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?

The number of operators available for flights from Chicago to Anguilla is 1 as of July 2025.

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.

$351 Cheap Flights from Chicago to Anguilla in 2025

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Find the cheapest flights from Chicago to Anguilla

Round-trip

One-way

Cheap round-trip flights

8:57 pm - 2:18 pmORD-AXA

15h 21m2 stops

5:05 pm - 7:05 amAXA-ORD

16h 00m2 stops

$602American Airlines

Find Deal

Fri, Nov 14 - Fri, Nov 21

4:40 pm - 2:18 pmORD-AXA

19h 38m1 stop

5:05 pm - 9:25 amAXA-ORD

18h 20m1 stop

$612American Airlines

Find Deal

Fri, Nov 14 - Fri, Nov 21

6:55 pm - 2:05 pmORD-AXA

17h 10m1 stop

5:30 pm - 9:02 amAXA-ORD

17h 32m1 stop

$1,087American Airlines

Find Deal

Mon, Dec 29 - Sun, Jan 4

5:09 am - 4:10 pmORD-AXA

9h 01m2 stops

5:30 pm - 9:02 amAXA-ORD

17h 32m1 stop

$1,201American Airlines

Find Deal

Mon, Dec 29 - Sun, Jan 4

8:52 am - 5:15 pmORD-AXA

31h 23m2 stops

9:35 am - 9:16 pmAXA-ORD

12h 41m2 stops

$1,522

Find Deal

Thu, Oct 23 - Thu, Oct 30

6:55 pm - 2:05 pmORD-AXA

17h 10m1 stop

5:30 pm - 12:18 amAXA-ORD

8h 48m1 stop

$1,807American Airlines

Find Deal

Sat, Dec 27 - Fri, Jan 2

8:45 pm - 2:05 pmORD-AXA

15h 20m2 stops

5:30 pm - 12:18 amAXA-ORD

8h 48m1 stop

$1,865American Airlines

Find Deal

Sat, Dec 27 - Fri, Jan 2

6:55 pm - 12:40 pmORD-AXA

15h 45m1 stop

5:30 pm - 12:18 amAXA-ORD

8h 48m1 stop

$1,991American Airlines

Find Deal

Fri, Dec 26 - Fri, Jan 2

2:37 pm - 3:08 pmORD-AXA

22h 31m2 stops

3:30 pm - 9:55 amAXA-ORD

20h 25m2 stops

$2,047

Find Deal

Mon, Dec 29 - Sun, Jan 4

8:45 pm - 2:05 pmORD-AXA

15h 20m2 stops

5:30 pm - 12:18 amAXA-ORD

8h 48m1 stop

$2,270American Airlines

Find Deal

Fri, Dec 26 - Fri, Jan 2

American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets

American Airlines

Nov 14

ORD8:57 pmChicago O'Hare Intl

15h 21m

2 stops

AXA2:18 pmThe Valley Wallblake Intl

Nov 21

AXA5:05 pmThe Valley Wallblake Intl

16h 00m

2 stops

ORD7:05 amChicago O'Hare Intl

$602

Find similar

American Airlines

Nov 14

ORD4:40 pmChicago O'Hare Intl

19h 38m

1 stop

AXA2:18 pmThe Valley Wallblake Intl

Nov 21

AXA5:05 pmThe Valley Wallblake Intl

18h 20m

1 stop

ORD9:25 amChicago O'Hare Intl

$612

Find similar

American Airlines

Dec 29

ORD6:55 pmChicago O'Hare Intl

17h 10m

1 stop

AXA2:05 pmThe Valley Wallblake Intl

Jan 4

AXA5:30 pmThe Valley Wallblake Intl

17h 32m

1 stop

ORD9:02 amChicago O'Hare Intl

$1,087

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 11/14

8:57 pm-2:18 pm

2 stops15h 21m

The Valley Wallblake Intl

Fri 11/21

5:05 pm-7:05 am

2 stops16h 00m

$602

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 11/14

4:40 pm-2:18 pm

1 stop19h 38m

The Valley Wallblake Intl

Fri 11/21

5:05 pm-9:25 am

1 stop18h 20m

$612

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 12/29

6:55 pm-2:05 pm

1 stop17h 10m

The Valley Wallblake Intl

Sun 1/4

5:30 pm-9:02 am

1 stop17h 32m

$1,087

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 12/29

5:09 am-4:10 pm

2 stops9h 01m

The Valley Wallblake Intl

Sun 1/4

5:30 pm-9:02 am

1 stop17h 32m

$1,201

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 10/23

8:52 am-5:15 pm

2 stops31h 23m

The Valley Wallblake Intl

Thu 10/30

9:35 am-9:16 pm

2 stops12h 41m

$1,522

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 12/27

6:55 pm-2:05 pm

1 stop17h 10m

The Valley Wallblake Intl

Fri 1/2

5:30 pm-12:18 am

1 stop8h 48m

$1,807

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 12/27

8:45 pm-2:05 pm

2 stops15h 20m

The Valley Wallblake Intl

Fri 1/2

5:30 pm-12:18 am

1 stop8h 48m

$1,865

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 12/26

6:55 pm-12:40 pm

1 stop15h 45m

The Valley Wallblake Intl

Fri 1/2

5:30 pm-12:18 am

1 stop8h 48m

$1,991

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 12/29

2:37 pm-3:08 pm

2 stops22h 31m

The Valley Wallblake Intl

Sun 1/4

3:30 pm-9:55 am

2 stops20h 25m

$2,047

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 12/26

8:45 pm-2:05 pm

2 stops15h 20m

The Valley Wallblake Intl

Fri 1/2

5:30 pm-12:18 am

1 stop8h 48m

$2,270

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first

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	$351
Fastest flight time	9h 01m
Direct flights	None
Airports in Anguilla	1 airport

The best one-way flight to Anguilla from Chicago in the past 72 hours is $351. The best round-trip flight deal from Chicago to Anguilla found on momondo in the last 72 hours is $602.

The fastest flight from Chicago to Anguilla takes 9h 01m

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)

Search flight deals

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?
The number of operators available for flights from Chicago to Anguilla is 1 as of July 2025.
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 Airlines	PriceFrom $614	Free Cancellation	Rating 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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Popular cities in Anguilla

Flights to The Valleyfrom $519

Cheap flights from Chicago to Anguilla from $351

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Anguilla departing on 9/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

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Filter for what you want

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American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets

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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

Fastest flight time

Direct flights

Airports in Anguilla

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

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?

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

Best airlines flying from Chicago to Anguilla

Compare and see reviews for airlines that fly from Chicago to Anguilla with momondo

Why use momondo?

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

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

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

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

An easier way to manage your Anguilla trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Anguilla

Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo