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 30m$132–605Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
9h 34m$222–955
Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Anguilla is to fly which costs $130 - $650 and takes 9h 30m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 30m and costs $130 - $650.
The distance between Chicago and Anguilla is 3566 km.
It takes approximately 9h 30m to get from Chicago to Anguilla, including transfers.
Anguilla is 1h ahead of Chicago. It is currently 10:54 PM in Chicago and 11:54 PM in Anguilla.
There are 1189+ hotels available in Anguilla.
What companies run services between Chicago, IL, USA and Anguilla?
American Airlines, United Airlines, and five other airlines fly from Chicago O'Hare International Airport (ORD) to Clayton J. Lloyd International Airport (AXA) 4 times a day.
- Website
- anguillaairservices.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 7h 2m
- When
- Saturday
- Estimated price
- $130–600
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 30m
- When
- Saturday
- Estimated price
- $220–950
- Website
- worldticket.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 7h 2m
- When
- Saturday
- Estimated price
- $130–600
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 30m
- When
- Saturday
- Estimated price
- $220–950
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 8h 1m
- When
- Every day
- Estimated price
- $150–650
- Website
- timbisair.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Baltimore
- Ave. Duration
- 7h 5m
- When
- Monday
- Estimated price
- $400–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Baltimore
- Ave. Duration
- 7h
- When
- Monday
- Estimated price
- $600–1,700
- Website
- united.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 8h 55m
- When
- Saturday and Sunday
- Estimated price
- $140–600
- Website
- flytradewind.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 6h 45m
- When
- Every day
- Estimated price
- $140–600
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 Need to know: Jadrolinija, South Korea: Travelling from Seoul to Busan , and The beginner’s guide to the 2018 World Nomad Games - to help you get the most out of your next trip.