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Cheap flights from Chicago to Anguilla from $565

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 8/5. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:10 pm - 2:21 pm
ORD
-
AXA
17h 11m
1 stop
American Airlines Logo
5:20 pm - 9:28 am
AXA
-
ORD
18h 08m
1 stop
$712American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
6:00 am - 4:26 pm
ORD
-
AXA
8h 26m
1 stop
American Airlines Logo
5:06 pm - 12:38 am
AXA
-
ORD
9h 32m
1 stop
$712American Airlines
Tue, Jan 19 - Wed, Jan 27
American Airlines Logo
8:58 pm - 2:21 pm
ORD
-
AXA
15h 23m
2 stops
American Airlines Logo
5:20 pm - 7:42 am
AXA
-
ORD
16h 22m
1 stop
$717American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
8:55 pm - 2:23 pm
ORD
-
AXA
15h 28m
2 stops
American Airlines Logo
5:06 pm - 7:27 am
AXA
-
ORD
16h 21m
2 stops
$717American Airlines
Tue, Jan 19 - Wed, Jan 27
United Airlines Logo
8:40 pm - 5:35 pm
ORD
-
AXA
18h 55m
2 stops
United Airlines Logo
9:46 am - 10:18 pm
AXA
-
ORD
14h 32m
2 stops
$1,644United Airlines
Mon, Nov 16 - Thu, Nov 19
United Airlines Logo
8:40 pm - 5:35 pm
ORD
-
AXA
18h 55m
2 stops
United Airlines Logo
9:46 am - 10:18 pm
AXA
-
ORD
14h 32m
2 stops
$1,679United Airlines
Mon, Nov 16 - Thu, Nov 19
Multiple Airlines Logo
8:55 am - 5:35 pm
ORD
-
AXA
31h 40m
2 stops
Multiple Airlines Logo
9:46 am - 8:05 pm
AXA
-
ORD
11h 19m
2 stops
$1,717Multiple Airlines
Tue, Aug 18 - Tue, Sep 1
Multiple Airlines Logo
8:55 am - 5:35 pm
ORD
-
AXA
31h 40m
2 stops
Multiple Airlines Logo
9:46 am - 8:05 pm
AXA
-
ORD
11h 19m
2 stops
$1,752Multiple Airlines
Fri, Oct 9 - Mon, Oct 12
Multiple Airlines Logo
8:55 am - 5:35 pm
ORD
-
AXA
31h 40m
2 stops
Multiple Airlines Logo
9:46 am - 8:05 pm
AXA
-
ORD
35h 19m
2 stops
$1,864Multiple Airlines
Thu, Sep 24 - Sun, Sep 27
United Airlines Logo
8:55 am - 5:35 pm
ORD
-
AXA
31h 40m
2 stops
United Airlines Logo
9:46 am - 10:15 pm
AXA
-
ORD
13h 29m
2 stops
$2,064United Airlines
Sat, Sep 12 - Sat, Sep 19

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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
ORD7:10 pmChicago O'Hare Intl
17h 11m
1 stop
AXA2:21 pmThe Valley Wallblake Intl
Dec 15
AXA5:20 pmThe Valley Wallblake Intl
18h 08m
1 stop
ORD9:28 amChicago O'Hare Intl
$712
American Airlines
Dec 8
ORD8:55 pmChicago O'Hare Intl
15h 26m
2 stops
AXA2:21 pmThe Valley Wallblake Intl
Dec 15
AXA5:20 pmThe Valley Wallblake Intl
16h 05m
2 stops
ORD7:25 amChicago O'Hare Intl
$717
American Airlines
Dec 30
ORD5:05 amChicago O'Hare Intl
9h 31m
1 stop
AXA4:36 pmThe Valley Wallblake Intl
Jan 7
AXA5:06 pmThe Valley Wallblake Intl
16h 21m
2 stops
ORD7:27 amChicago O'Hare Intl
$722

United Airlines flights from Chicago to Anguilla

Our best United Airlines deals on Chicago to Anguilla flight tickets
United Airlines
Nov 16
ORD8:40 pmChicago O'Hare Intl
18h 55m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Nov 19
AXA9:46 amThe Valley Wallblake Intl
14h 32m
2 stops
ORD10:18 pmChicago O'Hare Intl
$1,644
United Airlines
Nov 16
ORD8:40 pmChicago O'Hare Intl
18h 55m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Nov 19
AXA9:46 amThe Valley Wallblake Intl
14h 32m
2 stops
ORD10:18 pmChicago O'Hare Intl
$1,679
United Airlines
Sep 12
ORD8:55 amChicago O'Hare Intl
31h 40m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Sep 19
AXA9:46 amThe Valley Wallblake Intl
13h 29m
2 stops
ORD10:15 pmChicago O'Hare Intl
$2,064

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 July 30, 2026.
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

Cheapest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 12/8

7:10 pm-2:21 pm

1 stop17h 11m

The Valley Wallblake Intl

Tue 12/15

5:20 pm-9:28 am

1 stop18h 08m

$712
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 1/19

6:00 am-4:26 pm

1 stop8h 26m

The Valley Wallblake Intl

Wed 1/27

5:06 pm-12:38 am

1 stop9h 32m

$712

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 12/8

8:58 pm-2:21 pm

2 stops15h 23m

The Valley Wallblake Intl

Tue 12/15

5:20 pm-7:42 am

1 stop16h 22m

$717

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 1/19

8:55 pm-2:23 pm

2 stops15h 28m

The Valley Wallblake Intl

Wed 1/27

5:06 pm-7:27 am

2 stops16h 21m

$717

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 11/16

8:40 pm-5:35 pm

2 stops18h 55m

The Valley Wallblake Intl

Thu 11/19

9:46 am-10:18 pm

2 stops14h 32m

$1,644

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 11/16

8:40 pm-5:35 pm

2 stops18h 55m

The Valley Wallblake Intl

Thu 11/19

9:46 am-10:18 pm

2 stops14h 32m

$1,679

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 8/18

8:55 am-5:35 pm

2 stops31h 40m

The Valley Wallblake Intl

Tue 9/1

9:46 am-8:05 pm

2 stops11h 19m

$1,717

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 10/9

8:55 am-5:35 pm

2 stops31h 40m

The Valley Wallblake Intl

Mon 10/12

9:46 am-8:05 pm

2 stops11h 19m

$1,752

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 9/24

8:55 am-5:35 pm

2 stops31h 40m

The Valley Wallblake Intl

Sun 9/27

9:46 am-8:05 pm

2 stops35h 19m

$1,864

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 9/12

8:55 am-5:35 pm

2 stops31h 40m

The Valley Wallblake Intl

Sat 9/19

9:46 am-10:15 pm

2 stops13h 29m

$2,064

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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Cheap Chicago to Anguilla flight deals and tips

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

Fastest flight time

7h 55m

Direct flights

None
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.
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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?

  • 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 $529Free CancellationRating
7.1
11,841 reviews
Search American Airlines flights

Frequently asked questions about flying from Chicago to Anguilla

  • How do I get Price Alerts for flights from Chicago to Anguilla?

    Price Alerts will notify you by email when the price for flights to Anguilla from Chicago decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

  • How can I save money on flights from Chicago to Anguilla with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    momondo shows deals across 700+ competitors all at once. momondo is active in 30 international markets, so you can have access to a wide range of options from airlines and OTAs alike.

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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Find better results for your trip to Anguilla

Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo
Flights to The Valleyfrom $621