$573 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Anguilla departing on 11/7. 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 O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to Anguilla

Sat, Jan 31 - Wed, Feb 4
American Airlines Logo
7:30 pm - 2:23 pmORD-AXA
16h 53m1 stop
American Airlines Logo
5:06 pm - 12:30 amAXA-ORD
9h 24m1 stop
$573American Airlines
Find Deal
Sat, Jan 31 - Wed, Feb 4
American Airlines Logo
8:50 pm - 2:23 pmORD-AXA
15h 33m2 stops
American Airlines Logo
5:06 pm - 7:22 amAXA-ORD
16h 16m2 stops
$578American Airlines
Find Deal
Fri, Jan 2 - Wed, Jan 14
American Airlines Logo
7:35 pm - 12:38 pmORD-AXA
15h 03m1 stop
American Airlines Logo
5:06 pm - 9:05 amAXA-ORD
17h 59m1 stop
$598American Airlines
Find Deal
Fri, Jan 2 - Wed, Jan 14
American Airlines Logo
8:53 pm - 12:38 pmORD-AXA
13h 45m2 stops
American Airlines Logo
5:06 pm - 7:22 amAXA-ORD
16h 16m2 stops
$603American Airlines
Find Deal
Fri, Apr 10 - Tue, Apr 14
American Airlines Logo
5:10 am - 3:05 pmORD-AXA
8h 55m2 stops
American Airlines Logo
4:05 pm - 6:24 amAXA-ORD
15h 19m2 stops
$633American Airlines
Find Deal
Thu, Jan 1 - Tue, Jan 6
American Airlines Logo
5:00 am - 4:36 pmORD-AXA
9h 36m1 stop
American Airlines Logo
5:06 pm - 9:05 amAXA-ORD
17h 59m1 stop
$658American Airlines
Find Deal
Thu, Jan 1 - Tue, Jan 6
American Airlines Logo
8:53 pm - 2:13 pmORD-AXA
15h 20m2 stops
American Airlines Logo
5:06 pm - 7:22 amAXA-ORD
16h 16m2 stops
$663American Airlines
Find Deal
Thu, Jan 15 - Mon, Jan 19
American Airlines Logo
7:30 pm - 2:23 pmORD-AXA
16h 53m1 stop
American Airlines Logo
5:06 pm - 9:05 amAXA-ORD
17h 59m1 stop
$673American Airlines
Find Deal
Sat, Jan 3 - Sun, Jan 11
Multiple Airlines Logo
8:15 pm - 5:10 pmORD-AXA
18h 55m3 stops
Multiple Airlines Logo
7:25 pm - 7:13 amAXA-ORD
13h 48m1 stop
$896Multiple Airlines
Find Deal
Sat, Jan 3 - Sun, Jan 11
Multiple Airlines Logo
8:15 pm - 5:10 pmORD-AXA
18h 55m3 stops
Multiple Airlines Logo
7:25 pm - 11:42 pmAXA-ORD
30h 17m2 stops
$924Multiple Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Anguilla flights

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

Which airlines fly non-stop between Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Anguilla.

There is just one airline that flies from Chicago O'Hare Intl Airport 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 $602.

Good to know

Low seasonNovember
Cheapest flight$460
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago to The Valley

FAQs - booking Anguilla flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Anguilla.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Intl to Anguilla

 
Need help choosing which airline to fly with from O'Hare Intl 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 11030 reviews
7.5Boarding
7.2Comfort
8.0Crew
6.4Food
6.9Entertainment
Airline reviews

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.

2.0 MediocreAnonymous, Oct 2025ORD - PDX
Read more American Airlines reviews

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.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Everything you need to know for your flight from O'Hare Intl to Anguilla

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