There are 3 ways to get from Chicago to Anguilla by plane or train
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$152–705Train to General Mitchell International Airport, fly
- Take the train from Chicago Union Station to Milwaukeetrain
- Fly from General Mitchell International Airport (MKE) to Clayton J. Lloyd International Airport (AXA)plane MKE - AXA
12h 23m$324–1,416Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
9h 26m$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 $150 - $750 and takes 9h 13m.
The fastest way to get from Chicago to Anguilla is to fly which takes 9h 13m and costs $150 - $750.
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 11:42 AM in Chicago and 1:42 PM in Anguilla.
There are 1124+ 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
- 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
- $160–700
Flights from General Mitchell International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 8h 25m
- When
- Every day
- Estimated price
- $310–1,300
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 8h 11m
- When
- Thursday and Sunday
- 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
- $150–700
Flights from General Mitchell International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 20m
- When
- Monday to Saturday
- Estimated price
- $300–1,300
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 15m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $230–1,000
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 9h 10m
- When
- Saturday
- Estimated price
- $220–1,000
- 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
- Estimated price
- $150–700
Flights from General Mitchell International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 20m
- When
- Monday to Saturday
- Estimated price
- $300–1,300
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 15m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $230–1,000
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 9h 10m
- When
- Saturday
- Estimated price
- $220–1,000
- 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
- $430–1,300
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Baltimore
- Ave. Duration
- 6h 55m
- When
- Monday and Friday
- Estimated price
- $550–1,800
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Boston
- Ave. Duration
- 7h 55m
- When
- Saturday
- Estimated price
- $600–1,900
- Website
- flytradewind.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 6h 52m
- When
- Monday to Friday
- Estimated price
- $160–700
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 8h 2m
- When
- Saturday
- Estimated price
- $220–950
- 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, Saturday, and Sunday
- Estimated price
- $150–700
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–40
- Website
- https://www.amtrak.com/home.html
Want to know more about travelling around Anguilla
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide




