$195 Find Cheap Flights from San José to Chicago - Compare and Save

Among airlines operating San José to Chicago flights:

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

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

Only United Airlines operates flights between San José and Chicago.

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).

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
• JetBlue: a cabin bag in Economy Class class
• Azul: a cabin bag in Economy Class class

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

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

• Economy Class
• Business Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $319 round-trip via Fort Lauderdale (FLL), compared to $475 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$70 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

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

• Panama City Tocumen Intl (PTY) - 32% of one-stop connections
• Fort Lauderdale (FLL) - 21% of one-stop connections
• Houston George Bush Intcntl (IAH) - 15% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 7% of one-stop connections

Panama City Tocumen Intl (PTY) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 20% on the San José to Chicago route. Tuesday is the cheapest departure day at $440 round-trip on average, while Saturday is the most expensive at $544, a difference of $104. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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, 6% of flights were delayed in the past 3 months, with delays averaging 3 hours 38 minutes.

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

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.

Last-minute fares on this route - booked within 2 weeks of departure - run 7% above the route average of $489. Book 4 weeks before departure for the lowest fares.

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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $365 to $2,647. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from San José to Chicago are currently in line with typical prices for this route. Average one-way fares are about $339.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Guatemala City La Aurora (GUA) gives the shortest average 1-stop total travel time at 7h 52m, compared with 8h 04m via Atlanta Hartsfield-Jackson (ATL) and 8h 16m via Houston Hobby (HOU).

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.

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 from around $17:

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

Near Chicago Midway Airport (MDW) — daily rates from around $32:

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

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

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

Round-trip flights from San José to Chicago range from $393 to $592, with an average of $489 over the past 12 months. Anything below $393 counts as a good deal.