Things to Do in the Loop - cityguidetochicago.com

There is a wonderful mix of things to do in the Loop including museums and cultural activities, landmarks, exceptional parks, and kid-friendly activities. If you are visiting Chicago, this is a can’t-miss neighborhood.

The Loop is the heart of downtown Chicago. It is home to the city’s financial district, theater district, and several world-class museums.

Last updated: April 2022

Read More About The Loop:
Best Restaurants in the Loop

Where is the Loop:

Table of Contents

The Loop is bordered by the Chicago River on the North and West, Lake Michigan to the East, and Roosevelt Road to the South. The neighborhood gets its name since the el train tracks make a complete loop in this neighborhood.

How to Get to the Loop:

All of the el trains have stops in the Loop. Several of the trains make a square loop around the Loop, giving the neighborhood its name. In addition to the el trains, the Metra trains stops at Millennium Station, Van Buren Station, and Museum Campus.

Parks and Outdoor Activities:

Millenium Park

A park just north of Grant Park that is home to the Cloud Gate sculpture, the Crown Fountain, and an amphitheater. Events including concerts, movie nights, workouts, and Chicago Gourmet are hosted here.

Grant Park

One of the largest parks in Chicago, Grant Park span’s much of the Loop’s lakefront. The park is over 312 acres in size and contains gardens, tennis courts, a skate park, baseball diamonds, and the massive Buckingham Fountain. The park hosts Lollapalooza and is the location of the start and finish lines for the Chicago Marathon. Technically, Millennium Park, Maggie Daley Park, Museum Campus, and part of the Lakefront Trail are all within Grant Park.

Maggie Daley Park

Maggie Daley Park is the ultimate playground, or, actually, a series of playgrounds for children of different ages. In addition to elaborate playgrounds, the park has a skating ribbon and a rock climbing wall. Maggie Daley Park is located directly to the east of Millennium Park.

Landmarks:

Cloud Gate (The Bean)

Cloud Gate is the centerpiece of Millennium Park. The large highly reflective bean-shaped sculpture by Anish Kapoor is one of the most iconic symbols of Chicago.

The Art Institute of Chicago

The Art Institute is one of just two buildings constructed for the 1893 World’s Fair that still stands today. The Beaux-Arts style building was used as the World’s Congress Auxiliary Building during the World’s Fair, before being turned over to the Art Institute of Chicago. The bronze lions standing at the stairs were added in 1894, after the AIC took over the space. The museum is located within Grant Park.

Calder’s Flamingo

Alexander Calder’s towering 53 foot tall vermillion colored Flamingo sculpture can be found in Federal Plaza. Flamingo was unveiled in 1974 and is one of Calders “stabile” works. The term refers to the fact that the sculpture does not move, unlike Calder’s famed “mobile” works. The shade of vermillion red is named “Calder Red” and the sculpture was repainted in this exact hue in 2012.

The sculpture is a short walk from the Art Institute of Chicago, Grant Park, and Millennium Park.

Chicago Picasso

A large scale, 50 foot tall, abstract steel sculpture located in Daley Plaza. The sculpture is untitled and is usually referred to as “The Picasso” or the “Chicago Picasso”. Picasso said that the head of the sculpture was inspired by his Afghan Hound. Others say that the sculpture was inspired by a female muse or that it was meant to look like a baboon.

The Rookery

Located in The Loop’s financial district, The Rookery is a multistory office building originally designed by Daniel Burnham and John Root and later updated by Frank Lloyd Wright and then William Drummond. The building is known for its exceptional interior architecture. Tours of the Light Court and the Burnham Library are available through The Frank Lloyd Wright Trust.

Willis Tower (Sears Tower)

The Willis Tower has 110 stories, stands 1,450 feet tall, and is the tallest building in Chicago.

Buckingham Fountain

This Rococo-style fountain is the centerpiece of Grant Park. Inspired by a fountain at the Palace of Versailles, and dedicated in 1927, it is a symbol of Lake Michigan. The four sets of seahorses represent the four states that border Lake Michigan (Illinois, Indiana, Michigan, and Wisconsin). The fountain was donated to Chicago by Kate Sturges Buckingham in memory of her brother Clarence Buckingham.

Things to do in the Loop - the Art Institute

Museums:

Art Institute of Chicago

Considered to be one of the best museums in the world, the Art Institute of Chicago has an exceptional collection of Impressionist and Post Impressionist Art and hosts traveling exhibits. If you plan to see a special exhibit, you may want to purchase tickets in advance.

McCormick Bridgehouse & Chicago River Museum

A museum sharing the story of the Chicago River and its moveable bridges. The museum lets visitors enter a bridge house at river level and then climb up five stories to the top of the bridge house to take in 360 degree views of the city. This museum is open seasonally closes during the winter months.

Museum of Contemporary Photography

A Columbia College art museum that houses works from over 1,500 artists. Collection highlights include works by Alfred Stieglitz, Dorothea Lange, and Cindy Sherman.

Chicago Architecture Center

The center is home to the largest scale model of Chicago, which features over 4,250 miniature buildings. The exhibit explores Chicago’s diverse neighborhoods and architectural styles.

American Writers Museum

The first museum that is dedicated to American writers and their literary contributions. Exhibits explore the works of individual writers and themes like immigrant and refugee writers.

Design Museum of Chicago

A museum that explores the impact of design, ranging from choreography to street art, architecture, and urban planning.

Pritzker Military Museum and Library

A museum with a collection of books and materials focused on military history, military affairs, national security, and citizen soldiers. The museum discusses past, present, and future military and its role in maintaining democracy and protecting our nation.

The Color Factory

This new interactive museum immerses Chicagoans in art and color with experiences that engage all the senses including 15 new installations and exciting artist partnerships.

Museum of Illusions

An immersive museum for people of all ages. Here you can experience optical illusions that make for fun photo opps.

Mindworks: The Science of Thinking

Operated by the Center for Decision Research at the University of Chicago Booth School of Business, this is a behavioral science discovery center with interactive exhibits that let participants learn about themselves while providing data for research studies.

Museum Campus:

According to the city’s website for Grant Park, Museum Campus is located within Grant Park. Yet, the city’s official map of community areas places Museum Campus in the South Loop. Museum Campus is home to the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

Field Museum

Chicago’s famous T-Rex, Sue, can be found at this natural history museum along with cultural collections and anthropological artifacts from all over the globe. This museum has exhibits that visitors of all ages will enjoy, including young children.

Shedd Aquarium

Chicago’s aquarium is home to a wide range of animals including dolphins, penguins, sharks, sea otters, and more. If you visit in the summer, you might want to plan your visit around the Jazzin’ at the Shedd outdoor concert series.

Adler Planetarium

This was America’s first planetarium, and it’s the place to learn about astronomy and astrophysics. The planetarium has shows geared towards children (one involves Big Bird and Elmo) plus programming for adults. Each Wednesday, the planetarium is open until 10 pm for Alder at Night.

Things to Do in the Loop:

Skydeck at the Willis Tower (Sears Tower)

Both 30 and 60 minute tours of the Willis Tower are available. These tours include an interactive look at Chicago’s history and then a trip to the Skydeck, the building’s 103rd floor observation deck. On a clear day, the views span four states. The Skydeck is home of The Ledge, a glass box ledge that extends out from the Skydeck, 1,353 feet above the streets below. The Ledge requires an additional ticket.

The Riverwalk

The Riverwalk is a 1.25 mile long pedestrian-only path that runs along the south side of the Chicago River. From the Riverwalk, visitors can enjoy views of architectural landmarks including the Wrigley Building and Marina Towers. During the warmer months, several al fresco bars and restaurants can be found along the Riverwalk. Many host live music and entertainment. The Riverwalk is a perfect place to view Art on the Mart.

Art on the Mart

An art experience involving art being projected onto the massive Merchandise Mart building. The art is projected onto the side of the building facing the Chicago River so while Merchandise Mart is in River North, Art on the Mart is best viewed from the Riverwalk in the Loop.

Wabash Arts Corridor

An outdoor public art project run by Columbia College Chicago that spans South Wabash Street from the Loop to the South Loop. Murals of various sizes tackle topics like the Women’s Suffrage Movement, Native American Chicago, Polish culture, and themes like hope, the relationships between time and space, and hip hop culture. Guided tours are offered year-round.

Chicago Cultural Center

A stunning building with two stunning stained glass domes that is used as an event space for free lectures, music, theater, dance, art, and film events.

Fine Arts Building Studios

This building that is home to art studios hosts Open Studios events on the second Friday of each month from 5 pm until 9 pm. These events are free and open to the public.

Architecture Tour

Several tour companies run architectural boat tours that cruise down the Chicago River. The best tours are run by the Chicago Architecture Foundation Center aboard Chicago’s First Lady. In addition to the very popular architectural tour, evening cruises and photography cruises are available.

Bike Tour

Bobby’s Bike Hike leads bike tours, walking tours, and food tours. The Ultimate City Tour is a biking tour that has stops at Millennium Park, Grant Park, Cloud Gate, Buckingham Fountain, and the lakefront. The Family-Friendly Tour of Chicago caters to families with young children and combines a bike tour with a food tour.

Segway Tours

Several companies operate Segway tours in the Loop. Absolutely Chicago Segway Tours hosts tours of the Lakefront and Museum Campus, Art and Architecture, and City Lights and the Skyline in addition to themed tours like ghosts and gangsters.

Things to do in the Loop - The Theater District

Music Venues:

The Loop is home to Chicago’s Theater District. Many of the theater venues host concerts in addition to Broadway in Chicago musicals and plays. Theses theaters include the Auditorium Theater, Cadillac Palace, CIBC Theater, the Nederlander Theater, and the Broadway Playhouse at Water Tower Place.

The Chicago Theater

This theater in The Loop is the place to see concerts, comedy shows, and other touring shows. It is one of those rare theaters where every seat feels like a great seat. Another reason why this theater is one of the best is that it is located steps from the State and Lake el stop making getting to and from a show a breeze.

Buddy Guy’s Legends

A blues club with live music 7 nights a week. They also serve New Orleans inspired food. The club was opened in 1989 by blues musician Buddy Guy, and if you are very lucky he might just hop up on stage and perform. You might want to buy tickets in advance.

Theater:

Broadway in Chicago

There are five theaters in Chicago (Auditorium Theater, Cadillac Palace, CIBC Theater, the Nederlander Theater, and the Broadway Playhouse at Water Tower Place) that are home to Broadway in Chicago plays and musicals. Some are Chicago-based productions and others are touring shows. It is usually best to purchase tickets directly from the Broadway in Chicago website for the best pricing.

Drunk Shakespeare

A unique Shakespeare production that involves an actor taking five shots of whiskey and then performing a play in a hidden speakeasy library. Craft cocktails are available for the audience.

Annual Events in the Loop:

Many of these events take place in Millennium Park or Grant Park.

Chicago Gourmet

A weekend food festival held in Millennium Park at the end of September. The event features wine tastings, food samples from Chicago restaurants, and cooking demonstrations from chefs.

Taste of Chicago

The world’s largest food festival takes place over five days in July in Grant Park. The main attraction is the food with dozens of Chicago restaurants participating but there is also live music.

Lollapalooza

A massive multi-stage music festival that takes place over four days in the middle of summer. The festival takes over Grant Park and dozens of bands perform. Expect a mix of household names and emerging acts to be on the lineup.

Blues Fest

A free blue festival in Millennium Park that attracts 500,000 attendees.

Jazz Fest

A free festival that brings jazz music to Millennium Park in early September.

Movies in the Park

Chicago’s summertime Movies in the Park event takes place at parks all over the city, including Grant Park.

Millennium Park Summer Film Series

In 2022 this annual film series will be taking place on Tuesdays from July 12 through August 30. Attendance is free and guests can sit in the Jay Pritzker Pavilion or on the Great Lawn.

Millennium Park Summer Music Series

A series of free concerts at the Jay Pritzker Pavilion on Mondays and Thursdays that runs from the end of June through the end of August. The 2022 schedule hasn’t been announced yet but, usually the music series spans genres including jazz, indie rock, blues, salsa, and folk.

Chicago Theater Week

A one week event that takes place during the winter when theaters across the city offer deeply discounted ticket prices ($15-$30)

Dyeing the Chicago River Green

The Chicago River gets dyed a vibrant shade of green for St. Patrick’s Day. The event takes place at 8 am the Saturday before St. Patrick’s Day (or on St. Patrick’s Day if it falls on a Saturday). The river is dyed between Columbus and Wacker Drive and the color lasts a few days.

Millennium Park Summer Workouts

This free workout series takes place on Saturdays from Memorial Day through Labor Day.