Did you know that Chicago has an underground bar, a hidden cocktail lounge, and a Prohibition-era speakeasy? Did you know that the city also has a goat-centric pop-up diner, a gourmet donut shop, and an immersive dining experience that recreates the New England fishing experience? Did you know there are so many things to do in Chicago? It’s not all just hot dogs and skyscrapers!
Are you planning a trip to Chicago for the first time and looking for ideas on what to do? Or, are you a local and want to get out of your routine and try something new? Regardless of your situation, we have you covered. There are so many options when it comes to activities in Chicago. But not all of them are obvious or easy to find — especially if this is your first time visiting this city. To help narrow your list of potential activities, we’ve created this helpful guide on insider things to do in Chicago that aren’t common knowledge.
Observe the architecture on a River Walk tour
Chicago has some of the most beautiful architecture in the world. Its buildings are distinct and have been featured in many films and TV shows over the years. One way to appreciate the architecture is to take a River Walk tour. The tour begins at the dock behind The Magnificent Mile. From there, you’ll be taken by boat down the Chicago River and see many of the city’s iconic buildings up close. You’ll get a different perspective on the architecture and also learn some facts about the buildings. You’ll also get to see Lake Michigan and the Chicago skyline from a new vantage point. When you’re done with the tour, you can hop off the boat and explore some of the nearby sights. A few of the buildings you’ll pass are The Wrigley Building, The Chicago Cultural Center, and The Navy Pier. At the end of the tour, you’ll return to the dock where you started. This tour is offered year-round, and you can choose between morning and evening tours.
Enjoy the view from the top of Willis Tower
When you’re visiting Chicago, you’ll likely see one of its famous landmarks in almost every picture. That’s because the city has many landmarks that are photogenic and worth a picture of. One of the most famous landmarks in Chicago is Willis Tower. It’s the 2nd tallest building in the United States and has a glass-enclosed observation deck at the top. At 1,451 feet, you have a panoramic view of the entire city from that spot. It’s one of the most popular things to do in Chicago. When the weather is nice, the outside observation deck is open. But, when it’s cold, it’s enclosed. If you’re visiting in the winter, you can still see the city from the inside. The indoor view is just as spectacular and photogenic as the outdoor view. Plus, it’s more comfortable to stand inside. While you’re inside, you can learn more about Chicago with the help of an audio tour. It tells you about the architecture of the city, where famous buildings are and more. The observation deck at Willis Tower is open from 10 a.m. to 10 p.m. every day.
Go on a food tour and taste your way around Chicago
Chicago has a thriving food scene, and there are food tours for every type of cuisine. Whether you’re a foodie or just want to try local specialties, a food tour is a great way to explore Chicago and try new things. There are food tours for eating at famous Chicago restaurants, tasting the best hot dogs, indulging in sweets, learning about farm-to-table food, eating ethnic foods, and more. No matter your interests, there’s likely a food tour that can cater to you. A food tour is a great way to explore the city and learn more about the culture. Plus, you get to try a bunch of delicious food. It’s a win-win. You can go on a food tour during the day, or you can also go on an evening food tour. Some tours even include drinks.
Visit The Bean, or Millennium Park — and stay for the views
If you only see one thing in Chicago, it should be the view from The Bean. The famous blue reflective sculpture by Anish Kapoor is in the center of Millennium Park, one of the best places to visit in Chicago. You can either visit the park and The Bean or stay for the sunset. The park has many fountains, sculptures, walking paths, and other things to do. You can also check out some of Chicago’s architecture in the park, too. If you visit during the day, there are also free events in the park, like yoga classes and music concerts. If you visit during the summer, you can also go to the nearby Lake Michigan, which is a beautiful spot to view the city from. At night, The Bean transforms into an LED Light Sculpture. There are concerts and events at the park, too. If you’re visiting in the summer, Millennium Park is one of the best places to see the fireworks on the Fourth of July. If you’re visiting at any other time of year, it’s still worth seeing the park.
Check out The Art Institute of Chicago’s latest exhibits
The Art Institute of Chicago is one of the best museums in Chicago. It has a diverse collection of art, including American art, Asian art, African art, European art, Modern art, and more. Each year, they rotate the exhibits so that you can see the latest art. There are also special exhibitions throughout the year, too. Admission to the Art Institute of Chicago is free. While you’re there, make sure to check out the Modern Wing. It’s a modern art gallery that includes the best pieces from the collection. You can also take a tour of the entire museum. There are many guided tours available, and each one is different and highlights different pieces of art. If you only have a few hours to spend at the museum, you can take a quick tour. If you have more time, you can take a long tour. There are also self-guided tours, where you can learn about the art and history on your own.
Catch a game at Wrigley Field and see the Cubs in action
The Chicago Cubs are one of the most famous sports teams in the world. That’s because they haven’t won a World Series in 108 years. You can visit Wrigley Field, the Cubs’ stadium, and see them play during a game. While the game may not go their way, you can still say you saw the Cubs play live. The stadium is quite small and has a vintage feel to it. You’ll experience the Cubs’ home games as if you’re a part of the crowd. There are tour options where you can go behind the scenes, too. You can visit Wrigley Field year-round. During the regular baseball season, there are daily games from April to October. You can buy tickets for any game, but you need to purchase them in advance because they sell out fast.
Celebrate with food at one of Chicago’s famous festivals
Chicago is known for having great food, so it only makes sense that the city hosts some of the world’s biggest food festivals. You can indulge in everything from pizza to ribs and everything in between while you celebrate Chicago’s rich culinary culture. If you visit in September, you can also catch the Chicago Food and Drink Festival, which is the city’s biggest food festival. If you visit at any other time of the year, there are plenty of other festivals to choose from, too. You can get recommendations for which festivals are worth attending based on the time of year you visit.
Go to an improv show and laugh it up in a comedy club
If you’re looking for things to do in Chicago that are fun and silly, you can’t go wrong with a night of improv comedy shows. There are many improv theaters in Chicago, so you can choose whichever one is most convenient for you. There are also some improv shows and comedy clubs that are open to the public. No matter which theater or club you choose, you’ll have a fun and silly night out that are sure to relieve the stress of daily life. Plus, you might even discover some new skills that you didn’t know you had. If you want to learn more about improv comedy, it’s best to visit one of the theaters during off hours to take a class.
Shreck Meadows Nature Centre
Shreck Meadows Nature Centre is a beautiful nature center located on the city’s southwest side. This nature center features a large natural area that is perfect for exploring, as well as an indoor gallery space. Additionally, the center also features a gift shop where visitors can purchase souvenirs, as well as a small cafe serving delicious snacks and drinks. If you’re interested in getting a close-up look at some of the most beautiful natural landscapes in the Chicago area, then Shreck Meadows Nature Centre is worth checking out. This nature center features a large field that is perfect for walking, hiking, and exploring, as well as several different gardens that allow visitors to get a close-up look at several different plant species.
River wading pools
If you’re interested in getting up close and personal with some of the most unique fauna in the Chicago area, then the river-wading pools are worth checking out. Located in the Northerly Island area of the Chicago Harbourfront Centre, the river-wading pools are a series of natural pools that are fed by the nearby Chicago River. These river wading pools are home to numerous species of fish, frogs, and other aquatic wildlife, and are a great place to explore if you’re interested in getting a close-up look at some of the most unique creatures in the Chicago area. These river-wading pools are open year-round and are a great place to explore with friends and family. If you’re interested in checking out the river wading pools, be sure to check the Northerly Island area’s events calendar to make sure the river wading pools are open during the day you want to go.
Jackson Park and the Museum of Science and Industry
Jackson Park and the Museum of Science and Industry is a stunning park located on Chicago’s south side. This park is especially popular among locals during the warmer months, as it features several different outdoor attractions in Chicago that are perfect for spending time outdoors with friends and family. If you’re looking for a beautiful park to explore during your time in the city, then Jackson Park and the Museum of Science and Industry is a great place to start. This park features numerous attractions, such as the nearby Museum of Science and Industry, the Japanese-style Garfield Park Conservatory, and the gorgeous Rookery. Additionally, the park also often hosts several different events, such as outdoor fitness classes and garden-based exhibitions.
Northerly Island and the Chicago Harbourfront Centre
Northerly Island and the Chicago Harbourfront Centre is a beautiful green spaces located on the city’s waterfront. This green space is especially popular during the warmer months, as it features a large outdoor area that is perfect for spending time outdoors with friends and family. If you’re looking for a gorgeous green space to explore while in the city, then Northerly Island and the Chicago Harbourfront Centre is a great places to start. This green space features a large outdoor area that is perfect for spending time outdoors with friends and family, as well as a variety of interesting attractions in Chicago. Additionally, the southern end of the green space features a stunning overlook that is worth checking out.
McCormick Tribune Refuge for Rare and Endangered Species
If you’re interested in learning more about the preservation efforts surrounding several rare species in the Chicago area, then the McCormick Tribune Refuge for Rare and Endangered Species is a great place to start. This wildlife refuge features a stunning natural area that is home to several rare species of birds, reptiles, and wildlife. Additionally, the refuge also hosts several different events and exhibitions throughout the year that are worth checking out.
Chicago has a reputation as the most city-dwelling city in the country. And while it’s true that this bustling metropolis is home to some of the largest population centers, there are still plenty of smaller towns and even some rural areas to explore.
It can be easy for those unfamiliar with Chicago to overlook the city’s many hidden gems. This guide hopes to help you discover the best places to go on your next trip to Chicago. While this guide will focus on Chicago, it is by no means an exhaustive list—much of what makes Chicago special is outside of the city limits.