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Cheap flights from Chicago to Anguilla from $589

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 12/7. 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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0 bags

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Cheap round-trip flights

American Airlines Logo
5:00 am - 2:23 pmORD-AXA
7h 23m1 stop
American Airlines Logo
5:20 pm - 8:43 amAXA-ORD
17h 23m1 stop
$589American Airlines
Find Deal
Sun, Dec 7 - Sun, Dec 14
American Airlines Logo
8:50 pm - 2:23 pmORD-AXA
15h 33m2 stops
American Airlines Logo
5:20 pm - 8:43 amAXA-ORD
17h 23m1 stop
$593American Airlines
Find Deal
Sun, Dec 7 - Sun, Dec 14
American Airlines Logo
8:50 pm - 2:23 pmORD-AXA
15h 33m2 stops
American Airlines Logo
5:20 pm - 7:19 amAXA-ORD
15h 59m2 stops
$623American Airlines
Find Deal
Sun, Dec 7 - Sun, Dec 14
American Airlines Logo
7:09 pm - 2:10 pmORD-AXA
17h 01m1 stop
American Airlines Logo
4:30 pm - 9:05 amAXA-ORD
17h 35m1 stop
$663American Airlines
Find Deal
Sun, Mar 1 - Sun, Mar 8
American Airlines Logo
8:25 pm - 2:10 pmORD-AXA
15h 45m2 stops
American Airlines Logo
4:30 pm - 9:05 amAXA-ORD
17h 35m1 stop
$667American Airlines
Find Deal
Sun, Mar 1 - Sun, Mar 8
American Airlines Logo
7:01 am - 4:25 pmORD-AXA
7h 24m1 stop
American Airlines Logo
5:10 pm - 9:02 amAXA-ORD
17h 52m1 stop
$683American Airlines
Find Deal
Thu, Feb 19 - Sun, Feb 22
American Airlines Logo
8:25 pm - 2:10 pmORD-AXA
15h 45m2 stops
American Airlines Logo
5:10 pm - 9:02 amAXA-ORD
17h 52m1 stop
$687American Airlines
Find Deal
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
4:59 pm - 5:15 pmORD-AXA
23h 16m2 stops
Multiple Airlines Logo
9:35 am - 9:33 pmAXA-ORD
12h 58m2 stops
$1,120Multiple Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 23
United Airlines Logo
9:10 pm - 5:45 pmORD-AXA
18h 35m2 stops
United Airlines Logo
9:00 am - 6:45 pmAXA-ORD
11h 45m1 stop
$3,653United Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
United Airlines Logo
6:20 pm - 5:45 pmORD-AXA
21h 25m2 stops
United Airlines Logo
9:00 am - 6:30 pmAXA-ORD
11h 30m2 stops
$4,563United Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16

American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets
American Airlines
Dec 7
ORD5:00 amChicago O'Hare Intl
7h 23m
1 stop
AXA2:23 pmThe Valley Wallblake Intl
Dec 14
AXA5:20 pmThe Valley Wallblake Intl
17h 23m
1 stop
ORD8:43 amChicago O'Hare Intl
$589
Find similar
American Airlines
Dec 7
ORD8:50 pmChicago O'Hare Intl
15h 33m
2 stops
AXA2:23 pmThe Valley Wallblake Intl
Dec 14
AXA5:20 pmThe Valley Wallblake Intl
17h 23m
1 stop
ORD8:43 amChicago O'Hare Intl
$593
Find similar
American Airlines
Dec 7
ORD8:50 pmChicago O'Hare Intl
15h 33m
2 stops
AXA2:23 pmThe Valley Wallblake Intl
Dec 14
AXA5:20 pmThe Valley Wallblake Intl
15h 59m
2 stops
ORD7:19 amChicago O'Hare Intl
$623
Find similar

United Airlines flights from Chicago to Anguilla

Our best United Airlines deals on Chicago to Anguilla flight tickets
United Airlines
Nov 13
ORD9:10 pmChicago O'Hare Intl
18h 35m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Nov 16
AXA9:00 amThe Valley Wallblake Intl
11h 45m
1 stop
ORD6:45 pmChicago O'Hare Intl
$3,653
Find similar
United Airlines
Nov 13
ORD6:20 pmChicago O'Hare Intl
21h 25m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Nov 16
AXA9:00 amThe Valley Wallblake Intl
11h 30m
2 stops
ORD6:30 pmChicago O'Hare Intl
$4,563
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Anguilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 12/7

5:00 am-2:23 pm

1 stop7h 23m

The Valley Wallblake Intl

Sun 12/14

5:20 pm-8:43 am

1 stop17h 23m

$589

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 12/7

8:50 pm-2:23 pm

2 stops15h 33m

The Valley Wallblake Intl

Sun 12/14

5:20 pm-8:43 am

1 stop17h 23m

$593

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 12/7

8:50 pm-2:23 pm

2 stops15h 33m

The Valley Wallblake Intl

Sun 12/14

5:20 pm-7:19 am

2 stops15h 59m

$623

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 3/1

7:09 pm-2:10 pm

1 stop17h 01m

The Valley Wallblake Intl

Sun 3/8

4:30 pm-9:05 am

1 stop17h 35m

$663

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 3/1

8:25 pm-2:10 pm

2 stops15h 45m

The Valley Wallblake Intl

Sun 3/8

4:30 pm-9:05 am

1 stop17h 35m

$667

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 2/19

7:01 am-4:25 pm

1 stop7h 24m

The Valley Wallblake Intl

Sun 2/22

5:10 pm-9:02 am

1 stop17h 52m

$683

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 2/19

8:25 pm-2:10 pm

2 stops15h 45m

The Valley Wallblake Intl

Sun 2/22

5:10 pm-9:02 am

1 stop17h 52m

$687

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 10/16

4:59 pm-5:15 pm

2 stops23h 16m

The Valley Wallblake Intl

Thu 10/23

9:35 am-9:33 pm

2 stops12h 58m

$1,120

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 11/13

9:10 pm-5:45 pm

2 stops18h 35m

The Valley Wallblake Intl

Sun 11/16

9:00 am-6:45 pm

1 stop11h 45m

$3,653

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 11/13

6:20 pm-5:45 pm

2 stops21h 25m

The Valley Wallblake Intl

Sun 11/16

9:00 am-6:30 pm

2 stops11h 30m

$4,563

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

Direct flights

None
There are no direct flights from Chicago to Anguilla. There are no popular flight routes from Chicago to Anguilla.
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?

  • 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 $657Free 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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Popular flights according to clicks in the last 7 days on momondo
Flights to The Valleyfrom $460