$170 Find Cheap Flights from San Jose to Chicago Midway Airport - Compare and Save

Among airlines operating San Jose to Chicago Midway Airport flights:

• Southwest: offers free seat selection

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

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

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

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 San Jose to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $383 round-trip via San Diego (SAN), compared to $478 for nonstop.

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 and United Airlines. Other aircraft seen on the route include Boeing 737-800 Passenger/BBJ2 (winglets) variants.

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

• Denver Intl (DEN) - 67% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 11% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 11% of one-stop connections
• San Diego (SAN) - 11% of one-stop connections

Denver Intl (DEN) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 48% on the San Jose to Chicago Midway Airport route. Wednesday is the cheapest departure day at $407 round-trip on average, while Sunday is the most expensive at $776, a difference of $369. 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 San Jose to Chicago Midway Airport 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 Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

• Earliest: departs at 6:00 am and lands at 10:03 am
• Latest: departs at 11:00 pm and lands at 3:03 am.

The flight takes about 4h 03m.

Last-minute fares on this route - booked within 2 weeks of departure - run 87% above the route average of $496. Book 15 weeks before departure for the lowest fares.

A nonstop flight from San Jose to Chicago Midway Airport takes 4h 03m, 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $293 to $2,169. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from San Jose to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $178, which is 37% below the typical average for this route.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 07m, compared with 6h 29m via Phoenix Sky Harbor Intl (PHX) and 7h 33m via Atlanta Hartsfield-Jackson (ATL).

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

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Round-trip flights from San Jose to Chicago Midway Airport range from $395 to $588, with an average of $496 over the past 12 months. Anything below $395 counts as a good deal.