$69 Cheap flight deals from Chicago (CHI) to San Juan (SJU)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This Weekend's Flight Deals from Chicago to San Juan
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 $69 One Way, $138 Round Trip from Chicago to San Juan
Prices starting at $138 for return flights and $69 for one-way flights to San Juan were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
San Juan economy flight packages
Hotel Puerto Valdes
Jul 12 - Jul 17
Chicago (CHI) to San Juan (SJU)
Reviewed on Apr 21, 2026
San Juan packages with premium economy flights
Hotel Puerto Valdes
Jul 16 - Jul 19
Chicago (CHI) to San Juan (SJU)
Reviewed on Apr 21, 2026
Ocean Breeze Villa
Jul 16 - Jul 23
Chicago (ORD) to San Juan (SJU)
Reviewed on Jan 19, 2026
Coral by the Sea Hotel
Jul 16 - Jul 23
Chicago (ORD) to San Juan (SJU)
Reviewed on Mar 14, 2026
San Juan business class flight packages
Hotel Rumbao, a Tribute Portfolio Hotel
Jul 20 - Jul 24
Chicago (MDW) to San Juan (SJU)
Reviewed on Apr 20, 2026
San Juan Marriott Resort and Stellaris Casino
Jul 20 - Jul 24
Chicago (MDW) to San Juan (SJU)
Reviewed on Apr 17, 2026
Four Points by Sheraton Caguas Real Hotel & Casino
Jul 20 - Jul 24
Chicago (MDW) to San Juan (SJU)
Reviewed on Jan 8, 2025
San Juan first class flight packages
Hotel Puerto Valdes
Jul 17 - Jul 20
Chicago (ORD) to San Juan (SJU)
San Juan (SJU) to Chicago (ORD)
Reviewed on Apr 21, 2026
OLV Fifty Five - Adults Only
Jul 17 - Jul 20
Chicago (ORD) to San Juan (SJU)
San Juan (SJU) to Chicago (ORD)
Reviewed on Feb 19, 2026
More About Flying To San Juan from Chicago
Route Information for Flights from Chicago to San Juan
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SJU |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to San Juan
Getting a spectacularly low fare on Chicago to San Juan flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Chicago to San Juan, discount hotel accommodations, cheap car rentals, and more.
Research and Book Chicago to San Juan Flights on the Go
Our free cutting-edge mobile apps for iPad, Android, and iPhone make it easy to find the best fares when researching and booking flights from Chicago to San Juan. You can also use the apps to check your flight status, find baggage claims details, and get exclusive mobile discount rates on car rentals and hotels.
Earn Miles and Points for Your Frequent Flyer Program
Build up points or miles for your frequent flyer plan with qualifying Chicago to San Juan flights. Simply add your frequent flyer number when booking your domestic or international flights or enter the numbers in your Orbitz account profile to automatically add them to your bookings.
Flight Alerts Take the Hassle out of Travel
You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Chicago to San Juan. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.
Stay in Your Budget and Still Get Great Accommodations
Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Chicago to San Juanare always found on Orbitz.
Frequently asked questions
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to London
- Chicago to Washington
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
San Juan Airports
More Destinations
- 5 Star Hotels in San Juan
- Apartments in San Juan
- Chalets in San Juan
- Guest Houses in San Juan
- All Inclusive Resorts & in San Juan
- Gay Friendly Hotels in San Juan
- Hotels with Balconies in San Juan
- Hotels with Free Breakfast in San Juan
- Pet Friendly Hotels in San Juan
- Houseboats in San Juan
- Resorts in San Juan
- Villas in San Juan
- All Inclusive Resorts & in Puerto Rico
- Beach Resorts & in Puerto Rico
- Casino Resorts & in Puerto Rico
- Cheap Hotels in Puerto Rico
- Kid Friendly Hotels in Puerto Rico
- Gay Friendly Hotels in Puerto Rico
- Hotels with Pool in Puerto Rico
- Hotels with a Lazy River in Puerto Rico
- Hotels with Free Breakfast in Puerto Rico
- Hotels with Hot Tubs in Puerto Rico
- Hotels with Kitchenettes in Puerto Rico
- Luxury Hotels in Puerto Rico
- Oceanfront Hotels in Puerto Rico
- Pet Friendly Hotels in Puerto Rico
- Spa Resorts & in Puerto Rico
- Waterpark Hotels & Resorts in Puerto Rico
- Hotels with a Wedding Venue in Puerto Rico
- Puerto Rico Hotels
- Farmstay in Puerto Rico
- Apartments in Puerto Rico
- B&B in Puerto Rico
- Cabin Rentals in Puerto Rico
- Castles in Puerto Rico
- Chalets in Puerto Rico
- Condo Rentals in Puerto Rico
- Cottages in Puerto Rico
- Extended Stay Hotels in Puerto Rico
- Guest Houses in Puerto Rico
- Hostels in Puerto Rico
- Houseboats in Puerto Rico
- Lodges in Puerto Rico
- Motels in Puerto Rico
- Vacation Homes in Puerto Rico
- Rv Parks in Puerto Rico
- Ranches in Puerto Rico
- Resorts in Puerto Rico
- Safari Camps in Puerto Rico
- Town Houses in Puerto Rico
- Treehouses in Puerto Rico
- Villas in Puerto Rico
- Flights from Minneapolis - St. Paul to Manati
- Flights to Puerto Rico
- Flights from Atlanta (ATL) to San Juan (SJU)
- Flights from Austin (AUS) to San Juan (SJU)
- Flights from Hartford (BDL) to San Juan (SJU)
- Flights from Nashville (BNA) to San Juan (SJU)
- Flights from Boston (BOS) to San Juan (SJU)
- Flights from Baltimore (BWI) to San Juan (SJU)
- Flights from Charleston (CHS) to San Juan (SJU)
- Flights from Cleveland (CLE) to San Juan (SJU)
- Flights from Charlotte (CLT) to San Juan (SJU)
- Flights from Columbus (CMH) to San Juan (SJU)
- Flights from Cincinnati (CVG) to San Juan (SJU)
- Flights from Denver (DEN) to San Juan (SJU)
- Flights from Dallas (DFW) to San Juan (SJU)
- Flights from Detroit (DTW) to San Juan (SJU)
- Flights from Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
- Flights from Fort Lauderdale (FLL) to San Juan (SJU)
- Flights from Washington (IAD) to San Juan (SJU)
- Flights from Houston (IAH) to San Juan (SJU)
- Flights from Indianapolis (IND) to San Juan (SJU)
- Flights from Jacksonville (JAX) to San Juan (SJU)
- Flights from New York (JFK) to San Juan (SJU)
- Flights from Las Vegas (LAS) to San Juan (SJU)
- Flights from Los Angeles (LAX) to San Juan (SJU)
- Flights from Orlando (MCO) to San Juan (SJU)
- Flights from Miami (MIA) to San Juan (SJU)
- Flights from Minneapolis (MSP) to San Juan (SJU)
- Flights from New Orleans (MSY) to San Juan (SJU)
- Flights from Chicago (ORD) to San Juan (SJU)
- Flights from West Palm Beach (PBI) to San Juan (SJU)
- Flights from Portland (PDX) to San Juan (SJU)
- Flights from Philadelphia (PHL) to San Juan (SJU)
- Flights from Phoenix (PHX) to San Juan (SJU)
- Flights from Pittsburgh (PIT) to San Juan (SJU)
- Flights from Providence (PVD) to San Juan (SJU)
- Flights from Raleigh (RDU) to San Juan (SJU)
- Flights from Fort Myers (RSW) to San Juan (SJU)
- Flights from San Diego (SAN) to San Juan (SJU)
- Flights from Seattle (SEA) to San Juan (SJU)
- Flights from San Francisco (SFO) to San Juan (SJU)
- Flights from St. Louis (STL) to San Juan (SJU)
- Flights from Philipsburg (SXM) to San Juan (SJU)
- Flights from Tampa (TPA) to San Juan (SJU)
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.