$350 Find Cheap Flights from Chicago O'Hare Airport to Anguilla - Compare and Save

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 11/24. 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.
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1 adult, Economy, 0 bags

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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

Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
7:10 pm - 2:21 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
17h 11m1 stop Miami
American Airlines Logo
5:20 pm - 9:28 amAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
18h 08m1 stop Miami
$712American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
8:58 pm - 2:21 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 23m2 stops Washington, D.C. Reagan-National Miami
American Airlines Logo
5:20 pm - 7:42 amAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
16h 22m1 stop Miami
$717American Airlines
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:55 am - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
31h 40m2 stops San Juan Luis Munoz Marin Intl Saint Thomas Island Cyril E King
Multiple Airlines Logo
9:46 am - 6:45 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
9h 59m1 stop Saint Thomas Island Cyril E King
$1,569Multiple Airlines
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:55 am - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
31h 40m2 stops San Juan Luis Munoz Marin Intl Saint Thomas Island Cyril E King
Multiple Airlines Logo
9:46 am - 11:49 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
15h 03m2 stops Saint Thomas Island Cyril E King Newark
$1,569Multiple Airlines
Mon, Nov 16 - Thu, Nov 19
United Airlines Logo
8:40 pm - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
18h 55m2 stops Newark Saint Thomas Island Cyril E King
United Airlines Logo
9:46 am - 10:18 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
14h 32m2 stops Saint Thomas Island Cyril E King Newark
$1,644United Airlines
Tue, Aug 25 - Fri, Aug 28
Multiple Airlines Logo
8:55 am - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
31h 40m2 stops San Juan Luis Munoz Marin Intl Saint Thomas Island Cyril E King
Multiple Airlines Logo
9:46 am - 8:05 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
35h 19m2 stops Saint Thomas Island Cyril E King San Juan Luis Munoz Marin Intl
$1,744Multiple Airlines
Thu, Nov 26 - Tue, Dec 1
United Airlines Logo
1:27 pm - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
26h 08m2 stops Newark Saint Thomas Island Cyril E King
United Airlines Logo
9:46 am - 9:47 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
14h 01m2 stops Saint Thomas Island Cyril E King Newark
$1,784United Airlines
Sat, Sep 12 - Sat, Sep 19
United Airlines Logo
8:55 am - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
31h 40m2 stops San Juan Luis Munoz Marin Intl Saint Thomas Island Cyril E King
United Airlines Logo
9:46 am - 11:40 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
14h 54m2 stops Saint Thomas Island Cyril E King Washington, D.C. Dulles Intl
$2,333United Airlines
Mon, Nov 16 - Thu, Nov 19
United Airlines Logo
8:40 pm - 5:35 pmORD  Chicago O'Hare Intl-AXA The Valley Wallblake Intl
18h 55m2 stops Newark Saint Thomas Island Cyril E King
United Airlines Logo
9:46 am - 10:18 pmAXA  The Valley Wallblake Intl-ORD Chicago O'Hare Intl
14h 32m2 stops Saint Thomas Island Cyril E King Newark
$2,395United Airlines
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 18h 55m.

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Good to know

Cheapest flight

$350
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.

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.
7.1
American AirlinesOverall score based on 11876 reviews
6.4Food
7.5Boarding
6.8Entertainment
7.9Crew
7.2Comfort
Airline reviews

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

6.0 GoodSyarifah Nadirah, Aug 2026
Read more American Airlines reviews

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

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

Information on your arrival and departure airports

Chicago O'Hare Airport (ORD)