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 October 2026.

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.

$381 Cheap Flights from Chicago to Anguilla in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Anguilla

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:50 pm - 2:54 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

17h 04m1 stop Miami

3:34 pm - 12:53 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

11h 19m1 stop Miami

$667American Airlines

Tue, Dec 8 - Tue, Dec 15

9:06 pm - 2:54 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

15h 48m2 stops Charlotte Douglas Miami

3:34 pm - 8:00 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

18h 26m1 stop Miami

$671American Airlines

Tue, Dec 8 - Tue, Dec 15

9:06 pm - 2:54 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

15h 48m2 stops Charlotte Douglas Miami

5:39 pm - 7:30 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

15h 51m2 stops Miami Philadelphia

$671American Airlines

Tue, Dec 8 - Tue, Dec 15

8:45 am - 5:30 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

30h 45m2 stops Toronto Pearson Intl Newark

1:30 pm - 1:13 pmAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

25h 43m2 stops Simpson Bay Princess Juliana Toronto Pearson Intl

$956Multiple Airlines

Fri, Feb 5 - Fri, Feb 12

8:45 am - 5:30 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

30h 45m2 stops Toronto Pearson Intl Newark

7:10 pm - 5:30 pmAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

24h 20m3 stops Newark Montreal Pierre Elliott Trudeau Intl Toronto Island

$1,106Multiple Airlines

Fri, Feb 5 - Fri, Feb 12

8:50 pm - 5:25 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

18h 35m2 stops Toronto Pearson Intl Simpson Bay Princess Juliana

7:55 am - 5:30 pmAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

35h 35m3 stops Providenciales Newark Toronto Island

$1,373Multiple Airlines

Thu, Feb 4 - Sun, Feb 14

7:05 am - 5:25 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

32h 20m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Simpson Bay Princess Juliana

7:55 am - 5:30 pmAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

35h 35m3 stops Providenciales Newark Toronto Island

$1,375Multiple Airlines

Thu, Feb 4 - Sun, Feb 14

12:15 pm - 1:10 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

22h 55m2 stops Toronto Island Boston Logan Intl

1:55 pm - 9:22 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

21h 27m2 stops Providenciales Toronto Pearson Intl

$1,416Multiple Airlines

Thu, Dec 24 - Thu, Dec 31

12:15 pm - 1:10 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

22h 55m2 stops Toronto Island Boston Logan Intl

1:55 pm - 11:07 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

23h 12m3 stops Providenciales Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$1,422Multiple Airlines

Thu, Dec 24 - Thu, Dec 31

9:35 pm - 5:35 pmORD Chicago O'Hare Intl-AXA The Valley Wallblake Intl

18h 00m2 stops Washington, D.C. Dulles Intl Saint Thomas Island Cyril E King

9:00 am - 12:01 amAXA The Valley Wallblake Intl-ORD Chicago O'Hare Intl

17h 01m2 stops Saint Thomas Island Cyril E King Washington, D.C. Dulles Intl

$1,584United Airlines

Fri, Dec 11 - Fri, Dec 18

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American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets

American Airlines

Dec 8

ORD7:50 pmChicago O'Hare Intl

17h 04m

1 stop

AXA2:54 pmThe Valley Wallblake Intl

Dec 15

AXA3:34 pmThe Valley Wallblake Intl

11h 19m

1 stop

ORD12:53 amChicago O'Hare Intl

$667

American Airlines

Dec 8

ORD9:06 pmChicago O'Hare Intl

15h 48m

2 stops

AXA2:54 pmThe Valley Wallblake Intl

Dec 15

AXA5:39 pmThe Valley Wallblake Intl

17h 51m

1 stop

ORD9:30 amChicago O'Hare Intl

$671

American Airlines

Nov 28

ORD5:00 amChicago O'Hare Intl

7h 57m

1 stop

AXA2:57 pmThe Valley Wallblake Intl

Dec 5

AXA1:25 pmThe Valley Wallblake Intl

10h 16m

1 stop

ORD9:41 pmChicago O'Hare Intl

$701

United Airlines flights from Chicago to Anguilla

Our best United Airlines deals on Chicago to Anguilla flight tickets

United Airlines

Dec 11

ORD9:35 pmChicago O'Hare Intl

18h 00m

2 stops

AXA5:35 pmThe Valley Wallblake Intl

Dec 18

AXA9:00 amThe Valley Wallblake Intl

17h 01m

2 stops

ORD12:01 amChicago O'Hare Intl

$1,584

United Airlines

Jan 8

ORD8:40 amChicago O'Hare Intl

30h 55m

2 stops

AXA5:35 pmThe Valley Wallblake Intl

Jan 15

AXA9:00 amThe Valley Wallblake Intl

16h 44m

2 stops

ORD11:44 pmChicago O'Hare Intl

$1,674

United Airlines

Jan 25

ORD5:10 pmChicago O'Hare Intl

22h 25m

2 stops

AXA5:35 pmThe Valley Wallblake Intl

Jan 28

AXA9:00 amThe Valley Wallblake Intl

11h 45m

1 stop

ORD6:45 pmChicago O'Hare Intl

$1,704

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

7:50 pm-2:54 pm

1 stop17h 04m

The Valley Wallblake Intl

Tue 12/15

3:34 pm-12:53 am

1 stop11h 19m

$667

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

9:06 pm-2:54 pm

2 stops15h 48m

The Valley Wallblake Intl

Tue 12/15

3:34 pm-8:00 am

1 stop18h 26m

$671

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

9:06 pm-2:54 pm

2 stops15h 48m

The Valley Wallblake Intl

Tue 12/15

5:39 pm-7:30 am

2 stops15h 51m

$671

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Fri 2/5

8:45 am-5:30 pm

2 stops30h 45m

The Valley Wallblake Intl

Fri 2/12

1:30 pm-1:13 pm

2 stops25h 43m

$956

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Fri 2/5

8:45 am-5:30 pm

2 stops30h 45m

The Valley Wallblake Intl

Fri 2/12

7:10 pm-5:30 pm

3 stops24h 20m

$1,106

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 2/4

8:50 pm-5:25 pm

2 stops18h 35m

The Valley Wallblake Intl

Sun 2/14

7:55 am-5:30 pm

3 stops35h 35m

$1,373

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 2/4

7:05 am-5:25 pm

3 stops32h 20m

The Valley Wallblake Intl

Sun 2/14

7:55 am-5:30 pm

3 stops35h 35m

$1,375

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 12/24

12:15 pm-1:10 pm

2 stops22h 55m

The Valley Wallblake Intl

Thu 12/31

1:55 pm-9:22 am

2 stops21h 27m

$1,416

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 12/24

12:15 pm-1:10 pm

2 stops22h 55m

The Valley Wallblake Intl

Thu 12/31

1:55 pm-11:07 am

3 stops23h 12m

$1,422

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Fri 12/11

9:35 pm-5:35 pm

2 stops18h 00m

The Valley Wallblake Intl

Fri 12/18

9:00 am-12:01 am

2 stops17h 01m

$1,584

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 airline that flies from Chicago to Anguilla?

American Airlines is the most popular carrier operating from Chicago to Anguilla

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	$381
Fastest flight time	7h 55m
Direct flights	None

The best one-way flight to Anguilla from Chicago in the past 72 hours is $381. The best round-trip flight deal from Chicago to Anguilla found on momondo in the last 72 hours is $667.

The fastest flight from Chicago to Anguilla takes 7h 55m

There are no direct flights from Chicago to Anguilla. There are no popular flight routes from Chicago to Anguilla.

Search flight deals

Frequently asked questions about flying from Chicago to Anguilla

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 October 2026.
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 $644	Free Cancellation	Rating 7.0 12,205 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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Flights to The Valleyfrom $404

Cheap flights from Chicago to Anguilla from $381

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 12/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets

United Airlines flights from Chicago to Anguilla

Our best United Airlines deals on Chicago to Anguilla flight tickets

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How to get the cheapest flight ticket from Chicago to Anguilla

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Cheap Chicago to Anguilla flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Chicago 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?

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

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According to popular flight searches on momondo this year

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List of cabin classes available on flights landing in Anguilla. Availability may vary depending on flight origin and airline.

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