Direct Flights from Chicago to San Juan
San Juan · Puerto Rico
Nonstop service from ORD and MDW to SJU on American, Frontier, Southwest, United. Here's the schedule at a glance — plus what to do once you land.
Which airports fly this route
Chicago has 2 airports with nonstop service to San Juan. Fares differ by airport — each row opens that exact search on Kayak.
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- Find flights ↗ORDSJUChicago O'Hare International
- Find flights ↗MDWSJUChicago Midway International
How rare is this nonstop?
36 cities have a nonstop to San Juan, Chicago among them.
How long to go to San Juan for, from Chicago
4h 40m in the air, 2,074 miles. A two-night trip loses most of two days to travel; three or four nights is where this one starts to make sense.
About San Juan
San Juan is the capital of Puerto Rico and its largest city, with 342,000 (2020) inhabitants in the municipality and 2,203,000 in the metropolitan area. Founded in 1521 by the Spanish conquistadors, San Juan is the oldest city under the jurisdiction of the United States. San Juan is located in the north-east coast of Puerto Rico and features distinctly centuries-old architecture, such as Spanish military forts built from the 1540s to 1800s, an active harbor, and a very active economic area in the Hato Rey and Santurce districts. San Juan has magnificent beaches, hotels, plazas, historic sites, and museums.
Summary from Wikivoyage (CC BY-SA).
Top things to do in San Juan
- San Juan National Historic Site in the Old San Juan section of San Juan, Puerto Rico, is a National Park Service-managed historic site which preserves and interprets the Spanish colonial-era fortification system of the c…
- The Metropolitan Cathedral Basilica of Saint John the Baptist, officially known as the Minor Basilica of Saint John the Baptist and Parish of Our Lady of Remedies, is the Catholic cathedral for the Archdiocese of San Jua…
- Caparra is an archaeological site containing the remains of Caparra, the first European settlement in the main island of Puerto Rico.
- The Pablo Casals Museum, located on San José Square in Old San Juan, San Juan, Puerto Rico, is a museum dedicated to the Catalan Puerto Rican cellist, composer and conductor Pablo Casals, who lived the last 17 years of h…
- Cathedral Dulce Nombre de Jesús, or in English, Sweet Name of Jesus Cathedral, is a cathedral of the Catholic Church in Caguas, Puerto Rico.
- The Museum of Art of Puerto Rico is an art museum in Santurce, a barrio of San Juan, Puerto Rico, with 18 exhibition halls.
- The Casa Roig Museum is a historic house museum and gallery in Humacao, Puerto Rico.
- Casa Alonso is a house museum and cultural center in Vega Baja Pueblo, the historic downtown of the municipality of Vega Baja, Puerto Rico. It was listed on the National Register of Historic Places in 1996.
- The San Juan Botanical Garden, officially known as the Botanical Garden of the University of Puerto Rico, is located in San Juan, the capital of Puerto Rico.
- The Catedral Santiago Apóstol, or in English, the Cathedral of St. James the Apostle, or Santiago Apóstol of Fajardo is a Catholic cathedral located on the town plaza in Fajardo, Puerto Rico.
- The Concatedral Dulce Nombre de Jesús or in English, Co-Cathedral of the Sweet Name of Jesus, is a Catholic cathedral located on the town plaza in Humacao, Puerto Rico.
- The Puerto Rico Museum of Contemporary Art, often abbreviated to MAC, is a contemporary art museum in Santurce, Puerto Rico.
Attraction descriptions from Wikipedia (CC BY-SA); place data from Wikidata (CC0).
San Juan weather, compared with Chicago
28° warmer than Chicago on average across the year, on daytime highs:
- January
- San Juan 83°F · Chicago 31°F · 52° warmer
- April
- San Juan 86°F · Chicago 59°F · 28° warmer
- July
- San Juan 89°F · Chicago 84°F · 5° warmer
- October
- San Juan 89°F · Chicago 62°F · 26° warmer
San Juan is the steadier of the two, moving 6° between its coldest and warmest months where Chicago moves 53°.
Average daily highs, 1991–2020 station normals from Meteostat (CC BY 4.0), measured at each city's airport.
Planning a trip to San Juan
- Best time to visit
- The best time to visit San Juan is December–March, when the weather is mildest, with daytime highs around 84°F.
- How long to stay
- San Juan rewards a longer visit — a full week lets you explore its many sights, from San Juan National Historic Site, Cathedral of San Juan, Puerto Rico, and Caparra Archaeological Site and beyond.
Frequently asked questions
- Is there a direct flight from Chicago to San Juan?
- Yes — you can fly nonstop from Chicago (ORD, MDW) to San Juan (SJU) on American, Frontier, Southwest, United.
- Which airlines fly nonstop from Chicago to San Juan?
- American, Frontier, Southwest, United fly nonstop between Chicago (ORD, MDW) and San Juan (SJU).
- Which Chicago airport has nonstop flights to San Juan?
- You can leave from 2 Chicago airports: ORD (Chicago O'Hare International) on American, Frontier, United; MDW (Chicago Midway International) on Southwest.
- How many nonstop flights are there from Chicago to San Juan?
- There are about 3 nonstop departures per day (roughly 21 per week) from Chicago to San Juan.
- How far is San Juan from Chicago?
- San Juan is about 2,074 miles from Chicago by air.
- Is there a direct flight from Chicago to Puerto Rico?
- Yes — San Juan (SJU) has nonstop service from Chicago on American, Frontier, Southwest, United, making it a nonstop gateway to Puerto Rico.
- What is there to do in San Juan?
- Popular things to do include San Juan National Historic Site, Cathedral of San Juan, Puerto Rico, Caparra Archaeological Site, Pablo Casals Museum, and more.
More nonstop destinations from Chicago near San Juan
Airports near Chicago
The closest other departure airports to Chicago — each opens up more nonstop destinations.