$159 Find Cheap Flights from Chicago to San Jose - Compare and Save

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

• Earliest: departs at 6:00 am and lands at 10:49 am
• Latest: departs at 9:15 pm and lands at 2:04 am.

The flight takes about 4h 49m.

Two cabin classes are available on flights from Chicago to San Jose:

• Economy Class
• First Class

A nonstop flight from Chicago to San Jose takes 4h 49m, covering 1,838 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 to San Jose range from $359 to $603, with an average of $450 over the past 12 months. Anything below $359 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 78% above the $450 route average. Book 5 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $328 round-trip via Portland (PDX), compared to $471 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Morning is the busiest departure period on Chicago to San Jose flights, with 67% of flights leaving in that window. Evening departures account for 33%, afternoon 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 $338 to $1,660. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from Chicago to San Jose are currently lower than usual. Average one-way flight prices are about $164, which is 40% below the typical average for this route.

San Jose Airport (SJC) hosts 5 major car rental companies, with daily rates averaging $59 for economy cars. Top options include:

• Europcar
• Fox
• Dollar
• Thrifty
• Hertz

Flights from Chicago to San Jose may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at San Jose (SJC).

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

• San Diego (SAN) - 48% of one-stop connections
• Seattle/Tacoma Intl (SEA) - 11% of one-stop connections
• Denver Intl (DEN) - 8% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 7% of one-stop connections

Yes. Flexible dates can save you up to 41% on flights from Chicago to San Jose. Thursday is the cheapest departure day at $423 round-trip on average, while Sunday is the most expensive at $709, a difference of $286.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

2 airlines operate flights between Chicago and San Jose. The airlines offering nonstop flights on this route include:

• Southwest
• United Airlines

Flying via Salt Lake City (SLC) gives the shortest average 1-stop total travel time at 6h 30m, compared with 6h 49m via Denver Intl (DEN) and 6h 55m via Las Vegas Harry Reid Intl (LAS).

San Jose is 2 hours behind Chicago (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 to San Jose flights:

• United Airlines: offers extra legroom; offers free seat selection
• 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:

• United Airlines: a cabin bag and a checked bag in Economy Class
• 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.

No. SJC is located in San Jose, California, in Silicon Valley. SJO is also a San Jose airport, but in Central America. SJO is the code for the Juan Santamaría International Airport located in San Jose, the capitol city of Costa Rica. These two airports are very easy to confuse when you are booking your ticket, so be extra careful.

Yes. United Airlines, American Airlines, and Alaska Airlines are among the carriers that fly nonstop from ORD to SJC. Southwest flies nonstop from MDW to SJC. United, American, Delta, Alaska, and Spirit Airlines all operate one-stop and two-stop flights from ORD to SJC with layovers and cities such as Minneapolis (MSP), Los Angeles (LAX) and Phoenix (PHX). Delta and primarily Southwest fly one and two-stop flights to from MDW to SJC with layovers and cities such as Minneapolis (MSP), Denver (DEN), and Las Vegas (LAS).

Yes. ORD has two USO lounges, and MDW has one. The lounges at ORD are located landside in Terminal 2 an airside in Terminal 3. The USO at Midway is post-security on Concourse C. Active-duty members of the US military and their families can enjoy the benefits of these lounges free of charge. Amenities include devices for connectivity and entertainment, comfy and relaxing furniture, refreshments, information, and more.

Yes, the Hilton Chicago O'Hare Airport hotel is across from Terminal 2 and connected to all the different terminals by way of an underground walkway. Amenities include an indoor pool, room service, a business center, wheelchair accessibility, and much more.