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Road trip from Chicago to Oakland
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Nature & Parks
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Museums
Fun & Games
ShoppingShow more (5+)
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Sights & LandmarksNature & ParksFood & DrinkWater & Amusement ParksMuseumsFun & GamesShopping
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Outdoor Activities
Spas & WellnessReset
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ITINERARY
36h 44m2,130 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 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.
16
Lake Merritt
Saltwater lake in the middle of the city.
17
Jack London's Cabin
Jack London's Yukon home during the winter of 1897-98.
Customize this Trip
OVERVIEW
Get ready for an epic adventure from the bustling streets of Chicago to the vibrant shores of Oakland! This cross-country journey will take you through diverse landscapes, spanning the vast Midwest, the rugged Rocky Mountains, and the serene Pacific coast. Along the way, you'll witness the grandeur of nature, explore historic cities, and discover hidden gems.
Prepare to be amazed by the towering skyscrapers of Chicago, the rolling hills of Nebraska, and the breathtaking vistas of Wyoming. As you venture westward, the majestic Rockies will unfold before you, offering unparalleled views from winding mountain passes. Embrace the thrill of traversing the Continental Divide and the awe-inspiring beauty of the Great Basin Desert.
As you approach the Pacific Ocean, the terrain transforms into a lush coastal paradise. California's fertile valleys and verdant hills will greet you, leading you to the vibrant city of Oakland. Here, you'll soak up the Bay Area's unique culture, explore its thriving arts scene, and revel in the beauty of its natural surroundings. Get ready for an unforgettable journey that will leave you with lasting memories and a profound appreciation for the wonders of America.
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 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.
16
Start:Lake Merritt
Oakland, California·
4.5
(926) review
Saltwater lake in the middle of the city.
17
Start:Jack London's Cabin
Oakland, California·
3.5
(90) review
Jack London's Yukon home during the winter of 1897-98.
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
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Frequently Asked Questions
What's the driving distance between Chicago and Oakland?
The distance is 2,130 miles
What's the travel time between Chicago and Oakland?
The driving time can vary depending on traffic conditions, but it is typically 36h 44m mins in normal traffic
What are some of the best cities to visit between Chicago and Oakland?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Oakland?
There are plenty! Here are some stops you shouldn’t miss on your way to Oakland
What’s the weather like in Oakland?
The weather in Oakland is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Oakland in January
Weather in Oakland in February
Weather in Oakland in March
Weather in Oakland in April
Weather in Oakland in May
Weather in Oakland in June
Weather in Oakland in July
Weather in Oakland in August
Weather in Oakland in September
Weather in Oakland in October
Weather in Oakland in November
Weather in Oakland in December
Interested in a detailed plan for your time in Oakland?
Plan your dream Oakland trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Oakland
A 2-day itinerary in Oakland
A 3-day itinerary in Oakland
A 4-day itinerary in Oakland
A 5-day itinerary in Oakland
A 6-day itinerary in Oakland
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
