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Cheap Flights from Chicago (CHIA) to San Jose (SJCA)

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Flight deals from Chicago to San Jose

Looking for a cheap last-minute deal or the best return flight from Chicago to San Jose? Find the lowest prices on one-way and return tickets right here.
San Jose.£126 per passenger.Departing Wed, 29 Apr, returning Mon, 4 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 29 Apr, arriving in San Jose International.Inbound indirect flight with Frontier Airlines, departs from San Jose International on Mon, 4 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From £126, select.
San Jose.£145 per passenger.Departing Mon, 4 May, returning Mon, 11 May.Return flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 4 May, arriving in San Jose International.Inbound indirect flight with Frontier Airlines, departs from San Jose International on Mon, 11 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From £145, select.
San Jose.£147 per passenger.Departing Wed, 22 Apr, returning Sun, 26 Apr.Return flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 22 Apr, arriving in San Jose International.Inbound indirect flight with Frontier Airlines, departs from San Jose International on Sun, 26 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From £147, select.
San Jose.£156 per passenger.Departing Thu, 12 Mar, returning Mon, 16 Mar.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Thu, 12 Mar, arriving in San Jose International.Inbound indirect flight with Alaska Airlines, departs from San Jose International on Mon, 16 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From £156, select.
San Jose.£169 per passenger.Departing Wed, 16 Sep, returning Tue, 22 Sep.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Wed, 16 Sep, arriving in San Jose International.Inbound indirect flight with Alaska Airlines, departs from San Jose International on Tue, 22 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From £169, select.
San Jose.£173 per passenger.Departing Wed, 20 May, returning Wed, 10 Jun.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Wed, 20 May, arriving in San Jose International.Inbound indirect flight with Alaska Airlines, departs from San Jose International on Wed, 10 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From £173, select.
San Jose.£178 per passenger.Departing Thu, 27 Aug, returning Mon, 31 Aug.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Thu, 27 Aug, arriving in San Jose International.Inbound indirect flight with Alaska Airlines, departs from San Jose International on Mon, 31 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From £178, select.
San Jose.£187 per passenger.Departing Sat, 10 Oct, returning Mon, 12 Oct.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Sat, 10 Oct, arriving in San Jose International.Inbound indirect flight with Alaska Airlines, departs from San Jose International on Mon, 12 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From £187, select.

Find the cheapest month to fly from Chicago to San Jose

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to San Jose flights are currently cheapest in May.
Feb
from £322
Mar
from £156
Apr
from £147
May
from £145
Jun
from £198
Jul
from £209
Aug
from £178
Sep
from £169
Oct
from £187
Nov
Find prices
Dec
from £266
Jan
Find prices

Direct flights from Chicago to San Jose

Alternative Chicago to San Jose routes

Looking for the cheapest, fastest or easiest route from Chicago to San Jose? You could fly into the following airports instead.

San Jose International

3 miles from central San Jose
Closest
from £126
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San Jose Reid-Hillview

4 miles from central San Jose
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Oakland Metropolitan Oak

32 miles from central San Jose
from £161
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San Francisco International

33 miles from central San Jose
Cheapest
from £92
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Concord

46 miles from central San Jose
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Carmel Monterey Peninsula

52 miles from central San Jose
from £206
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Sacramento Stockton

53 miles from central San Jose
from £199
Search flights

Chicago to San Jose: Flight information

The things to know before you go.
Cheapest flight found£126
Cheapest month to flyApril
Average flight time4 hrs, 44 mins
Most popular airlineSouthwest Airlines
Average flights per week88

Check out these San Jose hotels

Ready to plan your stay? Other travellers rate these San Jose hotels for cleanliness, service and location.
Towneplace Suites By Marriott San Jose Downtown
0.71 miles from city centre
£201
Per night
La Quinta Inn & Suites by Wyndham San Jose Airport-Downtown
1.73 miles from city centre
£112
Per night
Hampton Inn San Jose Cherry Ave, CA
5.49 miles from city centre
£141
Per night
Towneplace Suites By Marriott San Jose Downtown
0.71 miles from city centre
£201
Per night
La Quinta Inn & Suites by Wyndham San Jose Airport-Downtown
1.73 miles from city centre
£112
Per night
Hampton Inn San Jose Cherry Ave, CA
5.49 miles from city centre
£141
Per night
Explore top-rated hotels

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

There are 7 airports in San Jose: San Jose International, San Jose Reid-Hillview, Oakland Metropolitan Oak, San Francisco International, Concord, Carmel Monterey Peninsula, and Sacramento Stockton.
The best price we found for a return flight from Chicago to San Jose is £126. 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 44 minutes is the average flight time from Chicago to San Jose.
Southwest Airlines and United fly direct from Chicago to San Jose.
As of February 2026, there are 88 flights per week flying from Chicago to San Jose.
The cheapest month to fly from Chicago to San Jose is usually April.
If you're flying from Chicago, the cheapest airport near San Jose is San Jose International – which is 2.9 miles away from the centre of San Jose. We've found flights into this airport from £126.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to San Jose on Wednesday, 29 April 2026.
Yes – the average flight time is 4 hours and 44 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 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.
In February, the average temperature is usually around 10°C. August is typically the warmest month in San Jose, when it usually averages around 28°C. You can expect the least rain in July. The coldest month is January, with temperatures averaging 5°C. The rainiest month is February.
The cheapest airline that flies to San Jose is Frontier Airlines. And the cheapest airline that flies to San Jose Reid-Hillview Airport is Southwest Airlines.

Travelling from Chicago to San Jose: what you need to know

  • Start planning your holiday by checking out the departure points for your flight from Chicago to San Jose. Explore your options for leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.

  • When it comes to where you'll disembark, San Jose's primary entry point is Norman Y. Mineta San Jose International Airport (SJC).

  • The average length of a direct Chicago to San Jose flight is 4 hours 35 minutes.

  • San Jose's timezone is UTC-7, making San Jose two hours behind Chicago.

  • The busiest route for flights from Chicago to San Jose is from O'Hare International Airport (ORD) to Norman Y. Mineta San Jose International Airport (SJC). There are seven weekly services between these two airports. If you want to be on your way as soon as possible, the earliest flight from ORD to SJC is the 09:00 United Airlines option. If you prefer to travel later, the last scheduled departure is at 20:00 with United Airlines.

  • Allow plenty of time to catch your Chicago to San Jose flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • Flying during a peak time such as August? Major public holidays and other high seasons can lead to longer queues at check-in and security. Play it safe and get there up to four hours ahead of an international flight and two hours before domestic departures.

How to find the cheapest flights from Chicago to San Jose

  • At the moment, £75 is the lowest price we've found for a one-way ticket from Chicago to San Jose. The cheapest price for a return flight is £126. Remember fares can change due to demand at the time of booking.

  • Lock in cheap Chicago to San Jose flights by booking two months ahead. Based on our research, that's the ideal time for picking up a bargain.

  • The best month for finding cheap plane tickets from Chicago to San Jose is May. Use the 'Whole month' tool to compare flight prices, then choose the dates that offer the lowest fares.

  • Snapping up a cheap flight from Chicago to San Jose is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch when there's a better deal.

  • Tailor your trip using filters. Select your preferred departure and arrival times, total journey duration and airlines. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' Chicago to San Jose flights.

Flying from Chicago

O'Hare International Airport (ORD)

  • If you're after a direct flight from Chicago to San Jose, you can depart from O'Hare International Airport (ORD). Fly from ORD to Norman Y. Mineta San Jose International Airport (SJC) in one continuous trip.

  • United Airlines is a well-known airline that offers direct Chicago to San Jose plane tickets from ORD.

  • Located around 26 kms (16 miles) from central Chicago, ORD can be reached in about 35 minutes by car, depending on traffic. The journey on public transport will take roughly 55 minutes.

  • In search of a convenient hotel near O'Hare International Airport? If you've booked an early flight from Chicago to San Jose, these stays will have you sleeping moments from check-in:

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

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can book a direct flight from Chicago to San Jose out of Chicago Midway International Airport (MDW). Nonstop connections from MDW will get you to Norman Y. Mineta San Jose International Airport (SJC).

  • From MDW, you can lock in a direct Chicago to San Jose plane ticket with Southwest Airlines.

  • You can reach MDW from central Chicago in about 20 minutes by car (depending on traffic conditions). The journey on public transport will take roughly 45 minutes to cover the 14 kms (9 miles) or so.

  • Want to enjoy an extra night away before your flight from Chicago to San Jose? Unwind in a hotel near Chicago Midway International Airport before your trip officially starts. Consider one of these stays:

  • 78% of all departures from Chicago Midway International Airport make it to their destination as expected.

  • You'll find MDW at 5700 South Cicero.

Arriving in San Jose

Norman Y. Mineta San Jose International Airport (SJC)

  • Norman Y. Mineta San Jose International Airport (SJC) to central San Jose takes about 10 minutes by car. The centre is roughly 5 kms (3 miles) away.

  • It typically takes 45 minutes to get there when travelling by public transport.

  • The last thing you need is a long journey to your hotel if you're arriving on a late flight from Chicago to San Jose. Reserve one of these accommodation options near SJC instead:

  • Say yes to new adventures by picking up a Norman Y. Mineta San Jose International Airport rental car. Grab a set of wheels from Europcar, Fox - Rent A Car or Dollar to explore San Jose and beyond.

  • To lock in the lowest price, book your ride from Norman Y. Mineta San Jose International Airport about one week ahead of your Chicago to San Jose flight.

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

Best time to go to San Jose

  • It's time to figure out your trip dates for your flight from Chicago to San Jose. August is the most popular month for a trip to San Jose. If you like a more relaxed atmosphere, go in May.

  • When booking your Chicago to San Jose tickets, think about what kind of weather works for you. August is the warmest month in San Jose, with temperatures ranging from 11ºC (52ºF) to 32ºC (90ºF).

  • If you want cooler conditions, look for a cheap flight from Chicago to San Jose in January when temperatures average between 3ºC (37ºF) and 18ºC (64ºF).

More about San Jose

  • When it comes to searching for somewhere to rest your head, you'll find the best places to stay in San Jose right here. Browse these hotels after you've booked your flight from Chicago to San Jose:

  • Winchester Mystery House and Rosicrucian Egyptian Museum are a couple of top-rated attractions to put on your San Jose to-do list. Continue your sightseeing adventures at San Jose Museum of Art.

Explore more of United States

  • Los Angeles is just one of the many cities in United States waiting to be explored once you've seen San Jose. Around 310 miles to the south-east, popular attractions include Griffith Observatory, The Broad and La Brea Tar Pits & Museum.

  • If you're eager to discover another major destination in United States, head for San Francisco, roughly 40 miles north-west of San Jose. Golden Gate Bridge, Alcatraz Island and Lombard Street are key highlights.

Plan the rest of your trip from Chicago to San Jose

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