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Anguilla

$415+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Jul 22 — Jul 291
Wed 7/22
Wed 7/29
1 adult, Economy
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Cheap 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 June 22, 2026.

This American Airlines deal was found by Cheapflights users on 6/21. 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.
Tue 12/85:00 am
ORD
-
AXA
1 stop9h 40m
American Airlines
Tue 12/155:20 pm
AXA
-
ORD
1 stop9h 17m
American Airlines
Deal found 6/21$692
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Thu 12/37:07 pm
ORD
-
AXA
1 stop17h 14m
American Airlines
Mon 12/73:01 pm
AXA
-
ORD
1 stop9h 56m
American Airlines
Deal found 6/21$762
This American Airlines deal was found by Cheapflights users on 6/21. 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 7/255:59 pm
ORD
-
AXA
1 stop18h 12m
American Airlines
Sat 8/11:56 pm
AXA
-
ORD
1 stop9h 05m
American Airlines
Deal found 6/21$794
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Tue 7/75:00 am
ORD
-
AXA
1 stop10h 19m
American Airlines
Wed 7/224:59 pm
AXA
-
ORD
1 stop8h 27m
American Airlines
Deal found 6/21$804
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 7/155:59 pm
ORD
-
AXA
1 stop18h 12m
American Airlines
Sat 7/181:56 pm
AXA
-
ORD
1 stop11h 30m
American Airlines
Deal found 6/18$829
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Tue 7/75:07 am
ORD
-
AXA
2 stops10h 12m
American Airlines
Wed 7/154:59 pm
AXA
-
ORD
2 stops14h 39m
American Airlines
Deal found 6/20$839
This American Airlines deal was found by Cheapflights users on 6/21. 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 7/55:59 pm
ORD
-
AXA
1 stop21h 20m
American Airlines
Wed 7/81:51 pm
AXA
-
ORD
1 stop11h 35m
American Airlines
Deal found 6/21$904

Find flight deals from Chicago to Anguilla

Keep the following information in mind while searching for Chicago to Anguilla flight deals. Data was last updated June 22, 2026.

Round-trip from

$692
(American Airlines)

One-way from

$380
(American Airlines)
From Chicago (CHI) to Anguilla
Search Deals
One-way flight from Chicago (CHI) to Anguilla
Search Deals

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 June 22, 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

8:50 pm-2:21 pm

2 stops15h 31m

The Valley Wallblake Intl

Tue 12/15

5:20 pm-8:49 am

1 stop17h 29m

$697

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 12/3

8:55 pm-2:21 pm

2 stops15h 26m

The Valley Wallblake Intl

Mon 12/7

5:20 pm-7:19 am

2 stops15h 59m

$767
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/25

5:59 pm-1:11 pm

1 stop18h 12m

The Valley Wallblake Intl

Sat 8/1

1:56 pm-10:01 pm

1 stop9h 05m

$794
Cheapest one-way
Quickest one-way

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 7/24

5:07 am-4:19 pm

2 stops10h 12m

$415

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

5:07 am-4:19 pm

2 stops10h 12m

$430

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 7/24

8:05 am-12:00 pm

3 stops26h 55m

$1,052

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/20

Sorted by cheapest first

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 June 22, 2026.
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
7.1
Good
11,729 reviews

Crew

7.9

Boarding

7.5

Entertainment

6.8

Overall

7.1

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,729 reviews
American Airlines
7.1
Good
11,729 reviews

Crew

7.9

Boarding

7.5

Entertainment

6.8

Overall

7.1

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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 $692, American Airlines can have you in Anguilla from Chicago in 7h 21m. 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

Browse thousands of different options on Cheapflights for your next trip

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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 June 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$529Average$768FlexibilityNo cancel feeOn-time71%

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