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Anguilla

$435+ Cheap flights from Chicago (CHI) to Anguilla

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Dec 1 — Dec 81
Mon 12/1
Mon 12/8
1 adult, Economy
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Cheap flight deals from Chicago to Anguilla

Keep the following information in mind while searching for Chicago to Anguilla flight deals. Data was last updated November 1, 2025.

Round-trip from

$479
(American Airlines)

One-way from

$435
(American Airlines)

Popular in

August

Cheapest in

January

Average price

$1,133
From Chicago (CHI) to Anguilla
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One-way flight from Chicago (CHI) to Anguilla
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Highest demand for flights based on searches. 21% potential increase in price ($313 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($98 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Chicago to Anguilla

Cheapest flights from Chicago to Anguilla
Explore the most affordable flight options available from Chicago to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 1, 2025.

This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:07 pmORD - AXA
1 stop15h 33mAmerican Airlines
Wed 12/105:20 pmAXA - ORD
1 stop17h 29mAmerican Airlines
Deal found 10/31$479
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:34 pmORD - AXA
3 stops19h 36mMultiple Airlines
Mon 11/1712:30 pmAXA - ORD
2 stops13h 57mMultiple Airlines
Deal found 10/30$659
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:00 amORD - AXA
1 stop10h 01mAmerican Airlines
Mon 12/15:41 pmAXA - ORD
1 stop17h 24mAmerican Airlines
Deal found 10/31$681
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:07 pmORD - AXA
1 stop17h 24mAmerican Airlines
Fri 11/213:11 pmAXA - ORD
1 stop9h 48mAmerican Airlines
Deal found 10/30$793
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/277:26 pmORD - AXA
1 stop16h 47mAmerican Airlines
Tue 12/302:53 pmAXA - ORD
1 stop10h 06mAmerican Airlines
Deal found 10/30$808

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated November 1, 2025.
Use the filters below to find and compare flights from Chicago to Anguilla that are best for you.

Fly from

Chicago

Fly to

Anguilla

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 12/5

7:07 pm-12:40 pm

1 stop15h 33m

The Valley Wallblake Intl

Wed 12/10

5:20 pm-8:49 am

1 stop17h 29m

$479

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 12/6

7:00 am-4:40 pm

1 stop7h 40m

The Valley Wallblake Intl

Fri 12/12

5:20 pm-12:37 am

1 stop9h 17m

$479

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 4/6

6:58 pm-1:10 pm

1 stop17h 12m

The Valley Wallblake Intl

Wed 4/15

4:05 pm-6:10 am

2 stops15h 05m

$578

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 4/1

6:58 pm-1:00 pm

1 stop17h 02m

The Valley Wallblake Intl

Wed 4/8

4:05 pm-8:48 am

1 stop17h 43m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 1/1

5:00 am-2:13 pm

1 stop7h 13m

The Valley Wallblake Intl

Thu 1/8

5:06 pm-12:30 am

1 stop9h 24m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/2

5:00 am-4:26 pm

1 stop9h 26m

The Valley Wallblake Intl

Sun 2/8

5:06 pm-9:05 am

1 stop17h 59m

$603

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 11/13

7:34 pm-5:10 pm

3 stops19h 36m

The Valley Wallblake Intl

Mon 11/17

12:30 pm-12:27 am

2 stops13h 57m

$659

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 11/10

7:07 pm-2:31 pm

1 stop17h 24m

$435

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 11/10

12:17 pm-1:30 pm

3 stops47h 13m

$454

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Best time to book a flight from Chicago to Anguilla

Have a flexible travel schedule? Discover the best time to fly to Anguilla from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Anguilla
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Anguilla

Get insights into the airlines that provide service to Anguilla. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Anguilla. Reviews last updated November 1, 2025.
Read through reviews of airlines operating flights from Chicago to Anguilla, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,031 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,031 reviews
American Airlines
7.2
Good
11,031 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.4

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Chicago to Anguilla. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Anguilla?

    For as low as $479, American Airlines can have you in Anguilla from Chicago in 15h 33m. Chicago and Anguilla are separated by a distance of 2197 mi.

  • Can I find deals for flights from Chicago to Anguilla that include hotel bookings?

    Yes. In addition to deals on Chicago to Anguilla flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Anguilla?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Anguilla.

  • Can I find deals for business class flights from Chicago to Anguilla?

    Yes. Cheapflights offers flight deals from Chicago to Anguilla by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Chicago to Anguilla

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Anguilla

Discover the top airline that operate flights from Chicago to Anguilla. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$602Average$786FlexibilityNo cancel feeOn-time71%

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