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Cheap Flights from Chicago Midway to San Jose International

Compare Chicago Midway to San Jose International flight deals

Find the cheapest month or even day of the year to fly to San Jose International

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Flight deals from Chicago Midway to San Jose International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to San Jose International Airport? If you want to travel next month, return fares start from R 4,187. Find the lowest prices on one-way and return tickets right here.
San Jose.R 1,946 per passenger.Departing Tue, 25 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 25 Aug, arriving in San Jose International.Price includes taxes and charges.From R 1,946, select.
San Jose.R 1,948 per passenger.Departing Tue, 5 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 May, arriving in San Jose International.Price includes taxes and charges.From R 1,948, select.
San Jose.R 2,107 per passenger.Departing Wed, 17 Jun.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 17 Jun, arriving in San Jose International.Price includes taxes and charges.From R 2,107, select.
San Jose.R 2,179 per passenger.Departing Thu, 4 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 4 Jun, arriving in San Jose International.Price includes taxes and charges.From R 2,179, select.
San Jose.R 3,145 per passenger.Departing Tue, 1 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Sep, arriving in San Jose International.Price includes taxes and charges.From R 3,145, select.
San Jose.R 3,225 per passenger.Departing Wed, 29 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 29 Apr, arriving in San Jose International.Price includes taxes and charges.From R 3,225, select.
San Jose.R 3,319 per passenger.Departing Thu, 2 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 2 Jul, arriving in San Jose International.Price includes taxes and charges.From R 3,319, select.
San Jose.R 3,347 per passenger.Departing Thu, 15 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 15 Oct, arriving in San Jose International.Price includes taxes and charges.From R 3,347, select.
San Jose.R 3,604 per passenger.Departing Sat, 7 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 7 Nov, arriving in San Jose International.Price includes taxes and charges.From R 3,604, select.
San Jose.R 4,543 per passenger.Departing Tue, 28 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Apr, arriving in San Jose International.Price includes taxes and charges.From R 4,543, select.
San Jose.R 8,205 per passenger.Departing Sun, 27 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sun, 27 Dec, arriving in San Jose International.Price includes taxes and charges.From R 8,205, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to San Jose International flights are currently cheapest in August.
Apr
from R 3,225
May
from R 1,948
Jun
from R 2,107
Jul
from R 3,319
Aug
from R 1,946
Sep
from R 3,145
Oct
from R 3,347
Nov
from R 3,604
Dec
from R 8,205
Jan
Find prices
Feb
Find prices
Mar
Find prices

Direct flights from Chicago Midway to San Jose International

Chicago Midway to San Jose International: Alternative routes

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

San Jose International

5km from central San Jose
Closest
from R 1,946
Search flights

San Jose Reid-Hillview

6km from central San Jose
Search flights

Oakland Metropolitan Oak

52km from central San Jose
from R 1,946
Search flights

San Francisco International

53km from central San Jose
Cheapest
from R 1,305
Search flights

Concord

74km from central San Jose
Search flights

Carmel Monterey Peninsula

83km from central San Jose
from R 2,646
Search flights

Sacramento Stockton

85km from central San Jose
from R 2,896
Search flights

Chicago to San Jose: Flight information

The things to know before you go.
Cheapest flight foundR 1,946
Cheapest month to flyAugust
Average flight time4 hrs, 32 mins
Most popular airlineSouthwest Airlines
Average flights per week15

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

The best price we found for a return flight from Chicago Midway to San Jose International is R 4,187. 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 32 minutes is the average flight time from Chicago Midway to San Jose International.
Southwest Airlines flies direct from Chicago Midway to San Jose International.
As of April 2026, there are 15 flights per week flying from Chicago Midway to San Jose International.
The cheapest month to fly from Chicago Midway to San Jose International is usually May.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Jose International Airport on Wednesday, 13 May 2026.
Yes – the average flight time is 4 hours and 32 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 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 San Jose is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to San Jose International.

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

  • Around 4 hours 35 minutes is how long you'll be travelling on a direct flight from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport.

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

  • Flights from MDW to SJC start at 08:10 — the first with Southwest Airlines. The last departure is at 20:20 with Southwest Airlines. Overall, there are eight weekly Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport flights.

  • Give yourself plenty of time to catch your MDW to SJC flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • During popular months like July, it's best to get to the airport earlier than normal. Arrive two hours before domestic departures and four hours ahead for an international flight whenever you're flying during a peak period in general.

  • Flying into San Jose (and then seeing more of United States!) is easy with Southwest Airlines. This popular airline offers direct flights from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport.

  • The airline that tops the list for bookings on this route is Southwest Airlines.

  • The most punctual carrier that operates MDW to SJC flights is Southwest Airlines. Its services arrive as scheduled 73.77% of the time.

  • We make it a piece of cake to book a flight with a stopover. To see all your options for tickets from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport, deselect 'Direct flights only.' Then, choose a flight offering a stop long enough to tour your chosen city. Some great stopovers between MDW and SJC include:

    • Denver International Airport

    • Minneapolis-St. Paul International Airport

    • Los Angeles International Airport

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

  • R 1,946 is currently the lowest price for a one-way Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport flight. A return flight starts from R 4,187. These prices may change based on demand.

  • To score cheap tickets from MDW to SJC, reserve your trip six months before your departure.

  • May is the cheapest month for flights from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport. If you need to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

  • Snapping up cheap flights from MDW to SJC is a breeze with Price Alerts. Simply create one of these automatic alerts and we'll let you know as soon as a new deal comes up.

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

Handy information about Chicago Midway International Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • Of the flights that depart from Chicago Midway International Airport, 77.88% arrive as scheduled at their destination.

  • To get to Chicago Midway International Airport from central Chicago, it'll take about 20 minutes if you're going by car. Of course, this depends on traffic conditions. It's approximately 19 kilometres from the airport to the city centre.

  • The journey on public transport usually takes 45 minutes.

  • Searching for a handy hotel close to MDW? If you're catching an early flight from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport, these stays will have you sleeping moments from your check-in counter:

Arriving at Norman Y. Mineta San Jose International Airport (SJC)

  • If you're landing on a late Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport flight, nothing beats the convenience of staying near the terminal. Pick up your bags from the carousel and then be tucked up in bed not long after at one of these options near SJC:

  • Pick up a Norman Y. Mineta San Jose International Airport rental car and explore San Jose and beyond with your own set of wheels. Europcar, Fox - Rent A Car and Dollar are popular providers you can book with here.

  • To secure the lowest price, book your vehicle from Norman Y. Mineta San Jose International Airport around one week before you travel.

Getting from Norman Y. Mineta San Jose International Airport (SJC) to central San Jose

  • SJC is located at 1701 Airport Boulevard, Suite B-1130.

  • Norman Y. Mineta San Jose International Airport to the centre of San Jose has a drive time of around 10 minutes. It's approximately 6 kilometres away.

  • It typically takes 45 minutes if you're travelling by public transport.

When to fly to Norman Y. Mineta San Jose International Airport (SJC)

  • The quietest month for a flight from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport is May, while August is the most popular. Choose the ideal time to visit San Jose based on whether you prefer a more relaxed vibe or a faster pace.

  • Before locking in your flight from Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport, think about the type of weather you enjoy. August is the warmest month in San Jose, with temperatures ranging from 11ºC (52ºF) to 32ºC (90ºF).

  • Look for cheap tickets from MDW to SJC in January if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between 3ºC (37ºF) and 18ºC (64ºF) on average.

Explore more of United States

  • You've done San Jose, now it's time to discover other parts of United States. Travel about 499 kilometres south-east to Los Angeles to tick off its leading attractions. From Griffith Observatory to The Broad and La Brea Tar Pits & Museum, your itinerary will be busy.

  • Around 64 kilometres north-west of San Jose, San Francisco is another favourite stop in United States. No visit is complete without checking out Golden Gate Bridge, Alcatraz Island and Lombard Street.

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