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Cheap Flights from Chicago to San Jose International

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      Compare Chicago to San Jose International flight deals

      Find the cheapest month or even day of the year to fly to San Jose International

      Book the best San Jose International fare with no extra fees

      Flight deals from Chicago to San Jose International

      Looking for a cheap last-minute deal or the best return flight from Chicago to San Jose International Airport? If you want to travel next month, return fares start from R 3,778. Find the lowest prices on one-way and return tickets right here.
      San Jose.R 1,488 per passenger.Departing Mon, 5 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 5 Oct, arriving in San Jose International.Price includes taxes and charges.From R 1,488, select.
      San Jose.R 1,507 per passenger.Departing Sat, 15 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 15 Aug, arriving in San Jose International.Price includes taxes and charges.From R 1,507, select.
      San Jose.R 1,588 per passenger.Departing Thu, 10 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 10 Sep, arriving in San Jose International.Price includes taxes and charges.From R 1,588, select.
      San Jose.R 1,938 per passenger.Departing Thu, 10 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 10 Sep, arriving in San Jose International.Price includes taxes and charges.From R 1,938, select.
      San Jose.R 1,938 per passenger.Departing Sat, 3 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in San Jose International.Price includes taxes and charges.From R 1,938, select.
      San Jose.R 1,938 per passenger.Departing Tue, 3 Nov.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 3 Nov, arriving in San Jose International.Price includes taxes and charges.From R 1,938, select.
      San Jose.R 1,940 per passenger.Departing Thu, 13 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 13 Aug, arriving in San Jose International.Price includes taxes and charges.From R 1,940, select.
      San Jose.R 2,095 per passenger.Departing Wed, 2 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 2 Dec, arriving in San Jose International.Price includes taxes and charges.From R 2,095, select.
      San Jose.R 2,932 per passenger.Departing Wed, 2 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Dec, arriving in San Jose International.Price includes taxes and charges.From R 2,932, select.
      San Jose.R 2,938 per passenger.Departing Mon, 1 Feb.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Mon, 1 Feb, arriving in San Jose International.Price includes taxes and charges.From R 2,938, select.
      San Jose.R 3,045 per passenger.Departing Fri, 31 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 31 Jul, arriving in San Jose International.Price includes taxes and charges.From R 3,045, select.
      San Jose.R 3,324 per passenger.Departing Wed, 6 Jan.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 6 Jan, arriving in San Jose International.Price includes taxes and charges.From R 3,324, select.
      San Jose.R 3,335 per passenger.Departing Mon, 1 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 1 Feb, arriving in San Jose International.Price includes taxes and charges.From R 3,335, select.
      San Jose.R 3,652 per passenger.Departing Fri, 31 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 31 Jul, arriving in San Jose International.Price includes taxes and charges.From R 3,652, select.
      San Jose.R 21,970 per passenger.Departing Thu, 3 Jun.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 3 Jun, arriving in San Jose International.Price includes taxes and charges.From R 21,970, select.

      Find the cheapest month to fly from Chicago to San Jose International

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to San Jose International flights are currently cheapest in October.
      Jul
      from R 3,045
      Aug
      from R 1,507
      Sep
      from R 1,588
      Oct
      from R 1,488
      Nov
      from R 1,938
      Dec
      from R 2,095
      Jan
      from R 3,324
      Feb
      from R 2,938
      Mar
      Find prices
      Apr
      Find prices
      May
      Find prices
      Jun
      from R 21,970

      Direct flights from Chicago to San Jose International

      Chicago to San Jose International: Alternative routes

      Compare routes from Chicago to San Jose below. You may find an airport to fly into that's cheaper, faster, or easier than San Jose International.

      San Jose International

      5km from central San Jose
      Closest
      from R 1,488
      Search flights

      San Jose Reid-Hillview

      6km from central San Jose
      Search flights

      Oakland Metropolitan Oak

      52km from central San Jose
      from R 1,310
      Search flights

      San Francisco International

      53km from central San Jose
      Cheapest
      from R 1,262
      Search flights

      Concord

      74km from central San Jose
      Search flights

      Carmel Monterey Peninsula

      83km from central San Jose
      from R 2,020
      Search flights

      Sacramento Stockton

      85km from central San Jose
      from R 2,343
      Search flights

      Chicago to San Jose: Flight information

      The things to know before you go.
      Cheapest flight foundR 1,488
      Cheapest month to flyOctober
      Average flight time4 hrs, 43 mins
      Most popular airlineSouthwest Airlines
      Average flights per week56

      Finding cheap flights from Chicago to San Jose International: Frequently asked questions

      The best price we found for a return flight from Chicago to San Jose International is R 3,778. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      4 hours and 42 minutes is the average flight time from Chicago to San Jose International.
      Southwest Airlines and United fly direct from Chicago to San Jose International.
      As of July 2026, there are 56 flights per week flying from Chicago to San Jose International.
      The cheapest month to fly from Chicago to San Jose International is usually August.
      After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to San Jose International Airport on Saturday, 15 August 2026.
      Yes – the average flight time is 4 hours and 42 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Jose International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Jose is around 40 days in advance, so don’t leave your flight to the last minute.

      Flying from Chicago to San Jose Mineta International Airport (SJC): What you need to know

      • The first chapter of your trip begins at one of Chicago's main airports, Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore the options for booking a flight from Chicago to San Jose Mineta International Airport (SJC) departing from either of these.

      • Expect to be in the air for 4 hours 40 minutes. That's the average duration of a direct Chicago to San Jose Mineta International Airport flight.

      • San Jose Mineta International Airport is located in San Jose. The city is in the UTC-8 timezone and is two hours behind Chicago.

      • The most popular route is from Chicago O'Hare International Airport (ORD) to San Jose Mineta International Airport (SJC). Take your pick of 6 direct services every week. United Airlines operates a 9am departure between ORD and SJC.

      • Get to the airport on time so you don't miss your flight from Chicago to SJC. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.

      • With more people on the move during busy months like July, be at your terminal even earlier. Two hours for domestic flights and up to four for international journeys will allow extra time for delays. Remember things also get busy during major holidays like Christmas.

      Airports in Chicago

      Chicago O'Hare International Airport (ORD)

      • Chicago O'Hare International Airport (ORD) is a convenient option for travelling directly to your destination. Nonstop flights from Chicago to San Jose Mineta International Airport (SJC) leave from this terminal.

      • When leaving from ORD, you can catch a direct flight from Chicago to San Jose Mineta International Airport with United Airlines.

      • The airline most travellers choose when flying between ORD and SJC is United.

      • United is the most punctual carrier on this route, with 68.87% of its services landing on time.

      • Located around 27 kilometres from the centre of Chicago, ORD can be reached in about 30 minutes by car, depending on traffic. The journey on public transport is roughly 45 minutes.

      • Planning to catch an early flight from Chicago to San Jose Mineta International Airport? Avoid the mad dash to the terminal (and sneak in some extra snooze time) by picking one of these stays near Chicago O'Hare International Airport:

      • Of all flights departing from Chicago O'Hare International Airport, 70% arrive as scheduled at their destination.

      • You'll find ORD at 10000 West O'Hare.

      Chicago Midway International Airport (MDW)

      • Consider beginning your travels from Chicago Midway International Airport (MDW). You can book a direct Chicago to San Jose Mineta International Airport (SJC) plane ticket with departures from this hub.

      • You can board a direct flight from Chicago to SJC with Southwest Airlines. This is one of the leading airlines operating this route out of MDW.

      • Southwest Airlines is the top choice for passengers flying from MDW to SJC.

      • Southwest Airlines is the most punctual carrier flying between Chicago Midway International Airport and San Jose Mineta International Airport, with 75.41% of its services arriving on schedule.

      • You can get to MDW from the centre of Chicago in approximately 25 minutes by car, depending on traffic conditions. The journey on public transport takes roughly 30 minutes to cover the 16 kilometres or so.

      • Catching the earliest flight? Think about staying at one of these accommodation options near Chicago Midway International Airport the day before your Chicago to SJC flight:

      • Chicago Midway International Airport has an on-time performance rate of 76%. This figure provides insight into how frequently flights that leave from this airport land at their destination on schedule.

      • MDW is located at 5700 South Cicero.

      Chicago Rockford International Airport (RFD)

      • The journey time to RFD from the centre of Chicago is around 2 hours on public transport. If you're planning to travel by car, it'll take you roughly 1 hour 40 minutes to cover the 145 kilometres or so.

      • Relax in bed for a little longer and still make your Chicago to San Jose Mineta International Airport flight without having to rush. These accommodation options near Chicago Rockford International Airport make it a breeze to get to the terminal if you're flying out first thing:

      • Flights that depart from RFD arrive at their destination as scheduled 71% of the time.

      • Chicago Rockford International Airport is located at 2 Airport Cir.

      About San Jose Mineta International Airport (SJC)

      • If you're arriving on a late flight from Chicago to San Jose Mineta International Airport, nothing beats the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and snoozing soon after at one of these options near SJC:

      • Lock in the best possible rate by booking your ride around one week before your Chicago to San Jose Mineta International Airport flight.

      • The address for SJC is 1701 Airport Boulevard, Suite B-1130.

      Getting from San Jose Mineta International Airport (SJC) to central San Jose

      • Central San Jose is around 6 kilometres from San Jose Mineta International Airport and takes about 10 minutes to reach by car. See what your options are for heading into the city, whether that's with a taxi, car hire or ride-share.

      • If you're travelling by public transport, expect a journey of about 30 minutes.

      How to find the cheapest flights from Chicago to San Jose Mineta International Airport (SJC)

      • R 1,488 is the best price for a one-way ticket from Chicago to San Jose Mineta International Airport. A return flight starts from R 3,778. These prices may change based on demand.

      • Booking ahead of time is often the key to scoring a cheap flight from Chicago to SJC. Flight prices rise as demand increases, so the closer you get to departure, the more you'll likely pay.

      • If you have some flexibility with your trip dates, use the 'Whole month' search tool. It'll show you the lowest price across each month when searching for your Chicago to San Jose Mineta International Airport ticket.

      • Snapping up a cheap plane ticket from Chicago to SJC is a piece of cake with Price Alerts. Simply set up one of these automatic alerts and we'll get in touch when prices go down.

      • Lock in a cheap flight from Chicago to San Jose Mineta International Airport by using the search filters. Select your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

      The best time to fly from Chicago to San Jose Mineta International Airport (SJC)

      • Think about the kind of holiday you want when planning your trip dates. December is the quietest month to go to San Jose. July is when most people book flights from Chicago to San Jose Mineta International Airport (SJC), which may be perfect if you enjoy travelling when it's busier.

      • Lock in a Chicago to SJC plane ticket departing in July if you're eager to visit the city during its warmest month. You can expect temperatures in San Jose to range from 12ºC (54ºF) to 33ºC (91ºF).

      • January has temperatures of between 3ºC (37ºF) and 18ºC (64ºF). Search for cheap tickets from Chicago to San Jose Mineta International Airport around that time if you like cooler conditions.

      More about San Jose

      • When it comes to searching for somewhere to lay your head, you'll find the most popular stays in San Jose right here. Explore these options as soon as you've booked your flight from Chicago to San Jose Mineta International Airport:

      • Winchester Mystery House and The Tech Interactive are just a couple of the top-rated attractions to add to your San Jose itinerary. Keep the sightseeing going at Santa Clara Valley.

      Explore more of the United States

      • San Jose has loads to offer, but there are so many other corners of the United States you should also see. About 209 kilometres east of San Jose, a trip to Fresno will keep your itinerary busy. Start with popular sights like Forestiere Underground Gardens, Shinzen Japanese Garden and Fresno Chaffee Zoo.

      • Around 137 kilometres north of San Jose, Sacramento is another favourite stop in the United States. Experience this destination's highlights firsthand at California State Railroad Museum, Old Sacramento State Historic Park and Crocker Art Museum.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.