Discover Chicago on Foot or Bike: The Ultimate Walking Guide for Tourists
Updated: May 2026
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, with a focus on being outdoors and experiencing Chicago’s green and blue spaces.
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 must-visit stops or break it up among several days in the city! Anyway you do it, enjoy!
Affiliate Disclaimer
Please note that some of the links on this website are affiliate links. This means that I may earn a commission if you click on the link and make a purchase at no additional cost to you. I only recommend products and services that I have personally used or thoroughly researched. Thank you for your support!
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.
Summer and Fall are ideal seasons to visit Chicago because of the nice weather, plethora of outdoor festivals and events, and manageable crowds. You will also have the best chance of a good weather day to make the most of this guide!
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
Walking
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! (Note: this walking guide is 6+ miles! There are other ways to get around from point to point in this guide that may be more suitable for you!)
Bus & Train
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.
Bike
Another great way to get around Chicago is by renting a bike or scooter. These are available all over from Divvy city bike rentals, to rental companies like Bobby’s Bike Hike (close to starting point of this guide). They are affordable, and help you get around the city quickly.
Uber
Rideshare apps like Uber and Lyft are an efficient, but pricier option to getting around Chicago.
Guided Tours
There are so many guided tours available to fit anyone and everyone’s mobility, interests, and budgets.
Viator is a great source for browsing these options (affiliate link). They may not necessarily follow exactly what I have put together in this blog, but offers an excellent range of tours with guides to explore what excites you most about Chicago!
Ultimate Chicago Walking Guide for Tourists
The total time this entire route takes is approximately 2.5 hours (about 6 miles) by foot, however, I would allot 1-2 more hours for sightseeing, picture taking, traffic, crowds, weather, popping into museums, lunch, etc. This can easily be an all day exploration! Riding a bike, scooter, or taking a bus/train/Uber between spots will cut down on time on your feet.
Overview of Chicago Walking Guide start to finish:
360 Chicago
Museum of Contemporary Art Chicago
Ohio Street Beach
Navy Pier
Chicago Riverwalk
Cloud Gate (The Bean)
Crown Fountain
BP Pedestrian Bridge
Maggie Daley Park
Clarence F. Birmingham Memorial Fountain
Lakefront Park
Northerly Island Park
Start
360 Chicago
Tilt over the city streets below! The 360 Chicago experience is located on the 94th floor in the John Hancock Building and is an enclosed moving platform of glass that tilts you 30 degrees over Michigan Avenue. Also available on the 94th floor is CloudBar, a place to grab a cocktail, socialize, and enjoy the view.
All in all, this is among the most popular Chicago attractions and recommended to go early in the day with pre-paid tickets!
📍Location: Get directions on Google Maps
↓ Walking time 360 Chicago to MCA👟: about 4 minutes (0.2 miles) ↓
Museum of Contemporary Art Chicago
Walk the curated collections of 2,500+ pieces dating back from the 1920s onward at the Museum of Contemporary Arts Chicago. Exhibits include paintings, sculptures, mixed media, books, and more.
NOTE: MCA is closed on Mondays
📍Location: Get directions on Google Maps
↓ Walking time MCA to Ohio Street Beach (via Lakefront Trail)👟: about 16 minutes (0.7 miles) ↓
Ohio Street Beach
Dip your toes in the sand if the weather is nice, with a skyline view! Ohio Street Beach faces North, making it directionally unique for views of the city. Even on a gloomy Chicago day, this beach is beautiful.
While Ohio Street Beach is open daily from 6 am to 11 pm, swimming is only permitted while lifeguards are on duty.
TIP: Garrett’s Popcorn is a famous Chicago-born popcorn brand. You can buy some at the Garrett’s Shop on the Navy Pier.
📍Location: Get directions on Google Maps
↓ Walking time Ohio Street Beach to end of Navy Pier👟: about 15 minutes (0.7 miles)↓
Left to right: Looking over Lake Michigan on a gloomy day, Flyover, Centennial Wheel, view of skyline from pier
Navy Pier
Navy Pier is a popular tourist spot jutting into the beautiful Lake Michigan, with views of the Chicago cityscape, lake, and has a number of indoor or outdoor activities and attractions (depending on the weather), suitable for all ages and interests.
Consider checking out at Navy Pier:
Flyover Chicago - Incredible experience connecting visitors with the spirit and sights of Chicago. One of my favorite activities at the pier.
Centennial Wheel - 200ft ferris wheel boasting 360 views of Lake Michigan and Chicago.
Observation deck - The far East end of Navy Pier opens up to a wide space with more benches and unobstructed views.
Shopping & Dining - Options are plentiful!
📍Location: Get directions on Google Maps
↓ Walking time end of Navy Pier to Chicago Riverwalk👟: about 33 minutes (1.5 miles) ↓
Left: Riverwalk Theatre; Right: The Wrigley Building & Tribune Tower
Chicago Riverwalk
Wave at the tour boat passersby and take in the famous Chicago 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 there are plenty of opportunities to enjoy the entertainment, dining, and recreation of the riverwalk.
Here are some Chicago Riverwalk highlights:
First Lady Architecture Cruise - My favorite river cruise provider offering architecture-focused guided tours
Riverwalk Theatre - Seating along the riverwalk
Marina City Towers - Twin towers that famously look like corn cobs, designed by architect Bertrand Goldberg
Tribune Tower - Neo-gothic skyscraper built with influence of the Rouen Cathedral
The Wrigley Building - Notable Chicago skyline building, built in 1924 with clock tower
McCormick Bridgehouse & Chicago River Museum - Exhibits Chicago’s river and moving bridge systems
Chicago Architecture Center - Non-profit showcasing exhibits and tours promoting Chicago architecture
📍Location: Get directions on Google Maps
↓ Walking time Chicago Riverwalk to Cloud Gate👟: about 12 minutes (0.5 miles) ↓
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) in Millenium Park.
📍Location: Get directions on Google Maps
↓ Walking time Cloud Gate to Crown Fountain👟: about 2 minutes (0.1 miles) ↓
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: Get directions on Google Maps
↓ Walking time Crown Fountain to BP Pedestrian Bridge👟: about 6 minutes (0.2 miles) ↓
Pass by:
Jay Pritzker Pavilion - Impressive music and event venue designed by architect Frank Gehry
Lurie Garden - 2.5 acre botanical garden
Photo by Kestner Brae De Vera on Unsplash
BP Pedestrian Bridge
Walk across this architecturally unique, snake-like pedestrian bridge to get from Millennium Park to Maggie Daley Park, called BP Pedestrian Bridge.
📍Location: Get directions on Google Maps
↓ Walking time BP Pedestrian Bridge to Maggie Daley Park👟: about 1 minute ↓
Left: Beautiful pavilions and benches; Right: Cancer Survivors’ Garden
Maggie Daley Park
Maggie Daley Park is a 20-acre park of greenery, rock climbing, skating ribbons, ice skating rinks, mini-golf, tennis, children’s play grounds, and picnic groves with cityscape views surrounding you.
📍Location: Get directions on Google Maps
↓ Walking time Maggie Daley Park to Buckingham Fountain👟: about 8 minutes (0.4 miles) ↓
Pass by:
Cancer Survivors’ Garden - Quiet, beautiful garden built to honor cancer survivors and celebration of life
Butler Field - Large, open field used by the public for recreation, picnics, etc when no events are on
North Rose Garden - A rose garden that is prettiest when blooming in the summer
Clarence F. Buckingham Memorial 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: Fountain only runs April through October
📍Location: Get directions on Google Maps
↓ Walking time Buckingham Fountain to Lakefront Park👟: about 1 minute ↓
Photo by Zander Betterton on Unsplash
Lakefront Park
Cross Lakeshore Dr from Buckingham Fountain to Lakefront Park! This park is a green space stretching along a portion of the Lake Michigan shoreline with wide paved paths perfect for walking and biking.
You can walk this path South all the way to Adler Planetarium and Northerly Island Park.
📍Location: Get directions on Google Maps
↓ Walking time Lakefront Park to Northerly Island Park👟: about 33 minutes (1.5 miles) ↓
Pass by:
Shedd Aquarium - Indoor aquarium with impressive variety of habitats
Field Museum - One of the largest natural history museums in the world
Photo by Acool rocket on Unsplash
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.
More things to discover at Northerly Island Park:
Adler Planetarium - Planetarium with exhibits and skygazing events
Northerly Island Park Visitor Center - Grab a souvenir and information for your visit to Northerly Island Park
Northerly Island Loop Trail - 2.1 mile loop around Northerly Island Park
12th Street Beach - Nice public beach
📍Location: Get directions on Google Maps
End
Left: Chicago architecture river cruise tour with First Lady; Right: The Chicago Theatre
More 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.
Medieval Torture Museum: This is such an interesting and interactive museum! Detailed remakes of torture devices are displayed throughout the museum, giving visitors the opportunity to read the grim history and interact with some of the devices.
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.
The Art Institute of Chicago: Chicago’s #1 must-visit art museum with rotating exhibitions ranging from Van Gogh to contemporary statues and paintings.
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!
Map with Pins
↓ read more illinois travel guides ↓
PIN FOR LATER!
