There is 1 way to get from Chicago to Anguilla by plane
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Anguilla is to fly which costs $130 - $600 and takes 9h 30m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 30m and costs $130 - $600.
The distance between Chicago and Anguilla is 3566 km.
It takes approximately 9h 30m to get from Chicago to Anguilla, including transfers.
Anguilla is 2h ahead of Chicago. It is currently 8:04 PM in Chicago and 10:04 PM in Anguilla.
There are 1188+ hotels available in Anguilla.
What companies run services between Chicago, IL, USA and Anguilla?
United Airlines, Cape Air, and three other airlines fly from Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) 3 times a day.
- Website
- united.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 39m
- When
- Saturday and Sunday
- Estimated price
- $130–550
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 58m
- When
- Every day
- Estimated price
- $140–600
- Website
- timbisair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Baltimore
- Ave. Duration
- 7h 5m
- When
- Monday
- Estimated price
- $390–950
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Newark
- Ave. Duration
- 7h 40m
- When
- Monday and Friday
- Estimated price
- $400–950
- Website
- anguillaairservices.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 6h 45m
- When
- Saturday
- Estimated price
- $130–550
- Website
- capeair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 24m
- When
- Saturday
- Estimated price
- $130–550
Want to know more about travelling around the world?
Rome2Rio's Travel Guide series provide vital information for the global traveller. Read our range of informative guides on popular transport routes and companies - including How to get from London to Edinburgh, The London Underground: Essential tips to navigate the Tube, and Getting to Rome from the airport - to help you get the most out of your next trip.