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
8h 54m$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
11h 53m$353–1,460Fly from Chicago Midway International Airport
- Fly from Chicago Midway International Airport (MDW) to Clayton J. Lloyd International Airport (AXA)plane MDW - AXA
10h 41m$252–1,105
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 8h 54m.
The fastest way to get from Chicago to Anguilla is to fly which takes 8h 54m and costs $150 - $750.
The distance between Chicago and Anguilla is 3566 km.
It takes approximately 8h 54m to get from Chicago to Anguilla, including transfers.
Anguilla is 1h ahead of Chicago. It is currently 1:01 AM in Chicago and 2:01 AM in Anguilla.
There are 1132+ hotels available in Anguilla.
What companies run services between Chicago, IL, USA and Anguilla?
United Airlines, Cape Air, 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 30m
- When
- Every day
- Estimated price
- $160–700
Flights from General Mitchell International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 7h 51m
- When
- Every day
- Estimated price
- $330–1,400
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Miami
- Ave. Duration
- 12h 13m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $260–1,100
- Website
- anguillaairservices.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 6h 45m
- When
- Saturday and Sunday
- Estimated price
- $150–700
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 30m
- When
- Monday to Friday
- Estimated price
- $250–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 8h 40m
- When
- Every day
- Estimated price
- $250–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Fort Lauderdale, St Maarten
- Ave. Duration
- 8h 10m
- When
- Sunday
- Estimated price
- $400–1,400
- Website
- worldticket.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via St Maarten
- Ave. Duration
- 6h 45m
- When
- Saturday and Sunday
- Estimated price
- $150–700
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Orlando, St Maarten
- Ave. Duration
- 8h 30m
- When
- Monday to Friday
- Estimated price
- $250–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Atlanta, St Maarten
- Ave. Duration
- 8h 40m
- When
- Every day
- Estimated price
- $250–1,100
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via Fort Lauderdale, St Maarten
- Ave. Duration
- 8h 10m
- When
- Sunday
- Estimated price
- $400–1,400
- 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 Saturday
- Estimated price
- $150–700
Flights from Chicago Midway International Airport to Clayton J. Lloyd International Airport via San Juan
- Ave. Duration
- 9h 24m
- When
- Saturday and Sunday
- Estimated price
- $250–1,100
- Website
- united.com
Flights from Chicago O'Hare International Airport to Clayton J. Lloyd International Airport via Charlotte Amalie
- Ave. Duration
- 7h 15m
- When
- Every day
- 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
- $20–50
- Website
- https://www.amtrak.com/home.html
Want to know more about travelling around Anguilla
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