By Huuk Team
Share Your Trip
Excited about your upcoming trip? Share the adventure with your friends!
Road trip from Chicago to San Jose
All Category
Sights & Landmarks
Nature & Parks
Outdoor Activities
Water & Amusement Parks
Museums
Fun & Games
ShoppingShow more (4+)
All Category
Sights & LandmarksNature & ParksOutdoor ActivitiesWater & Amusement ParksMuseumsFun & GamesShopping
Nightlife
Classes & Workshops
Spas & WellnessReset
Show less
ITINERARY
37h 30m2,167 miles17 stops
1
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
2
Boystown
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
3
Wrigley Field
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
4
Anderson's Bookshop
5
Riverwalk
6
Arista Spa & Salon
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
7
Fitness Sports
Iowa's first Specialty Running & Walking store with a emphasis on personal service. Ou r stone motto is "Where You have the Right to B-Fit". Est. in 1984.
8
Red Butte Garden
Red Butte Garden is the largest botanical garden in the Intermountain West and, together with the University of Utah, is the state arboretum. The Garden has welcomed guests since 1985 and consists of over 21 acres of developed gardens and five miles of hiking trails winding through an extensive Natural Area. All just minutes away from downtown Salt Lake City. The Garden is renowned for plant collections, themed gardens, over 560,000 springtime blooms, gorgeous private rental spaces, a world-class summer concert series, and award-winning horticulture-based educational programs.
9
Sugar House Park
Once the site of Utah Territorial Prison, this park is a lot more pleasant today, with a gently rolling landscape great for running.
10
Ryan's Saloon & Broiler
11
Wilbur D. May Center
MUSEUM/ GIFT SHOP/ ARBORETUM/ EVENT VENUE/ The Wilbur D. May Center is located in Rancho San Rafael Regional Park at 1595 North Sierra, Reno, Nevada. The Wilbur D. May Museum features rotating exhibits for the whole family, smaller art shows, the permanent collection of Wilbur May's travels around the globe, an adjoining botanical garden, and plays home to many events throughout the year such as weddings, executive fundraisers, and educational seminars.
12
Enchambered: Sacramento Escape Room
Real Escape games let you live the game. We have real-life escape games where teams of 3-12 people are locked into a custom built, challenging and entertaining environments to solve the many mysteries, puzzles and challenges. You need to unlock the final clues to open the door and escape the room. Escape Rooms are fun for all ages.
13
Old Sacramento Schoolhouse Museum
14
Funderland Amusement Park
Historic Funderland Amusement Park is now open for its 2024 78th Anniversary season! First opened in 1946, Funderland continues to delight generations of Northern California families. Located on two lovely acres in Sacramento's beautiful 100+ year-old William Land Park, Funderland features ten child-sized amusement rides and attractions (nine of which children can also share and ride with their parents and grandparents!), four fun photo ops (perfect for family group shots!), a FunderTreats concession stand featuring delicious food, amusement park treats, and drinks, and plenty of big, mature shade trees! Funderland offers families a delightful day outside in welcoming and comfortable surroundings, and is also the perfect place to have your next birthday party, fundraiser, group, or corporate event! Parking is always free, and Funderland's one-price Gate Admission gives guests of all ages both entry to the park AND unlimited rides for the entire day!
15
Oakland Zoo
Oakland Zoo was established in 1922 and is managed by the Conservation Society of California, a 501(c)3 non-profit organization dedicated to the conservation of wildlife both locally and globally. The Zoo is home to over 850 native and exotic animals. We're recognized for our outstanding animal care, particularly our elephant care program, and for our Leed-certified, 17,000 square foot, state-of-the-art veterinary hospital—the largest wild animal veterinary facility in Northern California. June 2018 introduced Oakland Zoo guests to an entirely new experience, California Trail, a monumental expansion furthering our commitment to animal care, education, and conservation with a focus on this state’s remarkable native wildlife—both past and present.
16
Joaquin Miller Park
17
Oakland California Temple & Visitors' Center
Open to the public, the Oakland California Temple & Visitors' Center is a beautiful and peaceful place to visit. Visitors can walk through the colorful gardens lined with towering palm trees, sit by the fountains and cascading waterfall, enjoy the beautiful view of the San Francisco Bay Area, and feel the peace of the grounds. While you're there, you can take a guided tour at the Visitors' Center, learn more about you're family's history at the FamilySearch Library, and attend events at the Temple Hill Auditorium. Only members of The Church of Jesus Christ of Latter-day Saints can enter the temple itself. A coveted location for photographers, the Oakland Temple is one of the best locations to enjoy a sunset over the Bay. At night, the Oakland Temple is brightly lit and can be seen throughout the Bay Area. Devotionals, concerts, and performances are hosted throughout the month in the Temple Hill Auditorium and most events are free.
Customize this Trip
OVERVIEW
Get ready for an unforgettable journey from the bustling metropolis of Chicago to the vibrant heart of Silicon Valley, San Jose! This epic adventure will take you through diverse landscapes, from the shores of Lake Michigan to the rolling hills of California. Along the way, you'll encounter iconic cities, historical landmarks, and breathtaking natural wonders. Embrace the spirit of exploration as you uncover the hidden gems and rich tapestry of American culture that unfolds before your eyes on this captivating cross-country voyage.
Prepare to be mesmerized by the urban energy of Chicago, a city known for its towering skyscrapers, world-class museums, and vibrant arts scene. Immerse yourself in the Windy City's charm before embarking on your westward journey. As you traverse the vast expanse of the country, marvel at the ever-changing scenery. Witness the serene beauty of the Great Plains, the rugged grandeur of the Rocky Mountains, and the lush greenery of the Pacific Northwest. Each mile traveled will bring you closer to the innovation hub of San Jose, a city brimming with technological advancements and a thriving cultural scene.
Upon arriving in San Jose, embrace the vibrant energy of Silicon Valley, where dreams are born and the future is shaped. Explore the cutting-edge tech companies, delve into interactive museums, and soak up the infectious enthusiasm that drives this region. San Jose offers a harmonious blend of urban sophistication and natural beauty, with its proximity to stunning beaches, redwood forests, and majestic mountains. Let the spirit of discovery guide you as you uncover the countless wonders that await you on this extraordinary journey from Chicago to San Jose.
1
Start:Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
2
Start:Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
3
Start:Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
4
Start:Anderson's Bookshop
Naperville, DuPage County, Illinois·
5.0
(9) review
123 W Jefferson Ave, Naperville, IL 60540-5310
5
Start:Riverwalk
Naperville, DuPage County, Illinois·
4.5
(803) review
West Branch of DuPage River, Naperville, IL
6
Start:Arista Spa & Salon
Naperville, DuPage County, Illinois·
4.0
(9) review
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
7
Start:Fitness Sports
Des Moines, Iowa·
5.0
(9) review
Iowa's first Specialty Running & Walking store with a emphasis on personal service. Ou r stone motto is "Where You have the Right to B-Fit". Est. in 1984.
8
Start:Red Butte Garden
Salt Lake City, Utah·
4.5
(925) review
Red Butte Garden is the largest botanical garden in the Intermountain West and, together with the University of Utah, is the state arboretum. The Garden has welcomed guests since 1985 and consists of over 21 acres of developed gardens and five miles of hiking trails winding through an extensive Natural Area. All just minutes away from downtown Salt Lake City. The Garden is renowned for plant collections, themed gardens, over 560,000 springtime blooms, gorgeous private rental spaces, a world-class summer concert series, and award-winning horticulture-based educational programs.
9
Start:Sugar House Park
Salt Lake City, Utah·
4.5
(99) review
Once the site of Utah Territorial Prison, this park is a lot more pleasant today, with a gently rolling landscape great for running.
10
Start:Ryan's Saloon & Broiler
Reno, Nevada·
4.5
(9) review
924 S Wells Ave, Reno, NV 89502-2522
11
Start:Wilbur D. May Center
Reno, Nevada·
4.5
(97) review
MUSEUM/ GIFT SHOP/ ARBORETUM/ EVENT VENUE/ The Wilbur D. May Center is located in Rancho San Rafael Regional Park at 1595 North Sierra, Reno, Nevada. The Wilbur D. May Museum features rotating exhibits for the whole family, smaller art shows, the permanent collection of Wilbur May's travels around the globe, an adjoining botanical garden, and plays home to many events throughout the year such as weddings, executive fundraisers, and educational seminars.
12
Start:Enchambered: Sacramento Escape Room
Sacramento, California·
5.0
(98) review
Real Escape games let you live the game. We have real-life escape games where teams of 3-12 people are locked into a custom built, challenging and entertaining environments to solve the many mysteries, puzzles and challenges. You need to unlock the final clues to open the door and escape the room. Escape Rooms are fun for all ages.
13
Start:Old Sacramento Schoolhouse Museum
Sacramento, California·
4.0
(98) review
1200 Front St, Sacramento, CA 95814-3247
14
Start:Funderland Amusement Park
Sacramento, California·
4.0
(99) review
Historic Funderland Amusement Park is now open for its 2024 78th Anniversary season! First opened in 1946, Funderland continues to delight generations of Northern California families. Located on two lovely acres in Sacramento's beautiful 100+ year-old William Land Park, Funderland features ten child-sized amusement rides and attractions (nine of which children can also share and ride with their parents and grandparents!), four fun photo ops (perfect for family group shots!), a FunderTreats concession stand featuring delicious food, amusement park treats, and drinks, and plenty of big, mature shade trees! Funderland offers families a delightful day outside in welcoming and comfortable surroundings, and is also the perfect place to have your next birthday party, fundraiser, group, or corporate event! Parking is always free, and Funderland's one-price Gate Admission gives guests of all ages both entry to the park AND unlimited rides for the entire day!
15
Start:Oakland Zoo
Oakland, California·
4.5
(710) review
Oakland Zoo was established in 1922 and is managed by the Conservation Society of California, a 501(c)3 non-profit organization dedicated to the conservation of wildlife both locally and globally. The Zoo is home to over 850 native and exotic animals. We're recognized for our outstanding animal care, particularly our elephant care program, and for our Leed-certified, 17,000 square foot, state-of-the-art veterinary hospital—the largest wild animal veterinary facility in Northern California. June 2018 introduced Oakland Zoo guests to an entirely new experience, California Trail, a monumental expansion furthering our commitment to animal care, education, and conservation with a focus on this state’s remarkable native wildlife—both past and present.
16
Start:Joaquin Miller Park
Oakland, California·
4.5
(42) review
3450 Joaquin Miller Rd, Oakland, CA 94602
17
Start:Oakland California Temple & Visitors' Center
Oakland, California·
5.0
(940) review
Open to the public, the Oakland California Temple & Visitors' Center is a beautiful and peaceful place to visit. Visitors can walk through the colorful gardens lined with towering palm trees, sit by the fountains and cascading waterfall, enjoy the beautiful view of the San Francisco Bay Area, and feel the peace of the grounds. While you're there, you can take a guided tour at the Visitors' Center, learn more about you're family's history at the FamilySearch Library, and attend events at the Temple Hill Auditorium. Only members of The Church of Jesus Christ of Latter-day Saints can enter the temple itself. A coveted location for photographers, the Oakland Temple is one of the best locations to enjoy a sunset over the Bay. At night, the Oakland Temple is brightly lit and can be seen throughout the Bay Area. Devotionals, concerts, and performances are hosted throughout the month in the Temple Hill Auditorium and most events are free.
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
EXPLORE MORE
Discover Exciting Road Trip Inspirations
Chicago to Philadelphia
758 miles
14h 3m
20 stops
Museums
Food & Drink
ToursSights & LandmarksShoppingChicago to San Jose
2,167 miles
37h 30m
26 stops
Sights & LandmarksNature & ParksOutdoor ActivitiesToursWater & Amusement ParksChicago to Columbus
355 miles
6h 49m
19 stops
Sights & LandmarksToursWater & Amusement ParksFun & GamesSpas & WellnessChicago to San Francisco
2,135 miles
36h 54m
27 stops
Sights & LandmarksNature & ParksFood & DrinkToursWater & Amusement ParksChicago to Seattle
2,055 miles
36h 4m
16 stops
Sights & Landmarks
OtherNature & ParksMuseumsFun & GamesChicago to Denver
1,002 miles
17h 42m
13 stops
Food & DrinkSpas & WellnessOtherShoppingToursEXPLORE OTHER
Check Out Different Road Trip Options
Provo to Santa Cruz
836 miles
14h 38m
29 stops
Sights & LandmarksOutdoor ActivitiesOtherToursShoppingAlbany to Visalia
2,904 miles
52h 9m
56 stops
MuseumsNature & ParksToursShoppingFood & DrinkSanta Cruz to San Jose
30 miles
0h 49m
26 stops
Outdoor ActivitiesNature & ParksSights & LandmarksFood & DrinkMuseumsGrand Rapids to Kissimmee
1,234 miles
23h 6m
28 stops
ShoppingSights & LandmarksToursNature & ParksMuseumsSeattle to Vallejo
775 miles
14h 56m
31 stops
ToursSights & LandmarksOutdoor ActivitiesNature & ParksFood & DrinkColumbus to Memphis
585 miles
10h 54m
27 stops
Sights & LandmarksFun & Games
Concerts & ShowsNature & ParksShoppingFAQ
Frequently Asked Questions
What's the driving distance between Chicago and San Jose?
The distance is 2,167 miles
What's the travel time between Chicago and San Jose?
The driving time can vary depending on traffic conditions, but it is typically 37h 30m mins in normal traffic
What are some of the best cities to visit between Chicago and San Jose?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to San Jose?
There are plenty! Here are some stops you shouldn’t miss on your way to San Jose
What’s the weather like in San Jose?
The weather in San Jose is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in San Jose in January
Weather in San Jose in February
Weather in San Jose in March
Weather in San Jose in April
Weather in San Jose in May
Weather in San Jose in June
Weather in San Jose in July
Weather in San Jose in August
Weather in San Jose in September
Weather in San Jose in October
Weather in San Jose in November
Weather in San Jose in December
Interested in a detailed plan for your time in San Jose?
Plan your dream San Jose trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in San Jose
A 2-day itinerary in San Jose
A 3-day itinerary in San Jose
A 4-day itinerary in San Jose
A 5-day itinerary in San Jose
A 6-day itinerary in San Jose
Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you
