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Anguilla

$380+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
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 May 9, 2026.

This American Airlines deal was found by Cheapflights users on 5/5. 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 7/75:59 pm
ORD
-
AXA
1 stop18h 12m
American Airlines
Wed 7/224:59 pm
AXA
-
ORD
1 stop17h 09m
American Airlines
Deal found 5/5$664
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/226:10 am
ORD
-
AXA
1 stop9h 05m
American Airlines
Fri 6/264:55 pm
AXA
-
ORD
1 stop8h 24m
American Airlines
Deal found 5/6$694
This American Airlines deal was found by Cheapflights users on 5/4. 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 7/255:07 am
ORD
-
AXA
2 stops10h 12m
American Airlines
Tue 7/284:59 pm
AXA
-
ORD
2 stops14h 31m
American Airlines
Deal found 5/4$704
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/94:05 pm
ORD
-
AXA
1 stop23h 10m
American Airlines
Wed 6/171:59 pm
AXA
-
ORD
1 stop9h 01m
American Airlines
Deal found 5/6$741
This American Airlines deal was found by Cheapflights users on 5/6. 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 8/14:59 pm
AXA
-
ORD
2 stops14h 31m
American Airlines
Deal found 5/6$764
This American Airlines deal was found by Cheapflights users on 5/5. 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 11/282:50 pm
ORD
-
AXA
1 stop21h 28m
American Airlines
Sat 12/51:00 pm
AXA
-
ORD
1 stop11h 57m
American Airlines
Deal found 5/5$777
This American Airlines deal was found by Cheapflights users on 5/5. 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 11/26:45 pm
ORD
-
AXA
2 stops17h 33m
American Airlines
Fri 11/132:58 pm
AXA
-
ORD
2 stops20h 07m
American Airlines
Deal found 5/5$789

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 May 9, 2026.

Round-trip from

$664
(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 May 9, 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 7/7

5:00 am-4:19 pm

1 stop10h 19m

The Valley Wallblake Intl

Wed 7/22

4:59 pm-9:08 am

1 stop17h 09m

$664

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

Tue 7/28

4:59 pm-9:08 am

1 stop17h 09m

$664

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

4:59 pm-6:30 am

2 stops14h 31m

$764
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 7/6

6:10 am-4:19 pm

1 stop9h 09m

The Valley Wallblake Intl

Mon 7/13

4:59 pm-6:30 am

2 stops14h 31m

$764

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 11/1

4:05 pm-2:18 pm

2 stops20h 13m

The Valley Wallblake Intl

Fri 11/13

2:58 pm-9:05 am

2 stops20h 07m

$789
Cheapest one-way
Quickest one-way

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

5:07 am-4:19 pm

2 stops10h 12m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

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 May 9, 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
11,668 reviews

Boarding

7.5

Comfort

7.2

Crew

7.9

Entertainment

6.9

Overall

7.1

Food

6.4

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
11,668 reviews
American Airlines
7.1
Good
11,668 reviews

Boarding

7.5

Comfort

7.2

Crew

7.9

Entertainment

6.9

Overall

7.1

Food

6.4

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 $664, American Airlines can have you in Anguilla from Chicago in 10h 19m. 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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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 May 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$529Average$768FlexibilityNo cancel feeOn-time71%

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