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 13m$172–755Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
9h 26m$232–1,005
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 $170 - $800 and takes 9h 13m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 13m and costs $170 - $800.
The distance between Chicago and Anguilla is 3566 km.
It takes approximately 9h 13m to get from Chicago to Anguilla, including transfers.
Anguilla is 2h ahead of Chicago. It is currently 12:40 AM in Chicago and 2:40 AM in Anguilla.
There are 1106+ hotels available in Anguilla.
What companies run services between Chicago, IL, USA and Anguilla?
American Airlines, United Airlines, and six other airlines fly from Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) 4 times a day.
- Website
- worldticket.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 6h 25m
- When
- Saturday
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 30m
- When
- Monday and Saturday
- Estimated price
- $240–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 9h 10m
- When
- Saturday
- Estimated price
- $230–1,000
- Website
- anguillaairservices.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 6h 25m
- When
- Saturday
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 30m
- When
- Monday and Saturday
- Estimated price
- $240–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 9h 10m
- When
- Saturday
- Estimated price
- $230–1,000
- Website
- timbisair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Baltimore
- Ave. Duration
- 7h 30m
- When
- Friday
- Estimated price
- $450–1,400
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Newark
- Ave. Duration
- 7h 45m
- When
- Thursday and Sunday
- Estimated price
- $460–1,400
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Baltimore
- Ave. Duration
- 6h 55m
- When
- Monday and Friday
- Estimated price
- $600–1,900
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 24m
- When
- Every day
- Estimated price
- $180–800
- Website
- flytradewind.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 6h 49m
- When
- Monday to Friday
- Estimated price
- $170–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 7h 59m
- When
- Saturday
- Estimated price
- $230–1,000
- Website
- capeair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 6h 55m
- When
- Tuesday, Thursday, Saturday, and Sunday
- Estimated price
- $170–750
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