$503 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 3/8. 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

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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, Mar 8 - Fri, Mar 13
American Airlines Logo
7:00 am - 3:28 pm
ORD
-
AXA
7h 28m1 stop
American Airlines Logo
4:08 pm - 12:37 am
AXA
-
ORD
9h 29m1 stop
$529American Airlines
Sun, Mar 8 - Fri, Mar 13
American Airlines Logo
5:00 am - 3:28 pm
ORD
-
AXA
9h 28m1 stop
American Airlines Logo
4:08 pm - 7:25 am
AXA
-
ORD
16h 17m2 stops
$534American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
6:01 am - 4:28 pm
ORD
-
AXA
8h 27m1 stop
American Airlines Logo
5:10 pm - 12:37 am
AXA
-
ORD
9h 27m1 stop
$573American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
5:00 am - 4:28 pm
ORD
-
AXA
9h 28m1 stop
American Airlines Logo
5:10 pm - 12:37 am
AXA
-
ORD
9h 27m1 stop
$574American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
8:51 pm - 2:30 pm
ORD
-
AXA
15h 39m2 stops
American Airlines Logo
5:10 pm - 7:25 am
AXA
-
ORD
16h 15m2 stops
$578American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
10:15 pm - 2:30 pm
ORD
-
AXA
14h 15m2 stops
American Airlines Logo
5:10 pm - 7:25 am
AXA
-
ORD
16h 15m2 stops
$579American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
6:58 pm - 1:15 pm
ORD
-
AXA
17h 17m1 stop
American Airlines Logo
4:57 pm - 12:27 am
AXA
-
ORD
8h 30m1 stop
$599American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
6:58 pm - 1:15 pm
ORD
-
AXA
17h 17m1 stop
American Airlines Logo
4:57 pm - 12:27 am
AXA
-
ORD
8h 30m1 stop
$600American Airlines
Mon, Feb 23 - Sun, Mar 1
American Airlines Logo
5:00 am - 2:30 pm
ORD
-
AXA
7h 30m1 stop
American Airlines Logo
5:10 pm - 8:53 am
AXA
-
ORD
17h 43m1 stop
$603American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
8:44 pm - 1:15 pm
ORD
-
AXA
15h 31m2 stops
American Airlines Logo
4:57 pm - 12:27 am
AXA
-
ORD
8h 30m1 stop
$604American 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$335
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.

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 11075 reviews
8.0Crew
6.9Entertainment
7.5Boarding
7.2Comfort
6.4Food
Airline reviews

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

8.0 ExcellentKim, Jan 2026
ORD - PHL
Read more American Airlines reviews

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

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.

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.