$96 Find Cheap Flights from San Jose to Chicago - Compare and Save

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

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

The flight takes about 4h 11m.

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

• Economy Class
• Premium Economy Class
• First Class

A nonstop flight from San Jose to Chicago takes 4h 11m, 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 San Jose to Chicago range from $362 to $584, with an average of $466 over the past 12 months. Anything below $362 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 77% above the $466 route average. Book 18 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $329 round-trip via Seattle/Tacoma Intl (SEA), compared to $495 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 San Jose to Chicago flights, with 50% of flights leaving in that window. Afternoon departures account for 25%, night flights for 25%, and evening 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 $317 to $1,749. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from San Jose to Chicago are currently lower than usual. Average one-way flight prices are about $117, which is 55% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

Near Chicago Midway Airport (MDW) — daily rates averaging $84:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

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

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

• San Diego (SAN) - 51% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 15% of one-stop connections
• Salt Lake City (SLC) - 12% of one-stop connections
• Denver Intl (DEN) - 9% of one-stop connections

Yes. Flexible dates can save you up to 43% on flights from San Jose to Chicago. Wednesday is the cheapest departure day at $414 round-trip on average, while Sunday is the most expensive at $716, a difference of $302.

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 San Jose and Chicago. 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 28m, compared with 6h 30m via Minneapolis St Paul (MSP) and 6h 43m via Denver Intl (DEN).

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

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating San Jose to Chicago 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.

Yes, there is an exchange rate center. Each terminal at O'Hare International Airport has a foreign currency exchange counter operated by Seaway Bank. Seaway is a service that assists passengers in getting ready for their trips to international locations by facilitating the acquisition of foreign currency before departure and currency exchange upon return. There are automated teller machines (ATMs) positioned throughout the airport, both before and after security checkpoints, as well as in each terminal. These ATMs are offered by both local and national financial organizations.

Yes, you can access a nursing room. The Nursing Rooms may be found just inside the door of the women's toilet (with the exception of the Gate 8 site), and they are furnished with a comfy chair, sink, changing station, and outlets.

Yes, there is car rental services. You don’t have to worry when traveling to Chicago O’Hare International Airport (ORD) because there are a variety of car rental services. Car rentals provide flexible rentals with no hidden fees. Rental companies include Alamo, Goldcar, Megadrive, Europcar, Centaura. They are located inside the terminal building, usually in arrivals.

When departing from San Jose International Airport, it is feasible to request special assistance to go through security and to your gate in advance. The airport has accessible facilities as well as additional assistance for those with concealed disabilities. O'Hare International Airport, the airport of arrival, also provides accessible services like wheelchairs and adapted facilities.