San Jose to Chicago flights from $333

Flights starting at $333. Choose between Alaska Airlines, Delta Air Lines, or United Airlines to find the best price.

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Travelers usually depart from San Jose International, San José Diridon Station, San Jose-Tufesa Bus Stop, San Jose, CA - Convention Center Station, or Reid–Hillview Airport when they travel from San Jose to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Rockford International, or Chicago Downtown Greyhound Station. The distance between San Jose and Chicago is 2940 km. The most popular airlines for this route are Alaska Airlines, Delta Air Lines, United Airlines, Spirit Airlines, and Frontier Airlines. San Jose and Chicago have 401 direct flights per week.

Weekly direct flights

MondaysTuesdaysWednesdaysThursdaysFridaysSaturdaysSundays
Direct flights1111111
Fly direct with

United Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

Check-in for a flight from San Jose to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
Alaska AirlinesASAASYesOpens 24 days before flight
Closes 1 hours before flight
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Spirit AirlinesNKSNKNoOpens 24 days before flight
Closes 1 hours before flight
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight

United States COVID-19 travel restrictions

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Latest COVID-19 restrictions

United States

Kiwi.com/COVID-19/United States
  • Travel is allowed

  • No proof of negative pre-departure COVID-19 test results required for Illinois

  • No quarantine required for Illinois

  • No quarantine required for vaccinated travelers going to Chicago

Latest COVID-19 travel restrictions in United States – 07/2022
Your trip summary

Most travelers from San Jose, SJC with proof of full COVID-19 vaccination can enter Chicago, MDW.

Departure

Travel restrictions
  • Travel is allowed

  • No proof of negative pre-departure COVID-19 test results required for Illinois

  • No quarantine required for Illinois

  • No quarantine required for vaccinated travelers going to Chicago

Return

Travel restrictions
  • Travel is allowed

  • No proof of negative pre-departure COVID-19 test results required

  • No quarantine required

Additional information
  • Health pass for large events in California may be required

  • Masks may be required

Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.

Learn more about COVID-19 restrictions in United States in our dedicated Stories article.

Frequently asked questions

How long does it take to travel from San Jose to Chicago?
A one-way nonstop (direct) flight between San Jose and Chicago takes around 4.3 hours.
What is the flight distance between San Jose and Chicago?
The flight distance between San Jose and Chicago is 2940 km.
What airlines offer nonstop (direct) flights between San Jose and Chicago?
Several carriers operate flights between San Jose and Chicago. Airlines offering nonstop (direct) flights include United Airlines.
What are the most popular routes to and from San Jose?
Travelers frequently search for route combinations, such as San Jose and Las Vegas, Denver, Atlanta, Guadalajara, Washington, D.C., Phoenix, Houston, Los Angeles, Dallas, San Diego, Austin, Mexico City, St. Louis, London, Seattle, Fort Lauderdale, Orlando, Raleigh, Santa Ana, Philadelphia.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and Phoenix, Las Vegas, Denver, Orlando, San Francisco, Los Angeles, Tampa, Miami, Salt Lake City, New York, Atlanta, London, Sacramento, Minneapolis, Mexico City, Paris, Austin, Washington, D.C., Fort Lauderdale, Fort Myers.
What airports are near San Jose?
The main airport in San Jose is San Jose International. It is also served by San Francisco International, Sacramento International, Oakland International, Fresno Yosemite International, San Jose International, Monterey Regional, Stockton Metropolitan, Charles M. Schulz–Sonoma County, Merced Regional, Buchanan Field.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, Dane County Regional, General Wayne A. Downing Peoria International, South Bend International, Fort Wayne International, Central Illinois Regional, Quad City International, Decatur, Kalamazoo/Battle Creek International.
What buses and trains depart from San Jose?
A number of bus and train companies depart from San Jose, including Amtrak train.
Is it possible to combine flights, buses, and trains in one itinerary when traveling between San Jose and Chicago?
Yes, it's possible to combine different modes of transport between San Jose and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between San Jose and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.
What is Virtual Interlining and how do I use it?
Which airlines fly between San Jose and Chicago?
When's the best time to travel between San Jose and Chicago?
What flights operate between San Jose and Chicago?
How many airports are there near San Jose?
How many airports are there near Chicago?
Is it possible to reach San Jose by bus or train?
What time do nonstop (direct) flights between San Jose and Chicago depart?
What time do nonstop (direct) flights between San Jose and Chicago arrive?
What time do flights between San Jose and Chicago depart?
What time do flights between San Jose and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.

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