Cheap flights from Silicon Valley (SJC) to Chicago (CHI)

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Lowest round trip fares by airline from Silicon Valley and Chicago

Cheapest prices ($54 One Way, $137 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is $96 per night from May 27 to May 28
$96
per night
May 27 - May 28
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.6/10 Good! (1,003 reviews)
"nice location and pretty bar inside the hotel"

Reviewed on May 6, 2024

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $112 per night from May 12 to May 13
$112
per night
May 12 - May 13
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.2/10 (1,635 reviews)
Amazing stay while in Chicago
"I had an amazing time staying here. Highly recommend. I felt safe and the staff was so accommodating. Clean room and literally under 20 minutes from the airport."

Reviewed on May 7, 2024

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $55 per night from May 14 to May 15
$55
per night
May 14 - May 15
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,171 reviews)
Convenient, clean, efficient
"This place has always been convenient, clean, friendly. The staff are really great. Estela at the front desk is an absolute gem. She will bend over backwards to accommodate you and can multitask like no other."

Reviewed on May 7, 2024

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Silicon Valley to Chicago

Origin
Silicon Valley
Destination
Chicago
Number of Daily Flights
76
Earliest Flight Departure Date
May 17
Latest Flight Departure Date
May 18
Popular Airlines
United Airlines

Cheap flights from San Jose to Chicago

After your flight from San Jose, you'll want to rent a car to see all of Chicago properly. From the airport, you can easily reach downtown by taking I-90 or I-94. Once downtown, you can bask in front of famous paintings in the Art Institute, catch a concert by the magnificent Chicago Symphony Orchestra or pose by Cloud Gate, a sculpture that's also nicknamed "The Bean" for its shape.

Key Facts

Chicago is a sports-centered city where you can catch a match by any major league sport; the Bulls, Blackhawks, Fire, White Sox and Cubs all call Chicago home. If sports don't excite you, take a leisurely walk along Lake Michigan on the Lakefront Trail, see animals at the free Lincoln Park Zoo, or have some laughs at a Second City performance. Foodies can appreciate authentic Mexican food in the Pilsen neighborhood, or a deep-dish pizza from one of the many pizzerias.

Hints and Tips

The flight from San Jose International Airport (SJC) to Chicago takes about five hours. Because Chicago O'Hare International Airport (ORD) is a major transportation hub, you can easily catch a connecting flight. If you have a long layover, head for Navy Pier to relax and check out the view.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.