18 Best Things to Do in Chicago: Off-Beat Adventures Locals Choose

Discover the best things to do in Chicago with our ultimate guide to 18 must-see attractions and off-beat adventures. We also cover practical tips, including the best time to visit, how to get around, where to stay, and how to stay connected with Jetpac eSIM USA.

Chicago is a city of vibrant neighborhoods, fascinating architecture, and a rich cultural scene. But there’s so much more to the city than the usual tourist spots!

Whether you’re a first-time visitor or returning for another adventure, knowing the best things to do in Chicago can make all the difference in experiencing the city like a local.

In this guide, we’ll take you beyond the typical tourist checklist and share 18 off-beat adventures, local favorites, and insider tips that show the real heart of Chicago.

Along the way, you’ll find practical advice on the best time to visit, how to get around, and even how to stay online, making your adventure smooth, memorable, and authentically Chicago.

Best Time to Visit Chicago

Choosing the right time to visit can make a big difference in how much of the city you can enjoy. In fact, one of the tips for first-time flyers is to plan your trip during a season that suits your interests. Picking the right time ensures you get the most out of your visit and can comfortably experience the city’s highlights.

Chicago experiences all four seasons, each allowing you to enjoy unique attractions and activities. Here’s a table to guide you:

Looking for more advice on when to visit Chicago? Read our comprehensive guide to the Best Time to Visit USA.

What’s the Best Way to Get Around Chicago

Chicago is a sprawling city with a mix of bustling downtown areas and vibrant neighborhoods. Knowing how to get around efficiently can help you experience more of the best things to do in Chicago without wasting time in traffic.

Public Transit

The Chicago Transit Authority (CTA) operates the “L” trains and buses, which are reliable, affordable, and cover most major neighborhoods. Using the “L” is ideal for visiting downtown attractions like Millennium Park or hopping between neighborhoods like Wicker Park and Logan Square.

Walking & Biking

Many of the Chicago best things to do are within walking distance of each other, especially in the Loop and along the Lakefront Trail. Divvy Bikes, the city’s bike-share program, is a convenient option for exploring scenic areas, parks, and local streets off the beaten path.

Rideshares & Taxis

Uber, Lyft, and local taxis are useful for longer trips or when public transit is less convenient. They’re also handy if you want to reach all the top Chicago attractions that are spread across neighborhoods, like the Art Institute or unique food spots in Pilsen.

Where to Stay: Neighbourhood Guide

Choosing the right neighborhood can make a big difference in how much of the city you experience. Chicago is a city of diverse areas. Each has a unique vibe and offers easy access to iconic sights and hidden gems.

Here’s a guide to help you decide where to stay while exploring the best things to do in Chicago.

Loop / Downtown

The Loop is Chicago’s bustling heart and ideal for first-time visitors. Staying here puts you within walking distance of famous attractions like Millennium Park, the Art Institute, and the Chicago Riverwalk. It’s perfect if you want to tick off the must do things in Chicago while enjoying the convenience of central hotels.

Wicker Park

Known for its trendy shops, vibrant nightlife, and street art, Wicker Park is a favorite among young travelers and creatives. From this neighborhood, you can easily explore the top things to do in Chicago off the beaten path, including local cafés, live music venues, and boutique stores.

Logan Square

If you’re seeking an artsy, laid-back vibe, Logan Square is the place to be. It’s filled with murals, independent galleries, and craft breweries, making it perfect for those who want to experience Chicago like a local. Staying here offers convenient access to the city’s offbeat attractions, from hidden food gems to live music spots.

18 Best Things to Do in Chicago

The list below covers the 18 best things to do in Chicago, including popular hotspots and off-beat adventures that make your trip truly memorable.

1. Explore hidden street-art & murals

Chicago’s neighborhoods are full of vibrant street art and murals that offer a colorful glimpse into the city’s creative soul. Exploring areas like Pilsen and Logan Square is one of the best things to do in Chicago for art lovers looking beyond the typical tourist spots. These murals are not only visually stunning but also showcase the city’s history and culture, making them some of the top Chicago attractions.

2. Kayak or paddle-board on the Chicago River

Gliding along the Chicago River by kayak or paddle-board offers a fresh perspective of the city’s stunning architecture. It’s an outdoor adventure that combines exercise, sightseeing, and scenic views all in one. Many travelers consider it one of the popular things to do in Chicago during the warmer months.

3. Take a neighbourhood food crawl

Chicago’s diverse neighborhoods are a haven for food lovers, offering everything from classic deep-dish pizza to international cuisine. A food crawl lets you sample local flavors while discovering hidden streets and independent eateries. This is a delicious way to explore some of the top Chicago attractions.

4. Join a “mob/ gangster history” walking tour

Step into the past with a walking tour focused on Chicago’s gangster era, including sites connected to Al Capone and Prohibition history. It’s a fascinating way to learn about the city’s notorious history while strolling through historic streets. It is a must for anyone interested in things to see in Chicago.

5. Visit an indie music venue or rooftop bar

Chicago’s indie music venues and rooftop bars offer lively evenings filled with local talent and panoramic skyline views. Experiencing this side of the city gives visitors a real taste of the city’s vibrant nightlife. No wonder it ranks as one of the best things to do in Chicago after dark.

6. Discover craft breweries or speakeasies

Chicago has a thriving scene for adults seeking unique experiences, from intimate speakeasies to innovative craft breweries. These hidden spots provide local flavor away from crowded tourist areas. Exploring them is a highlight among the popular things to do in Chicago.

7. Cycle or Stroll the Lakefront Trail

Spanning nearly 18 miles along Lake Michigan, the Lakefront Trail is an ideal spot for cyclists and avid walkers seeking fresh air and scenic views. You’ll pass beaches, parks, and city landmarks while enjoying the lake’s calming breeze. Exploring this path is one of the places to go in Chicago for outdoor enthusiasts who want a mix of nature and urban scenery.

8. Attend a Free Outdoor Concert in Summer

Chicago comes alive in the summer with music festivals and free concerts in parks across the city. From jazz performances at Millennium Park to indie bands at neighborhood venues, there’s something for every music lover. Experiencing live music under the open sky is one of the must do things in Chicago for both locals and visitors.

9. Visit Quirky Shops and Cafés

Wander through neighborhoods like Wicker Park and Logan Square to find eclectic boutiques, artisanal coffee shops, and hidden gems. These small businesses offer a unique taste of Chicago’s culture and creativity. Discovering them is a highlight for anyone exploring Chicago best things to do beyond the usual tourist spots.

10. Take an Architecture Boat Tour of the Downtown River

A boat tour along the Chicago River provides an unforgettable perspective of the city’s iconic skyline and historic buildings. Guided tours often include fascinating stories about architectural styles and the city’s development over time. This experience is considered one of the top things to do in Chicago for anyone interested in design, history, or photography.

11. Go Hunting for Quirky Public Art Installations

Scattered throughout Chicago are unexpected public artworks, sculptures, and interactive installations that showcase the city’s playful and creative side. From hidden murals to whimsical statues, discovering them is like a treasure hunt through the streets. Art lovers and curious travelers alike will find this one of the most engaging places to go in Chicago.

12. Have a Picnic or Relax at a Local Beach by Lake Michigan

Chicago’s lakeside beaches provide the perfect escape from the city’s hustle and bustle. Spread a blanket, enjoy the skyline view, or take a refreshing swim during warmer months. Relaxing by the water is a simple yet rewarding way to enjoy one of the must do things in Chicago while soaking in the beauty of Lake Michigan.

13. Visit a neighbourhood museum or gallery

Chicago’s neighborhoods are dotted with smaller museums and independent galleries that highlight local artists and community history. These spaces offer an intimate experience that you won’t find at the city’s larger institutions. Exploring one of these spots is a great way to discover things to see in Chicago beyond the main tourist hubs.

14. Hop on a ferry or a short boat ride on Lake Michigan

A ferry or short boat ride provides a different perspective of Chicago’s skyline and shoreline. Whether it’s a leisurely cruise or a quick hop to nearby parks, the water adds a refreshing element to your day. Many travelers consider this one of the popular things to do in Chicago for enjoying the city from a new vantage point.

15. Attend a local festival or pop-up event

Chicago hosts a wide variety of festivals and pop-up events throughout the year, celebrating food, music, art, and cultural traditions. From neighborhood street fairs to seasonal celebrations, there’s always something unique happening around the city. Experiencing one of these lively gatherings is a must for anyone exploring the best things to do in Chicago.

16. Eat like a local

Ditch the tourist traps and dive into the city’s authentic culinary scene, from family-run pizzerias to international street food markets. Sampling local specialties is a delicious way to immerse yourself in Chicago’s culture and vibe. Food-focused adventures are among the most popular things to do in Chicago.

17. Watch a local sports game

Whether it’s baseball at Wrigley Field, basketball at the United Center, or soccer at Soldier Field, attending a live game offers an electric atmosphere that’s quintessentially Chicago. The energy of fans and the city’s sports traditions make this a memorable experience. For both casual fans and sports enthusiasts, this is one of the things to see in Chicago.

18. Explore the city’s rooftops and skyline vantage points at dusk

Chicago’s skyline is stunning, and seeing it from a rooftop bar or observation point at dusk makes for unforgettable views. Capture the city bathed in golden light and watch the streets come alive below. Experiencing these elevated perspectives is often listed among the best things to do in Chicago for photographers and travelers seeking iconic vistas.

Jetpac eSIM USA: The Easiest Way to Stay Online on Your Chicago Adventure

Exploring Chicago is easier when you’re online. You'll need access to the Internet for things like finding hidden murals in Pilsen, navigating the “L” train, and checking out local restaurants and cafés. For hassle-free mobile data, Jetpac eSIM USA is the perfect solution. It’s widely regarded as the best eSIM for USA travelers, letting you skip physical SIM cards and expensive roaming fees.

With Jetpac eSIM, you can activate your plan instantly, even before you land in the United States. Once in Chicago, enjoy reliable 4G/5G coverage throughout the city and across the country. Use it to access maps to discover local favorites, share photos on social media, or book last-minute tickets! Jetpac keeps you connected wherever you go.

Unlike traditional SIM cards, an eSIM is fully digital, which means no store visits and no swapping cards. It’s ideal for anyone looking for eSIM USA travel solutions that are fast, convenient, and secure. You can even keep your WhatsApp number active while enjoying your private, high-speed connection.

Chicago offers plenty of free Wi-Fi, but it’s often unreliable and unsafe. With Jetpac eSIM USA, you have your own secure connection, giving you peace of mind as you explore neighborhoods like Logan Square, Wicker Park, and the Riverwalk.

FAQs

What are the best things to do in Chicago for first-time visitors?

First-time visitors should focus on a mix of iconic landmarks and local experiences to get the full Chicago vibe. Highlights include Millennium Park, the Art Institute of Chicago, Navy Pier, and a stroll along the Riverwalk. These spots often feature on lists of the top 10 things to do in Chicago.

What are some off-the-beaten-path things to do in Chicago?

For travelers looking beyond the tourist trail, neighborhoods like Pilsen, Logan Square, and Wicker Park offer vibrant murals, indie cafés, and quirky shops. Kayaking along the Chicago River or exploring local speakeasies adds an adventurous twist. These are some of the best things to do in Chicago for those seeking something unique and authentic.

What are some family-friendly things to do in Chicago?

Chicago is full of attractions suitable for families of all ages. Lincoln Park Zoo, the Chicago Children’s Museum, and Navy Pier’s rides and activities make for fun, educational outings. Many of these are among the top 10 things to do in Chicago for families, providing entertainment while showcasing the city’s culture and history.

When is the best time to enjoy outdoor things to do in Chicago?

Spring and fall are ideal for enjoying Chicago’s outdoor attractions, with mild temperatures and fewer crowds. Summer is perfect for lakefront activities, festivals, and open-air concerts, while winter offers a quieter experience for exploring festive markets or scenic winter walks. Planning your visit around the season ensures you can comfortably experience the best things to do in Chicago outdoors.

How many days do I need to see Chicago?

A 2–3 day trip is enough to cover major landmarks and a few local neighborhoods, hitting many of the top 10 things to do in Chicago. For a deeper experience, 4–5 days allow time to explore off-beat spots, attend events, and enjoy the city at a relaxed pace. Your itinerary can be tailored depending on whether you prefer iconic attractions or hidden gems.

Do I need a SIM card or eSIM to enjoy things to do in Chicago?

Staying connected is essential for navigation, ticket bookings, and finding local hotspots. While free Wi-Fi is available in some areas, a SIM card or eSIM ensures reliable coverage across the city. Using an eSIM lets travelers easily access maps and resources while checking off the best things to do in Chicago.