$171 Find Cheap Flights from Chicago Midway Airport to San Jose - Compare and Save

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

• Earliest: departs at 9:35 am and lands at 2:17 pm
• Latest: departs at 9:20 pm and lands at 2:02 am.

The flight takes about 4h 42m.

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

A nonstop flight from Chicago Midway Airport to San Jose takes 4h 42m, covering 1,832 miles.

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.

Round-trip flights from Chicago Midway Airport to San Jose range from $390 to $617, with an average of $471 over the past 12 months. Anything below $390 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 77% above the $471 route average. Book 17 weeks before departure for the lowest fares.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $467 round-trip, compared to $502 via a layover through Los Angeles (LAX).

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 Boeing 737-800 variants.

Morning is the busiest departure period on Chicago Midway Airport to San Jose flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $297 to $2,106. That means the highest observed fare was about 7x 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 $182, which is 38% below the typical average for this route.

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
• Dollar
• Thrifty
• Hertz

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

One-stop flights from Chicago Midway Airport to San Jose most commonly connect through:

• Denver Intl (DEN) - 33% of one-stop connections
• Los Angeles (LAX) - 33% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 17% of one-stop connections
• Guadalajara Miguel Hidal (GDL) - 8% of one-stop connections

Yes. Flexible dates can save you up to 46% on flights from Chicago Midway Airport to San Jose. 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.

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

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 18m, compared with 6h 20m via Phoenix Sky Harbor Intl (PHX) and 6h 29m via Los Angeles (LAX).

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.

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

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.

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 always check the fare details before booking.