₹29,407 Cheap Flights from San Jose (SJC) to Chicago (MDW)

View ₹29,407 flight on Thu, 7 Aug 2025Opens in a new window

Popular airlines from Norman Y. Mineta San Jose Intl. Airport (SJC) to Chicago Midway Airport (MDW)

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Cheap Flights from San Jose (SJC) to Chicago (MDW)

Prices were available within the past 7 days and start at ₹29,407 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from San Jose (SJC) to Chicago (MDW)

October is typically the cheapest month to fly

From ₹11,838 - ₹49,561 per traveller.

Graph displaying average flight prices per month

Flight from San Jose to Chicago route information
Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
Midway Intl.
Distance
2933 km
Average flight time
7 hours 55 mins

San Jose to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from San Jose to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with SJC to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind San Jose for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from San Jose Intl. Airport to Midway Intl. Airport (MDW)?
Pack your bags, because round-trip flights from San Jose Intl. Airport to Chicago Airport start from . That's based on airfares available within the last 7 days on Expedia for flights departing within the next year. Prices can rise quickly, so book now to score the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from San Jose Intl. Airport to Midway Airport?
Every air carrier has different terms and conditions. If you decide to cancel your escape, head to our Customer Service Portal.
How do I find cheap flights from San Jose Intl. Airport to MDW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for San Jose Intl. Airport to Midway Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from SJC to Midway Intl. Airport (MDW)?
The flight distance between Norman Y. Mineta San Jose Intl. Airport (SJC) (SJC) and Midway Intl. Airport (MDW) (MDW) is 3,000 kilometres. Close your eyes or finish that novel and the trip will zip by.
Which airlines fly direct from San Jose Intl. Airport to MDW?
A favourite with many travellers, Southwest Airlines (WN) operates 21 flights every month from San Jose Intl. Airport to Chicago Airport. Pick the one that fits in with your travel plans and book your seat today.
Are San Jose Intl. Airport to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Norman Y. Mineta San Jose Intl. Airport (SJC) to MDW can be hit-or-miss. You might be lucky and score a bargain, but then again, you could miss out entirely! If you'd prefer to play it safe and start your trip planning early on, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines advertise their prices that far in advance. Our advice? Check back often as updates are made frequently.

Explore a world of travel with Expedia

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