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Cheap flights from Chicago to Anguilla from $906

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Anguilla departing on 2/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Anguilla

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Anguilla that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Anguilla.

Cheap last minute flights

Planning a quick getaway from Chicago to Anguilla? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Anguilla, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Anguilla

Find recent round-trip train or bus tickets from Chicago to Anguilla.

All round-trip flight deals to Anguilla

The cheapest plane tickets to Anguilla found on KAYAK recently.
7:09 pm - 12:39 pmORD-AXA
15h 30m1 stop
5:00 pm - 9:02 amAXA-ORD
18h 02m1 stop
$906American Airlines
Find Deal
Fri, Feb 14 - Sat, Feb 22
7:09 pm - 12:39 pmORD-AXA
15h 30m1 stop
5:00 pm - 7:10 amAXA-ORD
16h 10m2 stops
$960American Airlines
Find Deal
Fri, Feb 14 - Sat, Feb 22
5:10 am - 4:19 pmORD-AXA
9h 09m2 stops
5:00 pm - 7:10 amAXA-ORD
16h 10m2 stops
$1,040American Airlines
Find Deal
Fri, Feb 14 - Sat, Feb 22

American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets
American Airlines
Feb 14
ORD7:09 pmChicago O'Hare Intl
15h 30m
1 stop
AXA12:39 pmThe Valley Wallblake Intl
Feb 22
AXA5:00 pmThe Valley Wallblake Intl
18h 02m
1 stop
ORD9:02 amChicago O'Hare Intl
American Airlines
Feb 14
ORD7:09 pmChicago O'Hare Intl
15h 30m
1 stop
AXA12:39 pmThe Valley Wallblake Intl
Feb 22
AXA5:00 pmThe Valley Wallblake Intl
16h 10m
2 stops
ORD7:10 amChicago O'Hare Intl
American Airlines
Feb 14
ORD5:10 amChicago O'Hare Intl
9h 09m
2 stops
AXA4:19 pmThe Valley Wallblake Intl
Feb 22
AXA5:00 pmThe Valley Wallblake Intl
16h 10m
2 stops
ORD7:10 amChicago O'Hare Intl

See travel insights to Anguilla from

How to get the cheapest flight ticket from Chicago to Anguilla

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Anguilla?

The cheapest day to depart from Chicago to Anguilla is on a Friday when prices can be found for as low as $650. The most expensive day to fly to Anguilla is Saturday, with ticket prices averaging around $990.

What is the cheapest time of day to depart on your flight to Anguilla?

Flying to Anguilla from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $607 when looking at flights departing in the afternoon. Flights in the morning are often more expensive with an average ticket price of $759.

Cheap Chicago to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Anguilla

Best Price Found

$906

Fastest flight time

9h 09m

Direct flights

None

Airports in Anguilla

1 airport
The best flight deal from Chicago to Anguilla found on momondo in the last 72 hours is $906
The fastest flight from Chicago to Anguilla takes 9h 09m
There are no direct flights from Chicago to Anguilla. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - The Valley Wallblake Intl Airport.
There is 1 airport near Anguilla: The Valley Wallblake Intl (AXA)

  • When did momondo last update prices for flights from Chicago to Anguilla?

    Prices for flights from Chicago to Anguilla are updated daily.

  • How many operators does momondo search for flights from Chicago to Anguilla?

  • How old do you have to be to fly from Chicago to Anguilla?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Anguilla.

  • What documentation or ID do you need to fly to Anguilla?

    The travel and health documents required for your trip to Anguilla can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Anguilla. We always recommend checking with your airline or a trusted third party such as IATA to get advice.


Best airlines flying from Chicago to Anguilla

Compare and see reviews for airlines that fly from Chicago to Anguilla with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $564Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Anguilla?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Anguilla. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Anguilla with flexible booking policies on momondo?

Yes. All flights to Anguilla from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Anguilla?

momondo provides multiple filters to help you find the best flight to Anguilla from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Anguilla right now. Can momondo alert me if prices change?

Price alerts on flights to Anguilla from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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