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$182–755Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
9h 53m$262–1,005
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 - $800 and takes 9h 16m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 16m and costs $180 - $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 10:10 AM in Chicago and 11:10 AM in Anguilla.
There are 1172+ 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
- $200–800
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 19m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $270–1,100
- 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
- $180–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 8h 10m
- When
- Every day
- Estimated price
- $260–1,000
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h
- When
- Monday to Friday
- Estimated price
- $260–1,100
- 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
- $180–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 8h 10m
- When
- Every day
- Estimated price
- $260–1,000
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h
- When
- Monday to Friday
- Estimated price
- $260–1,100
- 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
- $180–750
- 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
- $180–750
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