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Flights from Chicago to Anguilla

Flight deals from Chicago to Anguilla

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Flight Information from Chicago to Anguilla

Cheapest one-way flight price £555
Cheapest return ticket price £620
Off-season travel month June
Peak season for travel April
Flight distance 3,513.43km

Find the best time to fly from Chicago to Anguilla

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights
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  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27

  • Aug

    27 3
  • 3 10
  • 10 17
  • 17 24
  • 24 31

  • Sep

    31 7
  • 7 14
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

FAQ

  • When are flight tickets from Chicago (CHI) to Anguilla (AXA) the cheapest?

    Airlines adjust prices for flights from Chicago to Anguilla based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Chicago (CHI) to Anguilla (AXA) cost?

    According to Trip.com's data, the lowest price is around £880.

  • How many airports in Anguilla (AXA)?

    There are 1 airport(s) in Anguilla (AXA): Clayton J. Lloyd International Airport.

How to find a cheap flight from Chicago to Anguilla

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Anguilla. Book your flights at the right time and save more.
1
Be flexible with your travel dates to get the cheapest flight from Chicago to Anguilla.
Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Chicago to Anguilla over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Sat, Jul 5, with one-way flights priced at just £555.
2
Compare cheap flight deals from Chicago to Anguilla across hundreds of airlines.
With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Chicago to Anguilla. The cheapest airline for this route is United Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your journey from Chicago to Anguilla, you can easily keep an eye on ticket prices without having to check every day.
4
Don't miss out on cheap flight deals and promo codes from Chicago to Anguilla.
You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.
5
Book early or wait until the last minute.
It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.
6
Search for flights on the go.
For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Chicago to Anguilla and snag some exclusive deals just for you.

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