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$362+ Cheap flights from Chicago (CHI) to Caracas (CCS)

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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CCS
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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1. Tell us where you want to go

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Cheap flight deals from Chicago to Caracas

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Caracas (CCS). 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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$641
(Trip.com)

One-way from

$362
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Caracas Simon Bolivar flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Caracas Simon Bolivar flights.
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From Chicago (CHI) to Caracas Simon Bolivar
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One-way flight from Chicago (CHI) to Caracas Simon Bolivar
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Find flight deals from Chicago to Caracas

Cheapest flights from Chicago to Caracas
Explore the most affordable flight options available from Chicago to Caracas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

This Trip.com deal was found by Cheapflights users on 1/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/15:15 amORD - CCS
2 stops13h 45mMultiple Airlines
Fri 2/66:30 pmCCS - ORD
2 stops31h 17mMultiple Airlines
Deal found 1/4$641
This Trip.com deal was found by Cheapflights users on 1/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/45:15 amORD - CCS
2 stops13h 45mMultiple Airlines
Wed 2/114:30 pmCCS - ORD
3 stops44h 52mMultiple Airlines
Deal found 1/5$720
This Trip.com deal was found by Cheapflights users on 1/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/245:32 pmORD - CCS
3 stops25h 28mMultiple Airlines
Wed 1/284:30 pmCCS - ORD
3 stops44h 52mMultiple Airlines
Deal found 1/5$739
This Trip.com deal was found by Cheapflights users on 1/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/25:15 amORD - CCS
2 stops13h 45mMultiple Airlines
Sun 2/84:30 pmCCS - ORD
2 stops33h 17mMultiple Airlines
Deal found 1/5$759
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Tue 2/248:16 pmORD - CCS
2 stops22h 44mMultiple Airlines
Fri 2/278:30 amCCS - ORD
2 stops17h 17mMultiple Airlines
Deal found 1/6$892
This Mytrip deal was found by Cheapflights users on 1/5. 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.
Wed 2/45:15 amORD - CCS
2 stops13h 45mMultiple Airlines
Thu 2/58:30 amCCS - ORD
2 stops17h 17mMultiple Airlines
Deal found 1/5$910
This Mytrip deal was found by Cheapflights users on 1/4. 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.
Tue 1/205:32 pmORD - CCS
3 stops25h 28mMultiple Airlines
Thu 1/2210:20 amCCS - ORD
3 stops38h 22mMultiple Airlines
Deal found 1/4$936

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Caracas 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 January 6, 2026.
Use the filters below to find and compare flights from Chicago to Caracas that are best for you.

Fly from

Chicago

Fly to

Caracas

Route

Depart

Return

Price

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Sun 2/1

5:15 am-9:00 pm

2 stops13h 45m

Caracas Simon Bolivar

Fri 2/6

6:30 pm-11:47 pm

2 stops31h 17m

$641

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Wed 2/4

5:15 am-9:00 pm

2 stops13h 45m

Caracas Simon Bolivar

Wed 2/11

4:30 pm-11:22 am

3 stops44h 52m

$720

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Sat 1/24

5:32 pm-9:00 pm

3 stops25h 28m

Caracas Simon Bolivar

Wed 1/28

4:30 pm-11:22 am

3 stops44h 52m

$739

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Mon 2/23

8:16 pm-8:07 am

2 stops33h 51m

Caracas Simon Bolivar

Mon 3/9

9:12 am-9:20 pm

1 stop13h 08m

$926

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Mon 2/23

8:16 pm-8:07 am

2 stops33h 51m

Caracas Simon Bolivar

Wed 3/4

9:12 am-8:20 pm

1 stop13h 08m

$926

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Tue 1/20

5:32 pm-9:00 pm

3 stops25h 28m

Caracas Simon Bolivar

Thu 1/22

10:20 am-10:42 pm

3 stops38h 22m

$936

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Mon 2/23

8:16 pm-8:07 am

2 stops33h 51m

Caracas Simon Bolivar

Sun 3/8

9:12 am-9:20 pm

1 stop13h 08m

$945

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Fri 2/27

8:16 pm-8:07 am

2 stops33h 51m

Caracas Simon Bolivar

Fri 3/6

11:55 am-8:20 pm

1 stop10h 25m

$950

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Wed 3/4

10:20 pm-8:57 pm

2 stops20h 37m

Caracas Simon Bolivar

Wed 3/25

9:12 am-9:20 pm

1 stop13h 08m

$973

ChicagoCaracas

ORD - CCS

ORDCCS

Chicago O'Hare Intl

Wed 2/18

10:20 pm-8:57 pm

2 stops20h 37m

Caracas Simon Bolivar

Wed 2/25

9:12 am-8:20 pm

1 stop13h 08m

$973

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 15 results
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Compare providers for flights from Chicago to Caracas

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 Caracas in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice Accuracy2 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-Caracas flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Caracas flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Caracas flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Caracas flights, Cheapflights users trust eDreams the most. eDreams 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-Caracas 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 Caracas

Have a flexible travel schedule? Discover the best time to fly to Caracas 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 Caracas
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Caracas. 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 Caracas from Chicago?

    Caracas Simon Bolivar (CCS) is the airport you will fly into if you book a flight from Chicago to Caracas. You should not have trouble finding flights to Simon Bolivar from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Caracas airport from Chicago. It is only a 10.3 mi journey from Simon Bolivar (CCS) to Caracas’s city center.

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

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

  • How can I find direct flights from Chicago to Caracas?

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

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

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

See more FAQs

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