Flight tickets from San Jose International to Chicago

Compare San Jose International to Chicago flight deals

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Flight deals from San Jose International to Chicago

Looking for a cheap last-minute deal or the best return flight from San Jose International Airport to Chicago? If you want to travel next month, return fares start from ₹ 19,947. Find the lowest prices on one-way and return tickets right here.

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

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

Direct flights from San Jose International to Chicago

San Jose to Chicago: Flight information

The things to know before you go.
Cheapest flight found₹ 10,445
Cheapest month to flyMay
Average flight time4 hrs, 14 mins
Most popular airlineSouthwest Airlines
Average flights per week26

Finding cheap flights from San Jose International 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 International to Chicago is ₹ 19,421. 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 International to Chicago.
Southwest Airlines and United fly direct from San Jose International to Chicago.
As of May 2026, there are 26 flights per week flying from San Jose International to Chicago.
The cheapest month to fly from San Jose International to Chicago is usually May.
If you're flying from San Jose International Airport, 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 ₹ 19,421.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Jose International Airport to Chicago on Sunday, 24 May 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 May, the average temperature is usually around 13°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.
Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago.

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

  • The average length of a direct flight from Norman Y. Mineta San Jose International Airport to Chicago is 4 hours 40 minutes.

  • Chicago is two hours ahead of San Jose, where Norman Y. Mineta San Jose International Airport is located. Chicago observes the UTC-5 timezone.

  • The busiest route is from Norman Y. Mineta San Jose International Airport (SJC) to Chicago Midway International Airport (MDW). You can select from seven weekly services between these two airports. Southwest Airlines offers a 06:35 departure between SJC and MDW.

  • To avoid missing your SJC to Chicago flight, allow plenty of time to check in and drop off your luggage. Arriving two hours ahead of international departures and one hour before domestic flights is the general rule.

  • Delays at security and check-in are more likely if you're flying during high season, so allow some extra breathing room. A good general rule for peak times? Get there up to four hours ahead for international flights and at least two hours for domestic departures.

  • Start your journey at SJC and fly straight to O'Hare International Airport (ORD). That's where you can expect to land when searching for Norman Y. Mineta San Jose International Airport to Chicago tickets.

  • Book your ticket with Southwest Airlines. This leading carrier offers direct flights from Norman Y. Mineta San Jose International Airport to Chicago.

  • Located around 5 kilometres from the centre of San Jose, SJC can be reached in about 10 minutes by car, depending on traffic. Travelling on public transport takes roughly 45 minutes.

  • Want a stress-free start to your holiday? Stay near SJC. Whether you've booked an early flight from Norman Y. Mineta San Jose International Airport to Chicago or just don't like being rushed, these hotels are worth a look:

  • Norman Y. Mineta San Jose International Airport gets top marks for its on-time performance. 84.69% of flights that depart SJC land on time.

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

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

  • The lowest price we've seen for a one-way Norman Y. Mineta San Jose International Airport to Chicago flight is ₹ 10,445. The cheapest price for a return flight is ₹ 19,421. Bear in mind fares may change due to availability at the time of booking.

  • To secure cheap flights from SJC to Chicago, reserve your journey one month ahead of your departure date.

  • Organise your trip for May. That's the best month for landing the biggest deals on Norman Y. Mineta San Jose International Airport to Chicago tickets. If you're flexible with your dates, use the 'Whole month' tool to find the cheapest price across each month.

  • Snapping up a cheap flight from SJC to Chicago is a breeze with Price Alerts. Simply create one of these automatic notifications and we'll get in touch as soon as a cheaper option becomes available.

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

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes about 35 minutes to get to the centre driving.

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

  • Look into staying at a hotel close to ORD if you're coming in on a late flight from Norman Y. Mineta San Jose International Airport to Chicago. Choose one of these options and make your arrival easier:

  • Pick up an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are well-known companies to choose from here.

  • Lock in the lowest price by reserving your vehicle from O'Hare International Airport about four weeks ahead of your flight from SJC to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Norman Y. Mineta San Jose International Airport to Chicago has hit the runway, you can reach the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • If you travel by public transport, you'll reach the centre in 45 minutes or so.

  • You'll find some great places to park your luggage (and yourself) near MDW. Unwind and get cosy after your SJC to Chicago flight at one of these perfectly located options:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car quick and easy. These providers are located in or around the terminal and will have you behind the wheel before you know it.

  • Snap up the best price by securing your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from the centre of Chicago. It'll take you about 1 hour 25 minutes to reach the city centre by car once you've hopped off your flight from Norman Y. Mineta San Jose International Airport to Chicago.

  • The journey takes about 4 hours 15 minutes using public transport.

  • Enjoy a quiet, low-key start to your trip by staying at a hotel near RFD after your SJC to Chicago flight. Rest up after a long day of travel or just take a moment to find your footing in a new city at:

  • Begin your journey without worrying about how to get to your destination with a Chicago Rockford International Airport rental car. Book your ideal wheels with reliable companies here like Budget, Alamo and National.

  • Booking at least a few weeks in advance of your flight from Norman Y. Mineta San Jose International Airport to Chicago is a smart way to go. Along with better deals, you'll have a wider selection of vehicle makes and models at RFD.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your dates before securing your flight from Norman Y. Mineta San Jose International Airport to Chicago. The city buzzes in peak season, but hotel prices are often higher and major attractions can be busy. Visit Chicago in low season for a quieter vibe.

  • When booking your Norman Y. Mineta San Jose International Airport to Chicago flight ticket, think about what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • If you want to travel in cooler conditions, look for a cheap ticket from SJC to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

  • Start your Chicago trip right by choosing the ideal place to stay. After booking your flight from Norman Y. Mineta San Jose International Airport to Chicago, browse our range of accommodation options including:

  • Art Institute of Chicago and Millennium Park are just the start of the major attractions to add to your Chicago travel itinerary. Keep the momentum going by heading to LandShark Beer Garden at Navy Pier.

Explore more of United States

  • Chicago is always a good idea, but there are so many other parts of United States waiting to be explored. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep your itinerary packed. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another standout destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without dropping by 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.