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Anguilla

$282+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Mon 12/2912:30 pmAXA - ORD
2 stops29h 12mMultiple Airlines
Deal found 12/16$770
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/208:35 pmORD - AXA
1 stop15h 38mAmerican Airlines
Thu 12/252:53 pmAXA - ORD
1 stop11h 00mAmerican Airlines
Deal found 12/15$824
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Wed 12/3112:30 pmAXA - ORD
2 stops28h 32mMultiple Airlines
Deal found 12/16$826
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Sat 12/2712:30 pmAXA - ORD
2 stops14h 00mMultiple Airlines
Deal found 12/16$860
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/245:00 amORD - AXA
1 stop7h 13mAmerican Airlines
Mon 12/295:30 pmAXA - ORD
1 stop9h 13mAmerican Airlines
Deal found 12/17$943
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:00 amORD - AXA
2 stops10h 10mMultiple Airlines
Mon 12/2912:30 pmAXA - ORD
1 stop12h 55mMultiple Airlines
Deal found 12/16$967
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:26 pmORD - AXA
2 stops23h 44mMultiple Airlines
Mon 12/293:30 pmAXA - ORD
1 stop9h 55mMultiple Airlines
Deal found 12/16$979
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Sun 12/2810:30 amAXA - ORD
2 stops14h 55mMultiple Airlines
Deal found 12/16$993
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Thu 1/112:30 pmAXA - ORD
2 stops11h 54mMultiple Airlines
Deal found 12/16$1,013

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 December 18, 2025.

Round-trip from

$529
(American Airlines)

One-way from

$282
(Kiwi.com)
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 December 18, 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

Sat 2/21

7:13 pm-2:19 pm

1 stop17h 06m

The Valley Wallblake Intl

Thu 2/26

5:24 pm-9:02 am

1 stop17h 38m

$529

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 3/6

5:45 am-4:44 pm

1 stop8h 59m

The Valley Wallblake Intl

Mon 3/16

4:18 pm-9:05 am

1 stop17h 47m

$545

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 3/7

7:13 pm-3:38 pm

1 stop18h 25m

The Valley Wallblake Intl

Sat 3/14

4:35 pm-9:05 am

1 stop17h 30m

$567

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 2/18

7:00 am-4:44 pm

1 stop7h 44m

The Valley Wallblake Intl

Sun 2/22

5:24 pm-9:02 am

1 stop17h 38m

$584

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 3/12

6:00 am-3:38 pm

1 stop8h 38m

The Valley Wallblake Intl

Thu 3/19

4:18 pm-12:35 am

1 stop9h 17m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 2/17

5:00 am-2:19 pm

1 stop7h 19m

The Valley Wallblake Intl

Sat 2/21

5:24 pm-12:33 am

1 stop9h 09m

$689

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 1/17

5:32 pm-1:30 pm

2 stops41h 58m

$282

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 1/27

5:00 am-2:23 pm

1 stop7h 23m

$335

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 1/17

7:30 pm-2:23 pm

1 stop16h 53m

$360

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 1/16

7:30 pm-12:34 pm

1 stop15h 04m

$385

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 11 results
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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 December 18, 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
11,055 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,055 reviews
American Airlines
7.2
Good
11,055 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 $529, American Airlines can have you in Anguilla from Chicago in 17h 06m. 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

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$597Average$754FlexibilityNo cancel feeOn-time71%

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