Best Things To Do In Chicago: Video Guide

15 Best Things to Do in Chicago: Windy City Wonders

Welcome to the Windy City, where towering skyscrapers meet the shores of Lake Michigan, and world-class culture blends with Midwestern charm. Chicago, the jewel of Illinois, offers a treasure trove of experiences for every type of traveler. From iconic architecture to mouthwatering deep-dish pizza, we’ve rounded up the 15 best things to do in Chicago that will make your visit unforgettable. Let’s dive into the heart of the Midwest and discover why Chicago is a must-visit destination!

1. Reach New Heights at Willis Tower Skydeck

Start your Chicago adventure with a bird’s-eye view of the city from the Willis Tower Skydeck. At 1,353 feet high, the Skydeck offers breathtaking 360-degree views of Chicago and beyond. For the daring, step out onto The Ledge, a glass balcony extending four feet outside the 103rd floor. It’s a heart-pounding experience that will give you a whole new perspective on the Windy City.

Time-saving tip: Visit early in the morning or during weekdays to avoid long queues. Pre-booking your tickets online can also help you skip the line.

2. Explore Millennium Park and “The Bean”

No trip to Chicago is complete without a visit to Millennium Park, home to the iconic Cloud Gate sculpture, affectionately known as “The Bean.” This mirrored masterpiece reflects the city skyline and is a favorite spot for selfies. While you’re there, don’t miss the Crown Fountain and the beautiful Lurie Garden. In summer, catch free concerts at the Jay Pritzker Pavilion.

Photo op: Visit “The Bean” early in the morning for the best lighting and fewer crowds in your shots.

3. Cruise Along the Chicago River

One of the best ways to appreciate Chicago’s stunning architecture is from the water. Take an architecture river cruise to learn about the city’s famous buildings and their history. As you glide along the Chicago River, you’ll see iconic structures like the Tribune Tower, Wrigley Building, and Marina City.

Sunset suggestion: Opt for a twilight cruise to see the city transition from day to night, with buildings beautifully illuminated against the darkening sky.

4. Immerse Yourself in Art at the Art Institute of Chicago

Art enthusiasts, rejoice! The Art Institute of Chicago is one of the world’s premier art museums, housing an impressive collection of Impressionist and Post-Impressionist works. Don’t miss iconic pieces like Grant Wood’s “American Gothic” and Edward Hopper’s “Nighthawks.” With over 300,000 artworks, you could spend days exploring this cultural treasure trove.

Money-saving tip: Illinois residents get free admission on Thursday evenings. For others, consider purchasing a Chicago CityPASS for discounted entry to multiple attractions.

5. Catch a Game at Wrigley Field

Baseball fans and novices alike will love the experience of watching a Chicago Cubs game at historic Wrigley Field. Built in 1914, this iconic ballpark offers a nostalgic glimpse into America’s favorite pastime. Even if you’re not a sports fan, the lively atmosphere and traditions like singing “Take Me Out to the Ball Game” during the seventh-inning stretch are not to be missed.

Foodie tip: Try the famous Chicago-style hot dog at Wrigley Field, but remember – no ketchup allowed!

6. Stroll Along Navy Pier

Navy Pier is Chicago’s lakefront playground, offering entertainment for all ages. Ride the 200-foot Centennial Wheel for spectacular views of the city and Lake Michigan. Enjoy live music, street performers, restaurants, and shops. Don’t miss the Chicago Children’s Museum if you’re traveling with kids. In summer, catch the breathtaking fireworks displays on Wednesday and Saturday nights.

Budget-friendly option: Simply walking along the pier and enjoying the lake views is free and just as enjoyable.

7. Indulge in Deep-Dish Pizza

No visit to Chicago is complete without sampling its famous deep-dish pizza. This hearty pie, with its thick crust and generous layers of cheese and toppings, is a local institution. Popular spots include Lou Malnati’s, Giordano’s, and Pequod’s Pizza. Be prepared to wait – a proper deep-dish takes around 45 minutes to bake!

Local secret: Many locals swear by the thin-crust “tavern-style” pizza. Try both and decide which team you’re on!

8. Get Wild at Lincoln Park Zoo

One of the oldest zoos in North America, Lincoln Park Zoo is a 35-acre oasis in the heart of Chicago. The best part? It’s completely free! Home to a diverse array of animals from around the world, it’s a perfect destination for families or anyone looking to escape the urban hustle. Don’t miss the beautiful Kovler Lion House and the immersive Regenstein Center for African Apes.

Seasonal delight: Visit during the winter holidays to experience ZooLights, when the zoo transforms into a twinkling winter wonderland.

9. Shop ‘Til You Drop on the Magnificent Mile

Shopaholics, prepare yourselves for the Magnificent Mile! This upscale section of Michigan Avenue is home to high-end department stores, luxury boutiques, and famous brands. Even if shopping isn’t your thing, the stunning architecture and street performers make it worth a stroll. Don’t miss the historic Water Tower, one of the few structures to survive the Great Chicago Fire of 1871.

Viewpoint tip: Head to the 360 CHICAGO Observation Deck in the John Hancock Center for panoramic views of the city and lake.

10. Laugh Out Loud at The Second City

Chicago is renowned for its comedy scene, and The Second City is where it all began. This legendary comedy club has launched the careers of countless stars, including Bill Murray, Tina Fey, and Stephen Colbert. Catch an improv show or sketch comedy performance for a night filled with laughter and maybe even spot the next big comedy star!

Pre-show suggestion: Grab dinner in the nearby Old Town neighborhood, known for its Victorian-era buildings and eclectic dining options.

11. Discover Science at the Field Museum

Step into a world of natural wonders at the Field Museum. Home to Sue, the largest and most complete T. Rex skeleton ever found, this museum offers a fascinating journey through Earth’s history. From ancient cultures to the latest scientific discoveries, the Field Museum’s extensive collections will captivate visitors of all ages.

Time-management tip: With so much to see, consider purchasing a Basic Admission + 1 ticket, which allows you to choose one special exhibit or 3D movie in addition to the main exhibits.

12. Relax at Lakefront Trail

Escape the urban jungle and enjoy Chicago’s natural beauty along the Lakefront Trail. This 18-mile paved path offers stunning views of Lake Michigan and the city skyline. Rent a bike, go for a jog, or simply take a leisurely stroll. It’s a perfect way to experience Chicago like a local and catch your breath between sightseeing adventures.

Picnic spot: Pack a lunch and stop at one of the many beaches along the trail for a scenic picnic with a view.

13. Experience History at Chicago History Museum

Dive deep into the Windy City’s past at the Chicago History Museum. From the Great Chicago Fire to the city’s role in World War II, this museum offers a comprehensive look at the events and people that shaped Chicago. Interactive exhibits and fascinating artifacts bring history to life, making it an engaging experience for visitors of all ages.

Guided tour tip: Join one of the museum’s neighborhood walking tours to explore Chicago’s diverse communities and hidden stories.

14. Jazz It Up at Green Mill Cocktail Lounge

Step back in time at the Green Mill Cocktail Lounge, a former speakeasy once frequented by Al Capone. This historic jazz club has been swinging since 1907 and still offers nightly live jazz performances. With its art deco decor and vintage atmosphere, it’s the perfect spot to end your evening with some smooth tunes and classic cocktails.

Insider tip: The Green Mill is cash-only, so be sure to hit an ATM before you go. Arrive early on weekends to secure a good seat.

15. Explore the Unique Neighborhoods

Chicago is a city of neighborhoods, each with its own distinct character. Take time to explore areas like Wicker Park, known for its hipster vibe and vintage shops; Pilsen, with its vibrant Latino culture and colorful murals; or Lincoln Park, home to beautiful Victorian houses and trendy cafes. Each neighborhood offers a unique slice of Chicago life.

Foodie adventure: Take a food tour through different neighborhoods to sample Chicago’s diverse culinary scene, from Polish pierogi in Avondale to Mexican street food in Little Village.

Plan Your Chicago Adventure

Chicago offers a perfect blend of big-city excitement and Midwestern hospitality. Whether you’re an art lover, a foodie, a sports enthusiast, or just looking for a fun-filled city break, the Windy City has something for everyone. Remember to pack comfortable walking shoes and a good appetite – you’ll need both to fully experience all that Chicago has to offer!

Best Time to Visit

Chicago shines in the summer (June to August) with warm weather and numerous festivals. However, fall (September to November) offers mild temperatures and beautiful foliage. Winter can be harsh, but the city looks magical covered in snow, and you can enjoy ice skating in Millennium Park.

Getting Around

Chicago has an excellent public transportation system, including the famous ‘L’ trains and an extensive bus network. Consider purchasing a Ventra Card for easy access to public transit. The city is also bike-friendly, with numerous bike-sharing stations available.

Ready to Experience Chicago?

Start planning your Windy City adventure today:

• Find the best flight deals to Chicago O’Hare International Airport (ORD) or Midway International Airport (MDW) with our interactive flight pricing map. Compare real-time prices and choose the perfect flight to start your Chicago experience.
• Discover perfect accommodations, from luxury hotels along the Magnificent Mile to cozy B&Bs in charming neighborhoods. Book your Chicago hotel here.
• Want to explore beyond the city limits? Check out our car rental options for day trips to nearby attractions.
• Start your Chicago adventure stress-free with a pre-booked airport transfer.

Chicago is waiting to welcome you with open arms and endless possibilities. From its towering skyscrapers to its beautiful lakefront, from its world-class museums to its legendary deep-dish pizza, the Windy City promises an unforgettable adventure. Get ready to create lasting memories in one of America’s greatest cities!

FAQs:

What are the must-see attractions for first-time visitors to Chicago?

First-time visitors should prioritize iconic attractions such as Willis Tower Skydeck, Millennium Park (including “The Bean”), Art Institute of Chicago, Navy Pier, and a Chicago River architecture cruise. Don’t miss trying deep-dish pizza and exploring neighborhoods like Wicker Park or Lincoln Park.

How many days do I need to explore Chicago?

A minimum of 3-4 days is recommended to see Chicago’s main attractions. However, 5-7 days would allow for a more relaxed pace and the opportunity to explore neighborhoods, attend events, and take day trips to nearby areas.

What’s the best time of year to visit Chicago?

The best time to visit Chicago is from late spring to early fall (May to September). Summer offers warm weather and numerous festivals, while September and October provide mild temperatures and fewer crowds. Winter can be harsh but offers unique experiences like ice skating in Millennium Park.

Is the Chicago CityPASS worth it?

The Chicago CityPASS can be worth it if you plan to visit several of the included attractions. It offers admission to five top attractions at a discounted rate and often includes skip-the-line privileges. Calculate the cost of individual tickets to the attractions you want to visit and compare it to the CityPASS price to determine if it’s a good value for your itinerary.

What are some free things to do in Chicago?

Chicago offers many free attractions, including:

Lincoln Park Zoo
Millennium Park and Grant Park
Chicago Cultural Center
Navy Pier (entry is free, though some attractions inside have fees)
Garfield Park Conservatory
Free museum days (many museums offer free admission on certain days for Illinois residents)
Lakefront Trail and beaches
Window shopping along the Magnificent Mile
Exploring neighborhoods and admiring street art in areas like Pilsen

These free activities allow visitors to experience much of Chicago’s culture and beauty without spending a whole lot.