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Find cheap flights from Chicago to Anguilla

1 adult
0 bags
Thu 7/11
Thu 7/18

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In the last 7 days travelers have searched 44,212,782 times on KAYAK, and here is why:

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Good to know

Low season

May

High season

February
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 26% lower on average.

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 to Anguilla from Chicago 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 to Anguilla with an airline and back to Chicago 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 to Anguilla from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Anguilla

  • Morning departure is around 214% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
7.3
American AirlinesOverall score based on 14129 reviews
6.6Food
7.2Comfort
8.0Crew
7.6Boarding
7.1Entertainment
Airline reviews

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

8.0 ExcellentFarzaneh, May 2024ORD - LAX
Read more about American Airlines reviews

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

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