Hey there, fellow travelers! Journeying Jack here, back with another exciting edition of Suitcase Stories. Today, we’re diving into the Windy City to uncover some of the coolest things to do in Chicago. From its iconic skyline to its vibrant neighborhoods, Chicago is a city that never ceases to amaze. So, whether you’re a first-time visitor or a seasoned local, I’ve got you covered with this ultimate list of cool things to do Chicago style.
As we embark on this urban adventure, we’ll explore the city’s rich history, diverse culture, and mouth-watering cuisine. So, buckle up and get ready to discover the coolest things to do Chicago has to offer. Trust me, by the end of this post, you’ll be itching to pack your bags and head straight to the heart of the Midwest. Let’s get started, shall we?
Urban Adventure: Exploring Chicago’s Street Art Scene
If you’re looking for cool things to do in Chicago, exploring the city’s vibrant street art scene should definitely be on your list. From colorful murals to intricate graffiti, Chicago’s streets are filled with art that reflects the city’s diverse culture and history.
Where to Start
One of the best places to start your street art adventure is in the Pilsen neighborhood. This area is known for its vibrant murals that showcase the Mexican-American community’s rich culture and history. Take a stroll down 16th Street, and you’ll be greeted with colorful murals that depict everything from Aztec gods to Frida Kahlo.
The 606 Trail
Another great spot to check out Chicago’s street art scene is the 606 Trail. This elevated trail runs through several neighborhoods and features a variety of murals and graffiti. The trail is also a great place to take a bike ride or go for a jog while enjoying the city’s art.
Wabash Arts Corridor
The Wabash Arts Corridor is a must-visit for anyone interested in street art. This area is home to some of the city’s most impressive murals and installations, including a massive mural of a woman’s face by artist Justus Roe. The corridor is also home to several galleries and art spaces, making it a hub for Chicago’s art scene.
Tips for Exploring
When exploring Chicago’s street art scene, it’s important to be respectful of the artists and their work. Avoid touching or defacing any of the art, and be mindful of your surroundings. It’s also a good idea to bring a camera or smartphone to capture photos of your favorite pieces.
In conclusion, exploring Chicago’s street art scene is one of the coolest things to do in the city. From the colorful murals in Pilsen to the impressive installations in the Wabash Arts Corridor, there’s something for everyone to enjoy. So grab your camera and hit the streets to discover the beauty of Chicago’s street art.
Foodie Paradise: Must-Try Chicago Eateries
Chicago is a foodie paradise, with a diverse range of cuisines and dining experiences to choose from. Whether you’re a fan of deep-dish pizza or looking for something more exotic, there’s something for everyone in the Windy City. Here are some of the must-try Chicago eateries that should be on every foodie’s list:
Lou Malnati’s Pizzeria
No visit to Chicago is complete without trying the city’s famous deep-dish pizza. Lou Malnati’s Pizzeria is a local institution, serving up some of the best pizza in town since 1971. Their signature dish is the “Malnati Chicago Classic,” a deep-dish pizza with sausage, extra cheese, and vine-ripened tomato sauce. It’s a must-try for any pizza lover visiting the city.
Girl & the Goat
For a more upscale dining experience, head to Girl & the Goat in the West Loop. This trendy restaurant is known for its creative small plates and innovative flavor combinations. The menu changes frequently, but some of the standout dishes include the roasted pig face, goat empanadas, and wood-fired oysters. Be sure to make a reservation well in advance, as this place fills up fast.
If you’re looking for a classic Chicago-style hot dog, look no further than Portillo’s. This fast-food chain has been serving up hot dogs, Italian beef sandwiches, and other Chicago favorites since 1963. The hot dogs are served on a poppy seed bun with mustard, relish, onions, tomatoes, and a pickle spear. It’s a simple but delicious meal that’s perfect for a quick lunch or snack.
The Purple Pig
The Purple Pig is a Mediterranean-inspired restaurant located in the heart of the Magnificent Mile. The menu features a variety of small plates, charcuterie, and cheese boards, as well as larger dishes like lamb chops and pork shoulder. The restaurant has a lively atmosphere and a great selection of wine and beer. Be sure to try the signature dish, the “Milk-Braised Pork Shoulder,” which is slow-cooked in milk and served with mashed potatoes.
Chicago is a food lover’s paradise, and these are just a few of the must-try eateries in the city. Whether you’re in the mood for pizza, hot dogs, or something more exotic, there’s no shortage of cool things to do in Chicago when it comes to food.
Windy City Nightlife: Top Bars and Clubs
Chicago is known for its vibrant nightlife scene, with a plethora of bars and clubs to choose from. Whether you’re looking for a laid-back atmosphere or a high-energy dance floor, the Windy City has something for everyone. Here are some of the top bars and clubs to check out during your visit to Chicago:
1. The Green Mill Cocktail Lounge
If you’re looking for a classic Chicago experience, head to The Green Mill Cocktail Lounge. This historic bar has been around since the 1900s and has hosted famous jazz musicians like Al Capone and Frank Sinatra. Today, you can catch live jazz performances every night of the week while sipping on a signature cocktail.
2. The Violet Hour
For a more upscale experience, check out The Violet Hour. This speakeasy-style bar is known for its creative cocktails and intimate atmosphere. The bartenders here are true mixologists, using fresh ingredients and unique flavor combinations to create one-of-a-kind drinks.
If you’re in the mood for dancing, head to Smartbar. This iconic nightclub has been a staple of Chicago’s electronic music scene since the 1980s. With a state-of-the-art sound system and a rotating lineup of DJs, Smartbar is the perfect spot to dance the night away.
4. Three Dots and a Dash
For a tropical escape in the heart of the city, visit Three Dots and a Dash. This tiki bar is known for its elaborate cocktails served in whimsical tiki mugs. The decor is just as impressive, with bamboo walls, thatched roofs, and a giant octopus sculpture.
5. The Empty Bottle
If you’re looking for a more laid-back atmosphere, check out The Empty Bottle. This dive bar has been a favorite of locals since the 1990s and has hosted countless indie bands over the years. With cheap drinks and a cozy atmosphere, The Empty Bottle is the perfect spot to relax and enjoy some live music.
No matter what kind of nightlife experience you’re looking for, Chicago has plenty of options to choose from. These are just a few of the top bars and clubs to check out during your visit to the Windy City. Don’t miss out on these cool things to do in Chicago!
Cultural Gems: Chicago’s Iconic Museums and Theaters
Chicago is a city that is rich in culture and history. From world-renowned museums to iconic theaters, there are plenty of cool things to do in Chicago for those who love the arts. Here are some of the must-visit cultural gems in the city:
Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the United States. It houses an impressive collection of over 300,000 works of art, including paintings, sculptures, and photographs. Visitors can explore galleries dedicated to American art, European art, and contemporary art, among others. The museum also hosts special exhibitions throughout the year, making it a must-visit for art lovers looking for cool things to do in Chicago.
Museum of Science and Industry
The Museum of Science and Industry is one of the largest science museums in the world. It features over 400,000 square feet of exhibits, including a full-size replica of a coal mine, a German U-boat captured during World War II, and a 40-foot tornado. Visitors can also explore the museum’s interactive exhibits, which cover topics such as space exploration, genetics, and transportation.
The Second City
The Second City is a world-famous comedy theater that has launched the careers of many famous comedians, including Tina Fey, Steve Carell, and Stephen Colbert. The theater offers a variety of shows, including improv and sketch comedy, making it a great option for those looking for cool things to do in Chicago at night.
The Chicago Theatre is an iconic venue that has been entertaining audiences since 1921. The theater’s marquee, which features the words “Chicago” and “Theatre” in bold letters, is a popular spot for photos. Visitors can catch a variety of shows at the theater, including concerts, comedy shows, and Broadway productions.
Whether you’re a fan of art, science, or comedy, Chicago’s museums and theaters offer plenty of cool things to do in the city. Don’t miss out on these cultural gems during your next trip to Chicago!
Outdoor Escapes: Chicago’s Beautiful Parks and Beaches
Chicago is known for its stunning architecture, delicious food, and vibrant culture. But did you know that the city also boasts some of the most beautiful parks and beaches in the country? If you’re looking for cool things to do in Chicago, exploring the great outdoors is a must. Here are some of the top outdoor escapes in the city:
Grant Park is a massive urban park that spans over 300 acres. It’s home to some of Chicago’s most iconic landmarks, including the Buckingham Fountain and the Cloud Gate sculpture (also known as “The Bean”). The park also features beautiful gardens, walking paths, and stunning views of Lake Michigan.
Located in the heart of downtown Chicago, Millennium Park is a must-visit destination for anyone looking for cool things to do in Chicago. The park is home to the Jay Pritzker Pavilion, an outdoor concert venue that hosts free concerts throughout the summer. It’s also home to the Lurie Garden, a beautiful oasis in the middle of the city.
Lincoln Park is one of the largest parks in Chicago, spanning over 1,200 acres. It’s home to the Lincoln Park Zoo, which is free to visit and features over 1,000 animals. The park also features beautiful gardens, walking paths, and stunning views of Lake Michigan.
North Avenue Beach
If you’re looking for a cool place to hang out on a hot summer day, North Avenue Beach is the place to be. The beach features a wide stretch of sand, volleyball courts, and a beach house with concessions and restrooms. It’s also a popular spot for swimming, sunbathing, and people-watching.
Oak Street Beach
Oak Street Beach is another popular destination for beach-goers in Chicago. The beach features a wide stretch of sand, a beach house with concessions and restrooms, and stunning views of the city skyline. It’s also a popular spot for swimming, sunbathing, and playing beach volleyball.
Whether you’re a nature lover or just looking for cool things to do in Chicago, the city’s beautiful parks and beaches are not to be missed. So pack a picnic, grab your sunscreen, and head out to explore all that Chicago’s great outdoors has to offer.
Shop ‘Til You Drop: Unique Chicago Shopping Experiences
Chicago is a shopper’s paradise, with a wide range of shopping experiences that cater to every taste and budget. From high-end boutiques to vintage shops, there’s something for everyone. Here are some of the coolest shopping experiences in Chicago that you won’t want to miss:
1. Magnificent Mile
The Magnificent Mile is a shopper’s dream come true. This iconic shopping district is home to some of the world’s most famous brands, including Gucci, Louis Vuitton, and Burberry. But it’s not just about high-end luxury brands; there are also plenty of mid-range and budget-friendly options. The Magnificent Mile is a must-visit for anyone looking for a cool shopping experience in Chicago.
2. Wicker Park
Wicker Park is a trendy neighborhood that’s known for its unique shopping experiences. This area is home to a variety of independent boutiques, vintage shops, and record stores. If you’re looking for something cool and unique, Wicker Park is the place to be. Some of the must-visit shops in Wicker Park include Myopic Books, Reckless Records, and Kokorokoko.
Andersonville is a charming neighborhood that’s known for its eclectic mix of shops and boutiques. This area is home to a variety of independent retailers, including vintage shops, bookstores, and gift shops. If you’re looking for a cool shopping experience in Chicago, Andersonville is definitely worth a visit. Some of the must-visit shops in Andersonville include Women & Children First, Brimfield, and The Brown Elephant.
4. Lincoln Park
Lincoln Park is another great neighborhood for shopping in Chicago. This area is home to a variety of shops and boutiques, including high-end fashion retailers, vintage shops, and home decor stores. If you’re looking for a cool shopping experience in Chicago, Lincoln Park is definitely worth a visit. Some of the must-visit shops in Lincoln Park include Art Effect, Jayson Home, and Lori’s Shoes.
Whether you’re a fashionista or just looking for a unique shopping experience, Chicago has something for everyone. So, put on your walking shoes and get ready to shop ’til you drop! Don’t forget to check out these cool shopping experiences in Chicago for a truly unforgettable experience.
In conclusion, the Windy City is brimming with excitement and adventure, offering a plethora of cool things to do Chicago. From its iconic skyline to its vibrant neighborhoods, Chicago is a city that never ceases to amaze and inspire. As Journeying Jack, I’ve had the pleasure of exploring many of these fantastic experiences, and I can confidently say that there’s always something new and exciting to discover in this bustling metropolis.
Whether you’re a foodie, an art enthusiast, a sports fan, or just someone looking for a good time, you’ll find that the cool things to do Chicago are endless. So, pack your bags, put on your walking shoes, and get ready to create your own Suitcase Stories as you embark on an unforgettable journey through the heart of the Midwest.
Remember, the cool things to do Chicago are only limited by your imagination and willingness to explore. So, don’t be afraid to venture off the beaten path and uncover the hidden gems that make this city truly unique. After all, the best Suitcase Stories are the ones that are filled with unexpected surprises and unforgettable memories.
So, fellow travelers, as you set out to explore the cool things to do Chicago, I encourage you to embrace the spirit of adventure and let the city’s charm sweep you off your feet. And, as always, happy journeying!