C$637 Cheap Flights from Caracas to Chicago

Compare Caracas to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Find the cheapest month to fly from Caracas to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Caracas to Chicago flights are currently cheapest in May.

Caracas to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$640
Cheapest month to flyMay

Finding cheap flights from Caracas to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Caracas to Chicago is C$1,107. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Caracas to Chicago. But we found flights with one or more stops from C$1,101.
As of March 2026, there are no flights flying from Caracas to Chicago.
The cheapest month to fly from Caracas to Chicago is usually May.
If you're flying from Caracas Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from C$1,107.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Caracas Airport to Chicago on Wednesday, May 6, 2026.
No airlines currently offer direct flights between Caracas Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Wingo offers the cheapest flight tickets to Chicago.

Travelling from Simon Bolivar International Airport (CCS) to Chicago: what you need to know

  • Simon Bolivar International Airport is located in Caracas. Operating on the UTC-5 timezone, Chicago is 1 hour behind Caracas.

  • For a smooth journey, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to board your flight from CCS to Chicago.

  • You can expect bigger queues during popular months like July and other peak periods. Arriving up to four hours in advance for international flights and two hours for a domestic departure is a good idea.

  • Stopovers are the perfect opportunity to take a break from travelling — and possibly even explore a different city. When searching for flights from CCS to Chicago, deselect the 'Direct flights only' box to see where you can visit along the way. Some popular options include:

    • Istanbul Ataturk Airport (IST)

    • Adolfo Suarez Madrid-Barajas Airport (MAD)

    • Tocumen International Airport (PTY)

  • You will need an embassy visa for United States if you hold a passport from Venezuela and are travelling for tourism purposes. Visa and travel documentation requirements can be subject to change. So before you book your cheap ticket from Simon Bolivar International Airport to Chicago, check with your airline and your destination country's local consulate or embassy for the most recent updates.

  • CCS is about 27 kilometres from central Caracas. If you're catching a cab, ride-sharing or driving from the centre, it'll take you 28 minutes or so to get there, depending on the traffic.

  • Need a convenient hotel close to CCS? If you've booked an early flight from Simon Bolivar International Airport to Chicago, these stays will put you moments from your departure gate:

How to find the cheapest flights from Simon Bolivar International Airport (CCS) to Chicago

  • C$637 is the best price for a one-way ticket from Simon Bolivar International Airport to Chicago. Return flights start from C$1,107. These prices can change depending on availability and demand.

  • To score cheap tickets from CCS to Chicago, book as early as you can. Airlines usually offer lower prices when flights are first made available.

  • Finding cheap tickets from Simon Bolivar International Airport to Chicago is more likely if you can be flexible with your travel dates. Check out the 'Whole month' search function to show the best prices across the month and land a great deal.

  • Sign into your online account or use the app to create a Price Alert. We'll get in touch right away if there's a cheaper deal on this route. It doesn't take long, and it'll save you time checking for cheap tickets from CCS to Chicago every day.

  • Use the filters to tailor your flights from Simon Bolivar International Airport to Chicago. Simply select your ideal departure and arrival times, airlines and number of stops. Alternatively, sort your results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month to board a flight from Simon Bolivar International Airport to Chicago while February is the quietest. To work out the ideal time to go to Chicago, consider your preferred travel pace and style.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your flights from Simon Bolivar International Airport to Chicago in this month if you enjoy this type of weather.

  • Search for cheap flights from CCS to Chicago in January if you like cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • When it comes to looking for somewhere to lay your head, you'll find the most popular stays in Chicago right here. Check out these hotels once you've booked your flight from Simon Bolivar International Airport to Chicago:

  • Every great adventure has to include some sightseeing. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are must-visits when exploring Chicago.

Complete your Chicago trip with a car rental

  • Select one of our car rentals in Chicago and explore the city in your own time. Easily compare companies in one place to find your perfect ride once you've booked your hotel and cheap flights from Simon Bolivar International Airport to Chicago.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.