There are 2 ways to get from Anguilla to Chicago 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 to Chicago O'Hare International Airport
best- Fly from Clayton J. Lloyd International Airport (AXA) to Chicago O'Hare International Airport (ORD)plane AXA - ORD
8h 2m$139–594Fly to General Mitchell International Airport, train
- Fly from Clayton J. Lloyd International Airport (AXA) to General Mitchell International Airport (MKE)plane AXA - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
11h 48m$446–1,842
Clayton J. Lloyd International Airport (AXA) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Anguilla to Chicago is to fly which costs $130 - $600 and takes 8h 2m.
The fastest way to get from Anguilla to Chicago is to fly which takes 8h 2m and costs $130 - $600.
The distance between Anguilla and Chicago is 2229 miles.
It takes approximately 8h 2m to get from Anguilla to Chicago, including transfers.
Chicago is 1h behind Anguilla. It is currently 1:29 PM in Anguilla and 12:29 PM in Chicago.
There are 1197+ hotels available in Chicago.
What companies run services between Anguilla and Chicago, IL, USA?
American Airlines, Cape Air, and four other airlines fly from Clayton J. Lloyd International Airport (AXA) to Chicago O'Hare International Airport (ORD) 4 times a day.
- Website
- aa.com
Flights from Clayton J. Lloyd International Airport to Chicago O'Hare International Airport via Miami
- Ave. Duration
- 8h 19m
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $140–650
Flights from Clayton J. Lloyd International Airport to Chicago O'Hare International Airport via St Maarten
- Ave. Duration
- 7h 19m
- When
- Saturday
- Estimated price
- $130–600
Flights from Clayton J. Lloyd International Airport to Chicago O'Hare International Airport via San Juan
- Ave. Duration
- 7h 54m
- When
- Monday, Wednesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $140–600
Flights from Clayton J. Lloyd International Airport to General Mitchell International Airport via Miami
- Ave. Duration
- 8h 43m
- When
- Monday
- Estimated price
- $420–1,800
- Website
- united.com
Flights from Clayton J. Lloyd International Airport to Chicago O'Hare International Airport via Charlotte Amalie
- Ave. Duration
- 10h 44m
- When
- Every day
- Estimated price
- $130–600
Flights from Clayton J. Lloyd International Airport to Chicago O'Hare International Airport via St Maarten
- Ave. Duration
- 7h 15m
- When
- Saturday
- Estimated price
- $130–600
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $23–50
- Website
- https://www.amtrak.com/home.html
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