Discover Chicago on Foot: The Ultimate Walking Guide for Tourists (2023) — Away With Anna (2024)

Illinois

Written By Anna Rooker

(Updated: 2023)

A fulfilling way to spend a day's worth of a trip in a new city is just walking around and sightseeing! A lot of these in this list are free or affordable to do in Chicago and include many hot tourist spots for first-timers. Discover the best of Chicago on foot with this comprehensive tourist walking guide. Immerse yourself in the vibrant energy of the Windy City as you explore its iconic landmarks, cultural hotspots, and hidden gems. Get ready to lace up your walking shoes and embark on an unforgettable journey through the heart of Chicago!

You could also take public transit, rent a scooter or bike, or call an Uber between these spots if you prefer. Customize this list to your own must-visit stops or break it up among several days in the city! Any way you do it, enjoy!

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Table of Contents

When to Visit Chicago

How to Get Around Chicago

Where to Eat in Chicago

Ultimate Chicago Walking Guide for Tourists

Other Things to Do in Chicago

Map with Pins

When to Visit Chicago

Chicago weather is very cold and windy in the winter and boasts warm weather in the summer. There is precipitation of some kind nearly a third of the year and it has its nickname of “Windy City” for a reason! Sitting right off of massive Lake Michigan brings in lots of weather and wind.

Spring and Fall are ideal seasons to visit Chicago because of the nice weather, plethora of outdoor festivals and events, and manageable crowds.

On a long walking tour like I have put together, checking the weather before you get going is important so you are plenty prepared to make the most of your excursion. Such as having an umbrella or coat on you just in case! Besides the weather, coming prepared in comfy walking shoes is a must!

How to Get Around Chicago

Of course, I have called this a walking tour and have walked this myself so your own two feet are a great way to get around the city. Chicago is very walkable!

The CTA (Chicago Transit Authority) is reliable and personally, my ideal way to explore Chicago other than walking. There are plenty of bus and train stations that can help you quickly get between some of the hot spots on my list.

Another great way to get around Chicago is by renting a bike or scooter. These are available all over or through sites like Viator, they are affordable, and help you get around the city quickly.

Where to Eat in Chicago

When you think of eating in Chicago, deep-dish pizza and gourmet hot dogs may come to mind. These are both must-tries while in the Windy City, but there’s so much more that Chicago has to offer within their food scene. Here are some of the best restaurants in Chicago.

  • Lou Malnati’s: You can’t visit Chicago without eating deep-dish pizza. Malnati’s is considered the oldest name in pizza history.

  • Gino’s East: Another option for some deep-dish pizza. Gino’s has locations outside of Illinois so if you are in one of the lucky states with a Gino’s, you can enjoy some Chicago deep dish close to home!

  • Qing Xiang Yuan Dumplings: They are famous for their dumplings and I can vouch that they are worth your trip to Chinatown!

  • Niu B: The place for some incredible sushi and Asian dishes.

  • Dollop Coffee Co: A cute coffee shop on Wells St. Unfortunately, this was the only coffee shop we got to during our trip but it was a lovely experience.

  • Island Party Hut Tiki Bar & Grill: A laid-back, outdoor experience located on the Riverwalk. The perfect place to order some drinks and watch boats and cruises go by in the river.

  • Jim’s Original: Known as the World Famous Polish sausage stand in Chicago that opened in 1939. Order the Polish Sausage Sandwich that started this shop and is still served today.

  • Alinea: This is a luxury eating EXPERIENCE and comes with a hefty price tag. If you have the means (money and time), then book your experience now!

  • The Berghoff Restaurant: Berghoff is an original, historic, German restaurant, 100% family-owned for over a century

  • Gibson’s Bar & Steakhouse: Gibson’s has been labeled the best steakhouse in Chicago. Celebrities & locals alike visit for their incredible dishes.

Ultimate Chicago Walking Guide for Tourists

Start

360 Chicago

Tilt over the city streets below! The 360 Chicago experience is located on the 94th floor in the John Hanco*ck Building and is an enclosed moving platform of glass that tilts you 30 degrees over Michigan Avenue. Also available on the 94th floor is Bar 94, a place to grab a co*cktail, socialize, and enjoy the view. All in all, this is among the most popular Chicago attractions.

Location: 875 N Michigan Ave 94th floor, Chicago, IL 60611, United States - Get directions on Google Maps

Walking time 360 Chicago to MOCAC👟: about 4 minutes

Museum of Contemporary Art Chicago

Walk the curated collections of 2,500+ pieces dating back from the 1920’s onward at the Museum of Contemporary Arts Chicago. These artworks include paintings, sculptures, mixed media, books, and more.

Location: 220 E Chicago Ave, Chicago, IL 60611, United States - Get directions on Google Maps

Walking time MOCAC to Ohio Street Beach👟: about 15 minutes

Ohio Street Beach

Dip your toes in the sand with a skyline view! Ohio Street Beach faces North, making it directionally unique for views of the city, and is even an ideal beach for open water swim training as the Oak Street curve is just a half-mile North.

While the beach is open daily from 6 am to 11 pm, swimming is only permitted while lifeguards are on duty.

Location: Illinois 60611, United States - Get directions on Google Maps

Walking time Ohio Street Beach to Navy Pier👟: about 3 minutes

Navy Pier

Navy Pier is a popular tourist spot with views and fun that make the visit worth it! Ride the Centennial Ferris Wheel located on Navy Pier while surrounded by beautiful Lake Michigan. Catch a seat on one of the many benches around the perimeter to sit and enjoy the endless view of the water with some take-out. Dine in one of the several restaurants on the pier and more!

Location: 600 E Grand Ave, Chicago, IL 60611, United States - Get directions on Google Maps

Walking time Navy Pier to Chicago Riverwalk👟: about 20 minutes

Chicago Riverwalk

Wave at tour boat passer-byers and appreciate the architecture with a drink in hand in one of the MANY restaurants or pubs along the Chicago Riverwalk.

This pedestrian waterfront extends from Lake Shore Drive to Lake Street; so plenty of opportunities to enjoy the entertainment, dining, and recreation of the riverwalk.

Location: E Wacker Dr, Chicago, IL 60601, United States - Get directions on Google Maps

Walking time Chicago Riverwalk to Cloud Gate👟: about 12 minutes

Cloud Gate

The obvious tourist stop - stand back to appreciate, walk under, and take pictures in this fun and interactive art form in the city; Cloud Gate (The Bean).

Location: 201 E Randolph St, Chicago, IL 60602, United States - Get directions on Google Maps

Walking time Cloud Gate to Jay Pritzker Pavilion👟: about 1 minute

Jay Pritzker Pavilion

Jay Pritzker Pavilion is an impressive piece of architecture home to live performances year-round. Even if you don’t have a show to catch here during your visit, its location in Millenium Park makes it a convenient landmark to mark off the list while in the area.

Location: 201 E Randolph St, Chicago, IL 60601, United States - Get directions on Google Maps

Walking time Jay Pritzker Pavilion to Crown Fountain👟: about 3 minutes

Crown Fountain

Gaze at the faces of Chicago that light up on a glass brick tower called Crown Fountain; one of Chicago’s best-known public art features. On a warm day, you can also dip your feet into the reflecting pool.

Location: 201 E Randolph St, Chicago, IL 60602, United States - Get directions on Google Maps

Walking time Crown Fountain to BP Pedestrian Bridge👟: about 5 minutes

BP Pedestrian Bridge

Walk across this architecturally unique, snake-like pedestrian bridge to get from Millenium Park to Maggie Daley Park called BP Pedestrian Bridge.

Location: BP Pedestrian Bridge, Chicago, IL 60601, United States - Get directions on Google Maps

Walking time BP Pedestrian Bridge to Maggie Daley Park👟: about 1 minute

Maggie Daley Park

Maggie Daley Park is a 20-acre park of greenery, rock climbing, skating ribbons, ice skating rinks, mini-golf, tennis, and picnic groves with cityscape views surrounding you.

Location: 337 E Randolph St, Chicago, IL 60601, United States - Get directions on Google Maps

Walking time Maggie Daley Park to Cancer Survivors’ Garden👟: about 1 minute

Cancer Survivors’ Garden

Cancer Survivors’ Garden is a tranquil 2.25-acre park located in the Northeast part of Maggie Daley Park was built to honor the celebration of life and to act as a place of healing for cancer patients. There are a total of 3 garden pavilions. Each represents the 3 main stages of healing; acceptance, support, and celebration.

Location: 337 E Randolph St, Chicago, IL 60601, United States - Get directions on Google Maps

Walking time Cancer Survivors’ Garden to Butler Field👟: about 4 minutes

Butler Field

Butler Field is where Chicago festivals, concerts, fairs, and fun takes place. If there are no events at your time of visit, run around, play frisbee, or lay out a blanket and relax in the green fields.

Location: S Lake Shore Dr & E Monroe St, Chicago, IL 60601, United States - Get directions on Google Maps

Walking time Butler Field to Buckingham Fountain👟: about 4 minutes

Buckingham Fountain

Stand in awe of the size and power of such a grand fountain. Buckingham Fountain is one of the largest fountains in the world.

(Note: only runs April through October).

Location: 301 S Columbus Dr, Chicago, IL 60605, United States - Get directions on Google Maps

Walking time Buckingham Fountain to Spirit of Music Garden in Grant Park👟: about 7 minutes

Spirit of Music Garden in Grant Park

Stroll through ornamental gardens, greenery, and nature known as Spirit of Music Garden in Grand Park. Summer concerts are also held here.

Location: 601 S Michigan Ave, Chicago, IL 60605, United States - Get directions on Google Maps

Walking time Spirit of Music Garden in Grant Park to Northerly Island Park👟: about 21 minutes

Northerly Island Park

End your Chicago walking tour with a walk through the 91-acre man-made peninsula known as Northerly Island Park. Another great location to take in the view of the city skyline while hiking, fishing, or strolling.

Location: 1521 S Linn White Dr, Chicago, IL 60605, United States - Get directions on Google Maps

End

Other Things to Do in Chicago

  • Chinatown: Chicago’s Chinatown is the 3rd largest in the United States and home to incredible food, events, people, history, and culture. This area is easy to navigate via train from central Chicago.

  • Garfield Park Conservatory: This enclosed exhibit of nature and architecture is home to over 120,000 plants and over 600 different species since 1908. Entry is free with a preferable donation at the door.

  • The Chicago Theatre: Catch a Broadway show (or just stand outside and marvel at its iconic beauty) at The Chicago Theatre on State St.

  • Chicago River Cruise: A very popular activity while in Chicago is to take a cruise on the river. Whether that is one of the famous architecture cruises, a sunset cruise, or a dinner cruise, there are several options to book.

  • Magnificent Mile: Shop ‘til you drop on the Magnificent Mile; the one-stop-shop for posh hotels, food, and luxury storefronts lining North Michigan Ave.

  • Wrigley Field: Home of the Chicago Cubs. If you are a baseball fan and there happens to be a home game during your visit, you should make plans to attend! This city loves its Cubs. If there isn’t a game, you can still visit and go on a tour of the stadium.

  • Adler Planetarium: Learn about astronomy and astrophysics from this world-renowned museum.

  • The Art Institute of Chicago: Chicago’s #1 must-visit art museum with rotating exhibitions ranging from Van Gogh to contemporary statues and paintings.

  • Field Museum: The Field Museum is one of the largest natural history museums in the world. Whether you work this visit into your walking day or come back another time to fully enjoy its spectacles and artifacts at your own pace, this is a museum of Chicago to not miss!

  • Shedd Aquarium: Interact with 1,500 beautiful species of animals at the Shedd A. Experiences are available for visitors such as Shark Feeding Tours, Meet a Penguin, Trainer for a Day, and more!

  • Paid City Walking Tours: While my suggested walking itinerary can be very low cost or even free, there are many paid walking tours of Chicago landmarks with a guide that can be booked through sites like Viator. See some of the best Chicago walking tours below!

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Discover Chicago on Foot: The Ultimate Walking Guide for Tourists (2023) — Away With Anna (2024)

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