Direct Flights from San Jose to Chicago
Chicago · Illinois
Nonstop service from SJC to MDW and ORD on American, 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 from San Jose. Fares differ by airport — each row opens that exact search on Kayak.
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- Find flights ↗SJCMDWChicago Midway International
- Find flights ↗SJCORDChicago O'Hare International
How rare is this nonstop?
Chicago is one of the best-connected places in the country: 205 cities fly there nonstop, San Jose among them.
How long to go to Chicago for, from San Jose
4h 10m in the air, 1,833 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 Chicago
Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. "Stormy, Husky, Brawling / City of Big Shoulders," Chicago is a Heartland boomtown, its ethos defined by urban planner Daniel Burnham's immortal vision: "Make no little plans; they have no magic to stir men's blood." It is one of the world's great cities and the third largest city in the United States, behind only New York City and Los Angeles.
Summary from Wikivoyage (CC BY-SA).
Top things to do in Chicago
- The Art Institute of Chicago is a private, nonprofit art museum in Grant Park, Chicago, Illinois, United States.
- Millennium Park is a public park in the Loop community area of Chicago, Illinois, United States, operated by the Chicago Department of Cultural Affairs and Special Events (DCASE).
- The Field Museum of Natural History is a private–public natural history museum in Chicago, Illinois, and is one of the largest such museums in the world.
- The Griffin Museum of Science and Industry is a private, non-profit science museum located in Jackson Park, the Hyde Park neighborhood, Chicago, Illinois.
- The Institute for the Study of Ancient Cultures, West Asia and North Africa (ISAC), formerly known as the Oriental Institute (OI), is a research institute and museum of the University of Chicago, located in Hyde Park, Ch…
- Essanay Studios, officially the Essanay Film Manufacturing Company, was an early American motion picture studio. The studio was founded in Chicago by George Kirke Spoor and Gilbert M.
- The Adler Planetarium is a municipal public museum for astronomy in Chicago, Illinois, United States. It is operated by the Chicago Park District, a municipal government agency of the City of Chicago.
- Grant Park is a large urban park in the Loop community area of Chicago, Illinois. Located within the city's central business district, the 319-acre (1.29 km2) park's features include Millennium Park, Buckingham Fountain,…
- Indiana Dunes National Park is a national park of the United States located in northwestern Indiana managed by the National Park Service.
- Buckingham Fountain is a Chicago Landmark in the center of Grant Park, between Queen's Landing and the end of Ida B. Wells Drive. Dedicated in 1927 and donated to the city by philanthropist Kate S.
- Shedd Aquarium is a public aquarium in Chicago, Illinois, United States. It is one of the oldest continually operating non-governmental aquariums in the U.S.
- The Barack Obama Presidential Center is a museum, library, and education project in Chicago to commemorate the presidency of Barack Obama, the 44th president of the United States.
Attraction descriptions from Wikipedia (CC BY-SA); place data from Wikidata (CC0).
Chicago weather, compared with San Jose
11° cooler than San Jose on average across the year, on daytime highs:
- January
- Chicago 31°F · San Jose 60°F · 28° colder
- April
- Chicago 59°F · San Jose 69°F · 10° colder
- July
- Chicago 84°F · San Jose 80°F · 4° warmer
- October
- Chicago 62°F · San Jose 75°F · 12° colder
January bottoms out near 31°F — a real coat, not a layer. Chicago also swings harder through the year than San Jose does — 53° between its coldest and warmest months against 21°.
Average daily highs, 1991–2020 station normals from Meteostat (CC BY 4.0), measured at each city's airport.
Planning a trip to Chicago
- Best time to visit
- The best time to visit Chicago is May–June and September–October, when daytime highs are a comfortable 62–80°F.
- How long to stay
- Chicago rewards a longer visit — a full week lets you explore its many sights, from Art Institute of Chicago, Millennium Park, and Field Museum of Natural History and beyond.
Frequently asked questions
- Is there a direct flight from San Jose to Chicago?
- Yes — you can fly nonstop from San Jose (SJC) to Chicago (MDW, ORD) on American, Southwest, United.
- Which airlines fly nonstop from San Jose to Chicago?
- American, Southwest, United fly nonstop between San Jose (SJC) and Chicago (MDW, ORD).
- Which Chicago airport can I fly to nonstop from San Jose?
- Chicago has 2 airports with nonstop service from San Jose: MDW (Chicago Midway International) on Southwest; ORD (Chicago O'Hare International) on American, United.
- How many nonstop flights are there from San Jose to Chicago?
- There are about 2 nonstop departures per day (roughly 14 per week) from San Jose to Chicago.
- How far is Chicago from San Jose?
- Chicago is about 1,833 miles from San Jose by air.
- What is there to do in Chicago?
- Popular things to do include Art Institute of Chicago, Millennium Park, Field Museum of Natural History, Museum of Science and Industry (Chicago), and more.
More nonstop destinations from San Jose near Chicago
Airports near San Jose
The closest other departure airports to San Jose — each opens up more nonstop destinations.