Walking Chicago! 20 Things to Do, See and Eat

  • June 10, 2017

Walking Chicago! I started going to Chicago on a regular basis about three years ago. I work remotely for a company that is right downtown in “the Loop” as its called, and so I’ve had a lot of time to visit some of downtown Chicago’s best destinations. Chicago is very different than where I’m from in Southern California. Unlike  San Diegans who complain when the weather reaches 50 degrees in the winter, or more than 80 in the summer, Chicago’s hardy  citizen’s brave long, very cold winters and the summers are brief and sometimes really hot and humid. They deal with a lot of bad press about their city’s budget and politicians, crime and corruption. Yet, the people who live there are filled with immense pride in their city (especially now that the Cubs have finally won a World Series!).

And they should be proud, Chicago is filled with incredible history, beautiful masonry, different architecture styles, parks, museums, art, and culture that most cities in the U.S. can only dream about. And, don’t get me started on the food — I just watched an episode of Netflix’ Chef’s Table on the restaurant Alinea and I’ve added it to my bucket list of restaurants! Chicago even has its own style of deep dish pizza that is worth a visit alone!

One of the things that I’ve learned from my trips to the city is that you can really visit a majority of the sights in downtown Chicago on foot. I absolutely love walking in a new city. I think it provides a better view of the sights, smells and distinct nuances that you won’t pick up by taking a cab or Uber everywhere. This post is for the walkers. I put together some of my favorite things to do and see  by walking Chicago.


There are so many hotel options downtown. You can find all of the chains like Hilton’s, Mariott’s and smaller boutique chains like Kimpton’s as well. I have stayed in quite a few hotels. The below are close to the destinations that I’ll be chatting about in this post. (all hotels, restaurants and destinations are linked).

Chicago Athletic Association —- 12 S Michigan Avenue

Hip, historical, with a modern athletic and masculine feel, Chicago Athletic Association opened up just a few years ago. Taking over the historical site of the athletic association the hotel boasts a game room, the Milk Room (get some good milkshakes!) and it has a great rooftop bar and restaurant Cindy’s that overlooks the park. Only downside is that its a top watering hole for the after work crowd. If you want a quiet hotel this might not be the spot for you.

Public Chicago — 1360 N Lake Shore Drive

Modern with minimalistic monochrome décor, Public is a good option.

Fairmont Hotel — 200 North Columbus Drive

The Fairmont is in a good location for walking to the Art Institute of Chicago and through Millennium Park. The hotel is pretty traditional, clean, with some great views of downtown from the higher floors.

Walking Chicago
The night view from the Fairmont Hotel, Walking the lake shoreline


Below is a list of things to do and see on foot by walking Chicago. One way to save some money if you plan to visit a lot of sights is to get the Chicago CityPASS – For $99 (adult) you get admission to the Art Institute of Chicago’s permanent collection and non-ticketed special exhibitions, plus an audio tour. CityPASS also includes admission to the Shedd Aquarium, Skydeck Chicago, the Field Museum, and either the Museum of Science and Industry or 360 Chicago.

Art Institute of Chicago — In Millennium Park – One of the best collections of Art in the U.S. Enjoy, modern masters like Picasso, a huge collection of impressionists, as well as sculpture, and other art installations. You could easily spend all day here if you are a fan of art. (Price is $29 starting)

The Field Museum — Dinosaur lovers – this museum is a must see! The Field Museum has the largest T. rex ever found. (Price is adults $51 with Jurassic world experience)

Adler Planetarium —Learn about planets and the solar system, eclipses, and telescopes. (Price starts at $24 for adults and $20 for children)

Navy Pier — Navy Pier is pretty touristy but its fun to walk out on the Pier. Originally designed for shipping and recreational purposes, the facility has evolved into an entertainment center. The Pier also houses the Chicago Children’s Museum designed for children under 10.  Experience an interactive timeline of Navy Pier’s history at

Picnic in Grant Park — Grab some lunch to go and head to Grant Park. See the huge Buckingham Fountain and enjoy the view of the lake.

Architecture Boat Tour — This is one of my favorite things to do in Chicago. The city has a fascinating architectural history with styles like Art Deco, and modern. Step onto the boat, order a glass of wine and enjoy the views and history as you float down the river looking at the magnificent buildings. There are a few different companies Wendella’s 75 minutes long. I recommend an evening tour – the view of the sunset hitting the buildings is beautiful.

Shopping — Of course many people love shopping. I am not one of those people but if you are interested in shopping make your way to the famous Magnificent Mile were you can take in 460 stores and shop to your heart’s content.

Walk or Run Downtown — There are some amazing running paths along the lake, river and throughout the city. One of my favorite running apps is called MapMyCity. Youc an create your own map, or find other runners maps of places to walk and run in the city.

See the sculptures, Jay Pritzker Pavilion and the Bean in Millenium Park — Free! Don’t miss capturing a photo in front of the world famous Bean.

See a comedy show at The Second City -1616 N Wells St — Second City has been making people laugh for more than 50 years! Since its debut, The Second City has been a launching pad for comedians, actors, directors and others working in show business. Alumni include Alan Arkin, Dan Aykroyd, John Candy, Steve Carell, Stephen Colbert, Rachel Dratch, Chris Farley, Tina Fey, Amy Sedaris, Martin Short, among many others.

Bike the City with Divvy — For just $10 you can bike Chicago for the whole day. The only catch is that you can only do it in 30 minute increments. Divvy Bikes are everywhere in Chicago – in fact there for 580 docking stations. You pay, unlock your bike and then drop it off at another station within 30 minutes. You can keep unlocking bikes and returning for your daily fee. If you want to keep it for a longer increment – they will charge you a few extra dollars.

Walking Chicago Buckingham Fountain Chicago, Navy Pier Chicago
Buckingham Fountain, Ferris Wheel at Navy Pier


Cindy’s Rooftop – Chicago Athletic Association — The view from this rooftop bar and restaurant is amazing. Cindy’s has great food and cocktails and firepits looking out over the park and lake.


Cindy’s — Located in the Chicago Athletic Association Hotel – this restaurant has some of the best views around.

Mercat La Planxa — I love this tapas restaurant. The flavors are amazing and the small plates make everything more fun. Try the tasting menu to get a great selection of plates.

Prime and Provisions— This steakhouse is a relatively new addition to downtown. The steaks are great, but the roasted garlic and mashed potato sides are incredible.

RPM Italian — I wasn’t sure what to expect when I visited this Italian restaurant owned by reality TV couple Bill and Giuliana Rancic, but I loved it.  My table shared a lot of dishes so we tried everything from the steak to the pasta. My favorite part was actually the panna cotta desert.

Walking Chicago, The Chicago Bean, Flowers in Chicago, Millennium Park Chicago
The Bean, Flowers along the lake and a view of the Jay Pritzker Pavilion
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