Cheap Flights from Chicago to Basseterre

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 Airport

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 March.

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 found$2,778
Cheapest month to flyMarch

Check out these Basseterre hotels

Ready to plan your stay? Other travellers rate these Basseterre hotels for cleanliness, service and location.
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Finding cheap flights from Chicago to Basseterre: Frequently asked questions

The best price we found for a return flight from Chicago to Basseterre is $2,778. 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 $2,778.
As of March 2026, there are no flights flying from Chicago to Basseterre.
The cheapest month to fly from Chicago to Basseterre is usually March.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Basseterre Airport on Sunday, 22 March 2026.
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 United .

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

  • There are two main airports to choose from in Chicago. Check out your options leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) when booking your flight from Chicago to Robert L. Bradshaw International Airport (SKB).

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

  • Leave enough time to get on your flight from Chicago to SKB. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Planning to travel during a peak time like school or public holidays? Expect longer lines at check-in and security. To give yourself peace of mind, arrive up to four hours before international flights and two hours ahead of domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • We make it easy to find cheap flights from Chicago to SKB that include a stopover. To explore all the options leaving from O'Hare International Airport (ORD), deselect 'Direct flights only.' Then, simply select a flight offering a stop long enough to tour your chosen city. Some popular stopovers between ORD and SKB include:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Miami International Airport (MIA)

    • Luis Munoz Marin International Airport (SJU)

  • Travelling from central Chicago to ORD takes about 55 minutes on public transport. If you drive, ride-share or grab a cab, you'll cover the 40 kilometres in 35 minutes or so, depending on traffic.

  • Planning to catch an early flight from Chicago to Robert L. Bradshaw International Airport? Avoid the last-minute rush to the terminal (and sneak in some extra snooze time) by choosing one of these stays close to O'Hare International Airport:

  • 74.85% of flights that depart O'Hare International Airport touch down at their destination on schedule.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Cross another spot off your travel list or just take a moment to recharge with a stopover. If you'd like to split up your flight from Chicago to Robert L. Bradshaw International Airport, check out these options when departing from Chicago Midway International Airport:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Charlotte Douglas International Airport (CLT)

    • Luis Munoz Marin International Airport (SJU)

  • On public transport, you can travel from central Chicago to MDW in around 45 minutes. The terminal is roughly 19 kilometres away, and making the trip by car will take approximately 20 minutes.

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

  • Chicago Midway International Airport has an on-time performance of 77.88%. This figure reflects how often flights that leave from this airport make it to their destination on schedule.

  • The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 137 kilometres from central Chicago. The drive from the city centre to the terminal takes about 1 hour 25 minutes. If you're thinking about taking public transport, you can expect a journey of around 4 hours 15 minutes.

  • Sleep a little longer, move a little slower, and still make your Chicago to Robert L. Bradshaw International Airport flight with time to spare. These hotels near Chicago Rockford International Airport make departure day a breeze if you're jetting off early:

  • The on-time performance record of RFD is 76.19%. To put it simply, that's how frequently flights departing this airport reach their final stop as planned.

  • The street address of Chicago Rockford International Airport is 2 Airport Cir.

About Robert L. Bradshaw International Airport (SKB)

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

  • $1,106 is the best price for a one-way ticket from Chicago to Robert L. Bradshaw International Airport. A return flight starts at $2,778. These fares can change based on availability and demand.

  • To pick up cheap flights from Chicago to SKB, book early. Airlines typically offer their most competitively priced fares when tickets first go on sale.

  • The 'Whole month' tool shows you the cheapest Chicago to Robert L. Bradshaw International Airport tickets across the month. It's an easy way to snap up a bargain if your travel plans aren't set in stone.

  • Be the first to know about deals for flight tickets from Chicago to SKB by setting up a Price Alert. We'll send you an email or notification through the app when a new discounted fare appears.

  • Filters make it easier to track down a bargain for your flight from Chicago to Robert L. Bradshaw International Airport. Choose the departure times, carriers and stops that look good to you. Then sort the results by 'Cheapest' to find the lowest price right away.

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

  • June is when most people book flights from Chicago to Robert L. Bradshaw International Airport (SKB). Visit Basseterre in April if you'd rather be there when it's quieter.

  • Before locking in your Chicago to SKB flight ticket, consider the kind of weather you prefer. September is the warmest month in Basseterre, with temperatures ranging from 26ºC to 29ºC.

  • February has temperatures of between 22ºC and 26ºC. Look for cheap tickets from Chicago to Robert L. Bradshaw International Airport around that time if you'd rather travel in cooler conditions.

More about Basseterre

  • Start your Basseterre trip right by choosing the ideal place to stay. As soon as you've booked your flight from Chicago to Robert L. Bradshaw International Airport, check out our selection of accommodation options including:

  • Your visit to Basseterre should come with a bit of sightseeing. Top attractions worth exploring include St. Kitts Scenic Railway, Port Zante and Immaculate Conception Co-Cathedral Catholic Church.

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