Things To Do in the Loop Chicago

If the neighborhoods of Chicago were a body, the Loop would be the beating heart of the city as its home to the iconic Chicago Theater, the haunted Congress Plaza Hotel, and our number one visited tourist attraction, Millennium Park, with its world famous “Bean”.  The Loop is also the birthplace of the Modern Skyscraper, built in 1885 on the corner of Adams and Lasalle, The Home Insurance Building (RIP) was the building that started Chicago’s legacy of architecture. If you’re planning on visiting the Windy City, I guarantee you’ll find yourself walking around in this neighborhood that started it all.  

The Loop neighborhood borders the main stem of the Chicago River to the north and extends south ending at Roosevelt Road. The Loop received its name because of the cable cars that ran in a circle around the area before the construction in 1897 of the Union Elevated Railway, or as we call it today, the “El”.  The El tracks go in a loop around…The Loop, cementing the beloved name for generations.


How to Get to the Loop

 If you’re flying into O’Hare then you should take the Blue Line into the Loop getting off at one of the following stops:

  • Clark/Lake
  • Washington
  • Monroe
  • Jackson

If you’re flying in from Midway, then you’ll be entering the Loop from the Orange Line. You’ll want to disembark at one of the following stations:

  • Roosevelt (transfer to the red line)
  • Harold Washington Library- State/Van Buren
  • LaSalle/Van Buren
  • Quincy
  • Washington/Wells
  • Adams/Wabash

If you’re driving into the Loop, then you’ll most likely be taking either I-55, I-290 or I-90/94.  Traffic is always heavier during rush hour and is particularly bad on Friday nights and Sunday afternoons.  If your schedule allows it, we highly recommend avoiding peak travel times to shorten your commute.

Should I stay in the Loop?

 The short answer is yes!  There’s a ton of iconic and historic hotels in the loop ranging from nice to ultra-luxurious. As an extra bonus, the Loop is extremely walkable and with the El accessible from every inch of the area, you can get almost anywhere in the city without touching a car.

Below is a list of our top recommended places to stay!

The Palmer House: Built in 1873, the Palmer House is the longest continually operating hotel in the United States, and is the birthplace of the Brownie!

The Congress Plaza Hotel: Want something extra spooky? According to Leisure + Travel Magazine, The Congress is the most haunted place in Illinois.  Catch a glimpse of Al Capone’s ghost, or lovable ghosts such as Peg Leg Johnny and the little ghost boy.

London House: Dripping with luxury, the London House sports the most iconic views of the Chicago River and its famed architecture. Their rooftop bar is one of the highest rated in the city.

The Chicago Athletic Association: Another classic building in Chicago completed in 1893, this hotel overlooks Millennium Park and, like the London House, boasts a rooftop bar. Originally a private club for the more fortunate, it has been renovated and opened to be enjoyed by the public. Step back in time and see the world through the eyes of Chicago’s Elite.

What is there to do in the Loop? 

Take a Tour of Downtown Chicago and the Loop!

Travel Tip! The ultimate way to make the most of your time in Chicago is to get to know the area, and the best way to do that is by taking a guided tour at the start of your trip. Your guide will point out the obvious points of interest and provide historical information, while also pointing out local favorites.

Here at Bobby’s Bike Hike, we offer two tours that will provide you with the history of the loop and Chicago’s infamous foods!

If you would like to see the city by bike, then may we suggest our Family Food Biking Tour! This tour starts and ends at our headquarters located near Navy Pier, and will take you through the Gold Coast and The Loop. 

If you would prefer to stay on your own two feet, we have the Chicago Favorites Food walking tour, which starts on the Magnificent Mile and ends in The Loop at, none other than, the Palmer House Hotel.

Both are food tours suitable for all ages and will provide you with plenty of food, history, and fun.  This is a great way to get acquainted with the city before jumping into the rest of your adventure.


The Chicago Cultural Center

The Chicago Cultural Center, was built in 1897 as Chicago’s first public Library. These days it is a free museum full of exhibits from local artists and houses the largest of the Tiffany Domes. Entrance is free, so whether you come to admire the architecture or the exhibits you’re sure to be in for a treat. It is open from 10am – 5pm every day and is conveniently located across the street from Millennium Park.

Go Shopping on State Street

State Street is Chicago’s second major shopping district with stores such as Footlocker, Sephora, Zara, and most notably the Marshall Field and Company turned Macy’s in 2006. Visiting Macy’s is an activity within itself. Construction was finished in 1893, just in time for the Colombian Exhibition, Chicago’s very first World’s Fair. The Walnut Room located on the 7th Floor hosts a Holiday Tea which has become a local tradition for families. The Marshall Field and Company Building also homes one of the infamous Tiffany ceilings in Chicago that is available for public display during opening hours. The Holiday Season is the best time of year to come and enjoy its splendor and window displays, but the building is a work of art that can be appreciated year-round.


Experience Chicago Dining

The Berghoff is one of the city’s oldest establishments, opening in 1898 and boasts being a local family-owned business since its inception, selling traditional German style fair as well as brewing its own beer and sodas. Unlike many of its competitors, The Berghoff stayed afloat during Prohibition not by opening a speakeasy, but by selling “near beer,” a low alcohol substitute.  They also created the Bergo Soda Pop which would be the predecessor to The Berghoff’s famous Root beer. This restaurant, full of history and exceptional food, is closed on Sunday and Monday, so be sure to plan this dining experience accordingly.

If German food isn’t quite your style, then let us introduce you to another Chicago Loop staple, The Italian Village

This three-story dining experience is the oldest Italian restaurant in the city opening in 1927.  Although red sauce pastas were beloved, what would separate this establishment from the other Italian restaurants was its introduction of other regional Italian dishes such as manicotti, fettuccini alfredo, and cannelloni just to name a few.  In 1955 the Village would open it’s second restaurant La Cantina. In 1961 The Florentine Room, Chicago’s first gourmet Italian restaurant, would open on the ground floor and cement the Italian Village as “Chicago’s best Italian Restaurant” according to the Chicago Tribune. They have some of the best service in Chicago and are an excellent choice if you are looking to grab dinner before making your way to see a Broadway in Chicago show.


Have questions about the Loop?

  • Millennium Park
  • Chicago Cultural Center Est. 1897
  • Chicago Athletic Association Est. 1893 
  • The Auditorium Building Est. 1889
  • The Chicago Theater Est. 1921
  • Marshall Field and Company Building Est. 1893 and the Walnut Room (Now Macy’s)
  • Broadway in Chicago
  • Italian Village
  • The Berghoff
  • The Chicago Riverwalk
  • The Magnificent Mile 
  • Soldier Field
  • The Art Institute 
  • The Field Museum
  • The Shedd Aquarium

You could spend an entire weekend in the Loop and still have more to see and learn. We would recommend taking a walking or biking tour of the area so you can get to know its history and try the must-eat-Chicago foods.

There are also a couple colleges located in the Loop, and the area is made up of many college students.

Peak season is June – August, but you can find things to do year-round in the Loop.

It’s no secret that our winters can be a bit on the chilly side, if you choose to visit between November and March then be sure to pack warm clothes with lots of layers to accommodate the moody climate. That doesn’t go without saying, there are lots of things to do in Chicago during the winter, from ice skating on the river to catching a hockey game.

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The Loop is incredibly walkable, the best way to generally get around is on foot.

Every line of the “L” train converges in The Loop, making every area of the city accessible

Uber/Lyft or taxis can be used in every area for those who prefer to stay away from public transportation.

The Loop started it all. Today it is still the home of our most legendary restaurants, hotels, and tourist attractions. It is a mecca of culture with year-round concerts, Broadway in Chicago Shows, and Ballets at the Auditorium Theater. No matter your interests, photography style or historic preferences, you will find something to entertain and dazzle you. ­­­­If you’re still looking for specific things to do in the Chicago Loop, give us a call at Bobby’s Bike Hike. We can set you up with a private tour of Chicago and make sure you are getting the exact experience you’re looking for.