HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Anguilla

$425+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Sep 13 — Sep 201
Sun 9/13
Sun 9/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Anguilla with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 14, 2026.

This American Airlines deal was found by Cheapflights users on 8/13. 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 12/87:50 pm -
1 stop17h 07m
Tue 12/153:37 pm -
1 stop11h 07m
Deal found 8/13$712
This American Airlines deal was found by Cheapflights users on 8/11. 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 11/16:05 pm -
1 stop21h 00m
Wed 11/45:45 pm -
1 stop17h 45m
Deal found 8/11$728
This American Airlines deal was found by Cheapflights users on 8/12. 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 12/107:50 pm -
1 stop17h 07m
Tue 12/153:37 pm -
1 stop18h 23m
Deal found 8/12$747
This American Airlines deal was found by Cheapflights users on 8/12. 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 12/16:59 am -
1 stop8h 22m
Sun 12/65:45 pm -
2 stops15h 42m
Deal found 8/12$757
This American Airlines deal was found by Cheapflights users on 8/14. 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 12/35:00 am -
1 stop10h 05m
Mon 12/75:45 pm -
1 stop8h 59m
Deal found 8/14$782

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 August 14, 2026.

Round-trip from

$712
(American Airlines)

One-way from

$425
(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 August 14, 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 Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 12/8

7:50 pm-2:57 pm

1 stop17h 07m

The Valley Wallblake Intl

Tue 12/15

3:37 pm-12:44 am

1 stop11h 07m

$712
Quickest round-trip

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Tue 2/2

6:59 am-4:26 pm

1 stop7h 27m

The Valley Wallblake Intl

Mon 2/8

3:03 pm-11:33 pm

1 stop10h 30m

$747

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Wed 2/3

8:58 pm-2:23 pm

2 stops15h 25m

The Valley Wallblake Intl

Wed 2/10

5:06 pm-7:27 am

2 stops16h 21m

$757

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 12/3

9:06 pm-2:57 pm

2 stops15h 51m

The Valley Wallblake Intl

Mon 12/7

5:45 pm-7:27 am

2 stops15h 42m

$787
Cheapest one-way

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 12/10

5:00 am-5:05 pm

1 stop10h 05m

$425
Quickest one-way

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 2/4

5:05 am-2:23 pm

1 stop7h 18m

$425

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 12/10

8:19 pm-2:25 pm

3 stops40h 06m

$528

ChicagoThe Valley

ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl

ORDAXA

Chicago O'Hare Intl

Thu 2/4

11:45 am-3:25 pm

3 stops25h 40m

$655

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

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 August 14, 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
11,927 reviews

Boarding

7.5

Food

6.4

Crew

7.9

Overall

7.1

Comfort

7.2

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,927 reviews
American Airlines
7.1
Good
11,927 reviews

Boarding

7.5

Food

6.4

Crew

7.9

Overall

7.1

Comfort

7.2

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 $712, American Airlines can have you in Anguilla from Chicago in 17h 07m. 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 August 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$529Average$764FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.