$154 Find Cheap Flights from Chicago to San José - Compare and Save

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

• Earliest: departs at 7:02 am and lands at 12:16 pm
• Latest: departs at 7:30 am and lands at 12:44 pm.

The flight takes about 5h 14m.

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

• Economy Class
• Premium Economy Class
• Business Class
• First Class

Prices vary by airline.

A nonstop flight from Chicago to San José takes 5h 14m, 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 Chicago to San José range from $461 to $737, with an average of $570 over the past 12 months. Anything below $461 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 2% above the $570 route average. Book 7 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $401 round-trip via Monterrey Gen Mariano Escobedo (MTY), compared to $572 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 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 $407 to $3,086. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Chicago to San José are currently in line with typical prices for this route. Average one-way fares are about $291.

San José Juan Santamaria Intl Airport (SJO) hosts 5 major car rental companies, with daily rates starting from around $1 for economy cars. Top options include:

• Priceless
• Avis
• Budget
• Routes Car & Truck Rentals
• Payless

Flights from Chicago to San José 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 José Juan Santamaria Intl (SJO).

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 Chicago to San José route, 20% of flights were delayed in the past 3 months, with delays averaging 2h 29m.

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

• Panama City Tocumen Intl (PTY) - 26% of one-stop connections
• Fort Lauderdale (FLL) - 18% of one-stop connections
• Houston George Bush Intcntl (IAH) - 17% of one-stop connections
• Miami (MIA) - 8% of one-stop connections

Yes. Flexible dates can save you up to 24% on flights from Chicago to San José. Tuesday is the cheapest departure day at $529 round-trip on average, while Saturday is the most expensive at $690, a difference of $161.

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 Chicago and San José.

Flying via Houston Hobby (HOU) gives the shortest average 1-stop total travel time at 8h 06m, compared with 8h 13m via Charlotte Douglas (CLT) and 8h 20m via Atlanta Hartsfield-Jackson (ATL).

San José is 1 hour behind Chicago (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in San José are Parque Metropolitano La Sabana, Estadio Nacional de Costa Rica and Museo de Oro. These are among the most viewed places in San José on KAYAK.

Among airlines operating Chicago to San José 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
• Azul: a cabin bag and a checked bag in Business 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.

Passengers on flights from Chicago to San Jose release roughly 4433 lb of carbon, respectively. The eco-friendliest airlines servicing this route include Spirit Airlines, American Airlines, and Delta, which emit 39%, 38%, and 36% less carbon, respectively. American Airlines' green initiatives include implementing one-engine taxiing, Spirit Airlines features fuel-efficient aircraft, and Delta has reduced single-use plastics onboard.

Passengers arriving in San Jose from Chicago can take a bus, taxi, or shuttle to the city center. You can book a cab at the taxi kiosks near the Customs office inside SJO. The Station Wagon and Tuasa bus are across the main terminal exit and stop at Avenia 2 near Merced Park. Interbus operates shuttle buses, and you can book online or board one at the shuttle bus stop opposite the main terminal.

Frontier and United Airlines allow small dogs and cats on board, provided you comply with their guidelines. Ensure your pet containers are roomy, ventilated, and fit under an airplane seat. Pets entering San Jose should be vaccinated and have a Veterinary Certificate for Costa Rica issued by a licensed USDA veterinarian.

Depending on your airline, flights from Chicago to San Jose may have a connection. Spirit Airlines flights stop at Orlando International Airport (MCO) or Fort Lauderdale-Hollywood International Airport (FLL), American Airlines flights at Charlotte Douglas International Airport (CLT) or Dallas/Fort Worth International Airport (DFW), and United Airlines flights at George Bush Intercontinental Airport (IAH).