$573 Find Cheap Flights from Chicago to Anguilla

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Anguilla departing on 12/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Anguilla

Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Book Cheap Chicago to Anguilla Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Anguilla that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Anguilla

Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
5:00 am - 2:19 pm
ORD
-
AXA
7h 19m1 stop
American Airlines Logo
5:24 pm - 9:02 am
AXA
-
ORD
17h 38m1 stop
$573American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
5:00 am - 2:19 pm
ORD
-
AXA
7h 19m1 stop
American Airlines Logo
5:24 pm - 7:20 am
AXA
-
ORD
15h 56m2 stops
$578American Airlines
Mon, Feb 9 - Tue, Feb 17
American Airlines Logo
5:00 am - 4:26 pm
ORD
-
AXA
9h 26m1 stop
American Airlines Logo
5:24 pm - 12:33 am
AXA
-
ORD
9h 09m1 stop
$593American Airlines
Mon, Feb 9 - Tue, Feb 17
Multiple Airlines Logo
5:15 am - 5:10 pm
ORD
-
AXA
9h 55m2 stops
Multiple Airlines Logo
10:00 am - 9:22 am
AXA
-
ORD
25h 22m3 stops
$595Multiple Airlines
Tue, Mar 24 - Thu, Mar 26
American Airlines Logo
6:00 am - 3:38 pm
ORD
-
AXA
8h 38m1 stop
American Airlines Logo
4:18 pm - 12:35 am
AXA
-
ORD
9h 17m1 stop
$611American Airlines
Mon, Feb 9 - Tue, Feb 17
Multiple Airlines Logo
5:15 am - 5:10 pm
ORD
-
AXA
9h 55m2 stops
Multiple Airlines Logo
10:00 am - 11:47 pm
AXA
-
ORD
15h 47m2 stops
$612Multiple Airlines
Tue, Mar 24 - Thu, Mar 26
American Airlines Logo
7:00 am - 3:38 pm
ORD
-
AXA
7h 38m1 stop
American Airlines Logo
4:18 pm - 7:21 am
AXA
-
ORD
16h 03m2 stops
$616American Airlines
Thu, Mar 12 - Thu, Mar 19
American Airlines Logo
6:00 am - 3:38 pm
ORD
-
AXA
8h 38m1 stop
American Airlines Logo
4:18 pm - 12:35 am
AXA
-
ORD
9h 17m1 stop
$628American Airlines
Wed, Jan 21 - Wed, Jan 28
American Airlines Logo
5:00 am - 2:23 pm
ORD
-
AXA
7h 23m1 stop
American Airlines Logo
5:06 pm - 12:30 am
AXA
-
ORD
9h 24m1 stop
$633American Airlines
Wed, Jan 21 - Wed, Jan 28
American Airlines Logo
7:00 am - 4:26 pm
ORD
-
AXA
7h 26m1 stop
American Airlines Logo
5:06 pm - 7:22 am
AXA
-
ORD
16h 16m2 stops
$638American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Anguilla flights

Get data-powered insights and trends into flights from Chicago to Anguilla to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Chicago and Anguilla?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago to Anguilla.

There is just one airline that flies from Chicago to Anguilla direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is to The Valley (AXA) and costs $597.

Good to know

Cheapest flight$435
Flight from Chicago to The Valley

FAQs - booking Anguilla flights

  • How does KAYAK find such low prices on flights from Chicago to Anguilla?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Anguilla.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Anguilla?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Anguilla is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Anguilla?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Anguilla with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Anguilla?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Anguilla up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Anguilla?

    The cheapest time of day to fly to Anguilla is generally in the evening, when round-trip flights cost $607 on average. Morning departures are around 30% more expensive than evening flights, on average. The most expensive time of day to fly to Anguilla is generally in the morning, which is peak travel time and where the average cost of a ticket is $759.

Reviews of the top airline flying from Chicago to Anguilla

 
Need help choosing which airline to fly with from Chicago to Anguilla? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11054 reviews
6.9Entertainment
7.5Boarding
8.0Crew
7.2Comfort
6.4Food
Airline reviews

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

6.0 GoodDan, Dec 2025
ORD - ALO
Read more American Airlines reviews

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

Everything you need to know for your flight from Chicago to Anguilla

Cabin class types available on flights to Anguilla

Cabin classes available on flights to Anguilla. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.