SJC to MDW (San Jose to Chicago) Flights

Last Minute Flights from SJC to MDW

Best airfare and ticket deals for SJC to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
SJCChicagoApril 19 to April 26$615
*Prices include taxes and fees

Cheapest SJC to MDW Flights

Best airfare and ticket deals for SJC to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
SJCChicagoMay 7 to May 15$298
SJCChicagoMay 18 to June 4$318
SJCChicagoMay 19 to June 4$330
SJCChicagoMay 18 to May 31$338
*Prices include taxes and fees
SJC to MDW Flight Details
Origin airport
Norman Y. Mineta San Jose Intl.
Origin airport IATA code
SJC
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
1833 mi

Frequently asked questions

Which airlines with flights from San Jose, CA Airport (SJC-Norman Y. Mineta San Jose Intl.) to MDW allow free cancellation due to COVID-19?
Enter your origin, destination and travel dates, then click the big green “Find the best flight deals” button. Once the search results are displayed, check the “No change fee” box underneath the “Flexible change policies” filter on the left. Before you book your San Jose, CA Airport (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL Airport (MDW-Midway Intl.) seats, read the airline’s COVID-19 travel-related policies so you know exactly what can and can’t be changed.
What airlines fly direct from SJC to MDW?
Southwest Airlines (WN) does. Book a seat on one of the 30 monthly flights that take off from SJC and jet straight to Chicago Airport. Skipping an irritating stopover is a perfect way to start your getaway.
How many flights are there from SJC to MDW?
Approximately 51 a day. If you’re in a rush to fly to Chicago, see if you can find a last-minute deal from San Jose, CA Airport (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL Airport (MDW-Midway Intl.) and then lock it in right away!
How long does it take to fly from San Jose, CA Airport (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
Around 5 hours and 39 minutes. Booked on a daytime flight? Secure a seat next to the window and enjoy the views. Otherwise, if you’re jetting from San Jose, CA Airport (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL Airport (MDW-Midway Intl.) when it’s dark, catch some z’s and touch down in Chicago feeling rested and recharged.
What is the flight distance from San Jose, CA Airport (SJC-Norman Y. Mineta San Jose Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
A laptop full of cool stuff to watch will help fill in time on this medium-haul trip of 1850 miles (3000 km). While you’ll likely have some in-flight entertainment, there’s nothing like having an exciting TV series waiting for you to press play.
How many morning flights are there from SJC to MDW?
Fasten your seat belt and get from SJC to MDW on one of the 136 morning flights every week. Southwest Airlines (WN) operates 125 weekly services taking off before midday. 6:30AM is the earliest departure time you can book with this airline.
How many afternoon flights are there from SJC to MDW?
With 227 weekly afternoon and evening flights from SJC to MDW, you can forget about setting your alarm. Browse the deals with Southwest Airlines (WN) and book one of the 210 flights every week that jet out after midday. The first departs at 12:00PM.
What is the earliest departure time out of San Jose to Chicago?
6:30AM is the earliest scheduled departure out of SJC, touching down at MDW at 10:15PM. Save precious time in the morning by having your luggage packed and ready to be tossed in the boot.
What is the latest departure time out of San Jose to Chicago?
The latest flight is scheduled to depart SJC at 9:45PM and arrives at 3:00PM at MDW. You’ll have ample time to get ready for this trip.
What is the average price from San Jose to Chicago?
You can find a round-trip flight from SJC to MDW from around $298. The cheapest deals disappear quickly, so book as soon as you’ve figured out your travel dates. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

San Jose to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from San Jose to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from SJC to MDW, we’ve got you covered here at Flights.com.

We present you with some of the hottest deals on airfare so stop that Google flights search. We want you to spend less on your flight from San Jose to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.