The city of Chicago is the most populous city in the state of Illinois and the third most populous in the U.S. Among other names, it’s called ‘The Great Commercial Tree’ of America. There are so many places to visit in the city, making it hard to narrow down the best things to do in Chicago. However, witnessing the city’s architecture is a must! That way, you’ll end up discovering the best places to visit in this city.
Caution: The 20 best things to do in Chicago mentioned may inspire you to move to the city permanently.
Related: Find Rooms For Rent In Chicago
Explore the Outdoors in Chicago, IL
1. Washington Park
Another nickname of the city is ‘City in a Garden’. At Washington Park, you can visit a museum, explore the sanctuary, ride a boat in its lagoons, visit a refectory, and see Lorado Taft’s statue — The Fountain of Time.
2. Maggie Daley Park
So many of the best things to do in Chicago can be found here at Maggie Daley Park, where you can go rollerblading, scootering, and bungee jumping, while the non-adrenaline junkies among you can enjoy tennis, mini-golf, and drinks at the cafe
3. Grant Park
Affectionately known as the city’s front yard, Grant Park hosts the annual food and music events Taste of Chicago and the Grant Park Music Festival. Discover the historic Buckingham Fountain here, too.
Timings: Open all week from 6am to 11pm
4. Chicago Riverwalk
It’s not a park, but it’s outdoors! You will find a great mix of the best things to do in Chicago right here, in or out of the water. Here, the riverwalk is a lifestyle — and it’s unique to this city.
Museums in Chicago, IL
1. The Field Museum
A great collection of cultural and historical artifacts, all in one place. If you’re looking for the best things to do in Chicago, you should definitely check out the Field Museum.
2. Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the country. Other than the art, it is home to one of the most popular fine-dining restaurants in Chicago — Terzo Piano.
3. Shedd Aquarium
The Shedd Aquarium is an incredible live exhibit! Serene, otherworldly, and entirely captivating — it’s another one of the best places to visit in the city.
Admission includes all exhibits, animal presentation, and Stingray Touch (open late-May to Mid-Sept.).
Cultural Attractions in Chicago, IL
1. Absolutely Chicago Segway
One of the best things to do in this city is to view the dominant architecture the urban way — get on a Segway and whiz around with Absolutely Chicago Segway‘s, the city’s premier architecture tour.
2. The Bean (Cloud Gate)
3. Chicago Architecture Center
Located right above the riverwalk, the Architecture Center aims to educate you about the city’s infrastructure through interactive methods, such as virtual stories, models, and more.
4. Wrigley Building
A skyscraper recognized as an emblem of the city’s excellence in architecture and commerce. One of the many hallmark places to visit in the city.
Restaurants in Chicago
1. Uno Pizzeria & Grill
One of the best things to do in the city is to try a Deep Dish Pizza in the restaurant that started it all.
2. Table, Donkey and Stick
A must-visit when looking for restaurants in Chicago. Table, Donkey and Stick is an award-winning restaurant offering patio dining, takeout, and delivery.
Related: Roomi’s Guide To Moving To Chicago!
3. Bub City
For everything southern – country music, barbecue, and whiskey – visit Bub City. Live music events, including karaoke, plus the great food, will have you coming back for more. You can even book the venue out for private parties.
Sun – Mon | 11AM – 10PM
Tues – Wed | 11AM – 12AM
Thurs – Sat | 11AM – 1AM
Bars in Chicago
Hopleaf is a friendly neighborhood pub known for its craft beers. A place to drink, eat and be merry without television, distractions or games. The perfect spot to meet old friends, or make some new ones, if you’re new in town.
2. Halligan Bar Chicago
An Irish bar serving whiskey and everything risky (beers, cocktails, shots) in a friendly, authentic Irish atmosphere. They have a good deal on drinks most, if not all, of the time.
3. The Berghoff
The city’s oldest German restaurant. On top of the 121 years of history, they have genuinely good happy hours and offer splendid deals on drinks along with German-inspired bar bites.
Shopping in Chicago
1. Fashion Outlets of Chicago
Shopping is one of the best things to do in the city and anywhere else you visit or move. Here, you’ll find world-renowned brands and independent stores to shop from.
2. State Street Retail Historic District
Out of the many things to do in Chicago is to visit the State Street Retail District. Here, you will find all things American and trendy. You will also find many of the restaurants in the city concentrated here.
3. Shop Small Chicago
A great place to shop and support local businesses. Look at their tailor-made hats! A definite stop-to-shop when looking for the best things to do in the city. Plus, it’s conveniently located in the riverwalk!
D’you know what else Roomi does outside of helping its readers find the best things to do in Chicago? With our ever-increasing lists of rooms and roommates across the world, we’ll help you find your perfect match!