Road Trips

Chicago to Iowa Road Trip: Wicked Mid West!

chicago road trip
Written by Town & Tourist

Chicago to Iowa Road Trip is a short but sweet mid america road trip! Along the way you will drive through authentic Americana.  Line of sight you can travel the 236 miles  between Chicago & Iowa in approximately 4 hours!

However, we prefer to take the more scenic route to really experience old americana: Here are our Stops along the way.

  1. Chicago 
  2. Naperville
  3. Rockford
  4. Galena
  5. Dubuque
  6. Davenport
  7. Iowa City, Iowa 
  8. Bonus: Amana Colonies

Map of Chicago to Iowa Road Trip!

Dive into our Map below, for the best attractions to see on a road trip between Chicago & Iowa.  

 DIVE INTO OUR MAP! User Guide:  Simply Click the +/- buttons to zoom in & out, (Zoom out to see Blowing rock). Click on a favourite restaurant, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to share our map on facebook by clicking the link in the top right corner!)

Chicago to Iowa City Road Trip Itinerary:


Starting in the Windy City, Chicago, Illinois is a large metropolis on the Scenic Lake Michigan. The Skyline is punctuated with vast skyscrapers, such as the Willis Tower (Former Sears Tower) and the Legendary John Hancock Center at over 1,451ft high.

Chicago is also known for Chicago style pizza (Deep dish) , and Chicago hot dogs in addition to Jazz and of course the Notorious 1920s gangster Al Capone.


chicago-Road trip (Chicago to Iowa Road Trip Itinerary)

Is Chicago Better than New York City?

That is very difficult to say & based entirely on opinion. Of course New York is larger & busier but many have stated Chicago is more affordable and the people are nicer! Of course this is entirely opinion based, let us know your thoughts in the comments below!

Either way Chicago is an epic city and the ideal place to start your road trip, here are 5 classic things to do and 5 unique things to do in Chicago!

5 Classic Things to do in Chicago: 

1. Millennium Park – FREE! 

Millennium Park  is not just a public park, its a true expression of the Chicago experience! It is the largest public space inside the 319 acres of Chicagos Grant Park, located downtown. This area includes, gardens, sculptures and attractions.


(Chicago to Iowa Road Trip Itinerary)

Cloud Gate (The “Bean”)

A Large public sculpture weighing in at over 110tones and is over 66 feet long and 33 feet high. This is an astonishing sculpture to see and was designed by British Artist Anish Kapoor.

Cloudgate Chicago Bean

Cloudgate Chicago Bean. Source: (Chicago to Iowa Road Trip Itinerary)

Crown Fountain: 

Crown Fountain was designed by Spanish artist Jaume Plensa the fountain is made up of two 50 foot glass block towers which of display rotating images of over 1000 Chicago residents.

The fountain fires water out of the giant mouth and is really popular with kids during the summer months.

Crown Fountain Chicago

Crown Fountain Chicago is perhaps one of the strangest fountains you will ever see! Source: (Chicago to Iowa Road Trip Itinerary)

Other highlights at Millennium Park include, Lure Garden and Maggie Daley Park. A large 20 acre adventure park which includes rock climbing, slides and mirror walks.

Where is it?

201 E Randolph St, Chicago, IL 60602, United States

2. Willis Tower (“Sears Tower”) 

The Willis Tower is a 110-story, 1,450-foot skyscraper in Chicago. When it was completed in 1973, it surpassed the World Trade Center in New York to become the tallest building in the world!

Willis Tower Sears Tower

Willis Tower Sears Tower. Source: (Chicago to Iowa Road Trip Itinerary)

Skydeck Chicago offer views from 103rd floor of the former Sears Tower with clear observation boxes & views extending to four states!

3. Navy Pier

Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan. Here you will find many fairground rides & attractions including a 360 Chicago, (A Premiere observation deck), Centennial Wheel (Observation Wheel)  Museum of Contemporary Art, the Childrens Museum, River Cruises and many more!

Navy Pier Chicago

Navy Pier Chicago. Source: (Chicago to Iowa Road Trip Itinerary)

How much does it cost? 

It is FREE to enter Navy Pier, each attractions or  show has it’s own admission price.

4. Art Institute of Chicago 

Head to the world renowned Art Institute of Chicago  in downtown. Here you find many unique paintings such as Nighthawks, american gothic and even a paperweight gallery!

5. Shedd Aquarium 

Shedd Aquarium is one of the largest indoor Aquariums in the world! It was opened back in the 1930s and houses over 32,000 animals!

Shedd Aquarium Chicago

Shedd Aquarium Chicago. Source: the great (Chicago to Iowa Road Trip Itinerary)

6 Unique things to Do in Chicago: 

1. Check out Garfield Park Conservatory 

Garfield Park Conservatory  is a tranquil & breath taking botanical gardens which is an ideal place to visit whether it’s raining or not!

Here you will find a pleathora of gorgeous flowers, lush plants and majestic trees.

Garfield Park Conservatory Chicago itinerary

Garfield Park Conservatory Chicago itinerary. Source: Garfield (Chicago to Iowa Road Trip Itinerary)

Insider Tip:

Many Chicago locals come here during Chicagos cold winters! 

2. Head down to the Lakefront Promenade 

As Lake Michigan spans across the entire length of Chicago, you should really take advantage of these glistening waters! Head down to the The Lakefront Trail where you will find 18 miles of biking & walking with scenic lakefront views.

Best Summer Spot:

Beach? If you fancy a beach head to Oak Street Beach, which is on North Lake Shore Drive.

This is a hidden gem popular with the locals during the summer months. Relax on the sands, overlooking glistening lake Michigan, while admiring the Skyscrapers in the distance!

Oak Street Beach Chicago 1

Oak Street Beach Chicago ,. (Chicago to Iowa Road Trip Itinerary)

Two other places for great views of Chicago include Promontory Point and North Avenue Beach.

3. Pullman National Monument

If your a history Buff you have to head down to Pullman National Monument.  This is just off the beaten track in an historic 19th Century neighbourhood which was the first planned Industrial Town in America.

Your first stop should be the visitors centre to find out more about the Pullman Company, afterwards take a self guided tour around the neighbourhood!


Pullman_Chicago_Clock_Tower. (Chicago to Iowa Road Trip Itinerary)

4. Get Active at The 606! 

The 606  opened in 2015 and has fast become one of the most popular place to jog, walk and bike in Chicago.

This is an elevated trail which runs through  Logan Square, Humboldt Park, Wicker Park and Bucktown.

606 chicago park 2

606 chicago park 2. Source:

If you would like to try cycling, rent a Divvy bike, . There are plenty of bike share stations nearby.

5. Take a river cruise! 

Taking a River Cruise through Chicago is one of the most unique ways of seeing the city! It’s a great way to learn about the downtown area and get your bearing if you’ve never been here before.

Chicago River cruise

Chicago River cruise. Source: GettyImages. (Chicago to Iowa Road Trip Itinerary)

6. Green Mill Lounge – Can you spot Al Capone?? 

Head back to the 1940s at Chicagos Green Mill Lounge. Here you can find local Jazz Musicians, poets and was once a hangout for the Notorious Gangster Al Capone.

Green Mill Lounge Chicago Al Capones hangout

Green Mill Lounge Chicago Al Capones hangout


As you drive out of Chicago, take a drive through the WEALTHIEST CITY IN THE MIDWEST! Here the average home of this Chicago suburb has a value of $365,000!


  • Naper Settlement  – An outdoor Museum, which has roots as a 19th Century Pioneer Outpost.
  • Naperville Riverwalk –  A scenic riverwalk which curves along the Dupage River.
  • Centennial Beach – A swimming complex with a water slide, diving boards and a sand volleyball court!
  • DuPage Children’s Museum – An Interactive childrens museum with has hands-on exhibits.

Naperville-welcome to the suburbs!  Source: (Chicago to Iowa Road Trip Itinerary)

Places to Eat? 

Cooper’s Hawk Winery & Restaurant
High end chain which serves New American dishes paired with house-label wines in a modern setting. This is great for a romantic couples, date night! 
Address1740 Freedom Dr, Naperville, IL 60563, United States
Meson Sabika
Spanish tapas & sangria in an historic Mansion, with an outdoor landscaped garden!  What more do you need??
Address: 1025 Aurora Ave, Naperville, IL 60540, United States


Rockford has gotten a bad rep of being a DANGEROUS CITY! I’m not saying it doesn’t have it’s issues but there are still some hidden gems worth visiting here.

Anderson Japanese Gardens

Anderson Japanese Gardens is a lush 12 acre paradise in Rockford! This has been named one of the highest quality Japanese gardens in North America.

Here you will find a 13th-century style garden with many waterfalls and ponds, streams, rock formations, winding paths, and even a sukiya style tea house!

Address & Telephone Number: 318 Spring Creek Rd, Rockford, IL, USA +1 815 229 9390

Anderson Japanese Gardens Rockford

Anderson Japanese Gardens Rockford. Source:  Anderson Japanese Gardens. (Chicago to Iowa Road Trip Itinerary)

Burpee Museum of Natural History

Burpee Museum of Natural History offers gigantic dinosaur bones & native artifacts! Definitely worth a visit, great for families and curious people of all ages.

Address & Telephone Number: 737 N Main St, Rockford, IL, USA +1 815 965 3433

Burpee Museum of Natural History

Burpee Museum of Natural History. Source: Burpee Museum of Natural History. (Chicago to Iowa Road Trip Itinerary)

Where to Eat?

Abreo – Downtown Delight! 

Abreo is a fine dining restaurant which specialises in small tapas plates! Located in Downtown Rockford. Here you will find meticulously presented cuisine as the chef takes special care of each & every customers needs! Here you will find selections of fresh meat, seafood, vegetarian dishes and desserts.

Fun Fact: Wines are selected from 80 Locations around the world!

Fine dining Hours: 5pm – 12am (Mon – Sat)

Social Urban Bar & Restaurant  – Downtown

Social offers local foods and ingredients, merged with some of the most talented bartenders in town!

The Cocktails, wines and Microbrews here are some of the best in the state! Guests are seated on communal dining tables for a more interactive experience.


Galena is a historic small town in northwest Illinois. This little town down is old school americana at its best! Here you will find a host of 19th century buildings such as the 1826 Dowling House and Hourseshoe Mount which offers views of THREE STATES!

You can check out other ancient ceremonial sites at Casper Bluff.

Galena Illinois

Galena Illinois is an all american city. Source: (Chicago to Iowa Road Trip Itinerary)

Things to do: 

  • Home of Ulysses S Grant
  • Chicago Atheneum
  • The Dowling House
  • Galena Grant Park
  • Galena Ghost Tours.
  • Galena Trolley Tours

Dubuque, Iowa 

Take the short drive across the Mississippi and you will come to Dubuque in Iowa.

Dubuque, Iowa 

Dubuque, Iowa. Source:

Mississippi River Aquarium:

Dubuque is home to the National Mississippi River Museum & Aquarium , which explores aquatic life in & around the river!

Botanical Gardens:

Other highlights of Dubuque Iowa include, the Dubuque Arboretum and Botanical Gardens  which include rose, herb and landscaped Japanese gardens.

Historic Mansions (Mathias Ham House): 

For History Buffs, you have to visit Mathias Ham House  a 19th-century mansion with luxurious decor and an 1833 log cabin onsite!

Mathias Ham House 1

Mathias Ham House. Source: Flickr.  (Chicago to Iowa Road Trip Itinerary)

Hiking? Mines of Spain State Recreation Area:

For Hiking along a series of historic & scenic trails head to Mines of Spain state Recreation area. 

Skiing at Sundown Mountain Resort

At Sundown Mountain Resort, you can tackle a diverse range of ski runs & 2 terrain parks. Afterwards relax in the lodge with bar/grill. This resort also offers ski lessons.


Drive South on a scenic drive along the Mississippi River to reach Davenport City. Davenport was founded in 1836 and is known as a very green city with  pleathora of 50 local parks! These are great for walking or biking.

You should also check out The Village, an historic area of Davenport which was once it’s own independent community. These days you can check out it’s distinct style, entertainment and shopping areas.

Davenport Mansion Iowa

Davenport Mansion Iowa. (Chicago to Iowa Road Trip Itinerary)

Things to do:  

Lindsay Park: 

Lindsay Park offers 31 acres of land and sits in the Village of eastern Davenport. You will will find incredible views of the Mississippi River and a series of art sculptures along the riverfront! The Rivverssance Festival of Fine Art is held here each year.

For art lovers there are architectural sculptures that run along a section known as Riverfront Parkway and, should you be in the area at the right time, the park is home to the Rivverssance Festival of Fine Art which is held annually.

Chocolate Mansion:

Chocolate Mansion in Davenport offers a pleathora of Handmade Chocolate & candy treats which will melt in your mouth! The are all made from local ingridents, which makes this one of the SWEEST PLACES IN IOWA! 

Chocolate Mansion Iowa

Chocolate Mansion Iowa

Great River Brewery

Davenport Brewery creates over 3,000 barrels of craft beer each year! Visitors can tour the brewery and learn all about the beer making process.

Putnam Museum & Science Center:

Putnam Museum and Science Center was one of the first Museums in area and has been around since 1867! The Museum contains over 160,000 pieces in its collection and even a movie theater which shows topics from history to natural sciences.

Must see attractions here include the Aquarium and representation of cave & forest habitats.

Davenport Skybridge:

Davenport Skybridge was constructed in 2005 and stands 50 feet tall and over 575 feet long. It offers views over the city and is the perfect place to view the whole of Davenport.

Freight House Famers Market: 

Freight House Farmers Market  gives you the opportunity to sample the best local produce in Iowa. This includes, fresh fruit, vegetables, meats and baked treats.


freight-house-farmers market. Iowa. (Chicago to Iowa Road Trip Itinerary)

Where is it?

Freight House at 421 W River Dr, Davenport, Iowa.

Insider Tips: 

  • Outdoor Market: Begins May 4th
  • Saturday 8-1
  • Sunday 10-2
  • Wednesday 4-8.
  • Indoor Market is open all year round.

Vander Veer Botanical Park: 

Vander Veer Botanical Park is a lush 33-acre botanical garden. It was established in 1885 and features a range of displays.

Location: 215 W Central Park Ave, Davenport.

Credit Island:

Credit Island is a island on the Mississippi to the south west of Davenport. This was an historic native american trading area and spans 420 acres! These days it’s a vibrant community park which offers its own golf course including rugby, soccer and softball areas.

Credit Island-Davenport Iowa

Credit Island-Davenport Iowa (Chicago to Iowa Road Trip Itinerary)

Iowa City

Take the short drive into Iowa City, where you can immerse yourself in some American history & Culture. 

Iowa City 1

Iowa City. Source:

Things to Do:

Old Capitol Building: 

This was Iowas first Capitol and contains a Local History Museum.

Herbert Hoover Presidential Library & Museum:

Herbert Hoover Presidential Library and Museum is the presidential library and burial place of Herbert Clark Hoover! The 31st President.

University Of Iowa Museum of Natural History:

University of Iowa Museum of Natural History – Here you can observe prehistoric stone tools and eye catching taxidermy!

University Of Iowa Museum of Natural History guide

University Of Iowa Museum of Natural History guide. Source:

Devonian Fossil Gorge:

Devonian fossil Gorge  is an Archeological wonder, which captures the ancient remains of an ocean floor from over an estimated 375 million years ago!

Terry Trueblood Recreation Area: 

A 5,870 square foot recreation area  with a large lake great for Kayaking & paddle boarding.

Amana Colonies:

Opened in 1855, The Amana Colonies are seven villages on 26,000 acres located in east Iowa.

They are a unique live history experience, your first stop should be the Amana Heritage Museum. There is also many special events, festivals and workshops such as woodwork.

Amana Colonies Iowa

Amana Colonies Iowa. Source: (Chicago to Iowa Road Trip Itinerary)

Popular Festivals: 

  • Winterfest
  • Octoberfest
    Wurst Festival
  • Prelude to Christmas
  • Maifest

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About the author

Town & Tourist

A travel resource guide that has been carefully crafted and curated by travel bloggers to help you find the best places to travel to in the USA.