By Huuk Team
Share Your Trip
Excited about your upcoming trip? Share the adventure with your friends!
Road trip from Chicago to Medford
All Category
Outdoor Activities
Nightlife
Museums
Nature & Parks
Concerts & Shows
Water & Amusement Parks
ShoppingShow more (4+)
All Category
Outdoor ActivitiesNightlifeMuseumsNature & ParksConcerts & ShowsWater & Amusement ParksShopping
Sights & Landmarks
Fun & Games
Spas & WellnessReset
Show less
ITINERARY
38h 36m2,217 miles23 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
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.
6
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.
7
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.
8
Quad Cities Symphony Orchestra
9
Endless Brews
We are a bottle shop & craft beer bar with 20 taps and over 300 select bottles and cans for carry-out.
10
German American Heritage Center
11
Brenton Skating Plaza
12
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.
13
Hot Shops Art Center
14
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.
15
Joslyn Art Museum
This property is temporary closed
16
Fun Plex
17
The Farm at Lee Martinez Park
18
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.
19
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.
20
Great Salt Lake
This 20,000 square mile lake, the second saltiest in the world, is also a wildlife refuge attracting millions of migratory birds every year to the ten islands within it.
21
Rosewood Lakes Golf Course
Championship golf surrounded by the natural beauty of the Nevada desert: players wind through sixty acres of protected wetlands that are home to an abundance of wildlife and waterfowl.
22
Ryan's Saloon & Broiler
23
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.
Customize this Trip
OVERVIEW
Prepare to embark on an epic adventure from the bustling metropolis of Chicago to the serene landscapes of Medford. Our journey will traverse vast plains, majestic rivers, and rolling hills, connecting two distinct worlds. Along the way, we'll discover hidden gems and explore the rich history and culture that shape this captivating region.
As we set off from the vibrant streets of Chicago, we'll witness the transformation of the urban landscape into tranquil countryside. Verdant fields and sprawling forests will greet us, inviting us to embrace the serenity of nature. We'll traverse historic towns and charming villages, each with a unique story to tell, adding layers of intrigue to our adventure.
Our journey will not only be a physical one but also a cultural immersion. We'll encounter diverse communities, each with its own traditions and perspectives. From lively festivals to local cuisine, we'll delve into the heart of the region, gaining a deeper understanding and appreciation for the people and places that make it so special.
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: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.
6
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.
7
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.
8
Start:Quad Cities Symphony Orchestra
Davenport, Iowa·
4.5
(8) review
327 Brady St, Davenport, IA 52801-1508
9
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.
10
Start:German American Heritage Center
Davenport, Iowa·
4.5
(84) review
712 W 2nd St, Davenport, IA 52802-1410
11
Start:Brenton Skating Plaza
Des Moines, Iowa·
4.5
(9) review
520 Robert D Ray Dr, Des Moines, IA 50309-1824
12
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.
13
Start:Hot Shops Art Center
Omaha, Nebraska·
4.5
(96) review
13th & Nicholas, Omaha, NE 68102
14
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.
15
Start:Joslyn Art Museum
Omaha, Nebraska·
4.5
(901) review
This property is temporary closed
16
Start:Fun Plex
Omaha, Nebraska·
3.5
(92) review
7003 Q St, Omaha, NE 68117-1649
17
Start:The Farm at Lee Martinez Park
Fort Collins, Colorado·
4.5
(93) review
600 N Sherwood St, Fort Collins, CO 80521-2061
18
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.
19
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.
20
Start:Great Salt Lake
Salt Lake City, Utah·
4.0
(987) review
This 20,000 square mile lake, the second saltiest in the world, is also a wildlife refuge attracting millions of migratory birds every year to the ten islands within it.
21
Start:Rosewood Lakes Golf Course
Reno, Nevada·
3.0
(9) review
Championship golf surrounded by the natural beauty of the Nevada desert: players wind through sixty acres of protected wetlands that are home to an abundance of wildlife and waterfowl.
22
Start:Ryan's Saloon & Broiler
Reno, Nevada·
4.5
(9) review
924 S Wells Ave, Reno, NV 89502-2522
23
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.
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
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
EXPLORE MORE
Discover Exciting Road Trip Inspirations
Chicago to Philadelphia
758 miles
14h 3m
20 stops
Museums
Food & Drink
ToursSights & LandmarksShoppingChicago to San Jose
2,167 miles
37h 30m
26 stops
Sights & LandmarksNature & ParksOutdoor ActivitiesToursWater & Amusement ParksChicago to Columbus
355 miles
6h 49m
19 stops
Sights & LandmarksToursWater & Amusement ParksFun & GamesSpas & WellnessChicago to San Francisco
2,135 miles
36h 54m
27 stops
Sights & LandmarksNature & ParksFood & DrinkToursWater & Amusement ParksChicago to Seattle
2,055 miles
36h 4m
16 stops
Sights & Landmarks
OtherNature & ParksMuseumsFun & GamesChicago to Denver
1,002 miles
17h 42m
13 stops
Food & DrinkSpas & WellnessOtherShoppingToursEXPLORE OTHER
Check Out Different Road Trip Options
Queens to Murrieta
2,806 miles
49h 53m
37 stops
Outdoor ActivitiesMuseumsNature & ParksFun & GamesToursLittle Rock to Sioux Falls
786 miles
14h 6m
22 stops
Fun & Games
Traveler ResourcesSights & LandmarksNightlifeConcerts & ShowsBoston to St. Louis
1,183 miles
22h 21m
37 stops
ToursSights & LandmarksTraveler ResourcesMuseumsNature & ParksTucson to Sarasota
2,088 miles
36h 28m
32 stops
ToursShoppingNature & ParksSpas & WellnessNightlifeColumbia to Oxnard
2,454 miles
43h 38m
33 stops
MuseumsSights & LandmarksNature & ParksShoppingTraveler ResourcesQueens to Paterson
27 miles
0h 41m
11 stops
Concerts & Shows
Boat Tours & Water SportsFun & GamesShoppingToursFAQ
Frequently Asked Questions
What's the driving distance between Chicago and Medford?
The distance is 2,217 miles
What's the travel time between Chicago and Medford?
The driving time can vary depending on traffic conditions, but it is typically 38h 36m mins in normal traffic
What are some of the best cities to visit between Chicago and Medford?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Medford?
There are plenty! Here are some stops you shouldn’t miss on your way to Medford
What’s the weather like in Medford?
The weather in Medford is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Medford in January
Weather in Medford in February
Weather in Medford in March
Weather in Medford in April
Weather in Medford in May
Weather in Medford in June
Weather in Medford in July
Weather in Medford in August
Weather in Medford in September
Weather in Medford in October
Weather in Medford in November
Weather in Medford in December
Interested in a detailed plan for your time in Medford?
Plan your dream Medford trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Medford
A 2-day itinerary in Medford
A 3-day itinerary in Medford
A 4-day itinerary in Medford
A 5-day itinerary in Medford
A 6-day itinerary in Medford
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
