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By Huuk Team

Road trip from Chicago to Portland

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ITINERARY

36h 40m2,121 miles13 stops
1
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.
2
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
3
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.
4
Anderson's Bookshop
123 W Jefferson Ave, Naperville, IL 60540-5310
5
Riverwalk
West Branch of DuPage River, Naperville, IL
6
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.
7
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.
8
Therapeutix Mind & Body
2348 Kiesel Ave, Ogden, UT 84401-1964
Full Service Spa located in the Ogden Junction downtown. Wonderful services and amazing staff. Natural and Organic products!
9
25th Street Museum & Tour
238 25th St, Ogden, UT 84401-2302
The 25th Street Museum is located in a historic building with a rich and sometimes tragic history right in the heart of historic 25th Street. Our 1-hour indoor guided tour will use images, artifacts, and stories to take you back to a time when 25th Street was ranked the “second most dangerous city in America." Experience 25th Street and learn how this street and the city of Ogden changed Utah and America.
10
Talisman Brewing Co.
1258 Gibson Ave, Ogden, UT 84404-5541
11
Morrison Bridge
Connects Southeast Morrison and Belmont streets to Southwest Alder and Washington streets, Portland, OR 97204
12
Sellwood
SE 13th Ave & SE Miller St, Portland, OR 97202
Neighborhood with a pleasant, small shopping area with dozens of antique shops.
13
South Waterfront Lower Tram Terminal
3303 S Bond Ave, Portland, OR 97239
The Tram is a popular destination for tourists, locals and people just looking to try something fun. The lower tram terminal is at the intersection of South Moody Avenue & Gibbs Street --the most transportation-diverse intersection in the country. Besides one of the nation's only aerial commuter trams, you'll see cars, buses, a streetcar, a soaring pedestrian bridge, a cycle track and the densest bike parking in America's #1 biking city. Bike valet is offered free to the public at Portland Aerial Tram Monday through Friday. Exiting the upper terminal you'll see the largest enclosed sky bridge in North America. Take a right to access an outdoor patio with seating and views of the terminal, the cityscape, the Willamette River and, on a clear day, Mount Hood and Mount St Helens. The upper terminal links to the 4T Trail--a self-guided tour by train, trail, tram and trolley. Much of Marquam Hill is a natural area with several trails.
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OVERVIEW

The journey begins in the heart of the Windy City, where the skyscrapers stand tall and the energy is electric. From there, you'll embark on an adventure that will take you across vast landscapes, from the rolling hills of the Midwest to the towering mountains of the West. Along the way, you'll discover hidden gems, meet friendly locals, and create memories that will last a lifetime.

As you traverse the country, you'll witness the changing seasons, from the vibrant colors of autumn to the snow-covered peaks of winter. You'll encounter diverse cultures, from the bustling cities of the East Coast to the laid-back towns of the Pacific Northwest. And you'll experience a range of emotions, from awe and wonder to peace and tranquility.

The journey's end brings you to the vibrant city of Portland, nestled amidst lush forests and sparkling rivers. Here, you can explore eclectic neighborhoods, indulge in culinary delights, and immerse yourself in the arts and culture that define this unique city. Portland marks the culmination of your adventure, a place where you can reflect on the journey you've taken and the memories you've made along the way.

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.
333 Michigan Ave, Chicago, IL 60601-3901
2
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
3
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
4
Anderson's Bookshop
Naperville, DuPage County, Illinois·
5.0
(9) review
123 W Jefferson Ave, Naperville, IL 60540-5310
5
Riverwalk
Naperville, DuPage County, Illinois·
4.5
(803) review
West Branch of DuPage River, Naperville, IL
6
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
7
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
8
Therapeutix Mind & Body
Ogden, Utah·
5.0
(90) review
Full Service Spa located in the Ogden Junction downtown. Wonderful services and amazing staff. Natural and Organic products!
2348 Kiesel Ave, Ogden, UT 84401-1964
9
25th Street Museum & Tour
Ogden, Utah·
5.0
(9) review
The 25th Street Museum is located in a historic building with a rich and sometimes tragic history right in the heart of historic 25th Street. Our 1-hour indoor guided tour will use images, artifacts, and stories to take you back to a time when 25th Street was ranked the “second most dangerous city in America." Experience 25th Street and learn how this street and the city of Ogden changed Utah and America.
238 25th St, Ogden, UT 84401-2302
10
Talisman Brewing Co.
Ogden, Utah·
5.0
(9) review
1258 Gibson Ave, Ogden, UT 84404-5541
11
Morrison Bridge
Portland, Oregon·
3.5
(9) review
Connects Southeast Morrison and Belmont streets to Southwest Alder and Washington streets, Portland, OR 97204
12
Sellwood
Portland, Oregon·
4.5
(98) review
Neighborhood with a pleasant, small shopping area with dozens of antique shops.
SE 13th Ave & SE Miller St, Portland, OR 97202
13
South Waterfront Lower Tram Terminal
Portland, Oregon·
4.0
(993) review
The Tram is a popular destination for tourists, locals and people just looking to try something fun. The lower tram terminal is at the intersection of South Moody Avenue & Gibbs Street --the most transportation-diverse intersection in the country. Besides one of the nation's only aerial commuter trams, you'll see cars, buses, a streetcar, a soaring pedestrian bridge, a cycle track and the densest bike parking in America's #1 biking city. Bike valet is offered free to the public at Portland Aerial Tram Monday through Friday. Exiting the upper terminal you'll see the largest enclosed sky bridge in North America. Take a right to access an outdoor patio with seating and views of the terminal, the cityscape, the Willamette River and, on a clear day, Mount Hood and Mount St Helens. The upper terminal links to the 4T Trail--a self-guided tour by train, trail, tram and trolley. Much of Marquam Hill is a natural area with several trails.
3303 S Bond Ave, Portland, OR 97239

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Portland?
The distance is 2,121 miles
What's the travel time between Chicago and Portland?
The driving time can vary depending on traffic conditions, but it is typically 36h 40m mins in normal traffic
What are some of the best cities to visit between Chicago and Portland?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Portland?
There are plenty! Here are some stops you shouldn’t miss on your way to Portland
What’s the weather like in Portland?
The weather in Portland is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Portland in January
Weather in Portland in February
Weather in Portland in March
Weather in Portland in April
Weather in Portland in May
Weather in Portland in June
Weather in Portland in July
Weather in Portland in August
Weather in Portland in September
Weather in Portland in October
Weather in Portland in November
Weather in Portland in December
Interested in a detailed plan for your time in Portland?
Plan your dream Portland trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Portland
A 2-day itinerary in Portland
A 3-day itinerary in Portland
A 4-day itinerary in Portland
A 5-day itinerary in Portland
A 6-day itinerary in Portland
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