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Chicago to San Jose Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Chicago to San Jose

Departure Arrival Travel dates Round-trip
CHI SJO Wed, Oct 8 - Wed, Oct 22 $359
CHI SJO Mon, Jan 26 - Thu, Jan 29 $516
CHI SJO Thu, Feb 12 - Fri, Feb 20 $558
CHI SJO Tue, Sep 23 - Fri, Oct 3 $565
CHI SJO Fri, Jan 30 - Sun, Feb 1 $592
CHI SJO Mon, Sep 22 - Mon, Oct 6 $655
CHI SJO Mon, Sep 22 - Mon, Oct 6 $661
CHI SJO Tue, Sep 2 - Tue, Sep 9 $678
CHI SJO Wed, Jan 21 - Mon, Jan 26 $725
CHI SJO Wed, Feb 25 - Thu, Feb 26 $768

Chicago and San Jose airports and terminals

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from ORD to SJO

    Terminal Carriers
    Terminal 1 United Airlines
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Airports in San Jose , CR
map of airports in San Jose
  • 1

    Juan Santamaria Intl (SJO)

    Distance from City Center: 10 miles

    Terminals and carriers for flights from CHI to SJO

    Terminal Carriers
    Terminal M United Airlines
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Cheap flights from Chicago to San Jose

Sun Mon Tue Wed Thu Fri Sat
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24 25
$389
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$389
27 28 29 30
$389
31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured San Jose Airport Hotels

Hotel only $89

Courtyard San Jose Airport Alajuela

3 stars
4.0 / 5 27 reviews

Radial Francisco J. Orlich,Plaza Los Mangos Map

Rate Includes Breakfast

...Located just 4 minutes from the Juan Santamaria San Juan Airport Costa Rica, this LEED-constructed Alajuela hotel features a modern lobby with 24-hour Market and GoBoard information center, plus... More

Hotel only $96

Holiday Inn Express SAN JOSE COSTA RICA AIRPORT

3 stars
4.1 / 5 55 reviews

1 KM EAST OF JUAN SANTAMARIA ARPT Map

...Airport-adjacent hotel with a free breakfast buffet and 24-hour shuttle The Holiday Inn Express San Jose Costa Rica Airport sits just one mile from the international airport and only 10 miles... More

Alajuela Backpackers Airport Hostel

2 stars
1.0 / 5 1 reviews

SJO Airport Avenue, 4th street Map

Alajuela Backpackers hostel is located just 4km west of the Juan Santamaria International Airport (SJO).... More

Hotel only $88

El Rodeo Estancia Boutique Hotel and Steakhouse

3 stars
3.2 / 5 6 reviews

49-4005 Map

FREE WiFi & Breakfast

El rodeo is a four-star hotel located only 10 minutes away from the Juan Santamaria International Airport, and in the heart of the latest bustling business and commercial district Lindora Santa... More

Hotel only $54

Hotel Catedral Casa Cornejo

3 stars
Not yet reviewed

Avenue 1 Street 1 Northeast Corner of Cathedral Map

Special Rate! - Book Now and Save

...Located less than 5 minutes away from the International Airport Juan Santamaria.... More

Hotel only $92

Hampton Inn & Suites by Hilton San Jose-Airport

2 stars
4.2 / 5 34 reviews

Hwy 1 Airport Blvd Map

...San Jose hotel near the airport with free breakfast and a pool The Hampton Inn & Suites Airport-San Jose hotel sits just minutes from the international airport and downtown San Jose, making it... More

August

Cheapest weekend flights in August from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Aug 14 Chicago (ORD) San Jose (SJO) Spirit Airlines $531
Earn $5.31
Return Mon, Aug 18 San Jose (SJO) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in August from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Aug 26 Chicago (ORD) San Jose (SJO) Spirit Airlines $389
Earn $3.89
Return Wed, Sep 3 San Jose (SJO) Chicago (ORD) Spirit Airlines

Best one-week trip in August from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Aug 31 Chicago (ORD) San Jose (SJO) Spirit Airlines $424
Earn $4.24
Return Sun, Sep 7 San Jose (SJO) Chicago (ORD) Spirit Airlines
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September

Cheapest weekend flights in September from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 18 Chicago (ORD) San Jose (SJO) Spirit Airlines $419
Earn $4.19
Return Mon, Sep 22 San Jose (SJO) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in September from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Sep 7 Chicago (ORD) San Jose (SJO) Spirit Airlines $359
Earn $3.59
Return Sat, Nov 15 San Jose (SJO) Chicago (ORD) Spirit Airlines

Best one-week trip in September from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Sep 16 Chicago (ORD) San Jose (SJO) Spirit Airlines $359
Earn $3.59
Return Tue, Sep 23 San Jose (SJO) Chicago (ORD) Spirit Airlines
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October

Cheapest weekend flights in October from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 30 Chicago (ORD) San Jose (SJO) Spirit Airlines $359
Earn $3.59
Return Mon, Nov 3 San Jose (SJO) Chicago (ORD) Spirit Airlines

Lowest roundtrip airfare in October from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Oct 27 Chicago (ORD) San Jose (SJO) Spirit Airlines $359
Earn $3.59
Return Fri, Oct 31 San Jose (SJO) Chicago (ORD) Spirit Airlines

Best one-week trip in October from Chicago to San Jose

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 7 Chicago (ORD) San Jose (SJO) Spirit Airlines $359
Earn $3.59
Return Tue, Oct 14 San Jose (SJO) Chicago (ORD) Spirit Airlines
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Find Cheap Flights from Chicago to San Jose

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

San Jose Airport Information

When you use Orbitz.com to purchase your air ticket, you will have a variety of cheap flights to San Jose to choose from. There are nine air passenger carriers that service the Mineta San José International Airport. American Airlines, Delta, Hawaiian Airlines, JetBlue, United, US Airways and Volaris use Terminal A, while Southwest and Alaska Airlines use Terminal B. The airport offers easy access to the city, as it is less than five miles northwest of downtown San Jose.

Ground Transportation in San Jose

If you hop on the VTA Airport Flyer, you will be able to access the Amtrak, the Metro Light Rail and Caltrain railways, Greyhound buses and the Bay Area Rapid Transit (BART). The Monterey Airbus and Santa Cruz Airport Flyer also make scheduled stops at the airport. There are several cab companies that service the airport, with fares between $15 and $20 for transportation into downtown San Jose. Book your flight with Orbitz.com, and you can also find deals on hotels that offer free airport shuttle service, or you can simply rent a car so that you can get around during your stay.

San Jose Weather Information

San Jose gets very little rainfall, and the year-round temperatures are rather moderate. You can expect the winter months to be in the low 40s to high 50s, and the summer months rarely venture higher than the low 80s. Nights can be cool in San Jose, so make sure you pack a light jacket or layer your clothes to accommodate the change in temperature.

What to Do in San Jose

If you're traveling with children, be sure to visit the Raging Waters water park, the Happy Hollow Park and Zoo and the Children's Discovery Museum of San Jose. Adults might prefer to visit one of the many museums, art galleries and theaters in San Jose. Whatever you decide to do while you're there, don't forget to come back to Orbitz.com to book cheap flights to San Jose for your next trip.

Aircraft options between Chicago and San Jose

Equipment Carrier
Boeing 737-800 Passenger United Airlines