$74 Cheap flight deals from Chicago (CHI) to San Juan (SJU)
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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 $74 One Way, $144 Round Trip from Chicago to San Juan
Prices starting at $144 for return flights and $74 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
Hyatt Regency Grand Reserve Puerto Rico
Jan 12 - Jan 16
Chicago (CHI) to San Juan (SJU)
Reviewed on Nov 11, 2025
The Oliver Hotel
Dec 27 - Jan 3
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
OLV Fifty Five - Adults Only
Dec 26 - Dec 30
Chicago (CHI) to San Juan (SJU)
San Juan (SJU) to Chicago (CHI)
Reviewed on Aug 7, 2023
San Juan packages with premium economy flights
Jobos Luxury Condos
Jan 17 - Jan 20
Chicago (MDW) to San Juan (SJU)
San Juan (SJU) to Chicago (MDW)
Reviewed on Jul 28, 2025
The Beach Pad
Jan 17 - Jan 20
Chicago (MDW) to San Juan (SJU)
San Juan (SJU) to Chicago (MDW)
Reviewed on Jul 20, 2025
Lazy Parrot Inn
Jan 17 - Jan 20
Chicago (MDW) to San Juan (SJU)
San Juan (SJU) to Chicago (MDW)
Reviewed on Dec 16, 2024
San Juan first class flight packages
Hyatt Vacation Club at Hacienda del Mar, Dorado
Jan 15 - Jan 19
Chicago (CHI) to San Juan (SJU)
Reviewed on Nov 21, 2025
Aire de O:live
Jan 15 - Jan 19
Chicago (CHI) to San Juan (SJU)
Reviewed on Apr 9, 2025
Hyatt Regency Grand Reserve Puerto Rico
Jan 15 - Jan 19
Chicago (CHI) to San Juan (SJU)
Reviewed on Nov 11, 2025
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
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San Juan Airports
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- 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.