Exploring Chicago: A Comprehensive Guide

There are few cities more spectacular than Chicago. Nestled on the banks of Lake Michigan, Chicago has everything from sandy beaches and luxury shopping districts to vibrant cultural scenes and art galleries, ensuring there is something for everyone.

The Windy City is a fabulous year-round destination for those who crave art, culture, adventure, world-class restaurants, and hotels. From fancy shops like Tiffany & Company on Michigan Avenue to quiet neighborhoods like Andersonville and Hyde Park, the city offers an unparalleled travel experience. With so much to see and do in Chicago, it’s hard to fit it all in one trip! Here, discover the favorite attractions and activities that highlight the essence of this vibrant city.

Best Things to Do in Chicago

Chicago is a very walkable city, especially in downtown areas like the Loop, River North, and along the Magnificent Mile. Moreover, it is bike-friendly, featuring many bike lanes and trails, particularly along the Lakefront Trail. The city’s bike-sharing program, Divvy, provides an easy and affordable way to rent a bike for short trips.

Part One – Things to Do in Downtown / Waterfront

1. The Bean – Millennium Park and the Cloud Gate

The Bean at Millennium Park is one of the most iconic sculptures in Chicago, known officially as the “Cloud Gate” and created by world-famous sculptor Anish Kapoor. Visit the beautiful Millennium Park to take advantage of a wonderful photo opportunity with The Bean. Its gleaming mirrored finish provides a beautiful backdrop as it distorts the city’s skyline in creative ways.

Other Things to Do at Millennium Park

Millennium Park offers more than just Cloud Gate; there are numerous activities to make it a full day out. In winter, enjoy ice skating at the McCormick Tribune Ice Rink, which transforms into a rock-climbing wall during warmer months. Don’t miss the magnificent Crown Fountain and its two towering glass structures bordering the reflecting pool, showcasing video projections of Chicago faces.

While at Millennium Park, keep an eye out for designs by architect Frank Gehry. The Jay Pritzker Pavilion is a state-of-the-art outdoor concert venue hosting various music events, including the Grant Park Music Festival, free concerts, and movie screenings in the summer. The BP Pedestrian Bridge offers unique views as it connects Millennium Park to Maggie Daley Park.

2. Stroll the Chicago Riverwalk

Take a leisurely stroll along the downtown Chicago River, exploring the Chicago Riverwalk, a 1.25-mile-long path featuring shopping, dining, and museums. Additionally, it’s easy to catch a boat tour from the Riverwalk for a comfortable sightseeing experience.

3. Chicago Architecture River Cruises

One of the best ways to explore Chicago is through the Chicago Architecture River Cruise. This highly recommended tour showcases some of the most iconic buildings and architectural feats in the city, providing insights into its rich architectural history.

4. Chicago River Boat Tour

If you prefer a shorter experience, a 45-minute family-friendly boat tour along the Chicago River is an entertaining option. Experience the city’s skyline and architecture while enjoying a pleasant river journey.

5. SkyDeck Chicago at Willis Tower

To enjoy unparalleled views of the Chicago skyline and Lake Michigan, visit the Skydeck Chicago situated atop the Willis Tower. For the adventurous, the Ledge offers a thrilling glass enclosure with breathtaking city views from 103 floors above ground.

6. Art Institute of Chicago

Located in the heart of Grant Park, the Art Institute of Chicago houses an extensive collection of art from around the world. With its architectural beauty and impressive exhibits, it has been recognized as one of the best museums globally.

Best Money Saving Tip for Chicago

Take advantage of the CityPASS, which provides bundled access to many of the city’s top attractions, saving time and money.

7. Take a Chicago Food Tour

A walking food tour is an excellent way to savor Chicago’s culinary delights. Discover local favorites, including specialties like Chicago hot dogs and deep-dish pizza, while exploring the city’s rich history.

8. Enjoy The Crimes of Chicago Mob and Crime Bus Tour

For those intrigued by Chicago’s colorful criminal past, a unique bus tour takes you through the notorious areas associated with famous mob figures like Al Capone and John Dillinger.

9. The Magnificent Mile

The ‘Mag Mile’ spans a mile-long stretch featuring over 460 retailers, famous restaurants, and cultural sites, making it an iconic shopping district in the city.

10. TILT At John Hancock Center

For breathtaking views of the skyline, visit the John Hancock Center’s observation deck. Dare to experience TILT for an adrenaline-fueled experience as it tilts you over the edge of the building.

11. Tour the Wrigley Building

The Wrigley Building, opened in the 1920s, showcases Chicago’s architectural evolution. A walking tour here reveals the history of the renowned Magnificent Mile and its iconic structures.

12. Chicago Cultural Centre

Admire the stunning architecture of the Chicago Cultural Centre, highlighting breathtaking stained glass and offering free exhibitions and performances, perfect for art enthusiasts.

13. Navy Pier

Navy Pier is a vibrant event space featuring various attractions, including the iconic Centennial Wheel, serving as a perfect spot for family fun and beautiful views of downtown Chicago.

Part 2 – Sports and Entertainment in Chicago

14. Catch a White Sox Game

Baseball is a quintessential American pastime, and attending a Chicago White Sox game at Guaranteed Rate Field is a must for any sports enthusiast.

15. Catch a Game at Wrigley Field

Alternatively, watch a Chicago Cubs game at the historic Wrigley Field, sitting in a charming residential neighborhood that perfectly embodies the spirit of the city.

16. Cheer on the Bulls & Blackhawks at the United Center

A visit to the United Center is essential for any sports lover, hosting thrilling games of the Chicago Bulls and Blackhawks along with notable concerts and events.

17. The Second City

Famous for its comedy scene, The Second City in Lincoln Park has nurtured numerous iconic comedians. A night here promises laughter and entertainment, a true gem in Chicago’s cultural landscape.

18. Chicago Magic Lounge

Experience the art of Chicago-style magic at the elegantly designed Chicago Magic Lounge, featuring cabaret performances in a unique ambiance combining the allure of vintage speakeasies.

Part 3 – The Best Chicago Museums

19. Museum of Science and Industry

The Museum of Science and Industry, situated in Hyde Park, offers engaging exhibits, including a World War II submarine and interactive experiences for visitors of all ages.

20. Museum of Contemporary Art

Filled with interactive exhibits and performances, the Museum of Contemporary Art houses a diverse collection of contemporary works, making it a must-visit during your Chicago trip.

21. Field Museum of Natural History

The Field Museum is an excellent destination for families, showcasing a diverse array of exhibits, including a complete T-Rex fossil and artifacts from ancient civilizations.

22. National Museum of Mexican Art

Celebrating Mexican art and culture, the National Museum of Mexican Art in Pilsen offers a rich array of exhibits and free admission, embracing the spirit of diversity and creativity.

Part 4 – Parks and Outdoors in Chicago

23. Lincoln Park

Lincoln Park is an ideal setting for outdoor enthusiasts, featuring beautiful gardens, a zoo, and various outdoor activities along the scenic Lakefront Trail.

24. Garfield Park Conservatory

This stunning conservatory houses an impressive collection of gardens and plant species, providing a serene escape within the city and a chance to explore beautiful landscapes indoors.

25. Chicago Botanic Garden

Located just north of the city, the Chicago Botanic Garden is a lush oasis featuring 27 gardens, perfect for a peaceful retreat and connecting with nature.

26. Ping Tom Memorial Park

Hidden in Chinatown, Ping Tom Memorial Park offers picturesque views of the Chicago skyline and a tranquil environment to explore traditional Chinese landscapes.

27. North Avenue Beach

This lively beach along Lake Michigan is perfect for adventure seekers, providing activities like volleyball and kayaking while offering stunning views of the city skyline.

28. Jackson Park

A historic park, Jackson Park offers a range of recreational activities, beautiful gardens, and beaches, making it a lovely spot to unwind during your Chicago visit.

29. Chicago Jazz Festival

If you’re in Chicago during late summer, don’t miss the Chicago Jazz Festival, which features a lively lineup of performances, transforming Millennium Park into a music hub.

Where to Eat in Chicago

From street food to fine dining, Chicago boasts an array of restaurants to explore. Be sure to try the iconic Chicago Red Hot or indulge in a deep-dish pizza, a must-have culinary experience.

Purple Pig

With a tagline of ‘Cheese, Swine and Wine’, the Purple Pig promises an exceptional dining experience through a curated menu of delicious offerings set in downtown Chicago.

Lou Mitchell’s

This historic diner has been serving delicious breakfast and brunch since 1923. Known for its skillet eggs and sensational pancakes, Lou Mitchell’s is a beloved spot among locals.

Michael Jordan’s Steak House

Located in the InterContinental Hotel, this steakhouse showcases an extensive menu featuring premium cuts of meat and an incredible wine selection, perfect for steak lovers.

Rooftop Bars

Chicago’s vibrant bar scene features numerous rooftop bars that provide stunning views of the skyline, a fantastic way to enjoy a drink in this dynamic city.

• Suggested rooftop bars for great views of the city include:
  • Try LH on 21 at London House
  • Cindy’s Rooftop at Chicago Athletic Association Hotel
  • The Raised Bar, Chicago.

Lou Malnati’s

No visit to Chicago is complete without indulging in deep-dish pizza. Start with a fresh salad and savor their delicious signature pizzas; they even offer gluten-free options.

Portillo’s Hot Dogs

Portillo’s is a renowned spot for trying Chicago’s famous hot dogs. Choose from a variety of toppings or select from their diverse menu, which includes salads and pasta.

Getting Around the City of Chicago

The most efficient way to navigate Chicago is by using the L-Train, which connects various neighborhoods and even extends to O’Hare International Airport. Alternatively, water taxis provide a unique travel experience from May to October.

Consider taking a hop-on-hop-off bus tour, offering a perfect overview of the city’s highlights, including major attractions and neighborhoods.

In conclusion, Chicago is a city rich in attractions and experiences, making it an ideal destination for travelers. With so many things to do and see, this guide serves as a great starting point for your Windy City adventure.