$119 Find Cheap Flights from Chicago Midway Airport to San Jose - Compare and Save

Among airlines operating Chicago Midway Airport to San Jose flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Chicago Midway Airport and San Jose.

Flights from Chicago Midway Airport to San Jose usually depart from Chicago Midway (MDW) and arrive at San Jose (SJC).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Chicago Midway Airport to San Jose.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $470 round-trip, compared to $666 via a layover through Phoenix Sky Harbor Intl (PHX).

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest. Other aircraft seen on the route include Airbus A319 variants.

Most connecting flights from Chicago Midway Airport to San Jose pass through Phoenix Sky Harbor Intl (PHX), which handles 100% of one-stop traffic on this route. Other layover airports each see under 5%.

Yes. Being flexible with your travel dates can save you up to 46% on the Chicago Midway Airport to San Jose route. Tuesday is the cheapest departure day at $387 round-trip on average, while Sunday is the most expensive at $713, a difference of $326. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Chicago Midway Airport to San Jose flights, with 50% of flights leaving in that window. Night departures account for 50%, afternoon flights for 0%, and evening flights for 0%.

Some of the most popular sights in San Jose are San Jose McEnery Convention Center, SAP Center at San Jose and Santana Row. These are among the most viewed places in San Jose on KAYAK.

A nonstop flight from Chicago Midway Airport to San Jose takes 4h 34m, covering 1,832 miles.

These are the earliest and latest flight times available from Chicago Midway Airport to San Jose:

• Earliest: departs at 9:50 am and lands at 2:24 pm
• Latest: departs at 9:20 pm and lands at 1:54 am.

The flight takes about 4h 34m.

Last-minute fares on this route - booked within 2 weeks of departure - run 76% above the route average of $473. Book 17 weeks before departure for the lowest fares.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $243 to $2,277. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Chicago Midway Airport to San Jose are currently lower than usual. Average one-way flight prices are about $121, which is 57% below the typical average for this route.

San Jose is 2 hours behind Chicago Midway Airport (Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

San Jose Airport (SJC) hosts 5 major car rental companies, with daily rates starting from around $18 for economy cars. Top options include:
· Europcar
· Fox
· Thrifty
· Dollar
· Hertz

Round-trip flights from Chicago Midway Airport to San Jose range from $389 to $606, with an average of $473 over the past 12 months. Anything below $389 counts as a good deal.