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)ORD - AXA
9h 13m$182–755Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)MDW - AXA
10h 31m$222–955
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 13m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 13m and costs $180 - $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 2:35 PM in Chicago and 4:35 PM in Anguilla.
There are 1123+ 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) 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 22m
- When
- Every day
- Estimated price
- $190–800
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 11h 55m
- When
- Monday, Wednesday, and Saturday
- Estimated price
- $230–1,000
- 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 and Sunday
- Estimated price
- $180–750
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 20m
- When
- Monday, Tuesday, and Friday
- Estimated price
- $230–950
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 9h 10m
- When
- Every day
- Estimated price
- $230–950
- Website
- timbisair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Newark
- Ave. Duration
- 7h 50m
- When
- Thursday and Sunday
- Estimated price
- $490–1,400
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Baltimore
- Ave. Duration
- 8h
- When
- Monday and Friday
- Estimated price
- $550–1,600
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Boston
- Ave. Duration
- 8h 30m
- When
- Saturday
- Estimated price
- $600–1,700
- Website
- flytradewind.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 7h 13m
- When
- Every day
- Estimated price
- $180–800
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 8h 3m
- When
- Saturday
- Estimated price
- $220–950
- Website
- intercaribbean.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 6h 55m
- When
- Monday
- Estimated price
- $290–1,000
- Website
- capeair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 32m
- When
- Every day
- Estimated price
- $180–750
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 How to get from JFK to New York City, Travelling to the UK: What do I need to know?, and 4 of the smartest ways to explore Australia - to help you get the most out of your next trip.