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Chicago to San Juan Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Chicago to San Juan

Departure Arrival Travel dates Round-trip
CHI SJU Wed, Jan 21 - Mon, Jan 26 $283
CHI SJU Wed, Dec 3 - Tue, Dec 9 $298
CHI SJU Tue, Dec 9 - Tue, Dec 16 $298
CHI SJU Sun, Nov 9 - Thu, Nov 27 $318
CHI SJU Sun, Nov 9 - Fri, Nov 14 $318
CHI SJU Mon, Nov 17 - Mon, Dec 8 $349
CHI SJU Tue, Mar 17 - Tue, Mar 24 $1,169

Chicago and San Juan airports and terminals

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from ORD to SJU

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 3 American Airlines, jetBlue
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Airports in San Juan , PR
map of airports in San Juan
  • 1

    Luis Munoz Marin Intl (SJU)

    Distance from City Center: 6.7 miles

    Terminals and carriers for flights from CHI to SJU

    Terminal Carriers
    Terminal A jetBlue
    Terminal C US Airways, United Airlines
    Terminal D American Airlines
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Cheap flights from Chicago to San Juan

Sun Mon Tue Wed Thu Fri Sat
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
$301
16 17
$301
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23 24 25 26 27 28 29
30

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured San Juan Airport Hotels

Hotel only $113

Courtyard by Marriott San Juan Isla Verde Beach Resort

3 stars
4.0 / 5 350 reviews

7012 Bosa de Cangrejos Avenue Map

Save 25% on your stay

Blue Flag award-winning Isla Verde Beach is found in Puerto Rico's San Juan, and home to the Courtyard by Marriot Isla Verde Beach Resort. The beachfront establishment has a family-friendly feel,... More

Hotel only $249

The Ritz-Carlton, San Juan

5 stars
4.4 / 5 377 reviews

6961 Avenue of the Governors, Isla Verde Map

Rate includes 6th Night Free

Immerse yourself in total luxury and relaxation at The Ritz Carlton, San Juan, with two miles of sandy beaches to enjoy. Modern and sophisticated decor makes the 416 rooms both stylish and... More

Hotel only $160

Hotel La Playa

3 stars
4.0 / 5 14 reviews

6 Amapola St. Map

You will love the newly renovated and refurnished La Playa Hotel, located just 5 minutes from the San Juan airport, at the best location in Isla Verde - between two of the best beaches in Puerto... More

Hotel only $60

Coral by the Sea Hotel

1 star
2.7 / 5 144 reviews

Calle Rosa #2 Map

20% OFF

...Convenient to Luiz Muñoz International Airport Rooms.... More

Hotel only $120

ESJ Towers

3 stars
3.4 / 5 108 reviews

6165 Isla Verde Ave. Map

FREE BREAKFAST FOR 2, KITCHENETTE, WIFI & PARKING

The ESJ Towers Hotel San Juan has a design-led feel that focuses on local artistic traditions, from the 20th century modern prints in the Mano a Mano bar to the curving sofas wrapped around... More

Hotel only $129

El San Juan Resort and Casino

4 stars
3.7 / 5 380 reviews

6063 Isla Verde Avenue Map

Includes 2 breakfast buffet certificates

...Conveniently located just a five-minute drive from Luis Munoz Marin International Airport (SJU), the resort lies close to the heart of San Juan.... More

November

Cheapest weekend flights in November from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 1 Chicago (ORD) San Juan (SJU) American Airlines $355
Earn $3.55
Return Mon, Nov 3 San Juan (SJU) Chicago (ORD) American Airlines

Lowest roundtrip airfare in November from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 15 Chicago (ORD) San Juan (SJU) US Airways $301
Earn $3.01
Return Thu, Dec 4 San Juan (SJU) Chicago (ORD) US Airways

Best one-week trip in November from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Nov 28 Chicago (ORD) San Juan (SJU) American Airlines $302
Earn $3.02
Return Fri, Dec 5 San Juan (SJU) Chicago (ORD) American Airlines
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December

Cheapest weekend flights in December from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 11 Chicago (ORD) San Juan (SJU) US Airways $311
Earn $3.11
Return Mon, Dec 15 San Juan (SJU) Chicago (ORD) US Airways

Lowest roundtrip airfare in December from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 10 Chicago (ORD) San Juan (SJU) Spirit Airlines $283
Earn $2.83
Return Fri, Dec 12 San Juan (SJU) Chicago (ORD) Spirit Airlines

Best one-week trip in December from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Dec 9 Chicago (ORD) San Juan (SJU) American Airlines $298
Earn $2.98
Return Tue, Dec 16 San Juan (SJU) Chicago (ORD) American Airlines
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January

Cheapest weekend flights in January from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jan 22 Chicago (ORD) San Juan (SJU) Spirit Airlines $283
Earn $2.83
Return Mon, Jan 26 San Juan (SJU) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in January from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jan 27 Chicago (ORD) San Juan (SJU) Spirit Airlines $283
Earn $2.83
Return Tue, Feb 3 San Juan (SJU) Chicago (ORD) Spirit Airlines

Best one-week trip in January from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jan 27 Chicago (ORD) San Juan (SJU) Spirit Airlines $283
Earn $2.83
Return Tue, Feb 3 San Juan (SJU) Chicago (ORD) Spirit Airlines
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Trips from Chicago to San Juan

Visit the Caribbean without leaving the U.S. with a trip to San Juan, Puerto Rico. It's easy to travel from Chicago to San Juan when you use Orbitz.com to book your airline tickets and hotel accommodations online. Whether you are interested in exploring historic sites or sampling the best cuisine that Puerto Rico has to offer, San Juan has what you are looking for.

Leaving Chicago

When you travel from Chicago to San Juan, you can fly out of Chicago O'Hare International Airport or Chicago Midway International Airport. Typically, the only nonstop flight to San Juan from Chicago is on American Airlines leaving out of Chicago O'Hare International Airport, but you may be able to get a deal on a single-stop flight leaving from Midway.

Public buses serve both O'Hare and Midway, so you can catch a ride at various points downtown. For door-to-door service, local taxi companies and airport shuttle services are available to pick you up anywhere in Chicago and bring you to either airport. If you are driving to the airport, both O'Hare and Midway have economy lots located off-site. Free shuttles bring passengers from the economy lots to the terminals. You can also park at the garages located next to each airport. Both airports have restaurants, coffee shops, and stores where you can eat or shop while waiting to board your flight.

Travel to San Juan

Visitors to San Juan can enjoy colonial architecture, bustling nightlife, and plenty of outdoor adventures. You can fill your time in San Juan by visiting the city's many museums and historic sites or simply swimming and lying out on the beach. Whether you want an active vacation or a relaxing one, you can find something to suit your vacation tastes in San Juan.

Visiting San Juan

Visitors to San Juan arrive at Luis Munoz Marin International Airport, which is about 9 miles from the city center. Taxis are available at the airport to take you to your hotel and cost about $8 to get into town. Alternately, you can take a public bus into the city for just $0.25. If you plan to drive while in Puerto Rico, you can rent a car from one of the car rental agencies at the airport. Avis, Hertz, and National are just three of the many agencies with facilities at the airport.

Popular historic sites in San Juan include Castillo de San Cristobal, the San Juan Gate, and San Juan Cathedral. Make time to explore the various neighborhoods of San Juan while you are there. In addition to the historical Old City, check out the swanky Isla Verde neighborhood and Santurce, which has recently become a hot district for art galleries. If your vacation plans include relaxing on the beach for hours, check out Ocean Park Beach or Condado Beach.

San Juan's tropical location keeps temperatures fairly steady year round, with highs in the 80s and lows in the 70s. January through March is the dry season in Puerto Rico, so many travelers from Chicago enjoy escaping the cold and visiting during this pleasant season. Travelers visiting at other times of the year may want to bring rain gear in case of sudden showers. Hurricane season runs from June through November, so be sure to watch the weather reports to ensure that there are no tropical storms or hurricanes approaching the island during your planned travel time.

Traveling from Chicago to San Juan

When you are ready to explore the early history of the Americas, or are simply ready for a tropical getaway, check Orbitz.com for great deals on travel to San Juan. In addition to flights from Chicago to San Juan, you can book your lodging, car rentals, and tickets to popular attractions online.

Interesting facts about flights from Chicago to San Juan

    • 2 direct flights are operating from Chicago to San Juan today.
    • Today's average time for a direct flight is 4h 43m.
    • United Airlines flight 1688 (3:15 AM GMT, Boeing 737-900 Passenger) is today's earliest available flight from Chicago to San Juan.
    • jetBlue flight 1563 (4:00 AM GMT, Airbus Industrie A320) is today's latest available flight from Chicago to San Juan.
    • Today's shortest direct flight from Chicago to San Juan (jetBlue flight 1563, Airbus Industrie A320) takes 4h 41m.
    • Today's longest direct flight from Chicago to San Juan (United Airlines flight 1688, Boeing 737-900 Passenger) takes 4h 45m.
    • Flights from Midway Airport (MDW), O'Hare Airport (ORD) to Luis Munoz Marin Intl (SJU) are available for this route.