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Santa Cruz de la Sierra

$269+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VVI
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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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 October 23, 2025.

This Copa Airlines deal was found by Cheapflights users on 10/22. 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.
Mon 11/106:56 amORD - VVI
1 stop13h 50mCopa Airlines
Mon 11/1711:40 amVVI - ORD
1 stop14h 25mCopa Airlines
Deal found 10/22$417
This Copa Airlines deal was found by Cheapflights users on 10/23. 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.
Thu 11/66:56 amORD - VVI
1 stop13h 50mCopa Airlines
Sat 11/151:09 amVVI - ORD
1 stop13h 37mCopa Airlines
Deal found 10/23$571
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Mon 11/1010:52 amORD - VVI
2 stops14h 44mUnited Airlines
Mon 11/1711:40 amVVI - ORD
2 stops22h 01mUnited Airlines
Deal found 10/22$604
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Tue 11/119:15 amORD - VVI
3 stops40h 21mUnited Airlines
Tue 11/2511:40 amVVI - ORD
2 stops14h 35mUnited Airlines
Deal found 10/22$620
This United deal was found by Cheapflights users on 10/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1112:45 pmORD - VVI
2 stops36h 51mMultiple Airlines
Mon 11/243:40 amVVI - ORD
2 stops19h 37mMultiple Airlines
Deal found 10/22$627
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Sun 11/22:07 pmORD - VVI
1 stop30h 39mCopa Airlines
Fri 11/71:09 amVVI - ORD
1 stop24h 56mCopa Airlines
Deal found 10/21$630
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:07 pmORD - VVI
1 stop11h 29mCopa Airlines
Thu 12/2511:40 amVVI - ORD
1 stop27h 12mCopa Airlines
Deal found 10/20$652
This Avianca deal was found by Cheapflights users on 10/22. 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.
Mon 11/107:25 amORD - VVI
2 stops17h 10mAvianca
Sun 11/163:40 amVVI - ORD
1 stop18h 40mAvianca
Deal found 10/22$671
This Avianca deal was found by Cheapflights users on 10/21. 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.
Sun 11/27:35 amORD - VVI
2 stops17h 00mAvianca
Fri 11/73:40 amVVI - ORD
1 stop18h 40mAvianca
Deal found 10/21$683
This Avianca deal was found by Cheapflights users on 10/23. 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.
Thu 11/68:50 amORD - VVI
2 stops15h 45mAvianca
Sat 11/153:40 amVVI - ORD
1 stop18h 40mAvianca
Deal found 10/23$693

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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$417
(Copa Airlines)

One-way from

$269
(United)

Popular in

July

Cheapest in

March

Average price

$638
Provider with most accurate pricing for Chicago (CHI)-Santa Cruz de la Sierra Viru Viru Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Santa Cruz de la Sierra Viru Viru Intl flights.
Search Deals
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. 9% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 23, 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

Mon 11/10

6:56 am-10:46 pm

1 stop13h 50m

Santa Cruz de la Sierra Viru Viru Intl

Mon 11/17

11:40 am-12:05 am

1 stop14h 25m

$417

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Thu 11/6

6:56 am-10:46 pm

1 stop13h 50m

Santa Cruz de la Sierra Viru Viru Intl

Sat 11/15

1:09 am-12:46 pm

1 stop13h 37m

$571

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Mon 11/3

2:07 pm-3:36 am

1 stop11h 29m

Santa Cruz de la Sierra Viru Viru Intl

Tue 11/11

1:09 am-12:46 pm

1 stop13h 37m

$587

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Mon 11/3

6:56 am-3:36 am

1 stop18h 40m

Santa Cruz de la Sierra Viru Viru Intl

Wed 12/24

1:09 am-12:52 pm

1 stop13h 43m

$587

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Mon 11/3

6:00 am-3:36 am

2 stops19h 36m

Santa Cruz de la Sierra Viru Viru Intl

Thu 12/25

11:40 am-9:10 am

2 stops23h 30m

$604

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Mon 11/10

7:30 am-3:36 am

2 stops18h 06m

Santa Cruz de la Sierra Viru Viru Intl

Mon 11/17

11:40 am-11:43 pm

2 stops38h 03m

$604

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Sun 11/2

9:08 pm-3:36 am

2 stops28h 28m

Santa Cruz de la Sierra Viru Viru Intl

Sat 11/8

11:40 am-9:46 am

2 stops24h 06m

$604

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Tue 11/11

5:55 pm-3:36 am

2 stops31h 41m

Santa Cruz de la Sierra Viru Viru Intl

Tue 11/25

11:40 am-10:02 am

2 stops24h 22m

$604

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Mon 3/2

6:00 am-2:35 am

2 stops42h 35m

$269

ChicagoSanta Cruz de la Sierra

ORD - VVI

ORDVVI

Chicago O'Hare Intl

Mon 3/2

7:34 am-10:50 pm

1 stop13h 16m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 13 results
1
2

Compare providers for flights from Chicago to Santa Cruz de la Sierra

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Santa Cruz de la Sierra in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Santa Cruz de la Sierra flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Santa Cruz de la Sierra flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Santa Cruz de la Sierra flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Santa Cruz de la Sierra flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Santa Cruz de la Sierra flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, November is the cheapest month in which you can book a flight from Chicago to Santa Cruz de la Sierra (average of $258). Flying from Chicago to Santa Cruz de la Sierra in January is currently the most expensive (average of $899). 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 October 23, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 10% 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 October 23, 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
1,558 reviews

Comfort

7.4

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

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
1,558 reviews
Copa Airlines
7.6
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

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
8,991 reviews
Copa Airlines
7.6
Good
1,558 reviews

Comfort

7.4

Entertainment

6.8

Food

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

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 13h 50m. Fly via Copa Airlines to get the fastest option. Airlines will cover a distance of 4410 mi.

  • 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 12% 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, November is the cheapest month in which you can book a flight from Chicago to Santa Cruz de la Sierra (average of $258). Flying from Chicago to Santa Cruz de la Sierra in January is currently the most expensive (average of $899). 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

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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$566Average$776FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$581Average$619FlexibilityNo cancel feeOn-time69%

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