Flights from Chicago to Aguadilla

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Airfare Deals Chicago to Aguadilla

On HolidayPrice.com you will find 0 direct and 4 connecting flights from Chicago to Aguadilla at a price of . You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out CHI - BQN flight schedule to find best flight time, convenient departure and arrival airports.

Sun

The cost of airline tickets from Chicago to Aguadilla (Puerto Rico) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Aguadilla.

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Cheap flights to Aguadilla
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One way flight from Chicago to Aguadilla

Below are the prices of tickets for direct one-way flights from Chicago to Aguadilla. The cheapest flight from Chicago to Aguadilla starts – the departure date for this flight is 01 January 1970.

*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Chicago to Aguadilla

You can buy a round-trip ticket from Chicago to Aguadilla (Puerto Rico) and back using the table below. The best offer starts from $255, the flight dates are: there on 07 November 2025 year and back on 22 November 2025 year.

*Prices include: baggage, hand luggage, airline fees and charges.

Not found promotions and sales.

Flight Schedule Chicago to Aguadilla 2025

The current flight schedule for the route from Chicago to Aguadilla for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

Flight schedule not found

Select a date to search for cheap flights to the destination.

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Aguadilla from Chicago takes 04:51 minutes (excluding transfers). The distance between Chicago and Aguadilla is 2011 miles (3238 kilometers). Planes depart from Chicago between 00:40 and 22:40. The fastest flight from the company Southwest Airlines with flight number WN 3023. Flies for just 06:58 minutes with departure from Chicago Midway and arrival in Rafael Hernandez Airport.

Airlines

Direct flight

There are 0 airlines that fly directly from Chicago to Aguadilla. The most popular company carrying out non-stop flights is .

*Flight number

Flights with Transfers

Flights with transfers from Chicago to Aguadilla can be bought from 4 airlines:

Southwest Airlines: Orlando
American Airlines: Orlando
United Airlines: West Palm Beach, New York
JetBlue Airways: New York

*Transit cities

Airports

Airports serving the air communication between Chicago and Aguadilla. You can fly to Aguadilla from 2 Chicago airports. Planes arrive at 1 airport in Aguadilla.

Chicago airports:

Chicago Midway ~ 14 km* from $ 129O'Hare ~ 25 km* from $ 87

Aguadilla airports:

Rafael Hernandez Airport ~ 0 km*

*Distance from the airport to the city center

Aircraft

You can fly from Chicago to Aguadilla on board of 4 airlines that utilize 5 aircraft models.

Airbus A320
Airbus A321

Boeing 737-800
Boeing 737-900

Embraer 190

Connecting cities

The list of cities on transfer flights to Aguadilla from Chicago. The best options are to fly through: Orlando, West Palm Beach, New York.

Orlando
West Palm Beach

New York

Cheap airline tickets from Chicago to Puerto Rico

Here is a list of flights from Chicago to Puerto Rico purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Chicago - San Juan AA 1174 American Airlines Boeing 737-800

23:30 O'Hare

in a way 4 hours 38 min Direct

04:08 Luis Munoz Marin

Flights
from $74 09 February 2026

Chicago - Ponce NK 929 Spirit Airlines Airbus A320

22:20 O'Hare

in a way 7 hours 13 min 1 Stopover

05:33 Mercedita Airport

Flights
Find 12 November 2025

Chicago - Aguadilla WN 3023 Southwest Airlines Boeing 737-800

22:40 Chicago Midway

in a way 6 hours 58 min 1 Stopover

05:38 Rafael Hernandez Airport

Flights
Find 12 November 2025

Chicago - Mayaguez AA 395 American Airlines Boeing 737-800

14:40 O'Hare

in a way 8 hours 15 min 1 Stopover

22:55 Eugenio M. De Hostos Airport

Flights
Find 12 November 2025

All flights from Chicago

Flights from United States to Aguadilla

Here are the cheapest flight bookings from United States to Aguadilla made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Aguadilla B6 939 JetBlue Airways Airbus A320

13:00 John F. Kennedy

in a way 3 hours 44 min Direct

16:44 Rafael Hernandez Airport

Flights
from $88 15 November 2025

Los Angeles - Aguadilla AA 1297 American Airlines Boeing 777-300ER

21:00 Los Angeles

in a way 10 hours 8 min 1 Stopover

07:08 Rafael Hernandez Airport

Flights
Find 12 November 2025

Miami - Aguadilla NK 809 Spirit Airlines Airbus A319

18:50 Fort Lauderdale Executive Airport

in a way 2 hours 10 min Direct

21:00 Rafael Hernandez Airport

Flights
Find 12 November 2025

Chicago - Aguadilla WN 3023 Southwest Airlines Boeing 737-800

22:40 Chicago Midway

in a way 6 hours 58 min 1 Stopover

05:38 Rafael Hernandez Airport

Flights
Find 12 November 2025

San Francisco - Aguadilla UA 292 United Airlines Boeing 737-800

21:05 San Francisco

in a way 9 hours 54 min 1 Stopover

06:59 Rafael Hernandez Airport

Flights
Find 12 November 2025

All flights to Aguadilla

Tips for buying a ticket

Chicago – Aguadilla – Chicago round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Chicago to Aguadilla — Aguadilla city

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