$360 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 3/24. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Anguilla

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

mer., avr. 15 - mer., avr. 22
American Airlines Logo
5:00 am - 4:17 pm
ORD
-
AXA
10h 17m
1 stop
American Airlines Logo
4:57 pm - 12:25 am
AXA
-
ORD
8h 28m
1 stop
$624American Airlines
mer., avr. 15 - mer., avr. 22
American Airlines Logo
5:00 am - 4:17 pm
ORD
-
AXA
10h 17m
2 stops
American Airlines Logo
4:57 pm - 7:39 am
AXA
-
ORD
15h 42m
2 stops
$629American Airlines
sam., avr. 11 - ven., avr. 17
American Airlines Logo
5:00 am - 4:17 pm
ORD
-
AXA
10h 17m
2 stops
American Airlines Logo
1:55 pm - 11:54 pm
AXA
-
ORD
10h 59m
2 stops
$638American Airlines
sam., avr. 11 - mar., avr. 14
American Airlines Logo
7:00 pm - 1:15 pm
ORD
-
AXA
17h 15m
1 stop
American Airlines Logo
4:57 pm - 12:25 am
AXA
-
ORD
8h 28m
1 stop
$654American Airlines
sam., avr. 11 - mar., avr. 14
American Airlines Logo
7:00 pm - 1:15 pm
ORD
-
AXA
17h 15m
1 stop
American Airlines Logo
4:57 pm - 7:24 am
AXA
-
ORD
15h 27m
2 stops
$659American Airlines
ven., mai 1 - lun., mai 4
American Airlines Logo
5:00 am - 4:17 pm
ORD
-
AXA
10h 17m
1 stop
American Airlines Logo
4:57 pm - 12:25 am
AXA
-
ORD
8h 28m
1 stop
$674American Airlines
ven., mai 1 - lun., mai 4
American Airlines Logo
8:46 pm - 1:15 pm
ORD
-
AXA
15h 29m
2 stops
American Airlines Logo
1:55 pm - 12:25 am
AXA
-
ORD
11h 30m
1 stop
$679American Airlines
sam., avr. 11 - sam., avr. 18
American Airlines Logo
7:00 pm - 1:15 pm
ORD
-
AXA
17h 15m
1 stop
American Airlines Logo
4:57 pm - 8:30 am
AXA
-
ORD
16h 33m
2 stops
$684American Airlines
mar., mars 24 - mar., mars 31
American Airlines Logo
5:00 am - 3:29 pm
ORD
-
AXA
9h 29m
2 stops
American Airlines Logo
2:11 pm - 12:38 am
AXA
-
ORD
11h 27m
1 stop
$689American Airlines
dim., avr. 5 - dim., avr. 12
American Airlines Logo
5:00 am - 1:31 pm
ORD
-
AXA
7h 31m
1 stop
American Airlines Logo
4:57 pm - 12:11 pm
AXA
-
ORD
20h 14m
1 stop
$700American 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 15h 18m.

Good to know

Cheapest flight$288
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 11345 reviews
7.5Boarding
7.2Comfort
6.9Entertainment
8.0Crew
6.4Food
Airline reviews

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

2.0 MediocreThomas, Feb 2026
ORD - CVG
Read more American Airlines reviews

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

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.