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$152–705Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
9h 10m$232–1,105
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 $150 - $750 and takes 9h 18m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 10m and costs $230 - $1,100.
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 7:00 AM in Chicago and 8:00 AM in Anguilla.
There are 1140+ hotels available in Anguilla.
What companies run services between Chicago, IL, USA and Anguilla?
United Airlines, Cape Air, and four other airlines fly from Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) 5 times a day.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 59m
- When
- Every day
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 37m
- When
- Every day
- Estimated price
- $240–1,100
- 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
- $150–700
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
- $240–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h 5m
- When
- Every day
- Estimated price
- $240–1,100
- 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
- $150–700
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
- $240–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 9h 5m
- When
- Every day
- Estimated price
- $240–1,100
- Website
- united.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 27m
- When
- Every day
- Estimated price
- $160–700
- Website
- flytradewind.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 7h 24m
- When
- Every day
- Estimated price
- $250–850
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 6h 39m
- When
- Saturday
- Estimated price
- $230–1,100
- 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
- $160–700
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