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Road trip from Chicago to Anchorage
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Sights & Landmarks
Nature & Parks
Fun & Games
Spas & Wellness
Concerts & Shows
Nightlife
Zoos & AquariumsShow more (5+)
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ITINERARY
71h 48m3,583 miles15 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 Japanese Gardens
Anderson Japanese Gardens is proud of its longstanding reputation as one of the highest quality Japanese gardens in North America. Our passion, however, is how the Garden positively impacts individuals and the communities where they live. We are committed to presenting first-class programs, events, and opportunities that bring people together in this uplifting natural setting.
5
Alliant Energy Center
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
6
KOSA Spa
KOSA Spa provides a sanctuary; a place to retreat, to nourish body, mind, and spirit, and in so doing reconnect with one’s best self. KOSA Spa blends wellness best practices from the 5,000-year-old Indian tradition of Ayurveda with seasonal, organic, Wisconsin-sourced ingredients and artisanal products. KOSA Spa’s offerings include customized wellness balancing plans; treatments, including Abhyanga, Shirodhara, Pinda Sweda, Massage, and Facials; and personal retreats that include access to our hot-stone sauna, aromatherapy hydro-steam room, meditation studio, sanctuary lounge, and organic, Ayurvedic teas and foods.
7
Dinner Detective Murder Mystery Show
The Dinner Detective is the largest, award-winning, interactive comedic murder mystery dinner show in the United States. We are now running public and private shows in cities across the country every week. Our immensely popular shows are set in the present day. Unlike other murder mystery dinner shows, here you will find no cheesy costumes, no recited campy dialogue and no hokey song and dance.
8
Snake Discovery
9
Artists' Quarter
10
Phalen 18 Hole Golf Course
11
Textile Center
12
Norseman Distillery
Norseman Distillery, the first micro-distillery in Minneapolis, was founded with principles of using the very best local ingredients to produce small batches of exceptionally fine spirits. From our micro-distillery in northeast Minneapolis, we hand craft each batch with the hopes of inspiring legendary cheer in those who drink it.
13
Zero Hour Escape Rooms
You are trapped in a room. But it’s not an ordinary room, it’s a real life adventure game designed for small groups of friends, families, co-workers or strangers. You look around and begin to notice strange objects and messages – or are they clues? – scattered around. Can you and your team solve the puzzles, figure out the clues, find the key, and escape the room? You’ll have to think on your feet: our escape rooms require you to think your way out, not break your way out. You have 60 minutes, so be quick!
14
Twin Cities Car Service
Minneapolis Limo service provides dependable ground transportation services for your personal and professional needs Twin Cities Car Service - complete Minneapolis limousine service - airport transportation, corporate transportation, wedding limos, bachelor limos, tours & charters, roadshow limo services, shuttle services
15
Jazzy Gourmet Popcorn
Jazzy Gourmet Popcorn’s owner, Mr. Roland’s inspiration for starting this business was his brother, an owner of one of Houston’s most popular popcorn establishments. JGP offers free samples of over 50 flavors of gourmet popcorn. We have gourmet flavors to please every palate including sweet, savory or spicy. If you’re feeling a little nutty, we offer flavors with cashews, pecans, walnuts & more.
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OVERVIEW
Get ready for an epic adventure that will take you from the bustling streets of Chicago to the breathtaking wilderness of Anchorage. This once-in-a-lifetime journey will span thousands of miles and showcase the incredible diversity of our nation's landscapes and cultures. Along the way, you'll encounter friendly faces, sample delicious local cuisine, and create memories that will last a lifetime. Embrace the excitement and sense of wonder that comes with exploring new places and cultures.
From the towering skyscrapers of Chicago to the rugged peaks of the Rocky Mountains, this journey will traverse diverse and awe-inspiring landscapes. You'll witness the vast stretches of the Great Plains, the tranquil shores of the Mississippi River, and the majestic grandeur of the Cascade Range. Each stop will offer its own unique charm and adventure, inviting you to immerse yourself in the local culture and create unforgettable experiences.
As you make your way towards Anchorage, the scenery will transform into a breathtaking panorama of glaciers, snow-capped mountains, and pristine lakes. The journey culminates in the vibrant city of Anchorage, where you can explore its rich heritage and embrace the spirit of adventure that permeates the Alaskan wilderness. This epic journey promises an unparalleled blend of urban excitement and natural wonders, creating an unforgettable experience that will leave a lasting imprint on your soul.
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 Japanese Gardens
Rockford, Illinois·
4.5
(863) review
Anderson Japanese Gardens is proud of its longstanding reputation as one of the highest quality Japanese gardens in North America. Our passion, however, is how the Garden positively impacts individuals and the communities where they live. We are committed to presenting first-class programs, events, and opportunities that bring people together in this uplifting natural setting.
5
Start:Alliant Energy Center
Madison, Wisconsin·
4.0
(99) review
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
6
Start:KOSA Spa
Madison, Wisconsin·
5.0
(9) review
KOSA Spa provides a sanctuary; a place to retreat, to nourish body, mind, and spirit, and in so doing reconnect with one’s best self. KOSA Spa blends wellness best practices from the 5,000-year-old Indian tradition of Ayurveda with seasonal, organic, Wisconsin-sourced ingredients and artisanal products. KOSA Spa’s offerings include customized wellness balancing plans; treatments, including Abhyanga, Shirodhara, Pinda Sweda, Massage, and Facials; and personal retreats that include access to our hot-stone sauna, aromatherapy hydro-steam room, meditation studio, sanctuary lounge, and organic, Ayurvedic teas and foods.
7
Start:Dinner Detective Murder Mystery Show
Madison, Wisconsin·
4.5
(8) review
The Dinner Detective is the largest, award-winning, interactive comedic murder mystery dinner show in the United States. We are now running public and private shows in cities across the country every week. Our immensely popular shows are set in the present day. Unlike other murder mystery dinner shows, here you will find no cheesy costumes, no recited campy dialogue and no hokey song and dance.
8
Start:Snake Discovery
Saint Paul, Minnesota·
5.0
(7) review
831 Century Ave N, Saint Paul, MN 55119-3822
9
Start:Artists' Quarter
Saint Paul, Minnesota·
4.0
(9) review
Hamm Building, 7th Place and St. Peter, Saint Paul, MN
10
Start:Phalen 18 Hole Golf Course
Saint Paul, Minnesota·
4.0
(9) review
1615 Phalen Dr E, Saint Paul, MN 55106-1827
11
Start:Textile Center
Minneapolis, Minnesota·
4.5
(9) review
3000 University Ave SE, Minneapolis, MN 55414-3356
12
Start:Norseman Distillery
Minneapolis, Minnesota·
5.0
(98) review
Norseman Distillery, the first micro-distillery in Minneapolis, was founded with principles of using the very best local ingredients to produce small batches of exceptionally fine spirits. From our micro-distillery in northeast Minneapolis, we hand craft each batch with the hopes of inspiring legendary cheer in those who drink it.
13
Start:Zero Hour Escape Rooms
Minneapolis, Minnesota·
5.0
(694) review
You are trapped in a room. But it’s not an ordinary room, it’s a real life adventure game designed for small groups of friends, families, co-workers or strangers. You look around and begin to notice strange objects and messages – or are they clues? – scattered around. Can you and your team solve the puzzles, figure out the clues, find the key, and escape the room? You’ll have to think on your feet: our escape rooms require you to think your way out, not break your way out. You have 60 minutes, so be quick!
14
Start:Twin Cities Car Service
Minneapolis, Minnesota·
1.0
(1) review
Minneapolis Limo service provides dependable ground transportation services for your personal and professional needs Twin Cities Car Service - complete Minneapolis limousine service - airport transportation, corporate transportation, wedding limos, bachelor limos, tours & charters, roadshow limo services, shuttle services
15
Start:Jazzy Gourmet Popcorn
Anchorage, Alaska·
4.0
(7) review
Jazzy Gourmet Popcorn’s owner, Mr. Roland’s inspiration for starting this business was his brother, an owner of one of Houston’s most popular popcorn establishments. JGP offers free samples of over 50 flavors of gourmet popcorn. We have gourmet flavors to please every palate including sweet, savory or spicy. If you’re feeling a little nutty, we offer flavors with cashews, pecans, walnuts & more.
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 Anchorage?
The distance is 3,583 miles
What's the travel time between Chicago and Anchorage?
The driving time can vary depending on traffic conditions, but it is typically 71h 48m mins in normal traffic
What are some of the best cities to visit between Chicago and Anchorage?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Anchorage?
There are plenty! Here are some stops you shouldn’t miss on your way to Anchorage
What’s the weather like in Anchorage?
The weather in Anchorage is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Anchorage in January
Weather in Anchorage in February
Weather in Anchorage in March
Weather in Anchorage in April
Weather in Anchorage in May
Weather in Anchorage in June
Weather in Anchorage in July
Weather in Anchorage in August
Weather in Anchorage in September
Weather in Anchorage in October
Weather in Anchorage in November
Weather in Anchorage in December
Interested in a detailed plan for your time in Anchorage?
Plan your dream Anchorage trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Anchorage
A 2-day itinerary in Anchorage
A 3-day itinerary in Anchorage
A 4-day itinerary in Anchorage
A 5-day itinerary in Anchorage
A 6-day itinerary in Anchorage
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
