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Chicago, IL, USA to ANGUILLA from $172: 3 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
ANGUILLA, Anguilla

How to Get from Chicago to ANGUILLA: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$172 - PlaneBest price
3533 kmDistance
9h 35m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to ANGUILLA with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Plane
Average Duration
9h  35m
Estimated price
$242-805
Recommended
Company
various
Plane
Average Duration
10h  40m
Estimated price
$172-755
Cheapest
route map
Distance: 3533 km
Duration: 9h 35m

See more options

Company
Amtrak, various
Train
Plane
Average Duration
11h  36m
Estimated price
$286-990
Browse car rentalsExplore flights

Traveling From Chicago to Anguilla

Your journey from Chicago, an urban hub filled with bustling city life, to Anguilla, a tranquil island paradise with pristine beaches and crystal-clear waters, offers a striking contrast in experiences.

Best Neighbourhoods in Anguilla

Anguilla offers a variety of charming neighborhoods, each with distinct characteristics.

The Valley
• The capital and cultural hub of Anguilla.
• Home to local shops and authentic dining experiences.
Shoal Bay
• Famous for its stunning white sandy beach.
• Great for water sports and beachfront dining.
Meads Bay
• Known for luxury resorts and vibrant beach bars.
• Ideal for relaxation and picturesque sunsets.

Best Times To Visit Anguilla's Attractions

Timing your visit can elevate your experience at Anguilla's top attractions.

Shoal Bay Beach
Visit early in the morning for peaceful beach moments and stunning sunrises.
The Valley
Weekdays are quieter, allowing you to explore local shops without the crowds.
Meads Bay
Evenings offer breathtaking sunsets and fewer visitors, perfect for a romantic dinner.

Anguilla Weather: What to Expect Year-Round

Anguilla enjoys a warm tropical climate, with temperatures typically ranging between 75°F and 85°F throughout the year. The dry season from December to April ranks as the best time for outdoor activities and beach lounging, while the occasional rain in the summer can provide a refreshing break from the sun.

Dining in Anguilla: A Culinary Escape

Try the grilled lobster at Geraud’s in Anguilla, where the freshness of locally caught seafood meets tropical flavors, offering a stark contrast to the urban dining scene in Chicago. The beachfront setting, combined with an emphasis on fresh ingredients and laid-back island atmosphere, creates a dining experience that feels more like a celebration of the sea.

Chicago - ANGUILLA operators

Explore transport companies operating between Chicago and ANGUILLA, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane Show flights
Website
aa.com

Plane from Chicago O'Hare to Anguilla

Average Duration
7h 2m
Estimated price
$242350-2421

Plane from Milwaukee to Anguilla

Average Duration
7h 27m
Estimated price
$242380-2425

Plane from Chicago Midway to Anguilla

Average Duration
8h 29m
Estimated price
$242350-2421
Website
united.com

Plane from Chicago O'Hare to Anguilla

Average Duration
8h 41m
Estimated price
$242360-2421

Plane from Chicago O'Hare to Anguilla

Average Duration
14h 30m
Estimated price
$242380-2421
Website
worldticket.com

Plane from Chicago O'Hare to Anguilla

Average Duration
6h 49m
Estimated price
$242370-2421

Plane from Chicago Midway to Anguilla

Average Duration
8h 10m
Estimated price
$170-24220
Website
capeair.com

Plane from Chicago O'Hare to Anguilla

Average Duration
8h 15m
Estimated price
$2420-800
Website
airsunshine.com

Plane from Chicago O'Hare to Anguilla

Average Duration
9h 2m
Estimated price
$242380-2421
Train
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Chicago Union Station to Milwaukee

Average Duration
1h 29m
Estimated price
$2426-2422

Chicago to ANGUILLA: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and ANGUILLA offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🛫 Flying from Chicago to Anguilla requires a connecting flight with a total travel time of approximately 7 hours. 💸 Depending on the airline and time of booking, the price for a flight between Chicago and Anguilla can range from $242 to $805.
Departure Point
Chicago O'Hare Airport
Arrival Point
Anguilla Airport. The quickest flight takes 7h and has one stopover
Useful tips for plane travellers
• Since there are no direct flights from Chicago to Anguilla, consider booking your stopover with World Ticket, Silver Airways, or Air Sunshine, and check their flight schedules at World Ticket, Silver Airways, and Air Sunshine to minimize your layover time.
• Upon arrival at Anguilla Airport, expect a smooth immigration process, but be ready for possible weather surveillance checks; it’s advisable to have all your documentation handy, and customs can be expedited with mobile customs forms if needed. More information about airport navigation can be found here.
• Taxi fares from Anguilla Airport to the city center generally range around $20-$25; it’s best to confirm the fare with the driver before starting your journey to avoid surprises. For more details on local transportation options, check Anguilla Transportation.

Frequently asked questions

Find out more about the route from Chicago to ANGUILLA.

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The distance between Chicago and Anguilla is approximately 2195 miles. The typical travel time by plane from Chicago to Anguilla is 9 hours and 23 minutes. However, there are no direct flights between the two locations, so travelers will need to make a connecting flight. Travel times by other modes of transportation, such as driving or taking a ferry, will vary significantly and may not be practical options for reaching Anguilla from Chicago.
The most cost-effective and time-efficient transportation option for traveling from Chicago to Anguilla is to fly. Flying usually takes around 9 hours and 23 minutes and costs between $430 and $950. Another quick option is also flying, which takes around 9 hours and 1 minute and costs between $390 and $1200. These options are recommended as they provide the most efficient way to reach Anguilla from Chicago. Other modes of transportation would involve much longer travel times and may not be as convenient.
The flight duration between Chicago and Anguilla typically takes around 7 hours and 53 minutes with one stopover. However, please note that there are no direct flights available from Chicago O'Hare Airport to Anguilla Airport. Prices for flights between the two destinations typically range from $432 to $905. It is advisable to check with airlines for the most accurate and up-to-date information regarding flight schedules and prices.
There are over 760 hotels available in Anguilla, offering a range of options for accommodations. Prices start at $75 per night, providing a variety of choices to suit different budgets. Whether you prefer luxury resorts, cozy guesthouses, or beachfront villas, there is a place to stay near Anguilla that will meet your needs. Booking in advance is recommended, especially during peak travel seasons.

Trips from Chicago