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Find cheap flights from Chicago to Anguilla from $367

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 6/24. 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
0 bags
Sat 5/25
Sat 6/1

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Good to know

Low season

February

High season

December

Cheapest flight

$367
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly and prices are also 7% 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 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 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 14898 reviews
7.6boarding
6.6food
7.2comfort
7.1entertainment
8.0crew
Airline reviews

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.

10.0 ExcellentChristopher, Apr 2024ORD - HEL
Read more about American Airlines reviews

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.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Book cheap flights from Chicago to Anguilla

Recent round-trip flight deals

5/28Tue
1 stopAmerican Airlines
9h 05mORD-AXA
6/4Tue
1 stopAmerican Airlines
10h 57mAXA-ORD
$415
5/28Tue
1 stopAmerican Airlines
7h 05mORD-AXA
6/4Tue
2 stopsAmerican Airlines
16h 38mAXA-ORD
$420
5/15Wed
1 stopAmerican Airlines
21h 55mORD-AXA
5/20Mon
1 stopAmerican Airlines
18h 22mAXA-ORD
$477
6/8Sat
1 stopAmerican Airlines
17h 26mORD-AXA
6/13Thu
1 stopAmerican Airlines
8h 28mAXA-ORD
$517
6/8Sat
2 stopsAmerican Airlines
15h 42mORD-AXA
6/14Fri
2 stopsAmerican Airlines
10h 58mAXA-ORD
$519
6/8Sat
2 stopsAmerican Airlines
15h 42mORD-AXA
6/13Thu
2 stopsAmerican Airlines
16h 18mAXA-ORD
$520
6/9Sun
1 stopAmerican Airlines
22h 13mORD-AXA
6/13Thu
1 stopAmerican Airlines
8h 28mAXA-ORD
$530
6/9Sun
1 stopAmerican Airlines
22h 13mORD-AXA
6/14Fri
2 stopsAmerican Airlines
10h 58mAXA-ORD
$533
6/12Wed
1 stop
26h 02mORD-AXA
6/15Sat
1 stop
9h 09mAXA-ORD
$555
6/12Wed
2 stops
18h 30mORD-AXA
6/15Sat
1 stop
9h 09mAXA-ORD
$572

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Recent one-way flight deals

6/24Mon
2 stopsAmerican Airlines
8h 50mORD-AXA
$367
6/23Sun
1 stopAmerican Airlines
17h 26mORD-AXA
$368
6/23Sun
2 stops
41h 30mORD-AXA
$411
6/24Mon
3 stops
44h 36mORD-AXA
$444
6/23Sun
3 stops
38h 33mORD-AXA
$466

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Flights to Anguilla

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