Explore the Best Of Chicago: Top 10 attractions & Dining Picks

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Your foodie plans Team

Collage of top attractions, local dining, and iconic landmarks in Chicago including Millennium Park, Willis Tower, and Portillo’s.
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Discover the top things to do in Chicago, from must-visit places to local dining spots. A full itinerary to explore the best of chicago, landmarks and flavors.

introduction: Why Chicago Should Be on Your Bucket List

Chicago, often called the Windy City, is a dynamic metropolis that offers something for every traveler. Whether you’re drawn to stunning architectural landmarks, world-class museums, exciting local food, or beautiful green spaces, Chicago has it all. Known for its iconic skyline, rich cultural heritage, and culinary delights, Chicago is one of the most exciting cities to visit in the United States.

This guide will walk you through the top 10 things to do in Chicago, including must-visit attractions, cultural landmarks, and the best local dining spots. You’ll get insider tips on how to experience the city like a local, from hidden gems to classic Chicago musts. Get ready to embark on an unforgettable adventure through the heart of the Midwest.

Morning: A Flavorful Start to Your Day

1. Breakfast at Lou Mitchell’s

To kick off your day in Chicago, head straight to Lou Mitchell’s, a local institution famous for its hearty breakfast dishes. Located just a short walk from the Willis Tower, this charming diner has been serving up delicious meals since 1923. Known for its comforting, home-cooked breakfasts, Lou Mitchell’s offers everything from classic pancakes and omelets to signature cinnamon rolls.

Start with their famous hotcakes, which are thick, fluffy, and served with maple syrup. If you’re in the mood for something savory, try the omelet loaded with fresh ingredients, or the biscuits and gravy—a Chicago breakfast staple. Don’t forget to sample their freshly brewed coffee, and if you’re lucky, you might even get a free piece of candy when you walk in!

Mid-Morning: Iconic Landmarks and Cultural Experiences

2. Explore Millennium Park

A visit to Millennium Park is a must for any Chicago itinerary. This sprawling park, located in the heart of downtown Chicago, is home to some of the city’s most iconic landmarks. Begin your visit with a photo op at the Cloud Gate sculpture (affectionately known as “The Bean”). This polished, reflective structure is one of Chicago’s most photographed attractions and a symbol of the city’s architectural prowess.

Afterward, take a stroll through the beautifully landscaped Lurie Garden, or relax on the lawn with views of the Chicago skyline. If you’re visiting during summer, be sure to check out the Jay Pritzker Pavilion, a stunning open-air venue that hosts free concerts and cultural events.

Millennium Park also offers plenty of free events throughout the year, from yoga classes to movie screenings, making it an exciting place to visit, no matter the season.

3. Visit the Art Institute ,one of the best of Chicago gems

Just a short walk from Millennium Park, the Art Institute of Chicago is another essential stop to explore the best of Chicago. Home to over 300,000 works of art, this world-renowned museum houses pieces from renowned artists like Vincent van Gogh, Pablo Picasso, and Grant Wood. The museum’s collection spans over 5,000 years, from ancient Egyptian artifacts to contemporary masterpieces.

Don’t miss the American Gothic painting by Grant Wood or A Sunday on La Grande Jatte by Georges Seurat. The museum’s extensive collection of Impressionist paintings, including works by Monet and Renoir, is a must-see for art lovers. If you need a break, stop by the museum’s cafe or gift shop for a souvenir.

Lunch: Savor Chicago’s Famous Flavors

4. Lunch at Portillo’s

When it’s time to refuel, head to Portillo’s, a Chicago institution known for its signature dishes, including the iconic Chicago-style hot dog and Italian beef sandwich. Portillo’s is famous for serving up local favorites in a casual, family-friendly setting. Located in several locations around the city, this beloved restaurant offers a variety of Chicago staples.

Try the Italian beef sandwich—thinly sliced roast beef, served on a soft roll with optional giardiniera and sweet peppers. Another local favorite is the Chicago-style hot dog, which comes topped with mustard, onions, relish, tomatoes, pickles, and sport peppers—all served on a poppy seed bun. For dessert, don’t miss their famous chocolate cake; it’s rich, decadent, and the perfect sweet ending to your meal.

Portillo’s is the perfect place for a satisfying and affordable lunch that showcases the best of Chicago ’s culinary traditions.

Afternoon: Iconic Views and Scenic Walks

5. Willis Tower Skydeck

After lunch, take a short walk to the Willis Tower, one of the Chicago’s most recognizable landmarks. For some of the best views in the city, head to the Skydeck, located on the 103rd floor. The Skydeck offers a breathtaking 360-degree view of Chicago, Lake Michigan, and the surrounding areas. It’s one of the tallest observation decks in the United States, providing visitors with unparalleled views.

For an extra thrill, step out onto The Ledge, a glass-floored balcony that extends from the building, giving you the sensation of floating above the streets below.

6. Chicago Riverwalk

Next, take a stroll along the scenic Chicago Riverwalk. This pedestrian-friendly path stretches for 1.25 miles along the Chicago River, offering stunning views of the city’s architecture and landmarks. The Riverwalk is a beautiful place to relax and watch the boats pass by, and there are plenty of outdoor cafes where you can stop for a drink or snack.

For a unique perspective of the city, consider taking a Chicago River architecture tour. These boat tours offer insights into Chicago’s world-famous architectural history, showcasing iconic buildings and landmarks along the river.

Evening: Unwind with Great Food and Atmosphere

7. Dinner at The Signature Room at the 95th

As evening approaches, head to The Signature Room at the 95th for dinner with a view. Located on the 95th floor of the John Hancock Center, this upscale restaurant offers spectacular views of Chicago’s skyline and Lake Michigan. The restaurant’s menu features a variety of delicious dishes, from steak and seafood to seasonal specialties.

The elegant atmosphere and breathtaking vistas make it the perfect spot for a relaxing dinner after a full day of sightseeing. Don’t forget to try their signature cocktails or a glass of wine from their extensive list. Whether you’re dining with a special someone or enjoying a meal with friends, The Signature Room is an unforgettable dining experience.

8. Nightcap at The Aviary

For those who want to extend their evening, head to The Aviary, a high-end cocktail bar located in the Fulton Market District. Known for its innovative drinks and chic, intimate setting, The Aviary offers a unique and sophisticated night out. The expert mixologists craft creative cocktails using fresh ingredients and cutting-edge techniques, making it a must-visit for cocktail connoisseurs.

Enjoy a nightcap or two while soaking in the stylish atmosphere of one of the best of Chicago ‘s top cocktail bars. The Aviary is a great spot to unwind after a day of exploring the city.

Late Night: Chicago’s Sweet Treats

9. Stop by The Original Rainbow Cone, the best of chicago ice cream shops

Cap off your evening with a visit to The Original Rainbow Cone, a Chicago institution since 1926. This iconic ice cream shop is known for its signature Rainbow Cone, a multi-flavored treat made with layers of orange sherbet, pistachio, chocolate, strawberry, and Palmer House (a vanilla-based ice cream with cherries and walnuts). It’s the perfect way to indulge your sweet tooth while reminiscing about your Chicago adventure.

Grab your cone and take a leisurely stroll through the neighborhood or relax in one of the nearby parks to end your day on a sweet note.

Insider Tips: Making the best of Chicago Experience

  • Getting Around: Chicago’s public transportation system is easy to navigate, with the L train and buses taking you to nearly every major attraction. For more flexibility, consider using ride-sharing apps like Uber or Lyft.
  • Best Time to Visit: Chicago is beautiful year-round, but the summer months (May through September) offer pleasant weather for outdoor activities. Spring and fall are great times to visit if you want to avoid the crowds.
  • Local Favorites: Don’t miss out on the famous Chicago deep-dish pizza at places like Giordano’s or Lou Malnati’s. Another local favorite recognized as the best of chicago popcorn shops, is the Chicago-style popcorn at Garrett Popcorn Shops.

Contact Details

For more information on Chicago tours and attractions, check out the following resources:

Conclusion: Your Ultimate Chicago Adventure Awaits

With a blend of iconic landmarks, stunning views, and mouthwatering dining experiences, Chicago is a city that promises to delight every traveler. From Millennium Park to Portillo’s, this guide has covered the top 10 things to do in Chicago, offering you a mix of culture, history, and local flavor. Whether you’re exploring the city’s skyline or savoring its pizza, Chicago’s charm is sure to leave you wanting more. So pack your bags, explore the Windy City, and make memories that will last a lifetime!