$415 Find Cheap Flights from Chicago 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 Chicago to Anguilla departing on 11/14. 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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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

Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
7:10 pm - 2:21 pm
ORD
-
AXA
17h 11m
1 stop
American Airlines Logo
5:20 pm - 9:28 am
AXA
-
ORD
18h 08m
1 stop
$692American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
8:58 pm - 2:21 pm
ORD
-
AXA
15h 23m
2 stops
American Airlines Logo
5:20 pm - 7:42 am
AXA
-
ORD
16h 22m
1 stop
$697American Airlines
Wed, Dec 30 - Thu, Jan 7
American Airlines Logo
5:05 am - 4:36 pm
ORD
-
AXA
9h 31m
1 stop
American Airlines Logo
5:06 pm - 7:27 am
AXA
-
ORD
16h 21m
2 stops
$702American Airlines
Fri, Dec 4 - Tue, Dec 8
American Airlines Logo
7:10 pm - 2:21 pm
ORD
-
AXA
17h 11m
1 stop
American Airlines Logo
5:20 pm - 12:38 am
AXA
-
ORD
9h 18m
1 stop
$727American Airlines
Fri, Dec 4 - Tue, Dec 8
American Airlines Logo
8:55 pm - 2:21 pm
ORD
-
AXA
15h 26m
2 stops
American Airlines Logo
5:20 pm - 12:38 am
AXA
-
ORD
9h 18m
1 stop
$732American Airlines
Wed, Dec 30 - Thu, Jan 7
American Airlines Logo
8:58 pm - 2:13 pm
ORD
-
AXA
15h 15m
2 stops
American Airlines Logo
5:06 pm - 7:27 am
AXA
-
ORD
16h 21m
2 stops
$737American Airlines
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
7:10 pm - 2:21 pm
ORD
-
AXA
17h 11m
1 stop
American Airlines Logo
3:01 pm - 11:33 pm
AXA
-
ORD
10h 32m
1 stop
$762American Airlines
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
6:00 am - 4:40 pm
ORD
-
AXA
8h 40m
1 stop
American Airlines Logo
5:20 pm - 7:27 am
AXA
-
ORD
16h 07m
2 stops
$767American Airlines
Sun, Jul 26 - Sun, Aug 2
American Airlines Logo
5:59 pm - 1:11 pm
ORD
-
AXA
18h 12m
1 stop
American Airlines Logo
4:59 pm - 12:26 am
AXA
-
ORD
8h 27m
1 stop
$794American Airlines
Sun, Jul 26 - Sun, Aug 2
American Airlines Logo
8:54 pm - 1:11 pm
ORD
-
AXA
15h 17m
2 stops
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$799American 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.

How long does a flight from Chicago to Anguilla take?

The duration of a flight to Anguilla depends on your arrival airport. The shortest route to Anguilla from Chicago is to The Valley, which takes 16h 07m.

Good to know

Cheapest flight$415
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.
7.1
American AirlinesOverall score based on 11768 reviews
6.4Food
7.9Crew
6.8Entertainment
7.5Boarding
7.2Comfort
Airline reviews

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.

2.0 MediocreOnkar Pravin, Jul 2026
ORD - DFW
Read more American Airlines reviews

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

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

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.