$351 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 9/2. 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

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Cheap Flights from O'Hare Intl to Anguilla

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
The Valley
The Valley1 stop$598
The Valley
The Valley1 stop$598

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, Oct 11 - Wed, Oct 15
American Airlines Logo
5:00 am - 1:18 pmORD-AXA
7h 18m1 stop
American Airlines Logo
2:05 pm - 10:31 pmAXA-ORD
9h 26m1 stop
$598American Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
American Airlines Logo
5:00 am - 1:18 pmORD-AXA
7h 18m1 stop
American Airlines Logo
2:05 pm - 7:18 amAXA-ORD
18h 13m2 stops
$602American Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
American Airlines Logo
4:40 pm - 4:39 pmORD-AXA
21h 59m1 stop
American Airlines Logo
5:05 pm - 12:21 amAXA-ORD
9h 16m1 stop
$612American Airlines
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Thu, Aug 14 - Thu, Aug 21
 Logo
8:12 pm - 5:15 pmORD-AXA
20h 03m2 stops
 Logo
8:30 am - 9:22 amAXA-ORD
25h 52m3 stops
$1,317
Find Deal
Thu, Aug 14 - Thu, Aug 21
 Logo
8:12 pm - 5:15 pmORD-AXA
20h 03m3 stops
 Logo
8:30 am - 9:22 amAXA-ORD
25h 52m3 stops
$1,319
Find Deal
Thu, Aug 14 - Thu, Aug 21
 Logo
8:12 pm - 5:15 pmORD-AXA
20h 03m2 stops
 Logo
8:30 am - 11:43 pmAXA-ORD
16h 13m2 stops
$1,396
Find Deal
Fri, Oct 10 - Mon, Oct 13
 Logo
9:20 pm - 5:15 pmORD-AXA
18h 55m2 stops
 Logo
9:35 am - 8:03 pmAXA-ORD
11h 28m2 stops
$1,697
Find Deal
Sat, Oct 11 - Wed, Oct 15
 Logo
8:52 am - 5:15 pmORD-AXA
31h 23m2 stops
 Logo
9:35 am - 8:03 pmAXA-ORD
11h 28m2 stops
$1,714
Find Deal
Fri, Oct 10 - Mon, Oct 13
 Logo
9:20 pm - 5:15 pmORD-AXA
18h 55m2 stops
 Logo
9:35 am - 9:26 pmAXA-ORD
12h 51m3 stops
$1,782
Find Deal
Fri, Dec 26 - Fri, Jan 2
American Airlines Logo
6:55 pm - 12:40 pmORD-AXA
15h 45m1 stop
American Airlines Logo
5:30 pm - 12:18 amAXA-ORD
8h 48m1 stop
$1,991American 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.

How long does a flight from Chicago O'Hare Intl Airport to Anguilla take?

The duration of a flight to Anguilla depends on your arrival airport. The shortest route to Anguilla from Chicago O'Hare Intl Airport is to The Valley, which takes 7h 18m.


Good to know

Low seasonOctober
Cheapest flight$351
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 35% 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 10000 reviews
6.9Entertainment
6.5Food
7.5Boarding
8.0Crew
7.2Comfort
Airline reviews

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

2.0 MediocreAnonymous, Jul 2025ORD - RIC
Read more American Airlines reviews

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!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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

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