Selected fares from Chicago to San Juan

Mon, Oct 3 - Thu, Oct 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$99.80

roundtrip

Sat, Nov 5 - Tue, Nov 8
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$246.80

roundtrip

Wed, Oct 26 - Tue, Nov 1
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$236.61

roundtrip

Wed, Oct 26 - Thu, Nov 3
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$237.80

roundtrip

Wed, Oct 26 - Thu, Nov 3
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$246.80

roundtrip

Fri, Dec 9 - Tue, Dec 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$402.78

roundtrip

Mon, Oct 3 - Thu, Oct 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$172.80

roundtrip

Mon, Oct 3 - Thu, Oct 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$177.30

roundtrip

Fri, Nov 4 - Sat, Nov 5
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$180.30

roundtrip

Wed, Oct 5 - Wed, Oct 19
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$188.80

roundtrip

Sun, Oct 9 - Thu, Oct 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$192.80

roundtrip

Mon, Oct 3 - Sun, Oct 9
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$197.30

roundtrip

Mon, Oct 3 - Sun, Oct 9
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$199.80

roundtrip

Wed, Oct 5 - Wed, Oct 19
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$202.43

roundtrip

Fri, Nov 4 - Sat, Nov 5
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$225.80

roundtrip

Sun, Oct 9 - Thu, Oct 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$234.99

roundtrip

Mon, Oct 3 - Thu, Oct 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$236.30

roundtrip

Fri, Nov 4 - Sat, Nov 5
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$239.30

roundtrip

Sun, Oct 9 - Thu, Oct 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$239.60

roundtrip

Sun, Nov 13 - Wed, Nov 16
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$240.80

roundtrip

Sat, Nov 5 - Sat, Nov 12
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$241.80

roundtrip

Sun, Nov 13 - Wed, Nov 16
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$243.80

roundtrip

Fri, Oct 28 - Fri, Nov 4
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$244.80

roundtrip

Sat, Nov 5 - Mon, Nov 7
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$250.80

roundtrip

Wed, Nov 2 - Sun, Nov 6
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$253.79

roundtrip

Sun, Nov 13 - Wed, Nov 16
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$249.29

roundtrip

Tue, Oct 11 - Tue, Oct 18
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$256.34

roundtrip

Tue, Oct 11 - Tue, Oct 18
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$257.80

roundtrip

Tue, Oct 4 - Wed, Oct 19
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$258.60

roundtrip

Fri, Nov 4 - Sat, Nov 5
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$259.80

roundtrip

Sat, Nov 5 - Tue, Nov 8
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$253.79

roundtrip

Thu, Oct 20 - Tue, Oct 25
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$261.80

roundtrip

Sun, Nov 13 - Wed, Nov 16
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$265.30

roundtrip

Flights from Chicago

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.

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Save more with San Juan Flight + Hotel packages

Hotels in San Juan

See all 75 Hotels in San Juan
San Juan Marriott Resort and Stellaris Casino
San Juan Marriott Resort and Stellaris Casino
1309 Ashford Avenue, San Juan
4.0 out of 5.0
4.3 out of 5 (809 reviews)

Featuring a 24-hour casino and ocean-view dining, this Puerto Rico beachfront resort is in San Juan's fashionable Condado district, about 3 km (2 mi) east of ...

$179

$179
Sheraton Old San Juan Hotel
Sheraton Old San Juan Hotel
100 Brumbaugh Street, San Juan
4.0 out of 5.0
3.9 out of 5 (426 reviews)

Located along the water in Old San Juan, this contemporary Puerto Rico resort is across from cruise-ship piers and 3 blocks from the massive Fort San ...

$118

$118
Hotel Miramar
Hotel Miramar
606 Ponce De Leon Avenue, San Juan
3.0 out of 5.0
3.7 out of 5 (189 reviews)

Overlooking the Condado Lagoon and the Atlantic Ocean, this boutique hotel provides affordable lodging a quarter-mile from Condado Beach and 2 miles from Museum ...

$90

$90
Sheraton Puerto Rico Hotel & Casino
Sheraton Puerto Rico Hotel & Casino
200 Convention Boulevard, San Juan
4.0 out of 5.0
3.8 out of 5 (216 reviews)

Overlooking the Bay of San Juan, the hotel is adjacent to the Puerto Rico Convention Center and close to historic Old San Juan and the San Juan Marina. The airport ...

$127

$127
Caribe Hilton San Juan
Caribe Hilton San Juan
1 San Geronimo Street, San Juan
4.0 out of 5.0
4.0 out of 5 (478 reviews)

Set among 17 acres of lush tropical gardens, and featuring a private beachfront location, this family-friendly hotel offers spacious accommodations and a large ...

$185

$185
DoubleTree by Hilton San Juan
DoubleTree by Hilton San Juan
105 Avenida de Diego, San Juan
4.0 out of 5.0
4.2 out of 5 (141 reviews)

Centrally located in San Juan, this property is within walking distance of Ocean Park Beach, Museo de Arte de Puerto Rico, Plaza del Mercado, and Centro de Bellas ...

$110

$110
La Concha Renaissance San Juan Resort
La Concha Renaissance San Juan Resort
1077 Ashford Ave Condado, San Juan
4.0 out of 5.0
4.3 out of 5 (615 reviews)

Freshly updated with a chic 21st-century style, this landmark San Juan resort adjoins a sandy beach and the calm, clear Caribbean Sea.

$179

$179
CIQALA Luxury Suites
CIQALA Luxury Suites
752 Manuel Fernandez Juncos Ave, San Juan
4.0 out of 5.0
4.6 out of 5 (60 reviews)

Located in Miramar, guests can enjoy top city attractions such as the Pan-American Pier, Old San Juan, San Cristobal Fort, and the Port of San Juan. CIQALA Luxury ...

$99

$99
Best Western Plus Condado Palm Inn & Suites
Best Western Plus Condado Palm Inn & Suites
55 Condado Avenue, San Juan
3.0 out of 5.0
3.7 out of 5 (49 reviews)

This family-friendly San Juan hotel is located near the airport, within a 10-minute walk of Plaza Antonia Quinones, Condado Beach, and Parque Laguna del Condado ...

$107

$107
The Condado Plaza Hilton
The Condado Plaza Hilton
999 Ashford Avenue, San Juan
4.0 out of 5.0
3.9 out of 5 (445 reviews)

Overlooking the Atlantic Ocean and the Condado Lagoon, this resort is in the fashionable Condado resort/residential neighborhood; Old San Juan and cruise-ship ...

$149

$149

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. 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.