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Road trip from Chicago to Paradise
All Category
Sights & Landmarks
Concerts & Shows
Museums
Outdoor Activities
Fun & Games
Food & Drink
Spas & WellnessShow more (5+)
All Category
Sights & LandmarksConcerts & ShowsMuseumsOutdoor ActivitiesFun & GamesFood & DrinkSpas & Wellness
Water & Amusement Parks
Shopping
Nightlife
Nature & ParksReset
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ITINERARY
30h 35m1,756 miles18 stops
1
The Rat Pack is Back
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
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
3
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
4
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.
5
Anderson's Bookshop
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
Klehm Arboretum & Botanic Garden
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.
8
1 Hundred West
1 Hundred West, in Davenport, IA, is the leading bar and grille serving Davenport and surrounding areas. We offer craft cocktails and a supper club inspired menu, along with drink specials, nightly features, wings, burgers, beer, family-style chicken fry, ribs, signature drinks, all you can eat fish fry and much more. For your next meal, visit 1 Hundred West in Davenport.
9
Quad Cities Symphony Orchestra
10
Endless Brews
We are a bottle shop & craft beer bar with 20 taps and over 300 select bottles and cans for carry-out.
11
German American Heritage Center
12
LoDo Massage Studio
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.
13
Brenton Skating Plaza
14
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.
15
Hot Shops Art Center
16
Hollywood Candy
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.
17
Joslyn Art Museum
This property is temporary closed
18
Fun Plex
Customize this Trip
OVERVIEW
Prepare to be amazed as we embark on an unforgettable journey from the bustling metropolis of Chicago to the tropical paradise of your dreams. Along the way, we'll immerse ourselves in vibrant cultures, encounter breathtaking natural wonders, and create memories that will last a lifetime.
Our adventure begins in the heart of the Windy City, where towering skyscrapers and bustling streets paint a vibrant tapestry of urban life. We'll explore iconic landmarks, savor delectable cuisine, and soak up the city's infectious energy. From here, we'll embark on a scenic drive, winding through picturesque countryside and charming small towns.
As we approach our destination, the landscape transforms into a tropical paradise, where swaying palm trees, crystal-clear waters, and white-sand beaches beckon us to embrace the tranquility of island life. We'll bask in the warm sunshine, swim in azure seas, and indulge in the flavors of local delicacies. Whether you seek adventure or relaxation, this extraordinary journey offers an unforgettable fusion of urban excitement and tropical serenity.
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.
2
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.
3
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
4
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.
5
Start:Anderson's Bookshop
Naperville, DuPage County, Illinois·
5.0
(9) review
123 W Jefferson Ave, Naperville, IL 60540-5310
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: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.
8
Start:1 Hundred West
Davenport, Iowa·
4.0
(8) review
1 Hundred West, in Davenport, IA, is the leading bar and grille serving Davenport and surrounding areas. We offer craft cocktails and a supper club inspired menu, along with drink specials, nightly features, wings, burgers, beer, family-style chicken fry, ribs, signature drinks, all you can eat fish fry and much more. For your next meal, visit 1 Hundred West in Davenport.
9
Start:Quad Cities Symphony Orchestra
Davenport, Iowa·
4.5
(8) review
327 Brady St, Davenport, IA 52801-1508
10
Start: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.
11
Start:German American Heritage Center
Davenport, Iowa·
4.5
(84) review
712 W 2nd St, Davenport, IA 52802-1410
12
Start: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.
13
Start:Brenton Skating Plaza
Des Moines, Iowa·
4.5
(9) review
520 Robert D Ray Dr, Des Moines, IA 50309-1824
14
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.
15
Start:Hot Shops Art Center
Omaha, Nebraska·
4.5
(96) review
13th & Nicholas, Omaha, NE 68102
16
Start: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.
17
Start:Joslyn Art Museum
Omaha, Nebraska·
4.5
(901) review
This property is temporary closed
18
Start:Fun Plex
Omaha, Nebraska·
3.5
(92) review
7003 Q St, Omaha, NE 68117-1649
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 Paradise?
The distance is 1,756 miles
What's the travel time between Chicago and Paradise?
The driving time can vary depending on traffic conditions, but it is typically 30h 35m mins in normal traffic
What are some of the best cities to visit between Chicago and Paradise?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Paradise?
There are plenty! Here are some stops you shouldn’t miss on your way to Paradise
What’s the weather like in Paradise?
The weather in Paradise is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Paradise in January
Weather in Paradise in February
Weather in Paradise in March
Weather in Paradise in April
Weather in Paradise in May
Weather in Paradise in June
Weather in Paradise in July
Weather in Paradise in August
Weather in Paradise in September
Weather in Paradise in October
Weather in Paradise in November
Weather in Paradise in December
Interested in a detailed plan for your time in Paradise?
Plan your dream Paradise trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Paradise
A 2-day itinerary in Paradise
A 3-day itinerary in Paradise
A 4-day itinerary in Paradise
A 5-day itinerary in Paradise
A 6-day itinerary in Paradise
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
