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By Huuk Team

Road trip from Chicago to Thousand Oaks

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ITINERARY

36h 1m2,053 miles19 stops
1
The Rat Pack is Back
255 E Flamingo Rd Tuscany Suites and Casino, Las Vegas, NV 89169-4708
The number 1 Rat Pack show in the world, now in its' 24th year. The only show of its' kind with an award from the Congress of the United States of America, a full time show running in Las Vegas and national and international touring companies, appearances in over 40 states, 8000 performances and over 3 million satisfied customers.
2
Yorba Regional Park
7600 E La Palma Ave, Anaheim, CA 92807-2444
3
Anaheim Convention Center
800 W Katella Ave Suite 600, Anaheim, CA 92802-3496
4
MagIQ Room
1446 S Robertson Blvd, Los Angeles, CA 90035-3402
MagIQ Room is a creative family business, a Hungarian-American “co-production”. Based upon the undisputed success of live escape games, MagIQ Room has decided to bring the activity to the next level. Game plots are more immersive and action based, with amazing theming and more difficulty levels, the adventure will be interesting for all ages.
5
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
6
Boystown
Chicago, IL
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
7
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
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.
8
Anderson's Bookshop
123 W Jefferson Ave, Naperville, IL 60540-5310
9
Arista Spa & Salon
2155 City Gate Ln Ste 201, Naperville, IL 60563-7703
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.
10
Klehm Arboretum & Botanic Garden
2715 S Main St, Rockford, IL 61102-3925
This year-round garden, which started as a commercial nursery, includes 155 acres of trees and 300 woody plant species mapped and labeled. The gardens include: a Rhododendron and Azalea dell, Hosta Garden, Nancy Olsen's Children's Garden, Fountain Garden, Demonstration Garden, Peony Garden, Grasses Garden,Woodland Wildflower Garden and Plant-a-Row garden. There are several signature events hosted each year also. Botanica luncheon,Garden Fair, Plant Sale, Woodsong Concert Series, Autumn in the Arboretum and Twilight in the Garden are all popular annual events.
11
Quad Cities Symphony Orchestra
327 Brady St, Davenport, IA 52801-1508
12
Endless Brews
310 N Main St, Davenport, IA 52801-1410
We are a bottle shop & craft beer bar with 20 taps and over 300 select bottles and cans for carry-out.
13
German American Heritage Center
712 W 2nd St, Davenport, IA 52802-1410
14
Brenton Skating Plaza
520 Robert D Ray Dr, Des Moines, IA 50309-1824
15
Fitness Sports
8810 Swanson Blvd, Des Moines, IA 50325-6910
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.
16
Hot Shops Art Center
13th & Nicholas, Omaha, NE 68102
17
Hollywood Candy
1209 Jackson St Omaha, NE, Omaha, NE 68102-2826
Hollywood Candy is a giant candy store proudly serving Omaha’s Old Market since 2007. We offer a large selection of housemate chocolate candy including our chocolate covered bacon, chocolate potato chips, candy cookie pops and our famous Peanut Butter Surprise. We have all flavors or Jelly Belly jelly beans and a large selection of M&M’s. We offer the largest selection of bulk candy in the area including hard to find retro brands, favorite brands like Hershey’s and Oreo, rock candy, gummies, sour candy, and lollipops. Our Soda Shoppe offers over 200 varieties of familiar and unique soda brands. We have the largest collection of PEZ dispensers for everyone to enjoy plus a large assortment for sale.
18
LoDo Massage Studio
3101 Walnut St Ste 200, Denver, CO 80205-2330
Therapeutic Massage Services! At LoDo Massage Studio, we believe a good massage can be a powerful tool to reshape and restore how your body feels and functions. Our massage therapists are talented, licensed, experts who are passionate about providing transformational therapeutic bodywork. Our studio encourages our LMTs to use their unique experience and skill to customize your massage to your body’s exact needs by using a wide range of modalities. Looking for a place to start? Named for our beloved city, our signature Mile High Massage service is tailored to suit you just right. You could also choose a relaxing Swedish massage, invigorating Sports Massage, or effective Neuromuscular Massage. We also offer add-ons like Aromatherapy, and Hot Towels to create a massage bespoke for your body.
19
Fun Plex
7003 Q St, Omaha, NE 68117-1649
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OVERVIEW

Embark on an epic adventure from the bustling city of Chicago to the picturesque Thousand Oaks. This cross-country journey traverses diverse landscapes, from the towering skyscrapers of the Midwest to the rolling hills and serene shorelines of California. Along the way, you'll discover hidden gems and witness the beauty of the American heartland.

The adventure begins in the vibrant heart of Chicago, where you'll experience the city's iconic architecture and renowned cultural attractions. As you venture westward, the landscape transforms into vast farmlands and charming towns, each with its own unique story to tell. The journey continues through the majestic Rocky Mountains, where towering peaks and sparkling lakes create a breathtaking backdrop.

As you approach the Pacific coast, the terrain becomes more rugged and dramatic. The coastal mountains give way to a mesmerizing tapestry of lush forests and rugged cliffs. The journey culminates in the enchanting Thousand Oaks, known for its scenic beauty, outdoor recreation, and cultural attractions.

1
Start:The Rat Pack is Back
Las Vegas, Nevada·
4.0
(999) review
The number 1 Rat Pack show in the world, now in its' 24th year. The only show of its' kind with an award from the Congress of the United States of America, a full time show running in Las Vegas and national and international touring companies, appearances in over 40 states, 8000 performances and over 3 million satisfied customers.
255 E Flamingo Rd Tuscany Suites and Casino, Las Vegas, NV 89169-4708
2
Yorba Regional Park
Anaheim, California·
4.5
(97) review
7600 E La Palma Ave, Anaheim, CA 92807-2444
3
Anaheim Convention Center
Anaheim, California·
4.5
(976) review
800 W Katella Ave Suite 600, Anaheim, CA 92802-3496
4
MagIQ Room
Los Angeles, California·
5.0
(99) review
MagIQ Room is a creative family business, a Hungarian-American “co-production”. Based upon the undisputed success of live escape games, MagIQ Room has decided to bring the activity to the next level. Game plots are more immersive and action based, with amazing theming and more difficulty levels, the adventure will be interesting for all ages.
1446 S Robertson Blvd, Los Angeles, CA 90035-3402
5
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.
333 Michigan Ave, Chicago, IL 60601-3901
6
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
Chicago, IL
7
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.
1060 W. Addison St., Chicago, IL 60613-4566
8
Anderson's Bookshop
Naperville, DuPage County, Illinois·
5.0
(9) review
123 W Jefferson Ave, Naperville, IL 60540-5310
9
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.
2155 City Gate Ln Ste 201, Naperville, IL 60563-7703
10
Klehm Arboretum & Botanic Garden
Rockford, Illinois·
4.5
(83) review
This year-round garden, which started as a commercial nursery, includes 155 acres of trees and 300 woody plant species mapped and labeled. The gardens include: a Rhododendron and Azalea dell, Hosta Garden, Nancy Olsen's Children's Garden, Fountain Garden, Demonstration Garden, Peony Garden, Grasses Garden,Woodland Wildflower Garden and Plant-a-Row garden. There are several signature events hosted each year also. Botanica luncheon,Garden Fair, Plant Sale, Woodsong Concert Series, Autumn in the Arboretum and Twilight in the Garden are all popular annual events.
2715 S Main St, Rockford, IL 61102-3925
11
Quad Cities Symphony Orchestra
Davenport, Iowa·
4.5
(8) review
327 Brady St, Davenport, IA 52801-1508
12
Endless Brews
Davenport, Iowa·
4.5
(9) review
We are a bottle shop & craft beer bar with 20 taps and over 300 select bottles and cans for carry-out.
310 N Main St, Davenport, IA 52801-1410
13
German American Heritage Center
Davenport, Iowa·
4.5
(84) review
712 W 2nd St, Davenport, IA 52802-1410
14
Brenton Skating Plaza
Des Moines, Iowa·
4.5
(9) review
520 Robert D Ray Dr, Des Moines, IA 50309-1824
15
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.
8810 Swanson Blvd, Des Moines, IA 50325-6910
16
Hot Shops Art Center
Omaha, Nebraska·
4.5
(96) review
13th & Nicholas, Omaha, NE 68102
17
Hollywood Candy
Omaha, Nebraska·
4.0
(99) review
Hollywood Candy is a giant candy store proudly serving Omaha’s Old Market since 2007. We offer a large selection of housemate chocolate candy including our chocolate covered bacon, chocolate potato chips, candy cookie pops and our famous Peanut Butter Surprise. We have all flavors or Jelly Belly jelly beans and a large selection of M&M’s. We offer the largest selection of bulk candy in the area including hard to find retro brands, favorite brands like Hershey’s and Oreo, rock candy, gummies, sour candy, and lollipops. Our Soda Shoppe offers over 200 varieties of familiar and unique soda brands. We have the largest collection of PEZ dispensers for everyone to enjoy plus a large assortment for sale.
1209 Jackson St Omaha, NE, Omaha, NE 68102-2826
18
LoDo Massage Studio
Denver, Colorado·
5.0
(99) review
Therapeutic Massage Services! At LoDo Massage Studio, we believe a good massage can be a powerful tool to reshape and restore how your body feels and functions. Our massage therapists are talented, licensed, experts who are passionate about providing transformational therapeutic bodywork. Our studio encourages our LMTs to use their unique experience and skill to customize your massage to your body’s exact needs by using a wide range of modalities. Looking for a place to start? Named for our beloved city, our signature Mile High Massage service is tailored to suit you just right. You could also choose a relaxing Swedish massage, invigorating Sports Massage, or effective Neuromuscular Massage. We also offer add-ons like Aromatherapy, and Hot Towels to create a massage bespoke for your body.
3101 Walnut St Ste 200, Denver, CO 80205-2330
19
Fun Plex
Omaha, Nebraska·
3.5
(92) review
7003 Q St, Omaha, NE 68117-1649

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Thousand Oaks?
The distance is 2,053 miles
What's the travel time between Chicago and Thousand Oaks?
The driving time can vary depending on traffic conditions, but it is typically 36h 1m mins in normal traffic
What are some of the best cities to visit between Chicago and Thousand Oaks?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Thousand Oaks?
There are plenty! Here are some stops you shouldn’t miss on your way to Thousand Oaks
What’s the weather like in Thousand Oaks?
The weather in Thousand Oaks is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Thousand Oaks in January
Weather in Thousand Oaks in February
Weather in Thousand Oaks in March
Weather in Thousand Oaks in April
Weather in Thousand Oaks in May
Weather in Thousand Oaks in June
Weather in Thousand Oaks in July
Weather in Thousand Oaks in August
Weather in Thousand Oaks in September
Weather in Thousand Oaks in October
Weather in Thousand Oaks in November
Weather in Thousand Oaks in December
Interested in a detailed plan for your time in Thousand Oaks?
Plan your dream Thousand Oaks trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Thousand Oaks
A 2-day itinerary in Thousand Oaks
A 3-day itinerary in Thousand Oaks
A 4-day itinerary in Thousand Oaks
A 5-day itinerary in Thousand Oaks
A 6-day itinerary in Thousand Oaks
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
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