Top Things to Do in Chicago for First Timers

Chicago has a way of pulling you in almost immediately. One minute you’re standing beneath towering skyscrapers in Millennium Park, and the next you’re walking along Lake Michigan with water views so expansive you think you are at the coast.

I’ve visited Chicago many times over the years, and these are the top things to do that I always recommend to friends planning their first trip in the spring or summer.

From the Riverwalk to rooftop bars, Chicago is lively and walkable. You’ll love the lakefront, the patios that fill the sidewalks, and the outdoor attractions that become part of everyday city life.

#1. Millennium Park (The Bean) – One of the Top Things to Do in Chicago

Millennium Park is one of the top things to do in Chicago and the city’s most iconic public space.

It is home to Cloud Gate, known as The Bean, a mirrored sculpture that reflects the skyline and the surrounding park. It is one of the most photographed spots in the city for first-time visitors.

Just steps away, Lurie Garden offers a quieter escape with seasonal blooms, walking paths, and beautiful landscaping that feels tucked away in the middle of downtown.

The Crown Fountain adds a playful touch in warmer months, with interactive water features and digital displays that showcase Chicago residents.

From here, it’s an easy walk into Grant Park, often called “Chicago’s front yard.” Wide green spaces lead you toward Buckingham Fountain, one of the largest fountains in the world, and especially beautiful in the evening.

If you’re interested in art, the Art Institute of Chicago sits right nearby. It’s one of the most respected museums in the country and an easy add-on without going out of your way.

Nearby, the Chicago Cultural Center is worth a quick stop for its stunning stained-glass dome and free exhibits.

Trip Tip: For a guided art tour through the park, you can arrange for a free walking tour with chicagogreeter.com. You need to make arrangements at least ten days in advance. 

#2. Chicago Riverwalk – Best Waterfront Walk in Downtown Chicago

The Chicago Riverwalk is one of the best things to do in Chicago for first-time visitors who want a relaxed, scenic experience.

This pedestrian path runs along the Chicago River and offers restaurants, seating areas, public art, and constant views of architecture boats passing through downtown.

If you’ve ever walked the San Antonio Riverwalk, Chicago’s version feels bigger and more urban, with skyscrapers rising on both sides rather than historic buildings, but it has that same easy, relaxed feel.

It connects easily to Millennium Park, nearby hotels, and boat tour docks, making it one of the most walkable and convenient attractions in the city.

#3. Navy Pier – Classic Chicago Waterfront Attraction

Navy Pier is one of the top attractions in Chicago for visitors of all ages.

Located on Lake Michigan, it features restaurants, shops, entertainment, and the Centennial Wheel, which offers panoramic skyline and lake views from enclosed gondolas.

Here, you can hop on a Big Bus Chicago Hop-On, Hop-Off tour of the city, which is delightful in the Chicago summer weather.

Navy Pier is also where you can board a boat to cruise Lake Michigan. During the summer, you can book an evening cruise that includes fireworks set off over the lake. It’s an experience you’ll never forget.

#4. Chicago Architecture River Cruise

I didn’t expect to be blown away by an architecture tour, but the Chicago River architecture cruise I took was fascinating and quite scenic, too. 

You’ll glide down the Chicago River while learning about the city’s history and iconic buildings.

The boat tour takes you through the heart of downtown while guides explain the history and design of Chicago’s most famous buildings.

It is one of the best ways to understand how the city was built and why it is known as one of the world’s great architectural capitals.

#5. Museum Campus + CityPASS Day

If you want to bundle major attractions into one day, head to Chicago’s Museum Campus along the lakefront.

This area includes the Field Museum, Shedd Aquarium, and Adler Planetarium, all within walking distance of each other. It also offers some of the best skyline views in the city, with Lake Michigan right beside you.

Many visitors use a Chicago CityPASS here to save money on admission and streamline entry, especially for first-time trips. It’s an easy way to experience Chicago’s cultural side without overplanning every detail.

#6. Wrigley Field Cubs Game

Even if you’re not a baseball fan, a Cubs game at Wrigley Field is a true Chicago experience.

The energy in Wrigleyville is part of the fun and something you have to experience at least once. Bars, restaurants, and fans fill the streets before the first pitch, adding to the energetic vibe.

The stadium itself is one of the most historic in the country, and it still carries that old-school charm you don’t find everywhere anymore.

Take the “L” train like locals do, grab a hot dog, and settle in for an afternoon that feels very Chicago in the best way.

I promise you will sing the Go Cubs Go song long after you leave. It is one of the most infectiously catchy songs you’ll hear all year.

Trip Tip: Make sure to visit Guest Services if you are a first-time visitor. They will make you feel very special.

#7. Lincoln Park Zoo & Lakefront Trail

Lincoln Park Zoo is one of the best free things to do in Chicago, and it’s surprisingly peaceful for being so close to downtown.

You can easily pair it with a walk through Lincoln Park Conservatory or a stroll along the lakefront trail, which runs for miles along Lake Michigan.

This is where Chicago really shows off—skyline views on one side, water on the other.

In spring and summer, this area is full of walkers, bikers, and people simply enjoying the weather. It’s one of the simplest and most enjoyable ways to spend time in the city without spending much at all.

#8. Magnificent Mile & Michigan Avenue

The Magnificent Mile is Chicago’s most famous shopping stretch, running along North Michigan Avenue.

It’s more than shopping, though. You’ll pass historic architecture, flagship stores, and landmarks like the Chicago Water Tower along the way. It’s an easy walk, especially if you’re already exploring downtown.

This is also a great place to pick up something special to remember your trip or just enjoy a classic city stroll.

As you’re walking through this area, make a quick stop at the Chicago Theatre on State Street. The marquee is one of the most recognizable sights in the city and an easy photo stop if you’re already exploring downtown.

If you’re planning a girls’ trip, this part of the city is usually at the center of it all. I share more ideas in my Chicago girls’ weekend guide, including where to stay and how to plan your days.

#9. Visit a Chicago Observation Deck – The Best Skyline Views

One of the best ways to see Chicago is from the sky, and Chicago has two spots worth checking out.

360 Chicago is one of the best places in the city for skyline and lake views.

Located in the John Hancock Observatory, it offers panoramic views from the 94th floor and the thrilling TILT experience, which angles visitors outward over the city.

Another popular option is the Skydeck at Willis Tower, formerly Sears Tower, where visitors can step onto The Ledge, a glass box extending over the skyline.

Both are included in a Chicago City Pass, so to save money, make sure to check that out first before buying your tickets.

No matter which you choose, a bird ‘s-eye view of the city will make you appreciate it that much more.

#10. Chicago Food Experiences – Must Try Local Favorites

Chicago’s food scene deserves its own moment.

Start with deep dish pizza. Whether you choose Lou Malnati’s or Giordano’s, it’s a must at least once. Then try a Chicago-style hot dog loaded with toppings and never, ever ask for ketchup. That’s the rule.

If you want something more local, try an Italian beef sandwich dipped in jus until it’s messy in the best possible way.

Food is part of the experience here. You don’t just visit Chicago, you taste it.

#11. Rooftop Bars with Skyline Views

Chicago has so much to offer in terms of art and culture, but it also has some of the best rooftop bars around. That’s right, I said ROOFTOP BARS. 

And they’re not just any rooftops either. They’re bars with some of the most stunning views in the entire city.

The rooftop bars in Chicago offer spectacular sunsets in the spring and summer.

These are some of my favorite: 

LH Rooftop on the 21st floor of LondonHouse – The views of the Chicago River are unbeatable, especially at sunset.

Cindy’s Rooftop – Overlooking Millennium Park in the Chicago Athletic Association Hotel, this rooftop spot serves up creative cocktails and small plates. It’s perfect for an afternoon chill session with your girls.

Z Bar at The Peninsula – Combines chic and chill in one place with unbeatable views of the city

#12. Chicago Night Tours & Evening Experiences

Chicago offers some of its most interesting experiences after dark. When the sun goes down, Chicago takes on a different personality.

One of my favorite experiences is the Chicago Gangster and Ghost Tour. This tour takes you to the best parts of the Windy City, including stops at some of the most famous gangster hangouts.

You’ll hear stories about Al Capone and other notorious criminals. Hear stories about ghosts still haunting their old haunts, too. It’s not as scary as the one I took in New Orleans, but it comes close.

If you want something lighter, Chicago also has sunset cruises and a world-famous comedy scene that keeps the city buzzing after dark.

It’s the perfect way to end a first trip to Chicago—part history, part storytelling, and just the right amount of atmosphere.

Getting Around Chicago (Easy and Budget-Friendly Options)

Getting around Chicago is easier than it looks.

Many of the top attractions are within walking distance of each other, especially downtown. For longer distances, the “L” train is reliable and affordable.

For something more structured, a hop-on hop-off bus tour can be a simple way to move between major sights like Millennium Park, Navy Pier, and the Museum Campus without worrying about directions.

The bus tour also gives you a helpful overview of the city early in your trip.

If you enjoy cities like New York or Boston, you’ll likely find Chicago just as easy to navigate, with a similar walkable layout and plenty to see within a short distance.

2–3 Day Chicago Itinerary Snapshot

Most first-time visitors can see the top things to do in Chicago in 2 to 3 days.

A typical plan includes Millennium Park, the Riverwalk, Navy Pier, an architecture cruise, and time along the lakefront. Adding one neighborhood, like Wrigleyville or Lincoln Park, helps round out the experience.

If you’re deciding where to stay, choosing a hotel near downtown or the River North area makes it much easier to see these attractions without needing transportation.

I personally recommend these hotels:

• DoubleTree by Hilton Magnificent Mile
• The Royal Sonesta Chicago River North
• Swissôtel Chicago
• The Palmer House Hilton

What Will You Do in Chicago?

Chicago is a city that’s easy to enjoy without overcomplicating your plans.

These are the places I come back to and recommend again and again. They give you a real feel for the city, especially in spring and summer when everything feels open, walkable, and alive.

If it’s your first visit, this list will give you a strong starting point and likely a reason to come back.