
$75 Cheap flight deals from Chicago (CHI) to Aguadilla (SJU)
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This Weekend's Flight Deals from Chicago to Aguadilla
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $75 One Way, $144 Round Trip from Chicago to Aguadilla
Prices starting at $144 for return flights and $75 for one-way flights to Aguadilla were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Aguadilla economy flight packages

ESJ Beach Hotel
Jan 5 - Jan 12
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Jul 14, 2025


Aire de O:live
Jan 5 - Jan 12
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Apr 9, 2025
Aguadilla packages with premium economy flights

Hyatt Regency Grand Reserve Puerto Rico
Jan 5 - Jan 10
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Nov 11, 2025

OLV Fifty Five - Adults Only
Jan 5 - Jan 10
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Aug 7, 2023

Aire de O:live
Jan 5 - Jan 10
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Apr 9, 2025
Aguadilla business class flight packages

Aloft Ponce Hotel & Casino
Jan 9 - Jan 16
Chicago (ORD) to San Juan (SJU)
Reviewed on Oct 18, 2025

Courtyard by Marriott Aguadilla
Jan 9 - Jan 16
Chicago (ORD) to San Juan (SJU)
Reviewed on Apr 16, 2023

Aloft San Juan
Jan 9 - Jan 16
Chicago (ORD) to San Juan (SJU)
Reviewed on Oct 20, 2025
Aguadilla first class flight packages

The Tryst Beachfront Hotel
Jan 17 - Jan 19
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on May 13, 2025

OLV Fifty Five - Adults Only
Jan 17 - Jan 19
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Aug 7, 2023

Aire de O:live
Jan 17 - Jan 19
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Apr 9, 2025
More About Flying To Aguadilla from Chicago
Route Information for Flights from Chicago to Aguadilla
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SJU |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
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Flying from Chicago to Aguadilla
Airports in Chicago
The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.
Chicago Airport Parking
Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.
Chicago Airport Transportation
There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.
Chicago Airport Restaurants
Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.
Airports in Aguadilla
If you are looking to book cheap flights to Aguadilla, Puerto Rico, check Orbitz.com to find great deals on your air ticket. Orbitz.com will search many airlines to find tickets that fit your budget. Rafael Hernández Airport provides Aguadilla with international and domestic service. The airport is located about six miles from downtown Aguadilla and is accessible from both PR-107 and PR-110. JetBlue, Spirit and United Airlines provide flights to the United States.
Transportation from the Airport
Taxi service is available to transport you to and from the airport. Check with your hotel to see if they offer a shuttle service. There are also rental car companies located in the passenger terminal if you would prefer to rent a car. Among these are Hertz, Avis, Budget and Ace. Orbitz.com can help you find ground transportation when you are booking your air travel by working with rental car companies to find you the best rates.
Weather in Aguadilla
Aguadilla has a very pleasant, tropical climate. Highs reach into the 80s throughout the year, with lows in the high 60s to low 70s. There is a rainy season that lasts from April into November, so if you visit during these months, be sure to bring an umbrella.
Major Attractions in Aguadilla
You are in luck if you enjoy swimming and sunbathing. Aguadilla has 19 beaches, more than any other city on the island of Puerto Rico. Many of the beaches are among the best in the world for surfing. Aguadilla is also home to Las Cascadas Water Park and the Aguadilla Ice Skating Arena. If you are planning a trip, check Orbitz.com for cheap flights to Aguadilla.
Flights from Chicago
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.


