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Chicago, IL, USA to San Juan from $114: 5 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
San Juan, Puerto Rico

How to Get from Chicago to San Juan: 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.

$114 - Fly and DriveBest price
3325 kmDistance
7h 35m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to San Juan 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
Southwest Airlines
Plane
Average Duration
7h  35m
Estimated price
$484-1167
Recommended
Company
various
Drive
Average Duration
11h  1m
Estimated price
$114-414
Cheapest
route map
Distance: 3325 km
Duration: 7h 35m

See more options

Company
various
Drive
Average Duration
10h  31m
Estimated price
$124-414
Company
various
Drive
Average Duration
11h 
Estimated price
$200-680
Company
various
Plane
Average Duration
8h 
Estimated price
$494-1267
Browse car rentalsExplore flights

Traveling From Chicago to San Juan

The journey from the vibrant urban landscape of Chicago to the sunny beaches and rich culture of San Juan offers a striking contrast between city life and island relaxation.

Best Neighbourhoods in San Juan

San Juan features vibrant neighborhoods, each brimming with charm and activity.

Old San Juan
• Colorful colonial architecture and historic landmarks.
• Lively plazas filled with shops and restaurants.
Condado
• Trendy beachfront area with luxury hotels.
• Vibrant nightlife and chic dining options.
Santurce
• Art district known for murals and galleries.
• Local eateries serving authentic Puerto Rican cuisine.

Best Times To Visit San Juan's Attractions

Timing your visits to San Juan's attractions can elevate your experience.

El Morro
Early mornings or late afternoons offer cooler temperatures and fewer tourists.
San Juan Cathedral
Weekdays in the morning allow for peaceful exploration and fewer crowds.
La Perla beach
Visit during weekdays to enjoy a quieter beach atmosphere.

San Juan Weather: What to Expect Year-Round

San Juan boasts a tropical climate with warm temperatures all year, making it a desirable destination for sun-seekers. The best times to visit are during the cooler months from December to April, as pleasant weather enhances outdoor activities and sightseeing.

Dining in San Juan: A Culinary Adventure

Savor the vibrant flavors of mofongo at La Mallorquina, where this traditional Puerto Rican dish made from fried green plantains comes to life with garlic, chicharrón, and seafood. The open-air setting and the lively ambiance create a distinct dining experience that sets it apart from the more urban, bustling eateries in Chicago.

Chicago - San Juan operators

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

Plane Show flights
Website
southwest.com

Plane from Chicago Midway to San Juan

Average Duration
4h 30m
Estimated price
$4841-4847

Plane from Chicago Midway to San Juan via Orlando

Average Duration
6h 18m
Estimated price
$4848-4843

Plane from Chicago Midway to San Juan via Fort Lauderdale-Hollywood International

Average Duration
8h 45m
Estimated price
$4849-4843

Plane from Chicago O'Hare to San Juan via Orlando

Average Duration
7h 32m
Estimated price
$4848-4843
Website
flyfrontier.com

Plane from Chicago O'Hare to Ponce via Orlando

Average Duration
9h 56m
Estimated price
$11670-11671

Plane from Chicago O'Hare to Ponce via Atlanta, Orlando

Average Duration
8h 24m
Estimated price
$11670-11671

Plane from Chicago Midway to Ponce via Orlando

Average Duration
8h 21m
Estimated price
$4840-11671
Website
jetblue.com

Plane from Chicago O'Hare to Ponce via Orlando

Average Duration
6h 53m
Estimated price
$11672-11673

Plane from Chicago O'Hare to Ponce via New York JFK

Average Duration
10h 43m
Estimated price
$11674-4847

Plane from Chicago Midway to Ponce via Orlando

Average Duration
6h 43m
Estimated price
$11672-11673

Plane from Chicago O'Hare to Mayaguez via San Juan

Average Duration
8h 16m
Estimated price
$484530-11675

Plane from Chicago O'Hare to Mayaguez via Charlotte Amalie, San Juan

Average Duration
9h 30m
Estimated price
$484540-11676
Website
spirit.com

Plane from Chicago O'Hare to San Juan

Average Duration
4h 39m
Estimated price
$484540-11677

Plane from Chicago O'Hare to San Juan via Orlando

Average Duration
7h 10m
Estimated price
$484560-11677
Website
united.com

Plane from Chicago O'Hare to San Juan

Average Duration
4h 40m
Estimated price
$11678-4847

Plane from Chicago O'Hare to Mayaguez via San Juan

Average Duration
6h 38m
Estimated price
$484550-11679
Website
capeair.com

Plane from Chicago O'Hare to Mayaguez via San Juan

Average Duration
8h 16m
Estimated price
$484530-11675

Plane from Chicago O'Hare to Mayaguez via Charlotte Amalie, San Juan

Average Duration
9h 30m
Estimated price
$484540-11676
Website
aa.com

Plane from Chicago O'Hare to San Juan

Average Duration
4h 39m
Estimated price
$11674-4847

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

Traveling between Chicago and San Juan 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 Midway Airport to San Juan Airport is convenient with a direct flight that takes only 4 hours and 30 minutes with Southwest Airlines. ✈️ The journey from Chicago to San Juan by plane typically lasts around 7 hours and 35 minutes, offering passengers a comfortable and efficient travel experience. 💸 Travelers can find flight prices between San Juan and Chicago ranging from $484 to $1167, providing options to suit different budgets and preferences.
Departure Point
Chicago Midway Airport
Arrival Point
San Juan Airport
Useful tips for plane travellers
• Book your flight early with Southwest Airlines for the best fares; they often have promotions, and being flexible with your travel dates can save you significantly on the $484 to $1167 price range.
• Upon arriving at Luis Muñoz Marín International Airport (SJU) in San Juan, expect a bustling environment; the customs area can get crowded, so having all your documents ready will expedite your passage through immigration.
• For a taxi from SJU to downtown San Juan, expect to pay between $20 to $30; familiarize yourself with the official taxi stand located right outside the terminal to avoid any scams or high fares.

Frequently asked questions

Find out more about the route from Chicago to San Juan.

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The distance between Chicago and San Juan is approximately 2066 miles. The typical travel time by flying directly from Chicago to San Juan is 7 hours and 53 minutes. Another option is to fly from Chicago O'Hare to Aguadilla and then drive to San Juan, which takes about 10 hours and 59 minutes.
The most cost-effective and time-efficient transportation option for traveling from Chicago to San Juan is to fly. Flying is the quickest way to reach San Juan, taking approximately 7 hours and 39 minutes. The cost of a flight can range from $180 to $430, depending on the airline and time of booking. However, for those looking to save money, flying and driving is a cheaper option, costing between $110 and $350 and taking approximately 10 hours and 59 minutes.
The flight from Chicago O'Hare Airport to San Juan Airport typically takes around 4 hours and 32 minutes. The duration may vary depending on the specific flight and any layovers. The cost of a flight between San Juan and Chicago can range from $150 to $1667, depending on factors such as the airline, the time of booking, and any ongoing promotions or discounts. It is advisable to compare prices from different airlines and book in advance to secure the best deals.
There are over 567 hotels available in San Juan providing a range of accommodation options for visitors. Prices for these hotels start at $111 per night, making it possible to find a suitable option for various budgets. From luxury resorts to budget-friendly guesthouses, travelers can find a range of options to stay near San Juan and enjoy their time in Puerto Rico.

Trips from Chicago

Trips to San Juan