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Cheap Flights from San Jose International to Chicago O'Hare International

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      Travellers and cabin class, 1 Adult, Economy
      United

      Compare San Jose International to Chicago O'Hare International flight deals

      Find the cheapest month or even day of the year to fly to Chicago O'Hare International

      Book the best Chicago O'Hare International fare with no extra fees

      Flight deals from San Jose International to Chicago O'Hare International

      Looking for a cheap last-minute deal or the best return flight from San Jose International Airport to Chicago O'Hare International Airport? If you want to travel next month, return fares start from R 3,349. Find the lowest prices on one-way and return tickets right here.
      Chicago.R 1,491 per passenger.Departing Mon, 19 Oct.One-way 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.Price includes taxes and charges.From R 1,491, select.
      Chicago.R 1,674 per passenger.Departing Thu, 12 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Jose International on Thu, 12 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,674, select.
      Chicago.R 1,839 per passenger.Departing Thu, 24 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Jose International on Thu, 24 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,839, select.
      Chicago.R 1,886 per passenger.Departing Sat, 5 Dec.One-way flight with United.Outbound direct flight with United departs from San Jose International on Sat, 5 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,886, select.
      Chicago.R 1,886 per passenger.Departing Sat, 23 Jan.One-way flight with United.Outbound direct flight with United departs from San Jose International on Sat, 23 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,886, select.
      Chicago.R 2,056 per passenger.Departing Tue, 27 Oct.One-way flight with United.Outbound direct flight with United departs from San Jose International on Tue, 27 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,056, select.
      Chicago.R 2,056 per passenger.Departing Sat, 26 Sep.One-way flight with United.Outbound direct flight with United departs from San Jose International on Sat, 26 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,056, select.
      Chicago.R 2,740 per passenger.Departing Tue, 25 May.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from San Jose International on Tue, 25 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,740, select.
      Chicago.R 2,779 per passenger.Departing Tue, 9 Mar.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from San Jose International on Tue, 9 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,779, select.
      Chicago.R 2,856 per passenger.Departing Wed, 11 Nov.One-way flight with United.Outbound direct flight with United departs from San Jose International on Wed, 11 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,856, select.
      Chicago.R 3,141 per passenger.Departing Thu, 22 Jul.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from San Jose International on Thu, 22 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,141, select.
      Chicago.R 3,247 per passenger.Departing Sat, 13 Feb.One-way flight with United.Outbound direct flight with United departs from San Jose International on Sat, 13 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,247, select.
      Chicago.R 3,638 per passenger.Departing Mon, 12 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Jose International on Mon, 12 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,638, select.
      Chicago.R 3,910 per passenger.Departing Mon, 12 Apr.One-way flight with United.Outbound direct flight with United departs from San Jose International on Mon, 12 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,910, select.
      Chicago.R 4,024 per passenger.Departing Sun, 11 Jul.One-way flight with United.Outbound direct flight with United departs from San Jose International on Sun, 11 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 4,024, select.
      Chicago.R 4,281 per passenger.Departing Tue, 9 Mar.One-way flight with United.Outbound direct flight with United departs from San Jose International on Tue, 9 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 4,281, select.

      Find the cheapest month to fly from San Jose International to Chicago O'Hare International

      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 O'Hare International flights are currently cheapest in October.
      Sep
      from R 1,839
      Oct
      from R 1,491
      Nov
      from R 1,674
      Dec
      from R 1,886
      Jan
      from R 1,886
      Feb
      from R 3,247
      Mar
      from R 2,779
      Apr
      from R 3,638
      May
      from R 2,740
      Jun
      Find prices
      Jul
      from R 3,141
      Aug
      Find prices

      Direct flights from San Jose International to Chicago O'Hare International

      United

      San Jose International to Chicago O'Hare International: Alternative routes

      Compare routes from San Jose International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

      Chicago Midway

      14km from central Chicago
      Closest
      from R 1,886
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from R 1,491
      Search flights

      Chicago Rockford

      127km from central Chicago
      from R 2,593
      Search flights

      San Jose to Chicago: Flight information

      The things to know before you go.
      Cheapest flight foundR 1,491
      Cheapest month to flyOctober
      Average flight time4 hrs, 23 mins
      Most popular airlineUnited
      Average flights per week11

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

      The best price we found for a return flight from San Jose International to Chicago O'Hare International is R 3,349. 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 23 minutes is the average flight time from San Jose International to Chicago O'Hare International.
      United flies direct from San Jose International to Chicago O'Hare International.
      As of September 2026, there are 11 flights per week flying from San Jose International to Chicago O'Hare International.
      The cheapest month to fly from San Jose International to Chicago O'Hare International is usually October.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Jose International Airport to Chicago O'Hare International Airport on Friday, 9 October 2026.
      Yes – the average flight time is 4 hours and 23 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 O'Hare 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Frontier Airlines and United offer the cheapest flight tickets to Chicago O'Hare International.

      Travelling from San Jose International Airport (SJC) to Chicago O'Hare International Airport (ORD): what you need to know

      • Around 4 hours 25 minutes is how long you can expect to be in the air on a direct flight from San Jose International Airport to Chicago O'Hare International Airport.

      • Chicago's timezone is UTC-6, making Chicago two hours ahead of San Jose.

      • There are six San Jose International Airport to Chicago O'Hare International Airport flights every week to choose from.

      • To ensure you catch your SJC to ORD flight, leave enough time to check in and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the standard rule.

      • You'll likely experience longer lines during popular months like July. Arriving up to four hours in advance for international flights and two hours for domestic departures is a smart move.

      • United is your ticket to exploring Chicago (and perhaps some other great parts of the United States!). Browse the direct flights from San Jose International Airport to Chicago O'Hare International Airport offered by this airline.

      • Most passengers choose to fly with United on this route.

      • United ranks as the leading on-time carrier for SJC to ORD flights, with 90.57% of its services arriving on schedule.

      • If you'd like to include a stop along the way, simply deselect 'Direct flights only' when searching for your ticket from San Jose International Airport to Chicago O'Hare International Airport. These are the top stopovers between SJC and ORD:

        • Denver International Airport

        • Phoenix Sky Harbour Airport

        • Salt Lake City Airport

      Handy information about San Jose International Airport (SJC)

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

      • San Jose International Airport maintains a solid on-time record, reducing the likelihood of delays. Departures from SJC arrive on schedule 83% of the time.

      • To get to San Jose International Airport from central San Jose, it'll take about 10 minutes if you're going by car. Of course, this depends on traffic conditions. It's approximately 6 kilometres from the airport to the city centre.

      • The trip when using public transport takes about 30 minutes.

      • Taking an early flight from San Jose International Airport to Chicago O'Hare International Airport? Avoid the stress of rushing to the terminal (and get some extra shut-eye) by picking one of these stays near SJC:

      Arriving at Chicago O'Hare International Airport (ORD)

      Getting from Chicago O'Hare International Airport (ORD) to central Chicago

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

      • Chicago O'Hare International Airport is approximately 27 kilometres from central Chicago. Driving there takes about 30 minutes.

      • If you're taking public transport, expect a journey of roughly 45 minutes.

      When to fly to Chicago O'Hare International Airport (ORD)

      • It's time to plan your dates for your flight from San Jose International Airport to Chicago O'Hare International Airport. July is the busiest month to head to Chicago. If you prefer a more laid-back vibe, go in March.

      • When booking your flight from San Jose International Airport to Chicago O'Hare International Airport, think about the kind of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 16ºC (61ºF) to 28ºC (82ºF).

      • Look for cheap tickets from SJC to ORD in January if you like cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

      Explore more of the United States

      • Chicago has loads to offer, but there are so many other corners of the United States waiting to be discovered. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep you on the move. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in the United States. Experience this destination's highlights firsthand at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.