Chicago Lakefront Path: 36 Miles of Stunning Lake and Skyline Views

I have always wanted to spend the day riding along Chicago’s magnificent lakeshore biking path. Despite living in the city for more than 20 years, I never managed the opportunity. I had heard others rave about how wonderful it is, but somehow never got around to taking a ride. Most of my recent visits have taken place during the snowy winter months, so obviously biking was a no go.

Mike and I decided to finally plan a fall visit to the area, primarily to finally bike this spectacular trail. We have walked portions of it in the past, but never got to truly experience the entire length. The benefit of biking this trail is easy access to the city’s most iconic attractions.

In my opinion, September is the perfect time to take a lengthy bike ride or jog along Lake Michigan. The weather is not too hot, nor too cold. It is also not overly crowded with tourists, as typically is the case of the entire downtown during the summer months. Too much foot and bike traffic can make it hard to enjoy the ride. The path is pretty narrow; I can see the crowds being a problem during prime summer tourist season.

On the path, you will find cyclists, runners, skaters, and walkers. I prefer to bike as it enables you to see more of the city in a shorter period of time. Taking a guided segway tour is another option to look into. I have heard that these tours are worth every penny.

I prefer to get in a fitness workout so I would probably opt out, but it’s a good alternative for those who don’t want to complete a massive workout. Check out Bike and Roll Chicago for information on upcoming tours and prices.

Where to begin your ride

We parked in a garage around Millennium Park, which is around the halfway point (8.5 miles) of the path. We decided to park here as there was a restaurant we wanted to try in the area. Wildberry Pancakes and Cafe is a great pre-cycling breakfast choice. They offer all sorts of specialty pancakes and crepes, but we opted for a omelet and burrito for a more filling meal.

This is a great starting location because there are a lot of restaurants and attractions in this area. You can easily find restaurants on Randolph Street or N. Michigan Ave. Another benefit is the convenient location; just a short walk from the Magnificent Mile, where you can treat yourself to a great meal after all that exercise. There is a great mix of touristy and local restaurants to choose amongst over here.

Check the weather forecast!

We left around 6:30am to take advantage of the cooler temperatures and reduced traffic. Unfortunately, halfway through the path, the weather became incredibly windy true to the city’s nickname. The return route was much rougher than the first 18 miles.

I recommend checking the weather forecast in advance, although anywhere in the Midwest you can expect Jekyll and Hyde weather changes. You can expect a flat and fast ride as long as it is not a windy day. The beginning of the ride was incredibly smooth and easy. We barely had to pedal. The way back was a different story!

Despite the strenuous nature of the ride due to the strong winds, we still enjoyed the magnificent views of the lake and the skyline. This clean, well maintained path is your best opportunity to take in all this beautiful city has to offer. In my opinion, this is one of the top skylines in the country, tied with Pittsburgh.

Check out these cool tree sculptures we spotted near the southern end of the path

City highlights along the path

Along the course, you will pass many of The Windy City’s top attractions, including: top rated museums, Soldier Field (where the Bears play), Millennium Park, Buckingham Fountain, Lincoln Park Zoo, Navy Pier, and more! Riding your bike is a great way to bypass the hassle of driving to each attraction separately.

There’s lots to see and do along the way. If you are seeking budget fun, I recommend taking a stroll around the zoo and seeing the Buckingham fountain show as they are both free.

Take a lot of breaks and enjoy some of the city’s many attractions. The museums here are the best. I was lucky enough to get free library passes during my childhood (free passes only for cardholders) and enjoyed many free trips to The Field, The Shedd Aquarium, and The Adler Planetarium. Some of these museums also offer free admission the first full weekend of each month if you hold a Bank of America card (as part of their Museums on Us promotion). This is a great promo which I use in cities across the country.

The Field Museum

In my opinion, The Field Museum is the must-see museum of the city’s famous Museum Campus; the name for the 3 well renowned museums located near the lake. If I only had time for one, I would definitely pick this one for new tourists. The Field Museum features “Sue the T-Rex,” the most complete dinosaur fossil.

The Field is often rated one of the best museums in the world. In fact, CNN Travel recently rated it number 2 among their list of the top 10 dinosaur museums. I haven’t visited in a few years, however, the Ancient Egypt mummy exhibit is outstanding. There is also a really cool dinosaur sculpture outside, which makes for an excellent photo opportunity.

The Shedd Aquarium

Another world-class museum to add to your bucket list is The Shedd Aquarium. Like The Field Museum, the Shedd is also part of the Museum Campus. It’s one of the best aquariums I’ve ever visited. This was the hardest pass to obtain at the Chicago Public Library back in the day (unfortunately, this one was recently taken out of their free pass program).

The exhibits and shows are spectacular. I have been to several other aquariums and they do not even come close in terms of exhibits. I particularly like the sea horse; such a unique looking fish. The Wild Reef exhibit, featuring a variety of sharks, is also pretty cool.

Adler Planetarium

The 3rd member of the Museum Campus is the Adler Planetarium, which features excellent space exhibits and amazing shows in its’ dome theaters. The Grainger Sky Theater is the most technologically advanced in the world. For more info on sky shows, visit the Adler site.

Exhibits aside, the real highlight of the planetarium is the amazing location. The panoramic views of one of the country’s top skylines can’t be matched. Even if you are not planning a trip to the planetarium itself, make sure to stop by for some amazing skyline photos.

Soldier Field

You will pass right by Soldier Field, home to the Chicago Bears, on your journey along the Lakefront Path. Soldier Field is also located on the Museum Campus. Visit the Bears ticketing site for information on purchasing tickets to a game. I have never seen the Bears play here despite Mike being a big fan (I am actually a Patriots fan).

Update: We did see the Bears play a preseason game in Cleveland which was pretty cool. I have heard many people say it is better to stay home and watch the game, but I still want to experience watching a game outdoors on a crisp fall day. Sadly, the Bears will be moving to a new stadium out of the city into Arlington Park. It is expected to open in 2028 according to the website. Let’s hope we can get to a game before they leave this iconic stadium.

Grant Park

Grant Park is a large public park that is home to many festivals and events, especially during the summer months. Inside the park, you will find the Museum Campus (The Field, Shedd Aquarium, and Adler Planetarium), Millennium Park, the Art Institute of Chicago, and Buckingham Fountain. Many popular annual events such as The Taste of Chicago and the Chicago Marathon are held here. The Grant Park Music Festival is one of the city’s best free events. All concerts are free to the public all summer long.

My most memorable experience here was seeing Michael Jordan during the Bulls Championship Rally which was held in 1998. This was when the Bulls were at their prime and there was a lot of great energy in the city.

Buckingham Fountain

This beautiful fountain, which stands as one of the largest in the world, is an absolute must-see during your ride. Located conveniently just across the street around the midpoint of the path, the fountain is easily accessible and worth the small break. Be sure to come back at night for the amazing music and light show. The show runs from 8am-11pm, from May to October (weather dependent). A spirited 20 min light and music show starts at 9am each morning and runs every hour.

Millennium Park

This city park finally opened in 2004, 4 years after its’ expected opening. It opened with a big hoorah multi day festival and today it continues to be a hotspot for city events. The most notable feature here is the amazing Cloud Gate Sculpture. Plenty of unique photo opportunities (taking pics of your own reflection) are available by “the bean.” In the summer and fall months, you can take a leisurely stroll and enjoy the sculptures, gardens, and Crown Fountain. There is always some type of event going on – usually music festivals.

During the winter months, make sure to plan an ice skating date at the McCormick Tribune Ice rink. It’s one of the only free rinks in the country. I love the festive ambiance and the cityscape in the background.