The Top 10 Things To Do In Chicago, IL 2023
One of the best downtown areas in the U.S. is the bustling city of Chicago. Peruse Millenium Park to check out “The Bean” and one of its many museums. Cheer on the White Sox or Cubs and have a blast at Navy Pier! Enjoy the food, scenery, gorgeous architecture, and all that jazz!
#10 - Food Tour
Easily one of the best parts of any vacation is the food, and Chicago doesn’t disappoint when it comes to good eats. In fact, the city is known for so many different types of cuisines that choosing where to eat can be overwhelming. That’s why we opted to partake in a food tour hosted by a company called Read MoreBobby’s Bike Hike Chicago. The guided tour allowed us to try several Chicago staples in an expedited and fun way. We got a slice of famous Chicago deep dish pizza at one of the city’s most famous pizzerias, half of an Italian beef sandwich while overlooking the river, a Chicago-style hot dog at a Cubs-themed restaurant, and a delicious brownie at Palmer Hotel who claims to have created the famous dessert. It was a wonderful walking tour that not only allows you to eat great food but takes you around many of the city’s most famous landmarks. A great way to spend an afternoon in the Windy City!
#9 - Lake Michigan
A beautiful 26-mile stretch in Chicago, where land meets water and a busy metropolis eases into a relaxing beach setting. The lakefront includes an 18-mile trail, parks, gardens, museums, and several water sports opportunities. Stroll along the shore, ride a bike, jet ski, kayak, boat, you name it! Or simply enjoy a Read Morerefreshing beverage at the popular North Avenue Beach or play some volleyball and kick back at Oak Street Beach. There are at least 20 beaches open to the public to choose from, so make sure to step away from the skyscrapers to take in the scenery and fresh air.
#8 - Downtown Nightlife
And all that jazz! If nightlife is what you’re looking for, Chicago will not disappoint. With its many restaurants, bars, jazz venues, comedy clubs, nightclubs, theaters, concerts, and more, Chicago is consistently listed as a top city for nightlife and entertainment. Enjoy an improv show at the renowned Read MoreSecond City comedy club, see some live jazz at the Jazz Showcase, play vintage arcades at Replay Lincoln Park, or enjoy some food and drinks overlooking the Chicago River at one of the many restaurant options along the water. Take in a show at the vibrant theater district or dance the night away in one of the city’s clubs. From burlesque shows at the Untitled Supper Club and kickback lounges, from rooftop bars, such as J.Parker, to underground clubs, Chicago has something for everyone!
A sculpture outside of Soldier Field.
#7 - Football Game at Soldier Field
Da Bears! If you’re a fan of the NFL, you’ll have to pay a visit to one of the most famous fields in NFL history. Built in 1924 (!) and home to the Chicago Bears since 1971, Soldier Field is the 3rd oldest stadium in the United States, trailing only its neighbor to the north, Wrigley Field, and Fenway Park in Boston. Read MoreBetween its Lake Michigan adjacent location and being the smallest NFL stadium (seats 61,500), Soldier Field offers a truly unique experience. The stadium has hosted a plethora of non-football events, such as concerts, the Fifa World Cup, NHL games, the first-ever Special Olympics, and Rugby. Try to visit Soldier Field soon, as the Bears have talked about moving out to a new stadium in the suburbs.
#6 - Museums, Planetarium, Aquarium, & Zoo
Chicago is a bustling city with many things to do and places to visit. Some of their best stops include the Boeing Art Gallery, with outdoor art installations in Millennium Park, the Field Museum of Natural History with the famous bones of Sue, the T-Rex, and the Museum of Science and Industry with several exhibits Read Morefor the innovative thinker. Or learn about the stars at Adler Planetarium, stroll through Lincoln Zoo, a 35-acre zoo that is free to the public, and splash into Shedd Aquarium with its Caribbean Reef and Abbott Oceanarium. These are just some of the fantastic sites to visit that are great for all ages. Many of these attractions can be found on the Chicago City Pass at a cheaper rate. So make sure to plan ahead for a day of learning, fun, and exploration!
#5 - Architecture River Cruise
This is a great way to start your trip and get a lay of the land. There are many different options and companies to go with, but this time we rode the half river and half lake tour with the Wendella company, who were the first group to offer such tours in Chicago way back in 1935. We really enjoyed learning about the Read Morefamous architecture from our guide, seeing all the city skyscrapers towering above us, and the picturesque views of the skyline. We were able to see and learn more about some of the tallest buildings, including Willis Tower, Aqua, and the Aon. Being out on the lake offered some incredible views of Lake Michigan, Navy Pier, Soldier Field, and much more. We definitely recommend this tour!
#4 - Willis Tower & Hancock Tower
Chicago has no shortage of great views high atop the city. The most famous two are Willis Tower (formerly the Sears Tower) and the formerly named Hancock Tower (currently only officially known by its address: 875 North Michigan Avenue). The Willis was the tallest building in the world when completed in Read More1974. It has an amazing observation deck with 360, unparalleled views, over 100 stories above street level. If you’re brave enough, step out onto “The Ledge'' onto a glass floor for a great photo op. Even the walk to the deck is fun and interactive, giving you many places to take unique photos and learn more about the city’s history, food, and culture.
The formerly named Hancock Tower (now known simply as 200 Clarendon) is more north than Willis, closer to Magnificent Mile, and offers an outstanding 360 view of Lake Michigan and the surrounding city. You can visit the observation deck for a splendid lookout and hang on to “The Tilt” as you are lowered on a glass bottom over 1,000 feet above the city below. Yikes! Or you can choose to enjoy food and drinks at the tower’s Signature Room and Lounge on the 95th floor. Both towers offer stunning portrayals of the beautiful Windy City.
#3 - Baseball Games at Wrigley Field or Guaranteed Rate Field
Wrigley Field - Come visit the Friendly Confines, home to the Chicago Cubs for over a century! As the oldest ballpark in the National League, opening in 1914 as Weeghman Park, it has become an iconic symbol of the city. Visit the historic ivy wall, look up at the manually operated scoreboard, and behold its famous red Read Moresign. This area also features many restaurants, bars, shops, and live music. Enjoy a game and leave with a feeling of the Cubs’ historical charm.
Guaranteed Rate Field - On the south side of Chicago, you’ll find the home of the Chicago White Sox. This stadium boasts an Xfinity Kids Zone, Miller Lite Landing, a panoramic fan deck, a rain room, and an exploding scoreboard! Paying homage to the old stadium, you can check out the Comiskey home plate or the many players’ statues located in the outfield concourse. This stadium has been featured in many movies, such as Rookie of the Year, proving its place in the city’s history. Both parks are accessible by public transportation from Downtown and are great places to watch a fun game of America’s pastime.
#2 - Navy Pier
Take a walk down the 3,300-foot-long pier for great views of the beautiful Lake Michigan. Stop for lunch at one of its restaurants, such as Harry Caray’s Tavern, and enjoy the many outdoor attractions, including the Centennial Ferris wheel and carousel. Check out the Funhouse Maze and Crystal Gardens, the Read MoreChicago Children’s Museum, and Shakespeare Theater. This is a great place for souvenir shopping, daily cruises and tours, or just relaxing with a drink at the Miller Lite Beer Garden and Offshore Rooftop Bar and Grill. Navy Pier also hosts many events, including fireworks! This is a place where everyone is welcome, giving you a sense of what this dynamic city has to offer.
#1 - Millennium Park & Cloud Gate
As Chicago’s top tourist attraction, this park covers over 24 acres and is nestled along the beautiful Lake Michigan to one side and the downtown Loop area to the other. Part of the larger Grant Park, this park is within walking distance from hotels and premium shopping and offers public art installations, the gorgeous Read MoreBuckingham or artsy Crown Fountain, the secret Lurie garden, Pritzker Pavilion, and Maggie Daley Park that has playgrounds, rock climbing, and mini golf. There are also several museums in or nearby, such as the Boeing Art Gallery, Field Museum, the Planetarium, and Aquarium. If you come during the summer, partake in one of the many concerts or festivals hosted here, such as the Chicago Jazz Festival or Food Fest. Yum! Of course, we can’t forget about the famous Cloud Gate, better known as “The Bean”. Take some awesome photos here as you see yourself and the city skyline reflected in its silvery surface, encompassing all Millennium Park is meant to be.
Check out the top 10 things to do in New York City!
Chicago Travel Tips & Frequently Asked Questions
What do I need to know before traveling to Chicago? There are some things that you should definitely know before traveling to Chicago. First, you don’t need a car. There are loads of public transport and ride-share options that are cheaper than parking/rental car fees and you won’t have to stress about driving in a Read Morebusy city. You should also know what the expected weather is going to be like for your trip and pack accordingly.
How do I prepare for Chicago? You should prepare for your trip to Chicago by making dinner reservations ahead of time and planning the attractions you want to see. Visiting attractions that are close to each other on the same day will make your trip more efficient.
What is the safest way to get around Chicago? Public transportation is definitely the way to go in Chicago. There are a ton of options (buses, trains, etc.) and they provide a quick and affordable option to get around town.
How many days do you need for a Chicago trip? We would have to say that 4 days is the optimal amount of time for a visit to Chicago. It’s certainly doable to just do 3, especially if this isn’t your first visit there, but 4 days add in enough extra time so your days aren’t as packed and potentially stressful.
Which month is good to visit Chicago? As long as you avoid the peak summer or winter months, pretty much any month is a good month to visit. Our ideal months are April and October. The weather is great during those times and you can catch a Cubs game in April or a Bears game in October.