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Anguilla

$351+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
août 5 — août 121
mar. 8/5
mar. 8/12
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 juillet 31, 2025.

Round-trip from

$598
(American Airlines)

One-way from

$351
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$866
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. 27% potential increase in price ($388 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($95 potential savings vs. average RT price).
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Average for round-trip flights in July 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 juillet 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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.
sam. 10/115:00 amORD - AXA
1 stop7h 18mAmerican Airlines
mer. 10/152:05 pmAXA - ORD
1 stop9h 26mAmerican Airlines
Deal found 7/31$598
This United deal was found by Cheapflights users on 7/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 12/262:37 pmORD - AXA
2 stops22h 31mMultiple Airlines
ven. 1/29:30 amAXA - ORD
2 stops13h 46mMultiple Airlines
Deal found 7/30$2,705

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 juillet 31, 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

sam. 10/11

5:00 am-1:18 pm

1 stop7h 18m

The Valley Wallblake Intl

mer. 10/15

2:05 pm-10:31 pm

1 stop9h 26m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

ven. 12/26

2:37 pm-3:08 pm

2 stops22h 31m

The Valley Wallblake Intl

ven. 1/2

9:30 am-9:16 pm

2 stops13h 46m

$2,705

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

mar. 9/2

8:12 pm-3:40 pm

2 stops18h 28m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 juillet 31, 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
10,000 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.

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.

  • 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.

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Alternative routes for Chicago to Anguilla

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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 juillet 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$614Average$907FlexibilityNo cancel feeOn-time71%

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