Cheap Flights from Caracas to Chicago

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

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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 November.

Alternative Caracas to Chicago routes

Looking for the cheapest, fastest or easiest route from Caracas to Chicago? You could fly into the following airports instead.

Caracas to Chicago: Flight information

The things to know before you go.
Cheapest flight foundج.م.‏ 20,233
Cheapest month to flyNovember

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 ج.م.‏ 37,415. 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 ج.م.‏ 37,415.
As of June 2025, there are no flights flying from Caracas to Chicago.
The cheapest month to fly from Caracas to Chicago is usually June 2025.
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 ج.م.‏ 37,415.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Caracas Airport to Chicago on Thursday, 10 July 2025.
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 June, the average temperature is usually around 19°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

  • Chicago is one hour behind Caracas, where Simon Bolivar International Airport is located. Chicago runs on the UTC-5 timezone.

  • Leave plenty of time to catch your CCS to Chicago flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • If you're flying during a bank holiday or another peak period, give yourself more time. A good rule is two hours before domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

  • Think about adding a stopover to potentially save on your flight ticket from CCS to Chicago. Just deselect 'Direct flights only' during your search. Give yourself a breather (and maybe even a better deal) by stopping at one of these connecting airports:

    • Istanbul Ataturk Airport (IST)

    • Adolfo Suarez Madrid-Barajas Airport (MAD)

    • Tocumen International Airport (PTY)

  • Central Caracas to CCS is around 18 kilometres. Depending on traffic conditions, it'll take you about 30 minutes to get there if you're driving, catching a cab or ride-sharing.

  • Searching for a hotel near CCS? If you've booked an early flight from Simon Bolivar International Airport to Chicago, these stays set you up for a seamless send-off:

  • Of the departures from Simon Bolivar International Airport, 59.05% arrive as scheduled at their destination.

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

  • ج.م.‏ 20,233 is the cheapest price we've found for a one-way Simon Bolivar International Airport to Chicago flight. A round-trip ticket right now is ج.م.‏ 37,415. Depending on when you book and the availability, these fares can change.

  • To pick up cheap flights from CCS to Chicago, book in advance. Airlines usually offer lower prices when flights first go on sale.

  • If you have flexibility with your trip dates, try using the 'Whole month' tool. It'll find the cheapest price across every month when looking for a Simon Bolivar International Airport to Chicago ticket.

  • Never miss a deal on cheap flights from CCS to Chicago by setting up a Price Alert. We'll send you an email or notification through the app when a lower fare becomes available.

  • Tailor your trip with filters. Choose your preferred departure and arrival times, total journey duration and airlines. You can also sort the results by 'Fastest,' 'Best' or 'Cheapest' flights from Simon Bolivar International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you about 35 minutes to get to the centre driving.

  • Getting there on public transport takes around 55 minutes.

  • The last thing you want is a long journey to your hotel if you're landing late on a flight from Simon Bolivar International Airport to Chicago. Check in to one of these accommodation options near ORD instead:

  • Hit the road running by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's usual tourist stops.

  • Booking your ride from O'Hare International Airport around four weeks in advance of your flight from CCS to Chicago can help you get the lowest rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is around 19 kilometres from central Chicago. Once you've disembarked your flight from Simon Bolivar International Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a cab or ride-share.

  • The journey will take about 45 minutes on public transport.

  • Place the 'Do not disturb' sign on your door and relax at a hotel near MDW. Here are a few options where you can tuck yourself in after your CCS to Chicago flight:

  • Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car quick and easy. These providers are located in or around the terminal and will have you on the road before long.

  • Avoid paying more than you need to. Securing your ride four weeks ahead of your arrival at MDW will help you save.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 137 kilometres from central Chicago. It takes about 1 hour 25 minutes to get to the city centre in a ride-share or cab once you've hopped off your flight from Simon Bolivar International Airport to Chicago.

  • If you're travelling on public transport, expect a journey of about 4 hours 15 minutes.

  • If you don't want to make your way to the centre, choose a hotel near RFD. Settle in at one of these options after your CCS to Chicago flight:

  • Whether you're looking for a compact for a solo escape or an SUV to fit a group of friends, you'll find the right Chicago Rockford International Airport rental car for you. Explore the range of wheels available from suppliers such as Budget, Alamo and National.

  • Rental companies sometimes offer deals for early bookings, so reserve your vehicle from RFD a few weeks in advance of your flight from Simon Bolivar International Airport to Chicago. A bit of planning goes a long way in savings.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your dates before securing your flight from Simon Bolivar International Airport to Chicago. The city buzzes in peak season, but rates are generally higher and major attractions can get crowded. Plan your trip to Chicago in the off-season if you want a more relaxed vibe.

  • Before booking a Simon Bolivar International Airport to Chicago flight ticket, think about the kind of weather forecast you're hoping for. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • Look for cheap tickets from CCS to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered after you've experienced Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another essential stop in United States and is around 257 kilometres south-east of Chicago. No journey is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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