. 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. 11/149:07 pmORD - VVI
2 stops47h 39mUnited Airlines
mié. 1/141:15 amVVI - ORD
2 stops25h 13mUnited Airlines
Deal found 9/15$657
This Avianca deal was found by Cheapflights users on 9/15. 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. 9/1910:35 amORD - VVI
2 stops14h 15mMultiple Airlines
sáb. 9/202:50 amVVI - ORD
1 stop11h 25mMultiple Airlines
Deal found 9/15$695
This Avianca deal was found by Cheapflights users on 9/14. 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.
mié. 12/1710:20 pmORD - VVI
1 stop26h 15mAvianca
mié. 12/243:40 amVVI - ORD
1 stop18h 40mAvianca
Deal found 9/14$714
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/1310:27 amORD - VVI
1 stop17h 23mMultiple Airlines
dom. 10/192:50 amVVI - ORD
2 stops21h 55mMultiple Airlines
Deal found 9/13$746
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/1410:20 pmORD - VVI
1 stop26h 15mMultiple Airlines
jue. 1/1510:25 pmVVI - ORD
2 stops23h 55mMultiple Airlines
Deal found 9/15$823
This United Airlines deal was found by Cheapflights users on 9/15. 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. 11/229:10 pmORD - VVI
2 stops23h 36mUnited Airlines
sáb. 11/291:09 amVVI - ORD
2 stops32h 32mUnited Airlines
Deal found 9/15$825
This Avianca deal was found by Cheapflights users on 9/14. 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. 12/186:10 amORD - VVI
2 stops18h 25mAvianca
mié. 12/243:40 amVVI - ORD
1 stop18h 40mAvianca
Deal found 9/14$829
This United Airlines deal was found by Cheapflights users on 9/15. 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.
mié. 12/246:21 pmORD - VVI
2 stops26h 25mUnited Airlines
mié. 12/311:15 amVVI - ORD
2 stops34h 23mUnited Airlines
Deal found 9/15$832

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 septiembre 16, 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. 11/24

9:10 pm-10:46 pm

2 stops23h 36m

Santa Cruz de la Sierra Viru Viru Intl

sáb. 11/29

1:09 am-11:43 pm

2 stops48h 34m

$611

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

mié. 3/11

3:22 pm-3:38 am

1 stop11h 16m

Santa Cruz de la Sierra Viru Viru Intl

mié. 3/25

1:14 am-1:31 pm

1 stop13h 17m

$656

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

mié. 3/11

7:56 am-10:50 pm

1 stop13h 54m

Santa Cruz de la Sierra Viru Viru Intl

dom. 3/22

1:14 am-1:31 pm

1 stop13h 17m

$656

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

vie. 11/14

9:07 pm-10:46 pm

2 stops47h 39m

Santa Cruz de la Sierra Viru Viru Intl

mié. 1/14

1:15 am-12:28 am

2 stops25h 13m

$657

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

mié. 3/11

9:13 pm-10:50 pm

2 stops24h 37m

Santa Cruz de la Sierra Viru Viru Intl

mar. 3/24

1:14 am-8:51 pm

2 stops20h 37m

$711

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

mié. 3/11

6:00 am-10:50 pm

2 stops15h 50m

Santa Cruz de la Sierra Viru Viru Intl

lun. 3/23

1:14 am-12:10 am

2 stops23h 56m

$711

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

mié. 3/11

3:22 pm-3:38 am

1 stop11h 16m

Santa Cruz de la Sierra Viru Viru Intl

mar. 3/24

1:14 am-1:31 pm

1 stop13h 17m

$725

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

lun. 10/13

3:50 pm-1:50 am

2 stops33h 00m

Santa Cruz de la Sierra Viru Viru Intl

dom. 10/19

1:09 am-11:41 am

2 stops35h 32m

$752

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

sáb. 11/22

9:10 pm-10:46 pm

2 stops23h 36m

Santa Cruz de la Sierra Viru Viru Intl

sáb. 11/29

1:09 am-7:41 am

2 stops32h 32m

$825

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

jue. 10/16

5:05 am-1:50 am

2 stops19h 45m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
1
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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 septiembre 16, 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 septiembre 16, 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
7.6
Good
1,531 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Entertainment

6.8

Boarding

7.8

Overall

7.6

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,531 reviews
Copa Airlines
7.6
Good
1,531 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Entertainment

6.8

Boarding

7.8

Overall

7.6

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
8,924 reviews
Copa Airlines
7.6
Good
1,531 reviews

Comfort

7.4

Food

6.8

Crew

8.1

Entertainment

6.8

Boarding

7.8

Overall

7.6

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

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 16m. Fly via United Airlines or Copa 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 14% 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

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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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$566Average$776FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$581Average$649FlexibilityNo cancel feeOn-time69%

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