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Self-Guided Chicago Bike Tour

Updated: December 22, 2023
 By Mel

Chicago Bike tour Divvy bike station Biking in Chicago is a great way to experience the city!  If you need to rent a bike, check out our post on the best Chicago bike rental companies.

Although most of this tour utilizes the bike path, if you find yourself using streets, get a refresher on bike laws here.

For only $9.95 you may access Chicago's city bike rental program - the Divvy bikes - for an entire day.  All of the tour stops will be near Divvy bike stations. Just remember to lock your bike at a Divvy Station within the first 30 minutes in order not to get charged anything extra, and when you are done with a tour stop, just take a new bike.

We recommend having Divvy’s website handy on your smart phone so that you can easily spot the stations. Although this is not necessary, the Divvy website is convenient because it allows you to see a map of where stations are, how many bikes are at the station and how many openings are at the station.  Once you have your bike and understand how your bike-share operates, hop on and enjoy the ride!

Click for movable map. Choose the option to show the Divvy Bike Stations as well.

Self-guided bike tour chicago map



Chicago bike tour Bean 1) Millennium Park (201 E. Randolph St. at the intersection of Randolph and Michigan)

This is a great place to start since some of the bike rental stations are conveniently located here.  There are a few “all day” bike rentals if you don’t want to use the bike share program Divvy. I recommend grabbing your bike after you are done enjoying the sites here since bike riding is not allowed on some parts of the grounds.

Millennium Park was built to celebrate the millennia though it officially opened in 2004.  It is a lovely park with one of the top tourist attractions in Chicago: Cloud Gate a.k.a the Bean designed by Anish Kapoor. The Bean is a large mirrored sculpture that reflects the skyline.

Other notable sites to explore are: the Crown Fountain by Jaime Plensa which consists of two large LED towers that display videos of faces.  This fountain was inspired by a gargoyle.  Watch and see why!  Also look for Pritzker Pavilion by Frank Gehrey, a large outdoor concert venue made up of stainless steel ribbons that resemble a trumpet blaring.

Learn more about the Loop and Millennium Park on a walking tour.
Chicago Bike tour Crown Fountain

2) Maggie Daley Park

Walk your bike over the BP bridge to enter Maggie Daley Park.  The bridge is a pedestrian walk way that is directly east of Pritzker Pavillion and Cloud Gate.

Maggie Daley Park, named after our previous mayor’s wife, is our newest and most jovial park in Chicago!  This park was built for the kids or the young at heart.  It features various playgrounds, a skating ribbon, an enchanted forest, and a large rocking climbing wall.  Maggie Daley Park is also the location of the Cancer Survivors’ Garden that is a large metal pavilion containing themed gardens to represent the stages of healing: acceptance, support and celebration.


3) Buckingham Fountain in Grant Park (301 S. Columbus Dr. at the intersection of Columbus and Congress)

Ride or walk your bike east (towards the Lake) on Monroe or continued through Maggie Daley Park and cross the street to find the bike path.  Take a right on the bike path heading south. You will see your next destination on your right across the street.

Chicago bike tour Buckingham Fountain Grant Park is one of the oldest parks in Chicago dating back to 1835.  The large green space makes it a perfect place to hold events like the Chicago marathon and the Taste of Chicago, which is an annual Chicago festival.  The centerpiece of the park is one of the largest fountains in the world.  Buckingham Fountain, a rococo-style fountain, was given to Chicago as a gift in 1927.  The fountain was manually operated until 1980.  From 10am-11pm- there is a water display on the hour for about 20 minutes! Other notable sites to explore in Grant Park are: the Art Institute built in 1893 that has the second largest collection of impressionist artwork, and one of the five Lincoln Statues of Chicago is in Grant Park near Columbus drive.  It was made by Augustus Saint-Gaudens.  Of course, we in the Land of Lincoln love our Abe statues.


Chicago Agora 4) Agora (The corner of Michigan and Roosevelt)

Ride your bike south through the parks or south on Columbus.  Turn right on Roosevelt or ride through the parks east/away from the Lake.

Near the South/West corner of Grant Park you will come across a large skating park.  It can be very fun to watch the skaters in the park do ollies!  On the other side of the skate park is an art installation that you cannot miss: Agora. Polish artist Magdalena Abakanowicz created this small army of headless and armless 9 foot tall statues at the edge of Grant Park. Take a picture of yourself milling about with these statues.


Chicago Waffles


5) Chicago Waffles (1400 S Michigan Ave. Hours: 7am-3pm M-F; 7am-4pm S-S)

We recommend leaving your Divvy bike at the station near Agora and walk two block south on Michigan.  Chicago Waffles will be on your right.

At this point, if you are looking for something to snack on- head over to Chicago Waffles for something sweet!  They serve only breakfast food and their specialty is obviously waffles!  As they say, “A waffle is like a pancake with a syrup trap!”




6) Museum Campus (1300 S Lake Shore Dr. along Lake Michigan)

Cross the street heading east towards the Lake to get back onto the bike path. Take a right or ride south on this path towards the Museum Campus and along the Lake to the Adler Planetarium.

Chicago bike tour Museum Campus View The Museum Campus is the best view of the Chicago skyline.  Bike all the way to the end of the tiny peninsula to see the best view of the city on the west and the beautiful Lake to the east.  This is a good time to pop into one of the three museums on this campus: The Field Museum, The Adler Planetarium, or the Shedd Aquarium.  Each offers a unique and totally different experience.  As you bike past them, it will be clear which one is which.  The aquarium is topped with a trident and is covered with nautical elements, the planetarium has a planet-like dome, and the Field Museum has replicas of dinosaurs outside.  By the way, those dinosaurs will don the outfits of our winning sports teams during the season! Speaking of which, to the south of the Field Museum is the iconic Soldier Field that is the home to the Chicago Bears Football team.  This structure is a unique blend of modern and classical architecture. The original structure was built in 1922 and the renovated modern parts were added in 2003.


7) Northerly Island (1521 Linn White Drive)

Recharge your bike at the Planetarium quickly and then head South through what looks like a parking lot to the right of the Planetarium.  Follow the streets until you reach the Prairie preserve area that has a short Loop around the island.

Originally Northerly Island was meant to be part of Daniel Turnham’s 1909 city plan to have a lake front park.  Of course, these plans changed when the Wright Brother’s took their iconic first flight!  A small commuter airport called Meig’s Field was put on the land.  For years it operated solely as an airport; however, in an attempt to reclaim the land for park space in 2003 Mayor Daley demolished most of the airport in the middle  of the night without city permission.  The island is now used as a concert venue and a small section of the airport still exists as a tiny museum.  This museum is where the airport scenes in the movie “Witless Protection” took place. The majority of the island was converting in 2015 to a public prairie park and path that offers a gorgeous view of the Lake and the city.


8) Snack Stop at the Juicy (Monroe and Lakeshore Drive)

Along the bike path heading north towards Navy Pier on the right side after Buckingham Fountain.

If you need another snack break or Divvy recharge, during the warm seasons there is a little Juice and snack hut before you reach Navy Pier.  They offer snow cones, fresh corn on the cob (perfect for a state that’s main crop is corn), and hot dogs.


9) Navy Pier (600 E. Grand, off of Lake Michigan)

From the Museum Campus turn around to head back North passing the Buckingham Fountain along the way.  You will continue following the bike path but watch for signs and pedestrians as the area near the Pier tends to be filled with folks on foot.  Navy Pier is on the right.

Chicago bike tour Navy Pier Navy Pier is a great place to visit.  It offers another beautiful view of the city and is the home of great entertainment, food, tours, special events, and shopping.  The pier was first built in 1916 and used as a shipping yard.  Later during the Second World War, Chicago leased the pier to the Navy, which is what the pier is later named in honor of. Later the pier was the home for the University of Chicago and then it housed festivals like the Taste of Chicago.  Finally, in the 1990’s Navy Pier was shaped into a tourist destination. Between 2014-2016 it is being renovated again.  While navigating the pier, look for yummy snacks like Chicago’s favorite popcorn shop Garrett’s Popcorn.  Ride on a carnival ride like the Ferris wheel or the swings.  Walk up the stairs near the McDonald’s to see a tropical garden called Crystral Gardens. Near the end of the pier you will find an indoor stain glass museum that displays the work of Louis C. Tiffany.


10) Milton Lee Olive Park (Directly north of Navy Pier)

This park is directly North of Navy Pier and shares the same land the Pier is built on.  You cant miss it!

This lovely park feels like a quiet oasis since it is nestled directly between Navy Pier, a giant water filtration plant, and a bustling downtown Chicago.  Most Chicagoans do not know of the tranquility of this park.  It features five large circular fountains and “Hymn to Water” a statue by Milton Horn.  Also look for the monument to the Park’s namesake, Milton Lee Olive who was the first African American recipient of the Medal of Honor in the Vietnam War.


11) Oak Street Beach (1001 N. Lake Shore Dr, of Lake Michigan north of Navy Pier)

Continue North on the path. The route will curve drastically to the left and directly on your right you will see the Oak Street Beach and Café.  The Divvy station is up on the left near Michigan Ave if you need to charge up quickly.

Chicago bike tour view behind you after leaving Oak Street Beach Believe it or not, Chicago boasts 18 miles of public lakefront and a bike path and that includes several beaches.  Although most folks don’t think about visiting Chicago as a beach vacation, it is a fantastic place to step away from the city, if only a few steps.  The Oak Street Beach is perfect because it boasts a café.  You can enjoy a beverage and a snack while lounging near the beach.  They often have live entertainment and special events like bag tournaments!  Playing bags will make you a true Midwesterner. As you pass the beach, be sure to turn around and see the amazing view of the Hancock Building which is the 4th tallest building in Chicago.  If you need a break from the outdoors, this is a good time to dock your bike and head over to the Drake Hotel for a cocktail in one of their bars off of Michigan Ave.  You can miss it with it giant light up sign. If you like this neighborhood, check out our Gold Coast tour.


12) Lincoln Park Zoo (2001 N. Clark St.)

This is your longest stretch of path without a Divvy station so be prepared.  You will continue heading North on the path but will be getting off the path to go towards the Zoo from North Ave.

Chicago bike tour Lincoln Park Lincoln Park covers the green area north of the city.  It used to be a cemetery but was converted to a park.  You can still find the grave for Couch which was too heavy to move. The Lincoln Park Zoo is one of the few remaining free zoos in America. And it’s one of the oldest, opening in 1868!  The entire campus is beautiful and has hidden gems throughout it.  South of the actual zoo, there is a small swampy prairie preserve where you can imagine the early days before “Chicago”. Many of the natural plants and animals have made their home here.  Be cautious with your bike on the path and consider walking in some areas to avoid little kids and families walking.  You will see a large wooden arch on your route.  It was built by Jeanne Gang and was inspired by a tortoise shell.  Once you enter the actual zoo, look for the lions, penguins, monkeys, and polar bears.  Several of the zoo structures are landmarks, including the Lion House.

This is great place to end the tour so that you can enjoy the zoo and then head into the Lincoln Park neighborhood for dinner.

++Please also check out our pay-what-you-like walking tours of Chicago's most popular sights and neighborhoods.+++

About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: December 22nd, 2023
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