Flights from Chicago to San Juan

Selected fares from Chicago to San Juan

Departure Arrival Travel dates Round-trip
CHI SJU Thu, Oct 1 - Mon, Oct 5 $314
CHI SJU Thu, Oct 1 - Mon, Oct 5 $314
CHI SJU Sat, Oct 10 - Fri, Oct 16 $314
CHI SJU Thu, Oct 1 - Mon, Oct 5 $329
CHI SJU Wed, Oct 28 - Mon, Nov 2 $339
CHI SJU Fri, Oct 23 - Mon, Oct 26 $359
CHI SJU Wed, Aug 19 - Sun, Aug 23 $631
Sun Mon Tue Wed Thu Fri Sat
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21
$332
22
23 24
$332
25 26 27 28 29
30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Save more with San Juan Flight + Hotel packages

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 International Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from ORD to SJU

    Terminal Carriers
    Terminal 1 United Airlines
    Terminal 3 American Airlines, US Airways, 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 United Airlines
    Terminal D American Airlines, US Airways
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Featured San Juan Airport Hotels

From $130

Courtyard by Marriott San Juan Isla Verde Beach Resort

3 stars
4.0 / 5 350 reviews

7012 Bosa de Cangrejos Avenue Map

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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

From $199

The Ritz-Carlton, San Juan

5 stars
4.4 / 5 385 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

From $60

Coral by the Sea Hotel

1 star
2.7 / 5 145 reviews

Calle Rosa #2 Map

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From $133

San Juan Airport Hotel

3 stars
3.3 / 5 3 reviews

LMM International Airport Terminal D - Hotel Map

Award winning San Juan Airport Hotel is the only Hotel located at the airport, just steps from the Airline counters in Terminal D. We have received the Best of the Best Award and Best of the Best... More

From $99

ESJ Towers

3 stars
3.4 / 5 113 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

August

Cheapest weekend flights in August from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Aug 27 Chicago (ORD) San Juan (SJU) jetBlue $345
Earn $3.45
Return Sun, Aug 30 San Juan (SJU) Chicago (ORD) jetBlue

Lowest roundtrip airfare in August from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Aug 24 Chicago (ORD) San Juan (SJU) jetBlue $332
Earn $3.32
Return Fri, Aug 28 San Juan (SJU) Chicago (ORD) jetBlue

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

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Aug 21 Chicago (ORD) San Juan (SJU) jetBlue $332
Earn $3.32
Return Fri, Aug 28 San Juan (SJU) Chicago (ORD) jetBlue
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September

Cheapest weekend flights in September from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 17 Chicago (ORD) San Juan (SJU) US Airways $324
Earn $3.24
Return Sun, Sep 20 San Juan (SJU) Chicago (ORD) US Airways

Lowest roundtrip airfare in September from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Sep 25 Chicago (ORD) San Juan (SJU) jetBlue $314
Earn $3.14
Return Wed, Sep 30 San Juan (SJU) Chicago (ORD) jetBlue

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

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Sep 27 Chicago (ORD) San Juan (SJU) jetBlue $314
Earn $3.14
Return Sun, Oct 4 San Juan (SJU) Chicago (ORD) jetBlue
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October

Cheapest weekend flights in October from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 1 Chicago (ORD) San Juan (SJU) US Airways $314
Earn $3.14
Return Mon, Oct 5 San Juan (SJU) Chicago (ORD) US Airways

Lowest roundtrip airfare in October from Chicago to San Juan

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 13 Chicago (ORD) San Juan (SJU) jetBlue $314
Earn $3.14
Return Tue, Oct 20 San Juan (SJU) Chicago (ORD) jetBlue

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 13 Chicago (ORD) San Juan (SJU) jetBlue $314
Earn $3.14
Return Tue, Oct 20 San Juan (SJU) Chicago (ORD) jetBlue
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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.