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

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Delta Flights from SJC to MDW

How much is a Delta flight from San Jose (SJC) to Chicago (MDW)?

One-way flights start as little as and there are roundtrips available from . Get in! You can score some sweet deals with Wotif and Delta.

How many non-stop Delta flights from San Jose (SJC) to Chicago (MDW) are there per day?

Delta flies flights direct every day between San Jose (SJC) and Chicago (MDW).

How far is San Jose (SJC) from Chicago (MDW)?

It’s from San Jose (SJC) to Chicago (MDW).

What is the best airline to fly from Norman Y. Mineta San Jose Intl.?

At Wotif, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Norman Y. Mineta San Jose Intl. with: . 

Can I change or cancel my Delta tickets from San Jose to Chicago on Wotif?

Change of plans? No worries! We’re right here to make things as easy as possible. Check out the Delta rules and restrictions in your itinerary. You can also use the No Change Fees filter to find flexible plane tickets for future trips. For more information on how to cancel or change your flight on Wotif, visit our customer service portal.

How do I find the best deal on Delta flights from San Jose (SJC) to Chicago (MDW)?

Just review and compare all our awesome offers or enter your travel dates to see more terrific deals on Delta flights from San Jose. And remember you can save even more when you bundle a hotel with your flight as part of a Wotif package. Sweet!

What’s a good way to get cheap Delta flight tickets from San Jose to Chicago?

We have loads of cheap flights, so just enter your travel dates to see what’s available. If you can be flexible on when you fly, you’ll find even more epic flight deals. So get booking!

What is the cheapest time of year to fly from San Jose (SJC) to Chicago (MDW)?

The cheapest time of the year for a return trip is . One-way, the cheapest month to fly is . Check our deal cards for details.

How long does it take to fly from SJC to MDW?

It typically takes hours to fly directly from San Jose (SJC) to Chicago (MDW).

Epic Hotel in Chicago

Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
"Satisfied with the overall stay."

Reviewed on 4 May 2025

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Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
"It is a good place to stay as it is close to downtown and many attractions are in walking distance. I like that parking is available close by though it comes with a cost."

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Holiday Inn & Suites Chicago - Downtown by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
"AMAZING AMAZING AMAZING…LOVED IT SO MUCH VERY SECURED…everything is near and very walkable…the subway does make noise but we were both heavy sleepers so we didn’t mind……also extremely clean"

Reviewed on 3 May 2025

Sonder South Wabash
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.