Things to Do In Chicago (Ultimate Guide 2021)
Did you know that Windy City doesn’t refer to the actual wind, but the politics? There’s a little Chicago trivia to get us started. There are not too many cities like Chicago. It is nestled along the southern shore of Lake Michigan with the freshwater branching through the city in a beautiful river. The third most populous destination in the United States solidified its iconic identity with its architecture, skyscrapers, art scene, food, sports teams, and so much more. Almost everything has a story and history behind it in this midwestern metropolis. The public attractions are plentiful with the many museums and parks that are so compacted together. That’s what is so great about Chicago; it’s not as spaced out as a city like New York. All the neighborhoods are compacted together on the grid plan connecting Chicago’s various districts.
Neighborhoods like Hyde Park, The Loop, Pilsen, and Bronzeville are all accessible by the Chicago Transit Authority’s elevated subway, or as it is famously called the “L.” Almost 60 million tourists a year ride the rails around the city, hitting up the high-key and low-key destinations. But what are these destinations and where can you find them? Consider this your elongated cheat sheet to things to do when in Chicago.
Millennium Park and so Much More
If you’ve seen photos of Chicago, then a few of them have surely included the famed Millenium Park “Cloud Gate” sculpture or more famously referred to as “The Bean” due to its shape. The city has several parks, each with something making them unique and worth checking out. Grant Park, known for Lollapalooza, is close to Millenium Park offers a big space and garden atmosphere near the central business district with the Buckingham Fountain as the centerpiece of the whole park.
Lincoln Park is in the northern part of the city with its zoo and DePaul college campus atmosphere. In the same area is Oz Park –a modest, pleasant space featuring statues of the characters from L. Frank Baum’s classic storybook, The Wonderful Wizard of Oz. The Chicago Park District manages several other low-key parks in the area that make for a break from the metropolitan hustle and bustle.
There are other major parks like Jackson Park and Garfield Park. Garfield Park is in the western neighborhoods of Chicago and home to the Garfield Conservatory, which features Chicago’s largest indoor botanical garden. The park also includes a fishing lagoon. Jackson Park in the southern region of Chicago also offers a lagoon wetlands atmosphere. Then there is the Jackson Park golf course with its scenic holes along the lakeshore. You can never go wrong with a stroll through the park.
The Incredible Food And Restaurants of Chicago
You’ve probably heard people bragging about the restaurant and food scene in Chicago. Both the street food and gourmet establishments are all something to gloat about. There are world-famous establishments with Michelin star ratings, as well as pizza and hot dogs that can be found on any block. New Michelin star recipients this year are Yugen, Parachute, North Pond, and Spiaggia. Chicago also saw the addition of a Nobu location as well in the West Loop Area. The variety of these restaurants offers exquisite Asian and American cuisine.
When it comes to the famed Chicago-style hot dog, there are several independent, almost hole-in-the-wall places that all follow the same recipe with the same beef –Vienna Beef. Iconic hot dog vendors like Wolfy’s, Wiener Circle, Fatso’s Last Stand, and Devil Dawgs all sport the blue “V” like a badge of honor. Superdawgs and Portillos are other iconic hot dog places with their own recipes, both started by WWII veterans when they returned from overseas.
International cuisine is another Chicago specialty. You can find the best food based on the neighborhood. Greektown in the West Loop dominates the Greek food scene, Spanish and French cuisine thrive in River North, Chinatown has authentic Cantonese food, and the best Filipino food can be found in Bucktown. When it comes to the best Chicago pizza and deep-dish, check out Lou Malnati’s for the original.
The Museum Campus of Chicago
Just next to Grant Park in the heart of the city is Chicago’s natural science museum campus. The park grounds quite literally connect them together. During the days and nights when the Bears play at Soldier Field, this area becomes packed and takes on a life of its own. When people aren’t tailgating for an upcoming game, the museum campus is a learning-orientated environment. The Field Museum is home to a collection of 1000s of specimens from every family in the animal kingdom, along with the most complete T-Rex skeleton, Sue, and the largest dinosaur to ever live, Maximo. The ancient Egyptian and Chinese exhibits also house several unique artifacts from the time.
Next door is the Shedd Aquarium which doesn’t just specialize in freshwater fish along the lake, but even the larger ones that dwell in the Amazon and open ocean. For years, the aquarium has had its own cast of dolphins, belugas, and penguins that delight millions of visitors. The penguins are fan favorites. Next door to the aquarium is the Adler Planetarium. As if learning about the planet wasn’t enough, you can look at the study of astronomy made accessible and unravel the mysteries of the universe with their walk-through and interactive exhibits. On some days, they may even have the telescope up and running.
If you were to continue down Lake Shore Drive, past Soldier Field, and down to Jackson Park, then you’ll come to the Museum of Science and Industry still housed in its original 1893 Columbian Exposition World’s Fair building. If the architecture and location don’t impress you already, then its historical exhibits of industrial science will. The museum is home to U-505, a German submarine from WWII that was captured by American forces, and the original Pioneer Zephyr train, which ran the Chicago, Burlington, and Quincy Railroad in the 1930s. Step back in time and learn how far humans have come with technology.
You may not count it as part of the museum campus, but the Chicago Institute of Art is situated right in Grant Park. It’s one of the oldest and largest art museums in the country. As such, there are some recognizable pieces by legendary artists. Some highlights include George Seurat’s A Sunday on La Grande Jatte, Pablo Picasso’s The Old Guitarist, Edward Hopper’s Nighthawks, and Grant Wood’s American Gothic. National and international art from the present and past are neatly organized into artistic adventures.
Walk or Cruise The Chicago Riverwalk
The amenities of the riverwalk along the Chicago River offer just as much as the Loop or Lincoln Park. The restaurants, bars, shops, and hotels are just as diverse as they are on the Magnificent Mile, which connects directly to the Riverwalk via Michigan Avenue. Seats line the river canals as bridges of the major streets stretch over it. Rooftop bars like London House are popular weekend hotspots.
The Chicago River itself has a couple of seasonal activities. Cruises along the river and the lakeshore are offered by Chicago Fire Boat Tours along with other ferrying companies. The Chicago Architecture Center offers boat tours up the river as they show you the most intriguing building styles of Chicago from different periods of the city’s history, from neo-gothic to postmodernism. Kayaks are also available to rent. There’s no feeling quite like paddling down the river to the lake through the canal and underneath the historic bridges.
Shop at The Magnificent Mile
Michigan Avenue stretches a mile from Lakeshore Drive to the River. The shops and hotels along this street are what make this mile so magnificent. The more north you head, the more high-end and exclusive the stores become. You have a ton of classy stores to visit, including national brands like Tommy Bahama, Disney, Vineyard Vines, and Marc Jacobs. Along the way, you’ll also find several international names like Prada, Gucci, and Rolex. These are just a couple of specific examples. If you were to visit each shop, you would need more than a day to get to them all.
The Magnificent Mile is also home to the John Hancock Center, one of the tallest buildings in the world. It’s one of the two familiar skyscrapers which make Chicago’s skyline so well known. Directly next door is Water Tower Place –Chicago’s most active shopping center with seven stories. Other landmarks around the Magnificent Mile include the Tribune Tower, the Wrigley Building, and the Chicago Water Tower, which survived the Chicago Fire.
Visitors to the city often lodge around the Magnificent Mile, given its selection of renowned and acclaimed hotels. Tourists looking for luxury accommodations and service can get a room at the Four Seasons, the Ritz-Carlton, the Peninsula, the Drake, and several more that have landmark status. There’s something about waking up where all the action is.
Visit The Ultimate Lakeshore Destination –Navy Pier.
You’ve seen the Centennial Wheel in snow globes and postcards from Chicago. Now, see the real deal at Chicago’s non-profit amusement mile Navy Pier. In addition to the shopping center of 70 local vendors, Navy Pier is home to the Chicago Children’s Museum, Amazing Chicago’s Funhouse Maze, and the Crystal Gardens. The restaurants and bars on the pier offer all your favorites while on the go and a place to lounge and have a few drinks. The rooftop scene at the Offshore Rooftop and Bar is particularly impressive with the view it offers. Outdoors next to the Centennial Wheel are even more rides and attractions like the Drop Tower and the Wave Swinger.
Navy Pier underwent renovations in 2015. This included replacing the original wheel with a larger one. By now, everything is complete and ready to go with the exception of their Imax theater that closed during the pandemic. You also may be able to board a ferry cruise around the pier as several commercial vessels dock here. What’s more, Navy Pier is nonprofit and charges no entry fee. Every purchase benefits independent and local businesses. It’s also a regular venue for concerts and events, especially during the summer. There’s always something happening at Navy Pier.
Go to The Top of Chicago’s Iconic Skyscrapers.
Yes, you can absolutely take an express elevator to the top of Chicago’s tallest skyscrapers like the Willis Tower and John Hancock Center. When in Chicago, you truly can’t miss them. Both buildings have Skydecks that are visited by millions of tourists every year. A glass-bottomed ledge extends from the top floor enabling you to look down on the city and streets 1,353 feet below. If you were to look out to the horizon, you can see as far as Michigan and Indiana to the southeast and Wisconsin to the north. It can be a real treat for thrill-seekers.
See What Makes Chicago Sports Teams so Historic
The United Center, with its Michael Jordan statue, “The Spirit,” has been referred to as the Mecca of the sports world. The Bulls share that space with the Blackhawks. Wrigley Field has often been called the nicest baseball stadium in the United States. Wrigleyville, close by Lincoln Park, is also a great destination with its food and official Cubs stores. The bars around the field are always open. As mentioned before, Soldier Field rests on the museum campus by Grant Park. The White Sox play at Guaranteed Rate Field in the South Side. Cubs vs. Sox games always get the city buzzing.
However, stadiums are closed when there are no games. Fortunately, there is still a way to spend your day immersed in the world of Chicago sports. The Water Tower Place on Michigan Avenue is home to the interactive Chicago Sports Museum as well as Harry Caray’s restaurant. Celebrate Chicago sports legends like Walter Peyton, Scottie Pippin, and Joe Maddon. There are some activities where you can test your hoop or pigskin skills with professional analysis. Wrigleyville also offers tours of the field on nongame days.
Chicago’s major league sports are world-famous, but that doesn’t mean that their minor league teams aren’t worth boasting about. In recent years, Chicago started their own minor league baseball team –The Chicago Dogs who play by O’Hare International Airport. Since their creation, they’ve enjoyed a fan following and game attendance complete with beer and hot dogs. The entertainment district close by also makes for a great post-game destination.
Tour The City’s Places of Worship And Faith
The church architecture of Chicago is one of its distinguishing features. Some of the buildings have a significant number of years on them. Some ways north of the city is a house of worship that welcomes all faiths and is known around the world. The Bahai Temple is located in the north suburb of Wilmette. There are ten Bahai Temples around the world. In fact, this one was the first one to be built in 1953. The Islamic appearance of a Mosque is fused with the Gothic and Romanesque elements of a Christian church to create a neoclassical mixed-faith temple. The gardens around the beautiful dome structure complement it and are fun to walk through. It’s a treat for people interested in the faith and those who appreciate architecture.
Watch a Broadway-Tier Play in The Windy City
Chicago has its own piece of Broadway with over 200 theatres that come in all shapes and sizes. The Chicago Theatre itself has to be the most famous and well-known venue. Other incredible theatres include the Cadillac Palace, the Nederlander, CIBC, the Riviera, Steppenwolf, and so much more. These venues can be found all over the city, from Lincoln Park to the South Side. Broadway plays, concerts, and even celebrity shows are commonplace in Chicago. By the River, there’s also the House of Blues Chicago location which showcases independent artists.
As a side note, the movie scene in Chicago is just as celebrated as its theatre one. There’s numerous drive-ins, which have blown up during the pandemic as a way to go to the movies but stay socially distanced. Sometimes even Soldier Field hosts a movie night with a big projector screen, featuring the latest film and live entertainment.
Take in All The Sounds of The Music Scene
Chicago has a unique music scene. Second to Nashville, many musicians come here to get their start. Because of that, the city has become a very nurturing environment for music. While the venues previously listed for plays have musical guests, there are neighborhoods and venues where you can come across some hidden gems. Uptown is a particularly diverse neighborhood when it comes to culture. The Riviera theater acts as their main venue with several smaller ones all around, including the oldest Jazz club in Chicago, the Green Mill, which has been around since the prohibition era. Independent artists and creators often reside in this neighborhood.
Wicker Park is westward over on the other side of I-90. This is another hideout for local artists and musicians. Subterranean, located on North Ave is a music, comedy, and nightclub with two different floors and thus, two different events every night. Chop Shop is another nearby venue named so because of the auto body shop building it’s housed in. The butcher shop in its restaurant and bar is a welcome section too. This offers more space with a 20ft ceiling. The Hideout and the Empty Bottle are a couple of up-and-coming hangouts a little way outside Wicker Park. Another great entertainment hangout is Logan Square. The audience here is more hipster-based with the dive bars, art galleries, and lounges. There’s always nightlife present and the music takes more of an experimental tone. The Whistler acts as the foremost cocktail bar with a music label and venue. Many of the restaurants here serve food that is farm-to-table fresh. Concord Music Hall is where the more national acts come to perform. With no set genre, a rock group can be playing one night while a rapper performs the next.
Immerse Yourself in The Lesser-Known Museums
We’ve gone over all the major museums of Chicago, which everyone goes to. However, Chicago has several independent museums that often go under tourists’ radar. The Chicago History Museum is the perfect place to immerse yourself in the city’s past –from the Chicago Fire to the reign of Al Capone. The DuSable Museum of African American History was first opened in the living room of Chicago artist and civil rights activist Margret Taylor-Burroughs. Now, it’s housed in the old police station by Jackson Park. The Museum of Contemporary Art is located next to Water Tower Place. Here, one of the largest collections of post-WWII art is on display. You can further be immersed in art at the WNDR Museum, and The Museum of Illusions is fun if you enjoyed the maze over at Navy Pier. The American Writers Museum is another great art destination. Speaking of writers, you can also visit Ernest Hemingway’s childhood home turned museum.
Lodge in Historic Hotels
As previously mentioned, the Magnificent Mile is where the top-rated hotels of Chicago are located. The Peninsula and the Four Seasons are top contenders for the most booked. Luxury hotels are constant in their quality service beyond Michigan Avenue. But another aspect that makes staying in a hotel in Chicago is that it’s like lodging in a piece of history. Palmer House has been in the Loop since 1871. Liberace even started his piano career as a pianist in the lounge in the 40s. Chicago is home to many 20s-era hotels like the Drake and Intercontinental. The Blackstone is another historical hotel that was opened a decade before. The turn of the century architecture is present with all the modern renovations.
The Congress Plaza Hotel by Grant Park opened for the World’s Fair hosted at the future Museum of Science and Industry. Believe it or not, it’s become known as one of Chicago’s most haunted places. Yes, numerous hauntings have been reported throughout the decades since it opened. Supposedly, there’s a sealed door with no knob on the 12th floor. They offer cozy luxury at an affordable price, and the World’s Fair auditorium is still present. The Staypineapple is another historic landmark in the area housed in the Reliance Building built around the same time as the Congress Plaza. These buildings are commonly talked about by tour guides on architecture tours.
Bike Around The City And Lakeshore
Using a bike is easy in Chicago with bike-sharing companies like Divvy. They have their electronic bike racks all over the city, stretching all the way up to Evanston and down to Calumet City. You won’t be able to walk a block in the city itself without coming across one. With a bike, the trail along the shore of Lake Michigan is the ideal experience. You don’t have to be an experienced cyclist to enjoy it. Bike tours are also available with architecture, history, food, and even ghost tours. Touring the city on a segway is also an option.
Try The Locally Brewed Beers
You could settle with the same old Budweiser or Bud Light or try some of the beer brewed and served directly from the source. Chicago is home to several independent brewing companies –most of which have bier gartens. Some of the Windy City brewers like Goose Island, Lagunitas, and Revolution are national bestsellers. The Anti-Hero IPA is a city favorite. Marz is an honorable mention. Lincoln Park and the surrounding neighborhoods are particularly where you’ll find the best drinks if you’re a lager or ale connoisseur. The fact that they’re located in popular music neighborhoods can be a sweet combination for the weekend.
Cruise Lake Michigan in Various Watercrafts
We’ve talked about walking up and down the lakeshore and kayaking through the River. So, you’ve probably been wondering about the possibilities of boating or swimming in the lake itself. Lake Michigan may not be as clean as most freshwater lakes, but it’s still safe to swim in. July is peak swim season. But if you’re reluctant to get wet, there’s a multitude of watercraft services with their own route and something unique. These places can be found at Navy Pier and along the shore.
Some of the best ferry companies and tours are the Shoreline Sightseeing Classic Lake Tour, the Skyline Sail, and the water taxis. Thrill-seekers can take the tour by speedboat with the Seadog Lakefront Tour –it’s a roller coaster on water. Eating out on the lake is dreamlike with dinner and lunch cruises. Odyssey Chicago River takes its dinners from the River and out into the lake while the Spirit of Chicago Dinner Cruise sticks entirely to the lake. Both run for about two and a half hours with music played by a DJ and pre-arranged menus to pair the experience with.
Witness and Interact With The Animal Kingdom at The Zoos
The Field Museum is great, but their animals aren’t alive. At the Lincoln Park Zoo, wildlife from all around the world unties in Chicago’s front yard with nearly 200 residents. Some famous ones include the critically endangered black rhinoceroses and rare iguanas in the reptile house. This year, they’re welcoming new white-cheeked gibbons, meerkats, and red river hogs. Animal care and conservation are prestigious with an emphasis on community. The Lincoln Park Zoo is actually the fourth oldest zoo in the United States.
Also west of the city is the larger Brookfield Zoo. Residents and tourists flock by the thousands here to feed the giraffes. While they don’t house elephants and hippos anymore, they continue to house rhinoceroses, tapirs, and hippos in their pachyderm house. Walk with the dinosaurs at Dinosaurs Alive, this season’s featured event with several life-sized animatronic figures of the giants which once walked the Earth.
Head North to The Chicago Botanic Gardens
The Garfield Conservatory is tied in terms of beauty with the Chicago Botanic Gardens. There’s a bike trail in Gompers Park leading 16 miles up to Glencoe, where the Botanic Gardens reside. The facility features a fruit, vegetable, and rose garden. The Japanese and Waterfall Gardens are a whole other way of seeing nature. The Junior Railway is a garden of electric trains traveling through all Chicago’s landmarks and other recognizable scenes. During the holiday season, the light show attracts thousands of guests with a line leading out of the entrance.
Close by the Botanic Gardens is Highland Park’s Ravina venue. National acts come to perform here, from local talent like the Chicago Orchestra to Steve Martin and Martin Short. When journeying from the city to the suburbs, the Metra train is the most reliable, running from Kenosha all the way to the end of the line close by the loop.
Take Part in The Sport of Whirly Ball
Chicago Whirlyball has a convenient location right next to I-90 by Roscoe Village. Its enormous signs beckon all those who pass by on the expressway. Whirlyball combines everything we love about lacrosse, hockey, and bumper cars into a competitive event. As competitive as bumping your friends can be, that is. It’s mainly played for laughs, more so than glory. There are whirly ball places all around Chicagoland. A lot of them have an arcade and bar setting. Some may sport a laser tag arena as well.
See And Try Everything When in Chicago
When you’re looking for things to do in Chicago, the best way to approach it is to never be discriminative or close-minded. In short, go out there and experience everything you can. Chicago is a midwestern beacon of food, culture, views, media, and industry. In recent times, all major businesses and attractions have taken safety measures to protect against COVID-19. By now, all the places that were once closed are opening up again. All the best things to do in Chicago have hours of operation now –ready to get the tourist business running again. Tourists also need not fear as Chicago has been steady in delivering the vaccine to its residents. Now, one in every seven Chicago residents is vaccinated, with more on the way. Consult the city’s official government website for more information on how Chicago is working to fight COVID19.
Whether you’re planning an activity-filled day, hitting up as many attractions as you can, or taking it easy at the parks or bars, Chicago has an atmosphere for everything. The summers are hot, and the winters are frigid, so it helps to plan your visit seasonally.