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The Best Sights on Chicago’s Magnificent Mile!

Chicago’s Magnificent Mile Is one of the most famous metropolitan areas In the world for a reason & we’ve narrowed down some of the best sights to check out!

Apr 30, 202110 min read

Anecia Ascalon
Anecia Ascalon
Team Building Expert

Chicago’s Magnificent Mile Is One Of The Most Famous Metropolitan Areas In The World For A Reason!

The 13-block stretch of North Michigan Avenue, from the river bank to Oak Street, offers Chicago visitors a one-of-a-kind city experience.

The famed avenue showcases an array of trendy restaurants, notable attractions, top-rated hotels, luxe shopping, and endless entertainment. The mile has more than 460 stores, 275 restaurants, and 60 hotels along its length. It can be intimidating trying to navigate it all, but we’ve narrowed down some of the best sights to check out on the Magnificent Mile!


Chicago is known for its famous buildings and historic architecture! Take a closer look at these renowned skyscrapers that can be viewed right along the Magnificent Mile.

The Chicago Water Tower


Chicago Water Tower

Photo courtesy of Choose Chicago

Built in 1869 by William W. Boyington, the Historic Water Tower is one of the most prolific landmarks in Chicago. The limestone tower, with its chiseled buttresses and intricately carved stonework, serves as a beautiful example of Neo-Gothic architecture.

A common misconception is that the Water Tower was the only surviving building after the Great Chicago Fire of 1871. In reality though, large sections of the city were never burned, however the Water Tower was the most iconic structure left standing. Piercing boldly into the sky, The Water Tower became a rallying point for Chicago residents, representing a city determined to rise from its own ashes!

Listed on the National Register of Historic Places, today the Water Tower is home to the Chicago City Art Gallery. Visitors can browse the free gallery inside or catch a show from the Tony Award-winning Looking Glass Theatre Company.

The Tribune Tower


The Tribune Tower

Photo courtesy of Elite Traveler

The Tribune Tower is another architectural gem on The Mag Mile. The facade incorporates more than 150 fragments from historic buildings and sites, like the Winter Palace in Beijing and the Great Pyramids in Giza!

In 1922, the Chicago Tribune, a Pulitzer Prize-winning newspaper, held an international building design competition for their new downtown headquarters. The competition implored architects to create the most beautiful building in Chicago, with a $50,000 prize for the winner. There were more than 260 entries from 23 countries! New York architects Raymond Hood and John Mead Howells submitted the winning entry. The building is now a prestigious landmark and beacon of Neo-Gothic style.

Wrigley Building


Wrigley Building

The Wrigley Building is another of the dazzling skyscrapers that have come to define the Magnificent Mile. The building was added to Chicago’s skyline in 1924 and was originally constructed as the corporate headquarters of the Wrigley Company.

Done in a Spanish Colonial Revival style, the skyscraper is often revered as one of Chicago’s most attractive buildings. It has a unique facade composed of six different shades of sparkling white terra cotta that become gradually brighter toward the top of the structure. The clock stands a staggering 425 ft above street level and this building is easily one of downtown Chicago’s most recognized architectural icons.

The John Hancock Center


John Hancock Building

Photo courtesy of Chicago Architecture Center

The John Hancock Center is a 100-story, 1,000+ foot skyscraper that features a rooftop observation deck, fine dining restaurant, and panoramic city views. It’s easily recognizable on the city skyline for the two needle-like tips on the roof!

The groundbreaking engineering of the John Hancock Center was innovative in the journey to constructing buildings over 100 stories. The building occurred a name change in 2018 to “875 North Michigan Avenue,” however it is still more often called the John Hancock Center.

On the 95th and 96th floors are the Signature Room restaurant and lounge. This is a classy, picture perfect place to spend an evening getting drinks and admiring the downtown views.

The observation deck also holds 360 Chicago, a place where you can get panoramic views of the city! Tilt is a thrill-seeker’s deck that actually tilts guest over the city from the 94th floor!

Fun Activities

The Escape Game Chicago


The Escape Game Chicago

The Escape Game is America’s premier provider of escape rooms! Teams enter a themed room with 60 minutes to search for clues, solve puzzles, and complete missions in order to “escape” in time.

Everyone in a group can contribute to the action. Whether they’re 8 or 80, a new player or an enthusiast, everyone gets a chance to save the day!

Adventures here bring unforgettable, epic stories to life in one-of-a-kind immersive experiences.

The Friends Experience


Friends Experience

Photo courtesy of The Magnificent Mile

“The One in Chicago” gives guests the chance to step into the world of FRIENDS™ and explore recreations of the iconic show’s sets, like Monica and Rachel’s Kitchen, Joey and Chandler’s apartment, and Central Perk!

The interactive space features twelve look-alike rooms with fun photo ops, such as peeking around Rachel and Monica’s purple door or helping “PIVOT!” the couch with Ross. Of course, there’s also Central Perk where visitors can recline on the legendary orange couch or sing a verse of “Smelly Cat”!

The FRIENDS™ Experience closes in Chicago on May 31, 2021!

Chicago Sports Museum


Chicago Sports Museum

Photo courtesy of The Chicago Sports Museum

The Chicago Sports Museum is a 23,000-square-foot museum that’s perfect for athletic fans of all kinds. Measuring up hands with those of famous basketball players, trying to jump as high as Michael Jordan, or attempting to solve sports’ greatest mysteries are only a few of activities that can be done here! The museum also has the largest collection of Chicago Cubs World Series memorabilia in the city!

The Comedy Bar


The Comedy Bar

Photo courtesy of The Comedy Bar

Just off the Magnificent Mile sits The Comedy Bar, a great spot to share laughs with friends after a day of sightseeing and shopping. The bar’s original endeavor was to create an affordable, quality, and easily-accessible place for tourists and locals alike. The Bar has been featured in Chicago Magazine as one of the “Best Comedy Clubs in Chicago.” They also offer food, drinks, and deep dish pizza!



With over 460 retailers, The Magnificent Mile is one of the most iconic shopping areas in the world! There are department stores, luxury boutiques, and multi-story shopping centers all within walking distance of one another! The big malls are The Shops at North Bridge, Water Tower Place, and 900 North Michigan Shops. All three will deliver shopping bags to nearby hotels, allowing guests to spend more and carry less!

Popular Stores Include: Bloomingdales, Nordstrom, Macy’s, The American Girl Place, The LEGO Store, The Disney Store, Gucci, Chanel, Burberry, Coach, Nike, and Zara.

Dining + Desserts

Visitors don’t have to go far to find something delicious after a full day of exploring! Here are a few must-see eateries along The Mag Mile!



This hot dog stand is up-class and unrivaled street food. They’re well-known for a variety of menu items including Chicago-style hot dogs, Italian beef sandwiches, cheese fries, and chocolate cake shake. If you’ve never eaten here, their suggestion is: “Order an Italian beef, dipped with sweet or hot peppers (add mozzarella if you’re feeling cheesy), or a Chicago-style hot dog “dragged through the garden” and you’ll see what all the hype is about.”

Michael Jordan’s Steakhouse


Michael Jordan’s Steakhouse

Photo Courtesy of Michael Jordan Steakhouse

Although he no longer plays for The Bulls, Michael Jordan is still linked to Chicago culture! At this restaurant, “excellence is served daily.” They take pride in “Steaksmanship,” which is their principle of putting guest experience first. Here diners can find a large menu of high-quality and well-dressed food as well as signature cocktails. Try the Table 23 Experience, where you can sit at MJ’s table and enjoy a crafted menu of his favorite items!

Aster Hall


Dining with a large group of people or can’t decide what to eat? Try Aster Hall, a dining hall that has sixteen “vaults,” each featuring a different type of delicious cuisine!

Some of the cuisine options include tacos, vegan-friendly greens and grains, hamburgers, rotisserie varieties, pastas, and chocolates.

This multi-shop eatery has taken attention to detail when it comes to creating an aesthetically pleasing, airy, Instagram-able environment. They also serve coffee and dessert!

Starbucks Reserve Roastery Chicago


Starbucks Reserve Roastery Chicago

Photo courtesy of Starbucks Reserve

Did you know that one Starbucks could have four floors? Well it can! Along the Magnificent Mile is Starbucks largest public roastery in the world, with a seventeen-page menu of exclusive food items, cocktails, beers, wines, and of course, coffee! You will NOT find a menu like this at the hometown Starbucks!

Looking For Even More Places To Eat?

Check out our list of nineteen more top food destinations in the city!