Cheap Flights from Chicago to Basseterre

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Compare Chicago to Basseterre flight deals

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

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Flight deals from Chicago to Basseterre

Looking for a cheap last-minute deal or the best return flight from Chicago to Basseterre? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Basseterre

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

Chicago to Basseterre: Alternative routes

Compare routes from Chicago to Basseterre below. You may find an airport to fly into that's cheaper, faster, or easier than Basseterre.

Chicago to Basseterre: Flight information

The things to know before you go.
Cheapest flight found839 €
Cheapest month to flyJune

Finding cheap flights from Chicago to Basseterre: Frequently asked questions

The best price we found for a return flight from Chicago to Basseterre is 839 €. 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 Chicago to Basseterre. But we found flights with one stop from 839 €.
As of April 2025, there are no flights flying from Chicago to Basseterre.
The cheapest month to fly from Chicago to Basseterre is usually April 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Basseterre Airport on Monday, 2 June 2025.
No airlines currently offer direct flights between Chicago and Basseterre Airport. 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 Basseterre 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 Basseterre is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Basseterre is Spirit Airlines .

Flying from Chicago to Robert L. Bradshaw International Airport (SKB): what you need to know

  • Chicago is home to a couple of airports that could be the jumping-off point for your adventure. Check out your options for reserving a flight from Chicago to Robert L. Bradshaw International Airport (SKB) leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

  • Robert L. Bradshaw International Airport is located in Basseterre. The city operates in the UTC-4 timezone and is 1 hour ahead of Chicago.

  • Arrive at the airport on time so you don't miss your flight from Chicago to SKB. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.

  • If you're getting away during a popular month like August, make your way to the airport even earlier. It's smart to arrive up to four hours before an international flight and two hours ahead of domestic departures. Security lines will be longer during high seasons like spring break and summer.

Airports in Chicago

O'Hare International Airport (ORD)

  • Think about adding a stopover to potentially find a cheaper flight from Chicago to SKB. Just deselect 'Direct flights only' when searching for departures from O'Hare International Airport (ORD). Take a break from travelling at one of these airports:

    • Luis Munoz Marin International Airport (SJU)

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Miami International Airport (MIA)

  • From the centre of Chicago, ORD is around 40 kilometres away. Use navigation apps or visit the official airport website to find the best way to get there.

  • After a stress-free start to your holiday? Stay near O'Hare International Airport. Whether you've booked an early flight from Chicago to Robert L. Bradshaw International Airport or want to avoid feeling rushed, these hotels are perfect:

Chicago Midway International Airport (MDW)

  • Split up your flight from Chicago to Robert L. Bradshaw International Airport with a stop so you can freshen up or cross a new place off your list. Popular stopovers between Chicago Midway International Airport and SKB are:

    • Miami International Airport (MIA)

    • John F. Kennedy International Airport (JFK)

    • Hartsfield-Jackson Atlanta International Airport (ATL)

  • On public transport, you can travel from central Chicago to MDW in about 46 minutes. The terminal is roughly 19 kilometres away, and making the journey by car will take approximately 21 minutes.

  • Start your holiday early with an additional night away from home. Before your flight from Chicago to SKB, stay in one of these hotels near Chicago Midway International Airport:

About Robert L. Bradshaw International Airport (SKB)

Getting from Robert L. Bradshaw International Airport (SKB) to central Basseterre

  • From Robert L. Bradshaw International Airport, Basseterre is approximately 2 kilometres away. It takes around 3 minutes to get to the centre driving.

How to find the cheapest flights from Chicago to Robert L. Bradshaw International Airport (SKB)

  • Book a one-way ticket from Chicago to Robert L. Bradshaw International Airport from 302 € or travel return from just 839 €. The prices shown are based on availability and could change when you book.

  • Don't leave things to the last minute. You're more likely to get cheap tickets from Chicago to SKB if you book in advance. Airlines often have some fantastic early bird deals.

  • The 'Whole month' search function shows you the cheapest tickets from Chicago to Robert L. Bradshaw International Airport across each month. It's an easy way to find a bargain if your plans are flexible.

  • Create a Price Alert and keep track of changes on this route through email or push notifications. You'll know straight away when prices go down. Timing is key when finding cheap tickets from Chicago to SKB.

  • Customise your journey using filters. Choose the duration, number of stops, and departure and arrival times to find the ideal flight from Chicago to Robert L. Bradshaw International Airport. You can also sort the results to see the 'Best,' 'Fastest' or 'Cheapest' options first.

The best time to fly from Chicago to Robert L. Bradshaw International Airport (SKB)

  • April is the quietest time of year to fly to Basseterre. Alternatively, follow the crowds and go in June. This is the most popular month for flights from Chicago to Robert L. Bradshaw International Airport, but the best time to go is up to you.

  • The warmest month in Basseterre is September, with the temperature ranging between 26ºC and 29ºC. Book your flights from Chicago to SKB in this month if this is the type of weather you enjoy.

  • Look for cheap flights from Chicago to Robert L. Bradshaw International Airport in February if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between 22ºC and 26ºC on average.

More about Basseterre

Complete your Basseterre trip with a car rental

  • Once you've booked your hotel and cheap flight from Chicago to Robert L. Bradshaw International Airport, next up is choosing one of our car rentals in Basseterre. Explore the offers and easily compare your options on pick-up convenience, price, and more.

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