$380 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Anguilla departing on 7/7. 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, 0 bags

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Flight Deals

Book Cheap O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to Anguilla

Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
5:00 am - 1:11 pm
ORD
-
AXA
7h 11m
1 stop
American Airlines Logo
4:59 pm - 12:26 am
AXA
-
ORD
8h 27m
1 stop
$664American Airlines
Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
6:59 am - 4:19 pm
ORD
-
AXA
8h 20m
1 stop
American Airlines Logo
4:59 pm - 6:30 am
AXA
-
ORD
14h 31m
2 stops
$669American Airlines
Tue, Jul 7 - Mon, Jul 20
American Airlines Logo
6:10 am - 4:19 pm
ORD
-
AXA
9h 09m
1 stop
American Airlines Logo
4:59 pm - 12:26 am
AXA
-
ORD
8h 27m
1 stop
$699American Airlines
Mon, Jul 6 - Mon, Jul 13
American Airlines Logo
6:59 am - 4:19 pm
ORD
-
AXA
8h 20m
1 stop
American Airlines Logo
4:59 pm - 6:30 am
AXA
-
ORD
14h 31m
2 stops
$704American Airlines
Wed, Jul 1 - Mon, Jul 6
American Airlines Logo
5:00 am - 4:15 pm
ORD
-
AXA
10h 15m
1 stop
American Airlines Logo
4:59 pm - 8:52 am
AXA
-
ORD
16h 53m
2 stops
$709American Airlines
Tue, Jul 7 - Fri, Jul 24
American Airlines Logo
5:00 am - 1:11 pm
ORD
-
AXA
7h 11m
1 stop
American Airlines Logo
1:51 pm - 11:30 pm
AXA
-
ORD
10h 39m
1 stop
$724American Airlines
Tue, Jul 7 - Fri, Jul 24
American Airlines Logo
9:45 pm - 1:11 pm
ORD
-
AXA
14h 26m
2 stops
American Airlines Logo
1:51 pm - 11:30 pm
AXA
-
ORD
10h 39m
1 stop
$729American Airlines
Fri, May 29 - Tue, Jun 2
American Airlines Logo
6:08 am - 4:15 pm
ORD
-
AXA
9h 07m
1 stop
American Airlines Logo
4:55 pm - 12:24 am
AXA
-
ORD
8h 29m
1 stop
$759American Airlines
Fri, May 29 - Tue, Jun 2
American Airlines Logo
5:00 am - 1:19 pm
ORD
-
AXA
7h 19m
1 stop
American Airlines Logo
4:55 pm - 9:02 am
AXA
-
ORD
17h 07m
2 stops
$764American Airlines
Tue, Jul 7 - Tue, Jul 21
American Airlines Logo
5:00 am - 4:19 pm
ORD
-
AXA
10h 19m
1 stop
American Airlines Logo
4:59 pm - 7:04 am
AXA
-
ORD
15h 05m
2 stops
$779American Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Anguilla flights

Get data-powered insights and trends into flights from O'Hare Intl to Anguilla to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Anguilla?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Anguilla, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Anguilla is August, when tickets cost $0 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $1,428 and $1,182 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$380
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago to The Valley

FAQs - booking Anguilla flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Anguilla.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Anguilla?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport to Anguilla up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from O'Hare Intl to Anguilla

 
Need help choosing which airline to fly with from O'Hare Intl 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.
7.1
American AirlinesOverall score based on 11670 reviews
7.2Comfort
7.9Crew
6.9Entertainment
7.5Boarding
6.4Food
Airline reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

2.0 MediocreStella, Apr 2026
ORD - DCA
Read more American Airlines reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight from O'Hare Intl to Anguilla

Information on your arrival and departure airports

Chicago O'Hare Airport (ORD)