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 18m$182–805Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
10h 6m$282–1,305
Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) flights
Questions & Answers
The cheapest way to get from Chicago to Anguilla is to fly which costs $180 - $850 and takes 9h 18m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 18m and costs $180 - $850.
The distance between Chicago and Anguilla is 3566 km.
It takes approximately 9h 18m to get from Chicago to Anguilla, including transfers.
Anguilla is 1h ahead of Chicago. It is currently 8:26 AM in Chicago and 9:26 AM in Anguilla.
There are 1175+ 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) 3 times a day.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 56m
- When
- Every day
- Estimated price
- $190–850
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 35m
- When
- Every day
- Estimated price
- $290–1,300
- 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
- $180–800
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h 35m
- When
- Every day
- Estimated price
- $280–1,300
- 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
- $180–800
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h 35m
- When
- Every day
- Estimated price
- $280–1,300
- Website
- united.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 46m
- When
- Saturday
- Estimated price
- $180–800
- Website
- capeair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 40m
- When
- Saturday
- Estimated price
- $180–800
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