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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
Mon, Nov 30 - Tue, Dec 8
5:00 am - 2:57 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
7h 57m1 stop Miami
3:34 pm - 12:53 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
11h 19m1 stop Miami
$659American Airlines
Mon, Nov 30 - Tue, Dec 8
9:08 pm - 2:57 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 49m2 stops Dallas/Fort Worth Miami
5:39 pm - 12:53 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
9h 14m1 stop Miami
$659American Airlines
Mon, Nov 30 - Tue, Dec 8
9:08 pm - 2:57 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 49m2 stops Dallas/Fort Worth Miami
5:39 pm - 7:26 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
15h 47m2 stops Miami Washington, D.C. Reagan-National
$659American Airlines
Tue, Jan 19 - Tue, Jan 26
5:00 am - 4:55 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
9h 55m1 stop Miami
3:38 pm - 1:05 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
11h 27m1 stop Miami
$667American Airlines
Tue, Dec 8 - Tue, Dec 15
7:50 pm - 2:54 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
17h 04m1 stop Miami
3:34 pm - 12:53 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
11h 19m1 stop Miami
$667American Airlines
Tue, Dec 8 - Tue, Dec 15
9:06 pm - 2:54 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 48m2 stops Charlotte Douglas Miami
3:34 pm - 8:00 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
18h 26m1 stop Miami
$671American Airlines
Tue, Dec 8 - Tue, Dec 15
9:06 pm - 2:54 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
15h 48m2 stops Charlotte Douglas Miami
5:39 pm - 9:30 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
17h 51m1 stop Miami
$671American Airlines
Wed, Dec 23 - Sun, Dec 27
5:58 am - 1:10 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
29h 12m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
7:55 am - 12:00 pmAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
30h 05m3 stops Providenciales Newark Atlanta Hartsfield-Jackson
$1,266Multiple Airlines
Wed, Dec 23 - Sun, Dec 27
5:58 am - 1:10 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
29h 12m3 stops Atlanta Hartsfield-Jackson Miami Baltimore/Washington
7:55 am - 12:00 pmAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
30h 05m3 stops Providenciales Newark Atlanta Hartsfield-Jackson
$1,289Multiple Airlines
Thu, Mar 4 - Tue, Mar 9
6:20 pm - 4:40 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
20h 20m2 stops Toronto Island Newark
12:15 pm - 10:13 pmAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl
35h 58m3 stops Santo Domingo Las Americas Bogotá El Dorado Mexico City Benito Juarez
$1,607Multiple Airlines
Recent one-way flight deals from Chicago to Anguilla
Sat, Feb 20
6:00 am - 4:50 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
8h 50m1 stop Miami
$410American Airlines
Sat, Feb 20
9:45 pm - 2:25 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
14h 40m2 stops Philadelphia Miami
$416American Airlines
Sat, Feb 20
5:55 pm - 4:40 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl
44h 45m3 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson Newark
$460Multiple Airlines
Booking Insights
Price, demand and travel trends for Chicago to Anguilla flights
Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.
Prices
Airlines
More
What are the cheapest fares from Chicago to Anguilla right now?
The cheapest fare from Chicago to Anguilla in the last week was $659 round-trip, to The Valley Wallblake Intl (AXA).
Which airport in Anguilla is the cheapest to fly to from Chicago?
All flights from Chicago to Anguilla arrive at The Valley Wallblake Intl (AXA). On average, round-trip fares are around $774.
What are the most popular flight destinations in Anguilla?
The Valley is the most popular flight destination in Anguilla, based on KAYAK data from the past 3 months.
Key details for Chicago to Anguilla flights
High season | January |
|---|---|
Cheapest flight | $410 |
Your Chicago to Anguilla flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines and booking tips.
Your guide to booking Chicago to Anguilla flights
Get tips on when to book, when to fly and what to know before your trip.Reviews of the top airline flying from Chicago to Anguilla
7.0
American AirlinesOverall score based on 12231 reviews
6.4Food
6.8Entertainment
7.9Crew
7.2Comfort
7.4Boarding
Airline reviews
Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.
8.0 ExcellentAnonymous, Nov 2026
Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.
Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.
Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!
It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.
We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.
I have posted the comments in the first flight leg.
First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.
My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.
The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.
After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.
More options for your flight from Chicago to Anguilla
Complete your trip to Anguilla with a hotel stay or car rental
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.
Flights from other airports in Chicago to Anguilla
Flights from all airports in Chicago to Anguilla. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.