Cheap Flights from San Jose International to Chicago

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Compare San Jose International to Chicago flight deals

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

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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 $351. Find the lowest prices on one-way and return tickets right here.

Chicago.$351 per passenger.Departing Mon, 19 Oct, returning Wed, 21 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Jose International on Mon, 19 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 21 Oct, arriving in San Jose International.Price includes taxes and charges.From $351, select.

Chicago.$448 per passenger.Departing Fri, 9 Oct, returning Thu, 12 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Jose International on Fri, 9 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 12 Nov, arriving in San Jose International.Price includes taxes and charges.From $448, select.

Chicago.$458 per passenger.Departing Mon, 2 Nov, returning Thu, 5 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Jose International on Mon, 2 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 5 Nov, arriving in San Jose International.Price includes taxes and charges.From $458, select.

Chicago.$498 per passenger.Departing Sat, 17 Oct, returning Sat, 24 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Sat, 17 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 24 Oct, arriving in San Jose International.Price includes taxes and charges.From $498, select.

Chicago.$498 per passenger.Departing Sat, 31 Oct, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Sat, 31 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 7 Nov, arriving in San Jose International.Price includes taxes and charges.From $498, select.

Chicago.$498 per passenger.Departing Wed, 4 Nov, returning Wed, 11 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Wed, 4 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 11 Nov, arriving in San Jose International.Price includes taxes and charges.From $498, select.

Chicago.$527 per passenger.Departing Wed, 16 Dec, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Jose International on Wed, 16 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 5 Jan, arriving in San Jose International.Price includes taxes and charges.From $527, select.

Chicago.$535 per passenger.Departing Thu, 12 Nov, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Thu, 12 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Dec, arriving in San Jose International.Price includes taxes and charges.From $535, select.

Chicago.$577 per passenger.Departing Wed, 2 Dec, returning Wed, 9 Dec.Return flight with United.Outbound direct flight with United departs from San Jose International on Wed, 2 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 9 Dec, arriving in San Jose International.Price includes taxes and charges.From $577, select.

Chicago.$578 per passenger.Departing Thu, 21 Jan, returning Thu, 28 Jan.Return flight with United.Outbound direct flight with United departs from San Jose International on Thu, 21 Jan, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Thu, 28 Jan, arriving in San Jose International.Price includes taxes and charges.From $578, select.

Chicago.$589 per passenger.Departing Thu, 31 Dec, returning Thu, 14 Jan.Return flight with United.Outbound direct flight with United departs from San Jose International on Thu, 31 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Thu, 14 Jan, arriving in San Jose International.Price includes taxes and charges.From $589, select.

Chicago.$624 per passenger.Departing Mon, 1 Feb, returning Fri, 5 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Mon, 1 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 5 Feb, arriving in San Jose International.Price includes taxes and charges.From $624, select.

Chicago.$711 per passenger.Departing Tue, 20 Apr, returning Sun, 25 Apr.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from San Jose International on Tue, 20 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Sun, 25 Apr, arriving in San Jose International.Price includes taxes and charges.From $711, select.

Chicago.$753 per passenger.Departing Wed, 14 Apr, returning Sat, 17 Apr.Return flight with United.Outbound direct flight with United departs from San Jose International on Wed, 14 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 17 Apr, arriving in San Jose International.Price includes taxes and charges.From $753, select.

Chicago.$787 per passenger.Departing Mon, 26 Jul, returning Fri, 30 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from San Jose International on Mon, 26 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 30 Jul, arriving in San Jose International.Price includes taxes and charges.From $787, select.

Chicago.$788 per passenger.Departing Fri, 14 May, returning Fri, 28 May.Return flight with Delta.Outbound indirect flight with Delta, departs from San Jose International on Fri, 14 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Fri, 28 May, arriving in San Jose International.Price includes taxes and charges.From $788, select.

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 October.

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Direct flights from San Jose International to Chicago

Alternative San Jose International to Chicago routes

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

San Jose to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$351
Cheapest month to fly	October
Average flight time	4 hrs, 14 mins
Most popular airline	Southwest Airlines
Average flights per week	60

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

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from San Jose International to Chicago?

The best price we found for a return flight from San Jose International to Chicago is $351. 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.

How long does it take to fly from San Jose International to Chicago?

4 hours and 13 minutes is the average flight time from San Jose International to Chicago.

Which airlines fly direct from San Jose International to Chicago?

Southwest Airlines and United fly direct from San Jose International to Chicago.

How many flights are there a week from San Jose International to Chicago?

As of September 2026, there are 30 flights per week flying from San Jose International to Chicago.

When is the cheapest time to fly from San Jose International to Chicago?

The cheapest month to fly from San Jose International to Chicago is usually October.

Which is the cheapest airport to fly into in Chicago?

If you're flying from San Jose International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from $351.

Which upcoming date is cheapest to fly from San Jose International Airport to Chicago on?

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 Monday, 19 October 2026.

Can I get a direct flight from San Jose International Airport to Chicago?

Yes – the average flight time is 4 hours and 13 minutes.

How can I get the best flight deal from San Jose International Airport to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In September, the average temperature is usually around 20°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.

Which is the cheapest airline to fly from San Jose International Airport to Chicago with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago.

Travelling from San Jose Mineta International Airport (SJC) to Chicago: what you need to know

Expect to be in the air for 4 hours 40 minutes. That's the average time for a direct flight from San Jose Mineta International Airport to Chicago.
Chicago is two hours ahead of San Jose, where San Jose Mineta International Airport is located. Chicago observes the UTC-6 timezone.
With eight weekly flights between the two airports, San Jose Mineta International Airport (SJC) to Chicago Midway International Airport (MDW) is the busiest route. Hop on Southwest Airlines's 06:35 flight to get your trip from SJC to MDW underway.
Give yourself plenty of time to make your SJC to Chicago flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.
During popular months like July, it's a good idea to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead of international flights whenever you're flying during high season in general.
Start your trip at SJC and fly nonstop to Chicago O'Hare International Airport (ORD). That's where you can expect to land when searching for San Jose Mineta International Airport to Chicago tickets.
You can choose from various airlines that operate direct flights from San Jose Mineta International Airport to Chicago, including:
Located around 5 kilometres from central San Jose, SJC can be reached in about 10 minutes by car (depending on traffic). Travelling on public transport takes roughly 30 minutes.
In search of a hotel close to SJC? If you've booked an early flight from San Jose Mineta International Airport to Chicago, these stays set you up for a seamless send-off:
83% of flights departing from San Jose Mineta International Airport reach their destination as planned. With its strong on-time stats, you're unlikely to face delays when jetting out of SJC.
SJC is located at 1701 Airport Boulevard, Suite B-1130.

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

$163 is currently the lowest price for a one-way San Jose Mineta International Airport to Chicago flight. A return plane ticket starts at $351. These fares may change depending on availability and demand.
Booking ahead of time is often the key to locking in a cheap flight from SJC to Chicago. Fares tend to rise as seats fill up, so the closer you get to departure, the more expensive your ticket may be.
Landing cheap tickets from San Jose Mineta International Airport to Chicago is easier if you're flexible with your trip dates. Try using the 'Whole month' function to access the best prices across every month and snap up an awesome deal.
There's no need to check in daily to find out if fares have dropped when you set up a Price Alert. We'll update you the moment there's an even bigger deal on cheap flights from SJC to Chicago.
Pick your preferred arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from San Jose Mineta International Airport to Chicago by 'Best,' 'Fastest' or 'Cheapest.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) is around 27 kilometres from the centre of Chicago. If you're getting a taxi or a ride-share, the drive takes roughly 30 minutes.
Getting to the centre by public transport will take you around 45 minutes.
Book a hotel close to ORD if you're coming in on a late flight from San Jose Mineta International Airport to Chicago. Pick one of these options and make arrival day easier:
Lock in the best deal by reserving your vehicle from Chicago O'Hare International Airport around four weeks in advance 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 San Jose Mineta International Airport to Chicago has arrived, you can make your way to the city centre in about 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).
If you travel by public transport, the ride to the centre takes 30 minutes or so.
Hang the 'Do not disturb' sign on your door and rest at a hotel close to MDW. Here are a few options where you can put your feet up after your SJC to Chicago flight:
Score the best price by booking your ride from MDW four weeks ahead of time. You can also expect to have a greater range of vehicles.
You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Make your way to the city centre after your flight from San Jose Mineta International Airport to Chicago has arrived. Central Chicago is about 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to get to by car.
Public transport can get you there in about 2 hours.
Enjoy a low-stress, comfortable start to your break by staying at a hotel near RFD after your SJC to Chicago flight. Recover from a day of travel or simply give yourself time to settle into a new destination at:
Booking a couple of weeks ahead of your flight from San Jose Mineta International Airport to Chicago is smart. Along with better deals, you'll get a better selection of vehicle makes and models at RFD.
Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from San Jose Mineta International Airport to Chicago, while July is the busiest. Work out the ideal time to go to Chicago based on whether you want a bustling atmosphere or a more laid-back vibe.
The warmest month in Chicago is July, with temperatures ranging between 16ºC and 28ºC. Book your San Jose Mineta International Airport to Chicago plane ticket then if that's the weather you find most pleasant.
January sees average temperatures of between -12ºC and 3ºC. Search for a cheap ticket from SJC to Chicago around that time if you like cooler conditions.

More about Chicago

Start your Chicago trip right by choosing the ideal place to stay. Once you've booked your flight from San Jose Mineta International Airport to Chicago, browse our selection of hotels including:
There are so many things to discover in this city it can be tricky to know where to start. Art Institute of Chicago, Millennium Park and Willis Tower are top sights which should be on any good Chicago itinerary.

Explore more of the United States

You've visited Chicago, now it's time to discover other parts of the United States. Journey about 451 kilometres southeast to Columbus to check off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you'll have a full itinerary ahead.
If you're eager to discover another major stop in the United States, consider Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among its highlights.