$667 Find Cheap Flights from Chicago to Anguilla - Compare and Save

1 adult
1 adult, Economy, 0 bags

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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.

What are the cheapest fares from Chicago to Anguilla right now?

The cheapest fare from Chicago to Anguilla in the last week was $667 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 $771.

What’s the cheapest day to fly from Chicago to Anguilla?

Wednesday tends to be the cheapest day to fly from Chicago to Anguilla, while Thursday is the most expensive. Fares run about 52% higher that day, based on the past 12 months of KAYAK data.

Key details for Chicago to Anguilla flights

Cheapest flight

$667
The most popular month to fly with an average 21% increase in travelers.
Round-trip flight from Chicago O'Hare Intl Airport to The Valley

Your Chicago to Anguilla flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago to Anguilla?

    Yes. Fares from Chicago to Anguilla are low right now. As a rule of thumb, a round-trip under $697 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago to Anguilla?

    Over the past 12 months, round-trip fares from Chicago to Anguilla have ranged from $697 to $977.

  • What are the main airports serving Anguilla?

    Flights to Anguilla all arrive at The Valley Wallblake Intl (AXA).

  • What airlines fly nonstop from Chicago to Anguilla?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Chicago to Anguilla. One-stop options include United Airlines and American Airlines.

  • Which cabin classes are available on flights from Chicago to Anguilla?

    On flights from Chicago to Anguilla you can only book Economy Class.

Your guide to booking Chicago to Anguilla flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for December when flights are typically cheapest and avoid November when prices are at their highest.
  • Flying on Wednesday is usually the cheapest. Flights on Thursday cost about 52% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in The Valley, which is the most popular destination in Anguilla. From there, it's easy to continue on to other popular destinations such as West End Village, Long Bay Village and Shoal Bay.

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.
7.0
American AirlinesOverall score based on 12184 reviews
7.4Boarding
6.4Food
6.8Entertainment
7.1Comfort
7.9Crew
Airline reviews

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

8.0 ExcellentJennifer, Oct 2026
Read more American Airlines reviews

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.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

More options for your flight from Chicago to Anguilla

Complete your trip to Anguilla with a hotel stay or car rental