If you’re looking for the best things to do in Chicago for your first visit, allow me to show you around….well, I mean…virtually-speaking, of course. Every time I travel to a new city, I love exploring things that city is known for that makes it special…which usually means checking the “touristy” things off my list. In this post, I’ve listed all the must-see’s and do’s, plus included some hotel rec’s and pro tips for getting around below! But if you’re spending a weekend in the Windy City and you just can’t wait, click here to jump to the best things to do in Chicago for your first time.
Confession time: I never really had a desire to visit Chicago for most of my life, but that was mostly due to my own lack of knowledge about the city. I didn’t know much about Chicago other than the legacy left by Michael Jordan and the Chicago Bulls in the 90’s…and tbh, I’m not much of a basketball fan. Additionally, the nickname “The Windy City” left a lot to be desired for me. The Sunshine City, maybe…but wind?
- Fun Fact: The origin of the nickname “The Windy City” actually has nothing to do with weather, and instead, came from politics! The term was thrown out to criticize Chicago’s political leaders, implying that they were full of “hot air” and empty promises. Of course, if you’ve been to Chicago in the winter, you know it’s very windy, so this only added fuel to the fire.
ANYWAY…all that changed once I had to spend an impromptu night in Chicago due to missing a layover connecting flight. Now, whenever someone asks me my favorite U.S. city, I always say that it’s between New York and Chicago, depending on the day that you ask me. It’s crazy to think that for a long time, I didn’t realize how cool this city actually was!
Chicago is, IMO, one of the most beautiful cities in America, not to mention surprisingly clean for its size! It’s the 3rd largest city in the country behind New York and Los Angeles and seamlessly blends rich history, stunning architecture, and a vibrant cultural scene. In this guide, I’ll cover some of the best things to do and see to help you make the most of your first visit.
Hotel Recommendations
Chicago, Illinois
- Low Budget: Freehand Chicago
- Mid-range: Residence Inn by Marriott: Magnificent Mile, Allegro Royal Sonesta
- 5 star: The Drake, The Langham Chicago, The Peninsula
What’s The Best Way to Get Around Chicago?
Chicago is one of the most walkable cities in America, and walking is my favorite way to get around here. The city is laid out in a grid-like fashion, much like New York City. I have always found Chicago easy to navigate thanks to the landmark buildings and skyscrapers.
Another popular way to get around Chicago is to take the subway, more commonly referred to as “the L.” This is short for “elevated,” since Chicago’s subway system is not entirely underground.
- Safety Pro Tip: While the L is convenient, a lot of people avoid taking it due to safety reasons. I have taken the L before, but it has always been in the daytime when a lot of people are riding. I have been told to be extra cautious on the Red Line, since it is connected directly to the South Side, one of the most dangerous parts of Chicago. In the wintertime, homeless people tend to come on all different train lines here to avoid the cold.
If you want to get to a neighborhood outside the city and don’t want to take the L, there are a ton of Uber and Lyft options available. Keep in mind, traffic in Chicago is heavy and congested, but many people feel safer in a car.
The Best All-In-One Pass to See Chicago
The Chicago Pass from Go City
Choose from a 1, 2, 3, or 5 day All-Inclusive Pass or an Explorer Pass that lets you select the number of attractions you want to see.
The Best Things To Do in Chicago for Your First Time
1. Walk Around Millennium Park and Check Out The Bean
Millennium Park is located in The Loop and is arguably Chicago’s most famous park. People come here to relax, exercise, and check out the art and scenery. When the weather is nice, there are frequent cultural events, concerts at the Jay Pritzker Pavilion, and exhibitions held here. I have even seen yoga in the park before!
- Fun Fact: Millennium Park is actually part of Grant Park, which is similar to Central Park in NYC.
“The Bean” is Chicago’s famous Cloud Gate statue in Millennium Park that looks like…well…a bean. It was designed by British-Indian artist Anish Kapoor and is made of polished stainless steel plates, which create a highly reflective surface. Many people like seeing what types of creative photos they can take in the Bean’s reflection…but get here early if you want it all to yourself!
2. Take An Architecture Cruise
The first time I ever visited Chicago, this was hands-down my favorite “tourist” thing I did. Chicago’s skyline is absolutely gorgeous with massively high skyscrapers lining the Chicago River, and there’s no better way to see it than by boat. You can do this in the daytime or nighttime.
I booked my cruise through Get Your Guide with Wendella Tours and did the 8:30pm time slot. Seeing the city all lit up from the tour boat is a memory that will forever live in my head rent-free. It was indescribably beautiful. My tour guide was knowledgable, funny, and had a genuine love for Chicago that was evident through her storytelling. They also stop the boat every so often so you can take photos.
3. Visit Skydeck Chicago at the Willis Tower
Skydeck gives visitors an epic view of Chicago from the top of Willis Tower. You are able to ride an elevator up to the 103th floor and get your photo taken on The Ledge, a glass-paneled box that allows you to see all the way down to the ground below. You can even download an app that points out Chicago’s most notable buildings and sights to marvel from this high up.
Click here to get your Willis Tower Skydeck and The Ledge ticket from Get Your Guide
- Pro Tip: Although the Ledge is the highlight for most people, visitors to Skydeck are also able to learn about Chicago’s history through museum-quality exhibits.
4. Walk Down the Magnificent Mile and Go Shopping
IMO, one of the best things about visiting any big city is the shopping, but Chicago makes it easy by putting all its best stores on one street. North Michigan Avenue is home to a long stretch of shops, restaurants and attractions commonly referred to as the Magnificent Mile. This area is one of the most famous shopping streets in America and is home to many Chicago gems, such as:
- 360 CHICAGO, formerly the John Hancock Center – similar to Skydeck, visitors are able to see panoramic views of Chicago from 1,000 feet up. If you’re brave enough, check out TILT, which literally tilts you out over the city from the 94th floor.
- The original American Girl store (Wait…are American Girl dolls still popular? I don’t have kids, so I don’t know things like this. Someone help me out in the comments!)
- Chicago Sports Museum – an interactive museum celebrating the world of Chicago sports
- The Wrigley Building – the first major office building north of the Chicago River that is also associated with Wrigley chewing gum
In addition to all of the above, you’ll find everything from designer stores to Sephora, Bloomingdales, Aritzia, and more.
The Starbucks Reserve Roastery
Starbucks opened its Reserve Roastery in Chicago on the Magnificent Mile in November 2019. This is a 5, yes, five-story Starbucks coffee shop that gives visitors and inside look into the coffee roasting journey. There’s an authentic Italian bakery on the second floor, coffee flights and creations on the 3rd floor, and a rooftop terrace that is open when the weather is nice.
The Drake Chicago
At the end of the Magnificent Mile is The Drake, one of Chicago’s most famous hotels that serves afternoon tea in a traditional British style. You can make a reservation to sit in their Colonial Room and enjoy hot tea along with miniature pastries, homemade scone jam, and assorted finger sandwiches.
- Pro Tip: Year after year, the Drake is home of one of the swankiest New Year’s Eve parties in the city. I haven’t been to a NYE party here, but if you’re fancy like that, it seems like it would be very “Gatsby“
5. Explore the Chicago Riverwalk
You’ve heard me say it already, but the Chicago River and the surrounding scenery are one of the most beautiful parts of this city. One of the best places to take it all in is on the Chicago Riverwalk (aside from an architecture cruise, of course!).
The Chicago Riverwalk is a scenic waterfront path with a central starting location on Michigan Avenue, near the historic DuSable Bridge. Along the way, you’ll find riverfront restaurants and bars, public art instillations, and more. You’re even able to rent kayaks to paddle through the heart of the city! When the weather is nice, The Riverwalk also hosts seasonal events and live music, making it a vibrant destination both day and night.
As you probably guessed, this is a perfect spot to get Instagram pics with an epic background!
6. Visit the Navy Pier and Ride the Ferris Wheel
Navy Pier, often referred to as “The People’s Pier,” is a waterfront attraction in Chicago on the shoreline of Lake Michigan that hosts events, attractions, culture, dining, shopping and more. They also have free events throughout the year, the most popular one likely being their fireworks every Wednesday and Saturday nights between Memorial Day and Labor Day. Of course, the best time to visit is summertime when the weather is nice, but people frequent the area around the Navy Pier all year.
If you’re familiar with Navy Pier, you’ve likely heard about the Ferris wheel, called the Centennial Wheel, that’s in the middle of the pier. Many people love to ride the Centennial Wheel to get sky-level views of the city. It is also popular largely because the original Ferris wheel was invented in Chicago!
Book your Centennial Wheel ticket for Navy Pier here!
Photo by Gautam Krishnan on Unsplash
7. Snap a Pic of the Chicago Theatre
The Chicago Theatre is an iconic landmark and one of the city’s premier entertainment venues. It was built in 1921, and has a stunning French Baroque-style interior, complete with grand staircases, intricate murals, and a dazzling crystal chandelier.
Want to check out the inside for yourself? Book a tour of the Chicago Theater here!
The Chicago Theatre originally showcased silent films and live entertainment…but today, it hosts a variety of performances, from concerts and comedy shows to Broadway productions. If you’re a theatre person, you should definitely book a show here!
Even if you don’t go inside the theatre, you have to snap a pic of the massive, glittering “CHICAGO” marquee sign from the outside. IMO, photos don’t do it justice, but it’s gorgeous and one of the most photographed landmarks in the entire city.
8. Take a Crime Tour
Chicago has a lot of gangster, mobster, and criminal tours that let you learn about the city’s darker side. There are even tours that combine gangsters and ghosts that give you a peek into the city’s haunted past. Chicago was home to some of the most famous bad boys of all time, like Al Capone and John Dillinger, and it’s wild to learn about all the things they did back in the day.
Check out the tours from Get Your Guide below:
- Book the Chicago: Gangsters and Ghosts Guided Walking Tour
- Book the Chicago: Mob and Crime Bus Tour
- Book the Chicago Crimes Night Tour
9. Try the Famous Chicago Deep Dish Pizza
Chicago is one of the best foodie cities in America and is known for their hot dogs, Garrett’s popcorn, and Stan’s donuts. But out of all the food here, the city is probably best known for its signature deep dish pizza.
There are 2 popular pizza chains in Chicago that tout themselves as being the best: Lou Malnati’s and Giordano’s. In fact, the only Chicago rivalry more intense than the Cubs vs. the White Sox is probably Lou’s vs. Giordano’s. People have their favorite, and they will swear up and down that their chosen pizza chain is the best in the city.
So far, I have only tried Lou Malnati’s, and I thought it was…okay. Perhaps it was a little too hyped up and my expectations were way too high, but I was not mind-blown in the way that I thought I’d be. If you’re a Lou’s fan, you probably hate me. I’m sorry. I’m just being honest with you. I think you should still try whichever pizza chain you want, or ideally, both so you can compare. But if you’re anything like me, the thought of eating 2 deep dish pizzas in a small window of time is a little much.
So, talk to the locals, flip a coin, or head to whichever chain you run across first. If you want to try pizza that is supposedly great but less touristy, I’ve heard people rave about Pizzeria Portofino, which is right on the riverwalk. If you like truffle sauce, a pizza that I can personally vouch for is the mushroom truffle pizza from Siena Tavern. It isn’t “Chicago style,” but it’s one of my all-time favorite pizzas I’ve ever tried.
