149 € Cheap Flights from San Jose to Chicago

Compare San Jose to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from San Jose to Chicago

Looking for a cheap last-minute deal or the best return flight from San Jose to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from San Jose to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Jose to Chicago flights are currently cheapest in March.

Direct flights from San Jose to Chicago

San Jose to Chicago: Flight information

The things to know before you go.
Cheapest flight found149 €
Cheapest month to flyMarch
Average flight time4 hrs, 15 mins
Most popular airlineSouthwest Airlines
Average flights per week23

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from San Jose to Chicago is 149 €. 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 14 minutes is the average flight time from San Jose to Chicago.
Southwest Airlines and United fly direct from San Jose to Chicago.
As of February 2026, there are 23 flights per week flying from San Jose to Chicago.
The cheapest month to fly from San Jose to Chicago is usually March.
If you're flying from San Jose, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from 149 €.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Jose to Chicago on Monday, 16 March 2026.
Yes – the average flight time is 4 hours and 14 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Hawaiian Airlines. And the cheapest airline that flies to Chicago O'Hare International Airport is United.

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

  • Many exciting adventures kick off from San Jose's main airport, Norman Y. Mineta San Jose International Airport (SJC). Check out the options for reserving a flight from San Jose to Chicago leaving from this terminal.

  • When it comes to landing in Chicago, O'Hare International Airport (ORD) is a major hub. Another is Chicago Midway International Airport (MDW).

  • Book a direct San Jose to Chicago flight and you'll be travelling for an average of 4 hours 15 minutes.

  • Chicago's timezone is UTC-5, which makes Chicago two hours ahead of San Jose.

  • The busiest route for flights from San Jose to Chicago is from Norman Y. Mineta San Jose International Airport (SJC) to Chicago Midway International Airport (MDW). Take your pick of seven weekly services between these two airports. If you want to head off as soon as possible, the earliest flight from SJC to MDW is the 06:35 Southwest Airlines service. If you prefer travelling later, the final scheduled service is at 18:25 with Southwest Airlines.

  • For a relaxed travel experience, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to catch your San Jose to Chicago flight.

  • Travelling during a peak time such as August? School holidays and other popular periods can lead to longer lines and delays at security. Play it safe and arrive up to four hours before an international flight and two hours before a domestic departure.

How to find the cheapest flights from San Jose to Chicago

  • To snag cheap San Jose to Chicago flights, reserve your trip two months ahead of your planned departure.

  • Schedule your trip for May. That's the best month for landing great bargains on plane tickets from San Jose to Chicago. If you're flexible with your travel dates, use the 'Whole month' tool to see the cheapest price across each month.

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

  • Choose your preferred arrival and departure times, number of stops and airlines with the filters. Or sort your San Jose to Chicago flight results by 'Best,' 'Fastest' or 'Cheapest.'

Flying from San Jose

Norman Y. Mineta San Jose International Airport (SJC)

  • Start your journey at Norman Y. Mineta San Jose International Airport (SJC), which has a range of direct flights from San Jose to Chicago. From SJC, you can fly seamlessly to O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

  • Look out for deals with Southwest Airlines. This airline offers direct San Jose to Chicago plane tickets out of SJC.

  • SJC is about 5 kilometres from central San Jose. If you're ride-sharing, catching a cab or driving from the centre, it'll take 10 minutes or so to get there, depending on traffic conditions. If you're planning to take public transport, expect the travel time to be around 45 minutes.

  • After a relaxed start to your travels? Stay near Norman Y. Mineta San Jose International Airport. Whether you're boarding an early flight from San Jose to Chicago or just don't want to be rushed, these hotels are ideal:

  • Norman Y. Mineta San Jose International Airport maintains a solid on-time performance, making delays less likely. Departures from SJC land at their destination as scheduled 84.69% of the time.

  • SJC's address is 1701 Airport Boulevard, Suite B-1130.

Arriving in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is approximately 26 kilometres. It'll take you around 35 minutes to reach the centre driving.

  • If you're travelling on public transport, expect a journey time of about 55 minutes.

  • If you're coming in on a late flight from San Jose to Chicago, few things beat the convenience of staying close to the terminal. Grab your suitcases from the carousel and then be showered and sleeping not long after at one of these accommodation options near ORD:

  • Grab an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are top providers to choose from here.

  • Get the best deal by booking your ride from O'Hare International Airport around four weeks ahead of your trip.

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

Chicago Midway International Airport (MDW)

  • As soon as your flight from San Jose to Chicago has hit the runway, you can get to the city centre in around 20 minutes by car. Central Chicago is approximately 14 kilometres from Chicago Midway International Airport (MDW).

  • If you're travelling on public transport, it'll take around 45 minutes.

  • You'll find some great places ready to welcome you near MDW. Unwind after your San Jose to Chicago flight at one of these perfectly located options:

  • The fastest way to reach your destination is with a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and get going in the blink of an eye.

  • Lock in the lowest price by booking your ride from MDW four weeks ahead of time. You can also expect to have a bigger selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is roughly 129 kilometres from central Chicago. It'll take you about 1 hour 25 minutes to get to the city centre by car once you've hopped off your flight from San Jose to Chicago.

  • Public transport will get you there in about 4 hours 15 minutes.

  • Whether you'd like a budget-friendly compact just for you or a spacious SUV to transport your group, you'll find the ideal Chicago Rockford International Airport rental car for your needs. Explore wheels available from companies such as Budget, Alamo and National.

  • Booking a couple of weeks in advance of your flight from San Jose to Chicago is smart. Along with better deals, you'll likely have a better variety of makes and models to choose from at RFD.

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

Best time to go to Chicago

  • January is the quietest month for flights from San Jose to Chicago, while August is the most popular. Work out the ideal time to go to Chicago based on whether you want a laid-back vibe or a lively atmosphere.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your San Jose to Chicago ticket then if that's your ideal forecast.

  • Search for cheap flights from San Jose to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Chicago has plenty to offer, but there are so many other parts of United States waiting to be explored. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary busy. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another essential stop in United States and is around 257 kilometres south-east of Chicago. No trip is complete without experiencing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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