$335 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 7/2. 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 Chicago to Anguilla

 
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

Sat, Jul 26 - Fri, Aug 1
American Airlines Logo
6:57 pm - 1:25 pmORD-AXA
17h 28m1 stop
American Airlines Logo
4:25 pm - 12:17 amAXA-ORD
8h 52m1 stop
$603American Airlines
Find Deal
Sat, Jul 26 - Fri, Aug 1
American Airlines Logo
10:05 pm - 1:25 pmORD-AXA
14h 20m2 stops
American Airlines Logo
4:25 pm - 7:15 amAXA-ORD
15h 50m2 stops
$607American Airlines
Find Deal
Thu, Jul 31 - Sun, Aug 3
American Airlines Logo
5:00 am - 3:40 pmORD-AXA
9h 40m1 stop
American Airlines Logo
4:25 pm - 12:17 amAXA-ORD
8h 52m1 stop
$628American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
3:42 pm - 3:40 pmORD-AXA
22h 58m1 stop
American Airlines Logo
4:25 pm - 12:17 amAXA-ORD
8h 52m1 stop
$629American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
6:57 pm - 1:25 pmORD-AXA
17h 28m1 stop
American Airlines Logo
4:25 pm - 12:17 amAXA-ORD
8h 52m1 stop
$630American Airlines
Find Deal
Thu, Jul 31 - Sun, Aug 3
American Airlines Logo
8:45 pm - 1:25 pmORD-AXA
15h 40m2 stops
American Airlines Logo
4:25 pm - 7:15 amAXA-ORD
15h 50m2 stops
$632American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
10:05 pm - 1:25 pmORD-AXA
14h 20m2 stops
American Airlines Logo
4:25 pm - 12:17 amAXA-ORD
8h 52m1 stop
$633American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
6:57 pm - 3:40 pmORD-AXA
19h 43m1 stop
American Airlines Logo
4:25 pm - 7:15 amAXA-ORD
15h 50m2 stops
$634American Airlines
Find Deal
Thu, Jul 10 - Mon, Jul 14
 Logo
5:40 pm - 4:40 pmORD-AXA
22h 00m2 stops
 Logo
10:00 am - 3:31 pmAXA-ORD
30h 31m3 stops
Thu, Jul 10 - Mon, Jul 14
 Logo
4:36 pm - 4:40 pmORD-AXA
23h 04m3 stops
 Logo
10:00 am - 11:11 pmAXA-ORD
38h 11m3 stops
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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 18h 51m.


Good to know

High seasonJuly
Cheapest flight$335
Most popular time to fly and prices are also 17% lower on average.
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.

  • 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.

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.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
7.5Boarding
6.9Entertainment
7.2Comfort
8.0Crew
Airline reviews

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

6.0 GoodAnonymous, Mar 2025ORD - CLT
Read more American Airlines reviews

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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.

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