19 Of The Best Things To Do in Chicago

Ashley Akridge - Freelance Writer

This webpage contains affiliate links. If you choose to make a purchase through our link, we receive a commission at no extra cost to you.

Chicago is a city of incredible charm, history and vibrancy. From world-famous museums to top-notch restaurants, the Windy City has something for everyone. It's also an underrated travel destination. No matter your budget or style, here are the best things to do when you visit Chicago.

This article has three sections, the first is about what to see, the second is about where to stay, and the third is about what to eat. After you've finished reading this travel blog, you'll be salivating, so start planning your trip!

The Best Things To Do in Chicago

Visit the Chicago Art Institute

The Art Institute of Chicago Lions

The Art Institute of Chicago is one of the top museums in the U.S. (and the world). The museum has a massive collection of Impressionist, Post-Impressionist, Cubist and Modern art, including pieces by Van Gogh, Monet, Manet, Picasso, Rodin, Jackson Pollock, and Andy Warhol. This is a must-see place for art-lovers, but if it interests you, you can add it onto a package of several discounted attractions with the Chicago CityPass. See the link below for more details.


Ride a boat along the Chicago River

Chicago River Cityscape at Sunset

Chicago is also known for its shoreline, where you can go fishing, boating and swimming. The Chicago River is more than just a waterway in this city; it's still the lake that rules the town. Chicagoans never tire of looking at the river and the city skyline. It's beautiful, especially at night when the buildings are lit up. For around $50 you can take a cruise on the water to check out the sites in a very relaxing way.

Shedd Aquarium

Aerial View of Shedd Aquarium, Chicago, Illinois, USA

One of the best things to do in Chicago is to visit the Shedd Aquarium. It's one of the largest aquariums in the world, with more than 32,000 animals representing nearly 600 species. The aquarium also has a 4D theater, so you can watch movies while also getting sprayed with water and other stimuli. The Shedd Aquarium is free to the public, but there are small entry fees to the 4D theater. As mentioned above about the Chicago CityPass, the Shedd Aquarium is included in that package, so if you intend on seeing many of the top tourist spots it would be worth checking out their deal.

South Shore Cultural Center

South Shore Cultural Center Chicago

Suppose you're looking for more than just sea creatures, head to the South Shore Cultural Center. Here, you can enjoy live performances from up-and-coming local artists along with theatrical productions. If a night of quality entertainment among the arts is on your agenda, there's no better choice than this vibrant venue.

Walk Along Lake Shore Drive

Chicago and Lake Michigan at Sunset

Lake Shore Drive is Chicago's coastal drive, and it offers some of the best views of Lake Michigan in all of the city. This drive is located just east of the main tourist district and features a mix of beaches and residential areas. If you're looking to see some of the city's most amazing views without dealing with the crowds of the city, this is a great drive to take (and walk).

Navy Pier

Chicago's Navy Pier and ferris wheel along the Chicago River with cruise ship

One of the best things to do in Chicago is to take a walk around the lake and then go on the Ferris wheel at Navy Pier. The view from the Ferris wheel is amazing, not just of the city but of Lake Michigan too. There are plenty of attractions on the pier itself, including an aquarium and lots of bars and restaurants.

Willis Tower

Chicago cityscape with Willis Tower in focus

Don't let the name fool you. The "Willis Tower" has been home to the Chicago offices of the insurance giant for decades. However, this building is much more than a skyscraper. It's a prime destination for tourists from around the world, and it stands at an impressive 108-stories or 1,450feet (442 meters)! Nestled between downtown Chicago and the Magnificent Mile, the Willis Tower is an excellent option for sightseeing.

Aerial View of Chicago Rooftops and Chicago River from tourist attraction "glass ledges"

For an unforgettable experience, go up on the Glass Balcony. This is one of the highest points in Chicago, standing 1,353 feet (412 meters) above street level. Get set to have your breath taken away and witness unforgettable panoramic views across the city. The sky deck and glass balcony are open all year long, even in the winter! What better way to take amazing pictures of the city than from the top of a skyscraper?

If you purchased the Chicago CityPass, you're in luck, the Willis Tower Skydeck is included in your package!

Explore the Magnificent Mile

Magnificent Mile Chicago Illinois USA Michigan Avenue

The Magnificent Mile is a section of Michigan Avenue that cuts through Chicago's downtown. Part of Chicago's famous Loop, it's home to some of the city's greatest shopping, dining, and entertainment. Known as one of the top luxury shopping destinations in the U.S., you can find everything from high-end department stores to upscale boutiques here.

Chicago History Museum

Chicago History Museum East Façade

For history buffs, there's a lot to love about the Chicago History Museum. Housed in the 120-year-old former main post office, the museum is dedicated to telling the story of the city. There are more than 100,000 square feet of exhibit space, and you can learn about everything from urban history to the history of baseball. There are also some tremendous temporary exhibits worth checking out.

Grant Park

Aerial view of Buckingham Fountain in Grant Park, Chicago

When you are in Chicago, you can't miss visiting Grant Park. This is the largest of Chicago's parks, and it's where you can participate in some of the most exciting activities you can experience. The park boasts a wide variety of attractions that will delight anyone who loves nature. If you are interested in sports and outdoor activities, this is the right spot. Some of the most exciting activities that can be enjoyed in Grant Park include jogging, walking, biking and rollerblading. You can also go fishing or canoeing on Lake Michigan. If time permits, you can even enjoy a picnic with your family or friends on one of the many green areas within the park. They will also enjoy playing at Kids Field and Buckingham Fountain if you have children.

Here are some more exciting things to do in Grant Park:

Buckingham Fountain

Buckingham Fountain in Chicago at night

Buckingham Fountain is an iconic landmark that has been featured in many films and television shows set in Chicago. It was even designated as an American Water Landmark by the American Water Works Association. Built in 1927, it features water shooting up from its center during summertime. Even looking at pictures is breathtaking!

Millennium Park

Tourists visit Cloud Gate in Millennium Park in the evening with "The Bean" in focus

Millennium Park is one of Chicago's most iconic landmarks. It was designed by a world-renowned architect, Frank Gehry. Some of the most notable pieces of architecture in Millennium Park are the Cloud Gate, also known as 'The Bean'; and the Jay Pritzker Pavilion.

Maggie Daley Park

Maggie Daley Park, downtown Chicago, from above

The Maggie Daley Park is the largest and newest in Grant Park. This park is an excellent place for kids. In addition, there's a large water fountain and several water slides. It also has a vast complex that houses a climbing wall and rock climbing/bouldering. From a skatepark to a beach volleyball court, you will find something you like here. It is a fun park to visit, especially on a hot day because of the water!

Where To Stay In Chicago

Chicago Urban Skyine at Sunset Downtown Chicago Cityscape Panorama

Chicago is one of the premier cities in the United States and is a top destination for many travelers. You can find a variety of hotels in Chicago that offer upscale, mid-range, and budget accommodations. There are also a number of beautiful bed and breakfast inns available should you be looking for a more personal experience.

Nobu Hotel

The Nobu Hotel is Chicago's newest luxury hotel and a haven for relaxation. The 115-room property, located in the heart of downtown Chicago, offers the ultimate pampering experience with style. Step into the rooftop restaurant and enjoy panoramic views of the magnificent Chicago skyline. Then, indulge in an indoor tranquility pool or relax in the sanctuary-like bathroom. They even have their sushi bar downstairs! With its tall design, expansive bar and grill, and stunning views at every front door — the Nobu is one of those few hotels that feels like home away from home.
If this is not in your budget range, keep reading. We've included something for everyone on this list!

The Blackstone

The Blackstone is one of the most admired hotels in all of Chicago. Past guests such as Jimmy Carter, Teddy Roosevelt and a local legend Al Capone have all stayed at this historic landmark, a place you must consider if you're visiting Chicago. The Blackstone links to the past make it a top Chicago attraction with its classic design. So don't miss this chance to stay at one of Chicago's most iconic hotels.

One of the best things about The Blackstone hotel in Chicago is its view — it's close to both Grant Park and Lake Michigan, so you can see one or the other depending on what room you book. So, no matter the weather or your mood, you'll find a good view waiting for you at The Blackstone without breaking the bank!

FOUND Hotel Chicago

Looking for a budget stay in Chicago? The FOUND Hotel is a charming spot perfect for families and stylish travelers alike. Close to Millennium Park, the Art Institute of Chicago, and Navy Pier, this hotel is also near public transportation. For around $100 per night depending on the deals at the time, you'll get yourself a two-bedroom room featuring a queen-size bed and bunk beds in the second room for the little ones, perfect for a good night's sleep.

Where To Eat In Chicago

Outdoor Cafe in Chicago Illinois

Chicago is famous for two things: skyscrapers and deep-dish pizza. Of course, there are plenty of museums, parks, and cultural sights to see, but if you want to work up an appetite, you can always visit one of the seven Chicago-style pizzerias.

Chicago-Style Hot Dog

One of the best things to do in Chicago is to eat a Chicago-style hot dog. It's a Vienna Beef Hot Dog topped with yellow mustard, chopped white onions, neon green sweet pickle relish, dill pickle spear, tomato slices and a dash of celery salt on a poppy seed bun. There are many places to eat a Chicago-style hot dog, but Portillo's is famous. They have locations all over the Chicago area, and they're open until 3:00 in the morning. Here are a few other choices to eat a Chicago-style hot dog:

Hot Doug's
The Wiener's Circle
Gene and Jude's

Chicago Deep-Dish Pizza

Speaking of famous food, Chicago is also renowned for deep-dish pizza! Deep-dish pizza is one of the many great things about living in Chicago, and it's a unique feature of the city. It essentially means the crust is really thick and fluffy, and the toppings are piled on high. Not only are these pizzas delicious, but they are also fun to watch being made. There are a lot of places that serve fantastic deep-dish pizza in Chicago, Here are the top 3 deep-dish pizzas places worth tasting:

Lou Malnati's
Gino's East

Explore Chinatown's Food

Chinatown in Chicago is a great place to explore. It's not just the food that makes it an excellent place to visit, but there are also plenty of things to do in Chinatown. Tons of great restaurants are located here and offer a wide range of foods. So if you want to get adventurous with your taste buds, this area is where you should start. Look for the longest line if you can't decide where to eat! You can find anything from authentic Chinese cuisine to Thai cooking at these eateries.
Chinatown is also a fun place to go shopping, and there are plenty of options here too. You'll find all kinds of items from clothing stores and art shops to specialty stores selling things like incense, tea or souvenirs. So if you want something unique, Chinatown is the place to be!

Chinatown in Chicago is a great place for some authentic Asian food. There are many shops lined up in the area, and you can pick from Indian, Japanese, Chinese, Thai, Korean and Vietnamese restaurants. Here are a few fan favorites to eat in Chinatown:

Lao Sze Chuan
The People's Republic
Qing Xiang Yuan Dumplings
Snack Planet
BBQ King House

There are excellent local tours that take you throughout the city to try the absolute must-try foods, so if you want to get a total foodie experience with an expert, try one of these:

Final Thoughts on The Windy City

Chicago at Dusk - Aerial Cityscape

No matter how you slice it, Chicago is a brilliant place to go! Whether you're looking for family fun, unbelievable food, live comedy or cultural delights, there are plenty of things here to keep you satisfied all day long. We hope our blog has been helpful and we would like to wish you all the best on your trip to Chicago!

Scott and Yanling Contact Us Photo


Need some assistance for your trip?
Send us a message and we will do our best to help you out.

Try to be as detailed as you can with exactly what you need help with so we can best serve you.

Please complete the reCAPTCHA challenge