$216 Find Cheap Flights from San José to Chicago - Compare and Save

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

• Earliest: departs at 1:05 pm and lands at 6:38 pm
• Latest: departs at 1:55 pm and lands at 7:28 pm.

The flight takes about 5h 33m.

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

• Economy Class
• Business Class
• First Class

A nonstop flight from San José to Chicago takes 5h 33m, covering 2,211 miles.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Round-trip flights from San José to Chicago range from $399 to $618, with an average of $504 over the past 12 months. Anything below $399 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 12% above the $504 route average. Book 8 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $348 round-trip via Monterrey Gen Mariano Escobedo (MTY), compared to $488 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $50–$70 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $383 to $2,619. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from San José to Chicago are currently higher than usual. Average one-way flight prices are about $397, which is 11% above 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 José to Chicago usually depart from San José Juan Santamaria Intl (SJO) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Morning flights have the fewest delays on this route, while afternoon departures tend to have the most.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the San José to Chicago route, 5% of flights were delayed in the past 3 months, with delays averaging 3h 45m.

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

• Panama City Tocumen Intl (PTY) - 31% of one-stop connections
• Houston George Bush Intcntl (IAH) - 19% of one-stop connections
• Fort Lauderdale (FLL) - 12% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 11% of one-stop connections

Yes. Flexible dates can save you up to 19% on flights from San José to Chicago. Tuesday is the cheapest departure day at $469 round-trip on average, while Sunday is the most expensive at $574, a difference of $105.

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 United Airlines operates flights between San José and Chicago.

Flying via Houston Hobby (HOU) gives the shortest average 1-stop total travel time at 8h 14m, compared with 8h 18m via Charlotte Douglas (CLT) and 8h 19m via Atlanta Hartsfield-Jackson (ATL).

Chicago is 1 hour ahead of San José (Central Time vs Central 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 José to Chicago flights:

• United Airlines: offers extra legroom; 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
• Avianca: a cabin bag in Economy Class class
• Copa Airlines: a cabin bag in Economy Class class

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