Cheap flight deals from Chicago to Anguilla

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

Round-trip
One way

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

When is the cheapest time to fly from Chicago to Anguilla?

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

Cheapest flights

From price

6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8
8 15
15 22
22 29

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

Frequently Asked Questions

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

Airlines adjust prices for flights from Chicago to Anguilla based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Chicago (CHI) to Anguilla (AXA) cost?

According to Trip.com's data, the lowest price is around Rp 19,965,457.

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.

Be flexible with your travel dates to get the cheapest Chicago to Anguilla ticket.

Tap "Date" in the flight search bar to browse the calendar and find airfare from Chicago to Anguilla for the next six months in 2025. If you're looking to fly within the next three months, the lowest fare is Rp 11228555 for a one-way ticket on Sat, Apr 19.

Compare cheap Chicago to Anguilla flight deals from hundreds of airlines.

Our powerful search system compares prices from over 500 airlines. So you can find the cheapest flights from Chicago to Anguilla. The most affordable airline currently operating on this route is United Airlines.

Set up a Price Alert to track fare drops.

Set up a Price Alert for your Chicago to Anguilla route to track ticket prices effortlessly—no need to check manually every day.

Don't miss out on cheap Chicago to Anguilla flight deals and promo codes.

Stay updated on the latest deals with Trip.com Deals and Promo Codes for cheap flights. Sign up for a free membership to unlock even more exclusive flight discounts.

Book early or wait unitl the last minute to fine the best fares.

It's always better to book early! Airlines typically release their lowest fares about a year before departure, so check as soon as flights become available. If you miss that window, you may still find great deals closer to your travel date.

Search for flights on the go.

For the best booking experience on the go, download Trip.com and search for cheap flights from Chicago to Anguilla to access exclusive deals just for you.

Flight Info | Chicago to Anguilla

Cheapest one-way flight price	Rp 11,228,554
Off-season for travel	February
Peak season for travel	May
Flight distance	3,513.43 km
Popular airline	American Airlines