Stepping onto Chicago’s vibrant streets, I felt a rush of excitement. The Windy City is full of iconic attractions, world-class museums, and a food scene that’s unmatched. From the Willis Tower’s stunning architecture to Millennium Park’s calm, I knew I was in for an adventure.
Chicago has something for everyone, whether you’re visiting for the first time or are a seasoned traveler. In this guide, I’ll share 11 cool experiences. You’ll see famous spots like the Art Institute of Chicago and Navy Pier, as well as hidden gems known only to locals. So, pack your bags and get ready to explore the best of Chicago!
As you start your Chicago adventure, get ready to dive into the city’s history, diverse neighborhoods, and entertainment. From the Magnificent Mile to the Shedd Aquarium, every moment is a chance to make memories. And for couples, I’ve got a day trip guide for exploring history, architecture, and food on a budget.
So, let’s explore the 11 coolest things to do in Chicago. Trust me, you’re in for a treat!
1.Enjoy a Breathtaking 360-Degree View of the Windy City
Visiting Chicago is thrilling, especially when you see the city skyline from high up. Two famous spots, the Willis Tower Skydeck and 360 Chicago Observation Deck, give you amazing views.
2.Visit the Willis Tower Skydeck
The Willis Tower, once Sears Tower, is a top spot for city views. The Skydeck on the 103rd floor shows you the city and beyond. For a thrill, try The Ledge, a glass balcony that lets you look down.
The view from the Skydeck is simply breathtaking. On a clear day, you can see up to 50 miles in every direction, spotting iconic landmarks like Navy Pier, Millennium Park, and even the shores of Lake Michigan.
3.Take in the Views from 360 Chicago Observation Deck
The 360 Chicago Observation Deck is on the 94th floor of the John Hancock Building. It has huge windows for clear views of the skyline and Lake Michigan. For more excitement, try TILT, a moving platform that tilts you outward.
| Observation Deck | Height | Special Features |
|---|---|---|
| Willis Tower Skydeck | 1,353 feet (412 meters) | The Ledge glass balconies |
| 360 Chicago Observation Deck | 1,030 feet (314 meters) | TILT moving platform |
Both the Willis Tower Skydeck and 360 Chicago Observation Deck give you amazing views of Chicago. They are must-sees for anyone visiting the city. Whether you’re new to Chicago or live here, these views will create lasting memories.
4.Shop Till You Drop on the Magnificent Mile
No visit to Chicago is complete without a shopping spree on the Magnificent Mile. This stretch of Michigan Avenue has over 460 retailers. You’ll find everything from luxury brands to high-street favorites. Walking along, I felt excited about the endless shopping possibilities.
The Magnificent Mile is known for its upscale department stores. Places like Neiman Marcus, Saks Fifth Avenue, and Nordstrom offer a top-notch shopping experience. I got lost in the aisles, admiring the latest fashion trends and enjoying some retail therapy.
There are also many boutiques and specialty shops along the Magnificent Mile. You’ll find high-end designer boutiques like Tiffany & Co., Cartier, and Burberry. There are also more affordable options. The stunning window displays were a treat to see.
“The Magnificent Mile is a shopper’s paradise, offering an unparalleled selection of luxury brands, department stores, and specialty shops. It’s the perfect destination for a day of retail therapy and indulgence.”
Take a moment to admire the architecture along the Magnificent Mile. The historic Water Tower, a survivor of the Great Chicago Fire of 1871, is a beauty. Traveling alone to Chicago lets you fully enjoy the city’s history and architecture.
Whether you love fashion, bargain hunting, or just treating yourself, the Magnificent Mile has it all. Its endless shopping options and lively atmosphere make it a must-see for anyone visiting Chicago.
5.Unwind at LondonHouse Rooftop Bar
Make sure to visit the LondonHouse Rooftop Bar in Chicago. It’s on the 21st floor of the LondonHouse Chicago hotel. Here, you can enjoy amazing views of the Chicago River and skyline.
Sip Handcrafted Cocktails with a View
The mixologists at LondonHouse Rooftop Bar have made a special menu of cocktails. You’ll love the LH Gin & Tonic and the Smoked Old Fashioned. They also have a wide wine list and craft beers for everyone.
Sipping a handcrafted cocktail while taking in the stunning Chicago River views from the LondonHouse Rooftop Bar is an experience like no other.
Indulge in Delectable Small Plates
The bar also has a menu of tasty small plates. Try the Wagyu Beef Sliders, Crispy Octopus, Truffle Fries, and Charcuterie Board.
- Wagyu Beef Sliders
- Crispy Octopus
- Truffle Fries
- Charcuterie Board
The bar has both indoor and outdoor seating. It’s great for a romantic night or a fun evening with friends. The LondonHouse Rooftop Bar will surely impress you.
| Cocktail | Description | Price |
|---|---|---|
| LH Gin & Tonic | Hendrick’s Gin, Fever-Tree Tonic, Cucumber, Juniper Berries | $16 |
| Smoked Old Fashioned | Woodford Reserve Bourbon, Demerara, Angostura Bitters, Smoked | $18 |
| Rooftop Margarita | Casamigos Blanco Tequila, Cointreau, Lime, Agave | $17 |
6.Escape the Urban Bustle in Millennium Park
Chicago’s Millennium Park is a peaceful oasis in the city’s busy streets. It’s a 24.5-acre space that celebrates art, nature, and community. It attracts visitors from all over with its unique attractions.
Admire the Iconic Cloud Gate Sculpture
The Cloud Gate sculpture, or “The Bean,” is a famous landmark in Millennium Park. It’s a 110-ton stainless steel piece by artist Anish Kapoor. The sculpture’s mirrored surface shows the city and visitors, creating a stunning visual experience.
Relax in Lurie Garden
Lurie Garden is a 5-acre oasis in Millennium Park. It’s a lush space with diverse plants, celebrating Chicago’s growth. Walking through, you’ll see a colorful, ever-changing landscape, offering peace and a connection to nature.
Catch a Concert at Jay Pritzker Pavilion
Millennium Park is also a place for outdoor concerts and events. The Jay Pritzker Pavilion hosts free concerts all summer. It features a wide range of music, from classical to rock. It’s a great place to enjoy live music outdoors.
| Attraction | Highlights |
|---|---|
| Cloud Gate | Iconic 110-ton stainless steel sculpture, reflective surface, popular photo spot |
| Lurie Garden | 5-acre urban garden, diverse flora, seasonal displays, tranquil atmosphere |
| Jay Pritzker Pavilion | Frank Gehry-designed outdoor concert venue, free summer performances, diverse musical lineup |
Millennium Park is a special place for reflection, inspiration, or music. It shows Chicago’s spirit and its dedication to enriching lives. It’s a must-see destination in the city.
7.Explore the Vibrant Chicago Riverwalk
As I walked along the Chicago Riverwalk, I was amazed by the lively vibe. This 1.25-mile path along the Chicago River offers many outdoor activities. You can find dining, entertainment, and places to relax.
Renting a kayak or taking a guided river cruise is exciting. These activities give you a new view of the city. You can see the beautiful buildings and feel the city’s energy from the water. I saw cool public art, like the River Theater, while kayaking.
When I got hungry, I found many places to eat. Restaurants like City Winery and O’Brien’s Riverwalk Cafe offer great food with beautiful views. At night, the Riverwalk comes alive with music, making it fun and lively.
The Chicago Riverwalk is not just a place to walk; it’s a destination that invites you to immerse yourself in the city’s vibrant culture and enjoy an array of outdoor activities.
Looking for a calm spot? The Riverwalk has plenty. You can:
- Find a quiet spot to read a book or enjoy a picnic
- Engage in some people-watching and soak up the lively atmosphere
- Take a leisurely stroll and admire the stunning architecture along the river
| Activity | Description |
|---|---|
| Kayaking | Rent a kayak and paddle along the Chicago River for a unique perspective of the city |
| River Cruises | Join a guided river cruise to learn about the city’s history and architecture |
| Dining | Indulge in delicious bites at various restaurants and cafes along the Riverwalk |
| Live Music | Enjoy live music performances in the evening, creating a lively atmosphere |
The Chicago Riverwalk captures the essence of the Windy City. It offers fun, entertainment, and relaxation. Whether you live here or are visiting, this place is a must-see. It promises great memories and a true taste of Chicago’s charm.
8.Discover the Trendy West Loop Neighborhood
The West Loop in Chicago is a hotspot for foodies, art fans, and fashion enthusiasts. It’s a former industrial area now buzzing with new dining spots, art galleries, and trendy shops.
The West Loop’s food scene is top-notch, with many Michelin-starred restaurants. These places showcase Chicago’s culinary talent, offering dishes that are both tasty and creative.
Savor Innovative Cuisine at Michelin-Starred Restaurants
I got to try some of Chicago’s best restaurants in the West Loop. Girl & the Goat, run by Stephanie Izard, serves bold, flavorful dishes. The lively vibe and open kitchen make it a memorable spot.
Avec is another gem, known for its Mediterranean small plates and wide wine selection. It’s perfect for a cozy dinner with friends or a romantic evening.
The West Loop’s Michelin-starred restaurants are a testament to Chicago’s thriving culinary scene and the neighborhood’s status as a foodie destination.
Browse Unique Art Galleries and Boutiques
While exploring, I stumbled upon the West Loop’s art galleries and boutiques. Places like Kavi Gupta and Rhona Hoffman Gallery showcase contemporary art. I found exhibitions by both famous and new artists.
The boutiques in the West Loop are great for fashion and home decor. Stores like Notre and Free People offer trendy items with a personal touch. The staff is always ready to help you find what you need.
Exploring the West Loop’s art and shopping scene inspired me. The neighborhood’s creativity and support for local talent are truly inspiring.
| Restaurant | Cuisine | Chef |
|---|---|---|
| Girl & the Goat | New American | Stephanie Izard |
| Avec | Mediterranean | Paul Kahan |
| Blackbird | Contemporary American | Ryan Pfeiffer |
The West Loop is a must-see for anyone wanting to experience Chicago’s trendy side. With its innovative dining, art galleries, and boutiques, it’s a neighborhood that keeps surprising me.
9.Experience Rooftop Bliss at Noyane
Located on the 21st floor of the Conrad Chicago hotel, Noyane is a stylish rooftop bar. It offers a memorable experience. The moment I stepped onto the rooftop, I was struck by the stunning skyline views.
The modern decor and relaxed vibe make it ideal for any occasion. Whether you’re out with friends or on a date, Noyane is perfect.
The bar’s Japanese-inspired cuisine is a standout feature. It offers a variety of tasty small plates, great for sharing. The Wagyu Beef Gyoza and Spicy Tuna Crispy Rice were highlights for me.
These dishes were full of flavor and creativity. The chefs truly showcase their skills through the menu.
The Noyane Martini, a sake-based cocktail, is a must-try for anyone visiting this rooftop oasis.
Noyane also has a wide range of sake and sake-based cocktails. The Noyane Martini and Yuzu Sour were my favorites. They offer unique twists on classic drinks.
The bar also has Japanese whiskies and craft beers. There’s something for everyone’s taste.
Noyane has both indoor and outdoor seating. On a nice evening, the outdoor terrace is the best spot. You can enjoy the skyline views and your drink.
The rooftop bar’s atmosphere is peaceful. It’s a calm escape from the city’s hustle and bustle.
10.Take a Spin on Navy Pier’s Ferris Wheel
No visit to Chicago is complete without a trip to Navy Pier. This 3,300-foot-long pier on Lake Michigan offers entertainment for all ages. The pier’s highlight is the 200-foot-tall Ferris wheel, offering stunning views of the city and Lake Michigan.
Stepping into the Ferris wheel’s gondola filled me with excitement. The ride slowly showed off Chicago’s skyline and Lake Michigan’s waters. From up there, I saw the city’s skyscrapers, the lake, and the pier’s activity.
Enjoy Thrilling Rides and Attractions
Navy Pier has more than the Ferris wheel. It offers rides and attractions for kids and adults. Some top experiences include:
- Pepsi Wave Swinger: This classic swing ride gives a unique view of the pier and lake.
- Carousel: Enjoy a nostalgic ride on the carousel with 36 hand-painted animals and two chariots.
- Light Tower Ride: This ride sends you 100 feet up, offering an adrenaline rush.
The Chicago Children’s Museum on Navy Pier is great for families. It has interactive exhibits and hands-on activities. The pier also has an IMAX theater showing educational and fun films.
“Navy Pier is a must-visit destination for anyone traveling to Chicago. With its iconic Ferris wheel, thrilling rides, and endless entertainment options, it’s the perfect place to create unforgettable memories with family and friends.”
Watch Fireworks Light Up the Sky
Navy Pier hosts a weekly fireworks display in summer. It happens on Wednesday and Saturday evenings, weather permitting. Thousands come to see the dazzling show.
To enjoy the fireworks, get a spot on the pier or beach early. As the sun sets, the sky lights up with color and music starts.
| Day | Time | Location |
|---|---|---|
| Wednesdays (Memorial Day – Labor Day) | 9:30 PM | Navy Pier |
| Saturdays (Memorial Day – Labor Day) | 10:15 PM | Navy Pier |
The fireworks light up the night, filling me with awe. It’s a reminder of Chicago’s magic and beauty. Navy Pier is a must-see for unforgettable moments in the Windy City.
11.Get Lost in the Charm of Old Town
Step back in time in Chicago’s Old Town neighborhood. This area is full of architectural wonders, unique shops, and cozy cafés. You’ll feel like you’ve traveled back in time as you explore.
Visit the Instagrammable Kibbitznest Café
The Kibbitznest Café is a hidden gem in Old Town. It’s a bookstore, café, and vinyl record shop all in one. It’s the perfect spot to relax with a book, enjoy coffee, or listen to vinyl records.
The café’s vintage decor and warm atmosphere make it a must-see. It’s a place you’ll want to share on Instagram.
“Kibbitznest Café is a true oasis in the heart of Old Town. It’s the perfect place to escape the hustle and bustle of the city and immerse yourself in a world of books, music, and delicious coffee.”
Stroll Through Historic Streets and Architecture
As you explore Old Town, admire the stunning historic architecture. You’ll see the iconic St. Michael’s Church, which survived the Great Chicago Fire of 1871. There are also beautifully preserved Victorian-era homes.
Look out for these architectural highlights:
- The Second City: This renowned comedy club has been a launching pad for countless famous comedians, including Tina Fey, Steve Carell, and Stephen Colbert.
- Zanies Comedy Club: Another legendary comedy venue, Zanies has been entertaining audiences with stand-up performances since 1978.
- Old Town Triangle Association: This historic building, constructed in 1882, now serves as a community center and art gallery.
Whether you love history, architecture, or just want a charming place to spend the afternoon, Old Town is a must-see. So, put on your walking shoes, grab your camera, and get ready to fall in love with this timeless neighborhood.
Chicago tourist attractions, Things to do in Chicago, Chicago food tours
No trip to Chicago is complete without trying the famous deep dish pizza. Lou Malnati’s, Giordano’s, and Pequod’s Pizza are must-visits for this cheesy delight. For a deeper dive into Chicago’s food scene, join a Chicago food tour. You’ll get to try everything from classic Chicago hot dog stands to Michelin-starred dishes.
Chicago is also home to world-class museums. Spend time at the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry. A walk through Grant Park will take you to the Shedd Aquarium, with over 32,000 animals.
The Chicago River Architecture Tours give a unique view of the city’s architecture. These boat tours dive deep into Chicago’s iconic buildings and their history.
For a smooth visit, use a Chicago travel guide. With so much to see, a good plan ensures you enjoy the Windy City’s best.
| Chicago Tourist Attraction | What to Expect |
|---|---|
| Deep Dish Pizza | Thick, cheesy, and savory pizza that’s a true Chicago classic |
| Chicago Food Tours | Guided tours exploring the city’s diverse culinary scene |
| Chicago Hot Dog Stands | Iconic Chicago-style hot dogs topped with a variety of condiments |
| Chicago Museums | World-class museums showcasing art, history, science, and more |
| Shedd Aquarium | One of the largest indoor aquariums in the world with over 32,000 animals |
| Chicago River Architecture Tours | Guided boat tours offering a unique perspective on the city’s iconic architecture |
Chicago is a city that has something for everyone. You can see amazing architecture and visit places like the Willis Tower Skydeck and Cloud Gate. The city also has trendy neighborhoods and hidden spots to explore.
Whether you’re enjoying a view from a rooftop bar or trying amazing food, Chicago will capture your heart. You can also explore places like Millennium Park and the Riverwalk. Or, just wander through areas like the West Loop and Old Town.
Chicago’s history, friendly people, and endless adventures make it a place you’ll want to come back to. As you plan your trip, be open to new experiences. There’s always something new to find in Chicago.
So, pack your bags and get ready for an adventure in the Windy City. You’ll fall in love with it, I promise.
FAQ
What are some must-visit attractions in Chicago?
Top spots in Chicago include Millennium Park and the Art Institute of Chicago. Navy Pier, the Shedd Aquarium, and Willis Tower are also must-sees. The Magnificent Mile offers stunning views and great shopping.
Where can I find the best deep-dish pizza in Chicago?
For the best deep-dish pizza, try Lou Malnati’s, Giordano’s, or Pequod’s Pizza. Each place has its own twist on the classic dish. Be sure to try a few different ones.
What are some hidden gems in Chicago that I shouldn’t miss?
Don’t miss the Garfield Park Conservatory and the Chicago Riverwalk. The West Loop neighborhood and Kibbitznest Café in Old Town are also gems. They offer a glimpse into the city’s diverse culture and natural beauty.
What is the best way to see Chicago’s famous architecture?
The best way to see Chicago’s architecture is on a Chicago River Architecture Tour. These tours give you a close-up look at iconic buildings and their history. You’ll enjoy stunning views from the water.
Are there any good food tours in Chicago?
Yes, Chicago has many food tours. You can try deep-dish pizza, Chicago-style hot dogs, and more. Options include the Magnificent Mile Food Tour and the Chinatown Food Tour.
What are some fun activities for families in Chicago?
Chicago has lots for families, like Navy Pier and the Shedd Aquarium. The Field Museum and Museum of Science and Industry are also great. Don’t forget the Lincoln Park Zoo, a free zoo in the city.
What is the best time of year to visit Chicago?
Summer (June to August) is great for warm weather and outdoor fun. Fall (September to November) offers mild weather and beautiful foliage. Winter can be cold, but the city’s holiday lights and indoor spots are worth it.
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