15 Absolute Best Things to Do in Chicago for First-Timers

Planning a trip to Chicago and not sure what to see first? The Windy City is packed with incredible sights, world-class museums, amazing food, and some of the best skyline views in the country.

From walking along the Chicago Riverwalk to trying deep-dish pizza and catching sunset views over Lake Michigan, there’s no shortage of fun things to do in Chicago.

Whether it’s your first visit or you’re coming back for more, this Chicago travel guide covers the city’s top highlights, from classic landmarks to local favorites that you won’t want to miss.

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Best Things to Do in Chicago for First-Timers

1. Visit Millennium Park and see The Bean

Millennium Park is one of Chicago’s most famous attractions and the perfect place to start your Chicago itinerary. It’s home to Cloud Gate, the huge mirrored sculpture everyone calls The Bean, which has become one of the most photographed spots in the city.

You can walk right under it for fun reflections or capture the skyline mirrored on its surface, and it’s a must for any first-time visitor.

But there’s a lot more to Millennium Park than just The Bean. Stroll around to see the Crown Fountain with its digital faces and water displays, or the Jay Pritzker Pavilion, which hosts outdoor concerts and movie nights in summer.

If you’re visiting during winter, you’ll find an ice-skating rink set up nearby, turning the area into a festive hangout spot.

Millennium Park connects easily to the rest of downtown and is close to other major landmarks like the Art Institute of Chicago and the Lurie Garden.

2. Walk along the Chicago Riverwalk

The Chicago Riverwalk is one of the best places to take in the city’s architecture and waterfront views.

Stretching for about 1.25 miles through downtown, this pedestrian path runs right along the Chicago River and is lined with cafes, restaurants, and public art.

It’s a great place for a morning walk, a relaxed lunch by the water, or an evening stroll when the city is all lit up. You can stop for a drink at City Winery, grab ice cream from a local stand, or just sit on one of the benches and watch the boats go by.

If you want to explore even more, look for the Riverwalk’s small bridges and viewpoints that offer amazing photo spots of the skyline.

It’s a calm but lively part of downtown and one of those places that instantly makes you fall in love with Chicago.

3. Take an architecture boat tour

One of the best ways to see Chicago is from the water! The city is famous for its architecture, and the Chicago River runs right through the heart of it, making an architecture boat tour one of the top experiences to add to your Chicago bucket list.

These guided cruises take you past some of the city’s most impressive skyscrapers, while local experts share stories about how Chicago became a hub for innovative design after the Great Fire of 1871.

You’ll spot landmarks like the Wrigley Building, Marina City, and the Tribune Tower as you sail along the river.

Tours run throughout the day, but the early evening ones are especially popular when the light softens and the buildings start to glow. It’s a relaxing and fascinating way to learn about the city and easily one of the most memorable things to do in Chicago.

4. Get the best views in Chicago from Willis Tower Skydeck or 360 Chicago

If you want to see Chicago from above, head to one of its famous observation decks for unbeatable skyline views!

The two most popular options are the Skydeck at Willis Tower and 360 Chicago at the John Hancock Building, each offering a different but equally impressive perspective of the city.

At Skydeck Chicago, you can step out onto The Ledge, a glass box that extends four feet from the building and lets you look straight down at the streets below.

Over at 360 Chicago, you’ll find TILT, a glass platform that leans you out over Michigan Avenue for a quick adrenaline rush.

Both are great at any time of day, but if you visit close to sunset, you’ll catch the city from its most dramatic angle. Either way, you’ll walk away with some of the best views in Chicago.

5. Join a Chicago food tour

Chicago is a dream destination for food lovers, and joining a food tour is one of the best ways to taste your way through the city.

It’s a fun mix of local flavors and sightseeing, giving you the chance to sample Chicago’s signature dishes while learning a bit about the neighborhoods you’re walking through.

Most tours include deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches, plus a few sweet stops or local favorites depending on the route. It’s also a great way to find hidden gems that you might not discover on your own.

If you’re short on time, this is an easy way to try several must-eat spots in one go and learn what makes Chicago’s food scene so special.

6. Explore the Museum Campus

If you only have time for one area packed with major attractions, make it the Museum Campus. This scenic stretch along Lake Michigan brings together three of Chicago’s most famous museums: the Field Museum, Shedd Aquarium, and Adler Planetarium.

The Field Museum is home to Sue, the world’s largest and most complete T. rex skeleton, while the Shedd Aquarium features everything from sea otters and penguins to tropical fish and sharks.

For something different, the Adler Planetarium offers interactive exhibits about space and some of the best skyline views in the city from right outside its entrance.

You can easily spend half a day here, exploring the museums and taking photos along the lakefront. It’s one of the most popular things to do in Chicago and a must for anyone who enjoys history, science, or nature.

7. Eat deep-dish pizza

Deep-dish pizza is a Chicago classic and something every visitor should try at least once. It’s rich, cheesy, and baked in a deep pan so the crust turns golden and crisp around the edges.

The layers of melted mozzarella, tangy tomato sauce, and buttery dough make it unlike any other pizza you’ve had before.

Two of the most famous spots to try it are Lou Malnati’s and Giordano’s. Lou Malnati’s is known for its signature buttery crust and generous toppings, while Giordano’s is loved for its stuffed-style pizza that oozes with cheese.

Both are easy to find downtown and are perfect for a long lunch or early dinner.

Be prepared to wait a bit since deep-dish takes time to bake, but that first bite makes it totally worth it. It’s the kind of comfort food that keeps people coming back to Chicago for more!

8. Catch a Cubs game at historic Wrigley Field

Wrigley Field is one of those places that captures Chicago’s spirit. Even if you’re not a baseball fan, seeing a game here is a fun and unforgettable experience.

Built in 1914, it’s one of the oldest ballparks in the country, and the atmosphere on game day is something special.

The neighborhood around it, known as Wrigleyville, comes alive with fans before and after every game. You can grab a bite at one of the nearby bars, walk around the area, or just soak in the excitement as everyone heads toward the stadium.

Inside, you’ll find plenty of classic ballpark snacks, including Chicago-style hot dogs and popcorn. The energy of the crowd, the music, and the backdrop of the old scoreboard make it easy to see why locals love it so much.

Even if you don’t stay for the whole game, it’s worth going just to experience a piece of Chicago history.

9. Stroll around Lincoln Park

Lincoln Park is one of the most beautiful areas in the city and a must on any list of the best things to do in Chicago. It’s a huge green space that stretches along the lakefront, filled with walking paths, gardens, and peaceful spots to take a break from downtown.

One of the main highlights is the Lincoln Park Zoo, which is completely free to visit and home to everything from lions and gorillas to penguins and bears.

Right next door, the Lincoln Park Conservatory has lush indoor gardens and tropical plants that are worth a quick stop.

Before you leave, don’t miss the Honeycomb Pavilion near the South Pond. It’s one of the best photo spots in the park with the city skyline framed perfectly behind it.

Lincoln Park feels like a breath of fresh air right in the middle of Chicago, and it’s easy to spend a few hours wandering and taking it all in.

10. Visit North Avenue Beach

If you’re visiting Chicago in summer, North Avenue Beach is the perfect spot to relax and enjoy the city’s lakefront views.

It’s one of the most popular beaches in the city, located in the Lincoln Park area, and it has plenty of space for swimming, sunbathing, or just hanging out with friends.

There are beach bars, volleyball courts, and rental stands where you can grab a paddleboard or bike. The Lakefront Trail runs right past the beach, so you can walk or cycle while taking in the skyline views.

The view from the sand is one of the best in Chicago, with the tall buildings of downtown rising in the background. It’s a fun and easy way to take a break from sightseeing and see another side of the city.

11. Shop and stroll the Magnificent Mile

If you love shopping or simply want to take in Chicago’s lively downtown vibe, head to the Magnificent Mile. This stretch of Michigan Avenue is lined with everything from designer boutiques and department stores to cafes and landmarks.

You can spend a few hours browsing or window-shopping while admiring some of the city’s most impressive architecture.

The historic Water Tower and Tribune Tower are both worth a look, and you’ll find plenty of restaurants nearby when you need a break.

Even if shopping isn’t your main goal, the Magnificent Mile is a great place to walk around and feel the energy of the city. It’s one of those classic Chicago experiences that you shouldn’t miss.

12. Have some fun at Navy Pier

Navy Pier is one of Chicago’s most famous attractions and a fun stop for visitors of all ages. Stretching out into Lake Michigan, it’s packed with restaurants, shops, and entertainment options, making it a great spot to spend an afternoon or evening.

The main highlight is the Centennial Wheel, a 200-foot-tall Ferris wheel that gives you incredible views of the city and the lake. You’ll also find the Chicago Children’s Museum, theaters, seasonal events, and outdoor spaces perfect for a walk by the water.

In summer, Navy Pier often hosts fireworks and live music, adding to the lively atmosphere. Whether you go for the rides, the food, or just to enjoy the lake views, it’s one of the best things to do in Chicago during good weather.

13. Hunt down Chicago’s best street art

Chicago’s street art scene is full of color and creativity, and exploring it is one of the most unique things to do in Chicago. You’ll find huge murals, detailed graffiti, and community art projects scattered across different neighborhoods, each telling a story about the city’s culture and people.

Some of the best places to look are the Wabash Arts Corridor in the South Loop, Logan Square, and Pilsen, which is known for its vibrant community murals.

One of the most recognizable pieces is the Chicago Mural, with its bold letters and bright design. It’s a great photo stop if you’re nearby!

If you’re short on time, stick to one or two neighborhoods and plan your route in advance. That way, you’ll see some of the city’s most impressive murals without spending hours crisscrossing town.

14. Snap a photo with the Chicago Theatre sign

Few places say “Chicago” like the bright red sign outside the Chicago Theatre. It’s been lighting up North State Street for more than a century, and taking a photo here is almost a rite of passage for first-time visitors.

It’s one of the most photographed spots in the city, so try to stop by earlier in the day before the crowds arrive. The surrounding area has plenty of restaurants, shops, and historic buildings, so it’s easy to combine a quick photo stop with exploring downtown.

If you have time, check the schedule to see what’s on. The theater still hosts concerts, comedy shows, and special events throughout the year.

15. Catch the sunset at Milton Lee Olive Park

Milton Lee Olive Park is one of the best spots in Chicago to watch the sunset. It’s tucked behind Navy Pier and offers a quiet escape from the busy waterfront, with amazing views of both the skyline and Lake Michigan.

You can walk along the path, sit on one of the benches, or bring a snack and enjoy the view as the city starts to light up. It’s also a great place for photos, especially with the skyline reflecting on the water.

The park is usually less crowded than other downtown viewpoints, so it’s a nice way to end your day in Chicago without the noise and chaos of the city.

Where to Stay in Chicago

If it’s your first visit, The Loop and River North are the best areas to stay in Chicago. The Loop puts you close to Millennium Park, the Riverwalk, and the Art Institute, while River North has endless dining, shopping, and nightlife options.

Here are a few great places to stay:

• Trump International Hotel & Tower Chicago – A luxurious choice overlooking the Chicago River with spacious rooms, floor-to-ceiling windows, and incredible skyline views.
• Sofitel Chicago Magnificent Mile – A sleek, modern hotel near Michigan Avenue that blends French-inspired design with comfort. Great for travelers who want easy access to shops, restaurants, and downtown attractions.
• Arlo Chicago – A stylish mid-range option steps from Millennium Park. Rooms are compact but beautifully designed, and the central location makes it easy to explore on foot.
• Warwick Allerton Chicago – This historic property on the Magnificent Mile combines old Chicago charm with a modern touch. Perfect if you want to stay somewhere iconic.
• Hampton Inn & Suites Chicago-Downtown – A solid budget-friendly pick with comfortable rooms, free breakfast, and an unbeatable River North location.

If you’re still deciding which neighborhood fits your style, check out my full guide to the best areas to stay in Chicago for more hotel options and tips.

Where to Eat in Chicago

Chicago is a food lover’s dream, from deep-dish pizza and hot dogs to world-class restaurants and cozy brunch spots. You’ll find amazing places to eat in every neighborhood, but here are a few that stand out:

• Lou Malnati’s – A Chicago classic and one of the best spots to try authentic deep-dish pizza.
• Giordano’s – Another local favorite, famous for its stuffed pizza loaded with cheese.
• Portillo’s – The go-to spot for a true Chicago-style hot dog. Don’t skip the chocolate cake shake!
• Girl & the Goat – One of the city’s top restaurants serving creative small plates in the West Loop.
• The Purple Pig – A lively spot on Michigan Avenue with Mediterranean-inspired dishes and great wine.
• Wildberry Pancakes and Cafe – A popular breakfast and brunch spot right by Millennium Park.

From casual eats to fine dining, Chicago has something for every taste. Just be sure to come hungry, as the food scene here never disappoints!