Cheap Flights from Chicago to San Jose International

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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 ر.ق.‏ 830. Find the lowest prices on one-way and return tickets right here.

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 May.

Direct flights from Chicago to San Jose International

Chicago to San Jose: Flight information

The things to know before you go.
Cheapest flight foundر.ق.‏ 361
Cheapest month to flyMay
Average flight time4 hrs, 42 mins
Most popular airlineSouthwest Airlines
Average flights per week24

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 ر.ق.‏ 830. 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 April 2026, there are 24 flights per week flying from Chicago to San Jose International.
The cheapest month to fly from Chicago to San Jose International is usually May.
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 Friday, 29 May 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.

Travelling from Chicago to Norman Y. Mineta San Jose International Airport (SJC): What you need to know

  • Start your travels at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Check out your options for booking a flight from Chicago to Norman Y. Mineta San Jose International Airport (SJC) jetting off from either of these.

  • 4 hours 40 minutes is the average travel time for a direct Chicago to Norman Y. Mineta San Jose International Airport flight.

  • Norman Y. Mineta San Jose International Airport is located in San Jose. The city runs on the UTC-7 timezone and is two hours behind Chicago.

  • The most popular route is from O'Hare International Airport (ORD) to Norman Y. Mineta San Jose International Airport (SJC). Take your pick of 7 direct services each week. United Airlines operates a 9am departure between ORD and SJC.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport on time to board your flight from Chicago to SJC.

  • Peak season means busier airports, so show up even earlier. Give yourself at least two hours before a domestic flight and four hours for international journeys to stick to your schedule.

Airports in Chicago

O'Hare International Airport (ORD)

  • Enjoy an uninterrupted journey from O'Hare International Airport (ORD). Nonstop flights from Chicago to Norman Y. Mineta San Jose International Airport (SJC) are available from here.

  • Book your direct flight from Chicago to Norman Y. Mineta San Jose International Airport with United Airlines. This popular carrier operates departures from ORD.

  • United Airlines is the airline with the highest number of bookings for flights from ORD to SJC.

  • United Airlines is the most punctual carrier on this route, with 71.19% of its services arriving as planned.

  • Located around 40 kilometres from central Chicago, ORD can be reached in about 35 minutes by car, depending on traffic. The journey on public transport takes roughly 55 minutes.

  • Catching an early flight from Chicago to Norman Y. Mineta San Jose International Airport? Avoid rushing to the terminal (and get a little more snooze time) by choosing one of these hotels close to O'Hare International Airport:

  • 74.85% of flights that leave from O'Hare International Airport touch down at their destination on time.

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

Chicago Midway International Airport (MDW)

  • Thinking of flying out of Chicago Midway International Airport (MDW)? Direct Chicago to Norman Y. Mineta San Jose International Airport (SJC) flight tickets are available from here.

  • Southwest Airlines offers direct flights from Chicago to SJC departing from MDW. Book your favourite window seat and get to your destination in a single hop.

  • Southwest Airlines is the go-to airline for bookings on the MDW to SJC route.

  • The most reliable carrier is Southwest Airlines. Its Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport flights arrive as scheduled 73.77% of the time.

  • MDW is about 19 kilometres from central Chicago. It'll take 20 minutes or so to get to the airport by car from the city centre. Public transport takes roughly 45 minutes.

  • Flying out early in the morning? You might like to check in to one of these hotels near Chicago Midway International Airport the day before your Chicago to SJC flight:

  • As far as flight punctuality goes, Chicago Midway International Airport has an on-time arrival performance of 77.88%.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 137 kilometres from central Chicago. Driving from the city centre to the terminal takes about 1 hour 25 minutes. If you're thinking about using public transport, you can expect a journey of around 4 hours 15 minutes.

  • Set yourself up for a smooth departure — stay close to Chicago Rockford International Airport and know you'll be at your gate with time to spare. Get comfy at one of these hotels the day before if you're catching an early Chicago to Norman Y. Mineta San Jose International Airport flight:

  • Flights that take off from RFD arrive at their final stop on schedule 76.19% of the time.

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

About Norman Y. Mineta San Jose International Airport (SJC)

  • The last thing you need is a long journey to your hotel if you're arriving on a late flight from Chicago to Norman Y. Mineta San Jose International Airport. Get comfy at one of these accommodation options near SJC instead:

  • Explore without limits with a Norman Y. Mineta San Jose International Airport rental car. Pick up your wheels from Europcar, Fox - Rent A Car or Dollar and see more of San Jose and beyond.

  • To lock in the lowest price, reserve your vehicle around one week in advance of your Chicago to Norman Y. Mineta San Jose International Airport flight.

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

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

  • Norman Y. Mineta San Jose International Airport is about 5 kilometres from central San Jose. How long it takes to get there by cab or car hire will depend on the time of day. Do some research before you go.

  • Travelling on public transport takes about 45 minutes.

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

  • ر.ق.‏ 361 is the lowest price for a one-way ticket from Chicago to Norman Y. Mineta San Jose International Airport. Return flights start from ر.ق.‏ 830. These prices may change based on availability and demand.

  • To find cheap flights from Chicago to SJC, book early. Airlines typically offer lower fares when tickets are first released.

  • The 'Whole month' search tool will show you the cheapest Chicago to Norman Y. Mineta San Jose International Airport tickets across each month. It's a great way to find a bargain if your travel dates aren't set in stone.

  • Never miss a deal on flight tickets from Chicago to SJC by setting up a Price Alert. We'll send you an email or notification on the app when a lower fare becomes available.

  • Tailor your trip using filters. Pick your preferred departure and arrival times, total journey duration and airlines. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Chicago to Norman Y. Mineta San Jose International Airport.

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

  • May is the quietest month for flights from Chicago to Norman Y. Mineta San Jose International Airport (SJC), while August is the most popular. Work out the ideal time to visit San Jose based on whether you prefer a laid-back vibe or a lively atmosphere.

  • When booking your Chicago to SJC flight ticket, consider the weather you're most comfortable in. August is the warmest month in San Jose, with temperatures ranging from 11ºC to 32ºC.

  • Look for cheap tickets from Chicago to Norman Y. Mineta San Jose International Airport in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between 3ºC and 18ºC.

More about San Jose

  • Start your San Jose trip off on the right foot by choosing the perfect place to stay. Once you've booked your flight from Chicago to Norman Y. Mineta San Jose International Airport, explore our range of accommodation options including:

  • You'll find plenty of awesome things to do in San Jose when you're ready to get out and sightsee. Kick things off at Japantown (San Jose) followed by Winchester Mystery House and The Tech Museum of Innovation.

Explore more of the United States

  • You've seen San Jose, now it's time to explore other parts of the United States. Journey around 209 kilometres east to Fresno to tick off its leading attractions. From Forestiere Underground Gardens to Shinzen Japanese Garden and Fresno Chaffee Zoo, there's plenty to keep you on the go.

  • If you're interested in discovering another great destination in the United States, head for Sacramento, roughly 137 kilometres north of San Jose. Old Sacramento Waterfront, Fright Planet - America's Haunted Theme Park and California State Railroad Museum are the start of reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.