There are 2 ways 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.
Fly from Chicago O'Hare International Airport
best- Fly from Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA)plane ORD - AXA
9h 16m$172–755Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
10h 39m$222–905
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 $170 - $800 and takes 9h 16m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 16m and costs $170 - $800.
The distance between Chicago and Anguilla is 3566 km.
It takes approximately 9h 16m to get from Chicago to Anguilla, including transfers.
Anguilla is 1h ahead of Chicago. It is currently 12:02 AM in Chicago and 1:02 AM in Anguilla.
There are 1171+ hotels available in Anguilla.
What companies run services between Chicago, IL, USA and Anguilla?
American Airlines, United Airlines, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) 5 times a week.
- Website
- worldticket.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 6h 30m
- When
- Saturday
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 8h 5m
- When
- Monday, Wednesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $220–900
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h
- When
- Sunday
- Estimated price
- $230–950
- Website
- anguillaairservices.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 6h 30m
- When
- Saturday
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 8h 5m
- When
- Monday, Wednesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $220–900
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h
- When
- Sunday
- Estimated price
- $230–950
- Website
- united.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 36m
- When
- Saturday
- Estimated price
- $170–750
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 30m
- When
- Saturday
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via San Juan, Charlotte Amalie
- Ave. Duration
- 8h 40m
- When
- Saturday
- Estimated price
- $220–900
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 32m
- When
- Wednesday and Saturday
- Estimated price
- $190–800
- Website
- capeair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 30m
- When
- Saturday
- Estimated price
- $170–750
- Website
- flexflight.dk
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via San Juan, Gustavia
- Ave. Duration
- 8h 20m
- When
- Saturday
- Estimated price
- $220–900
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 Italian Lakes: Getting around by train, Flying into Beijing?, and Travelling by boat in Italy - to help you get the most out of your next trip.
