Chi-Town Checklist
Chicago is a city bursting with bold flavors, world class architecture, and iconic attractions that offer something for every type of traveler. Whether you’re strolling along the lakefront or diving into deep-dish pizza, the Windy City delivers an unforgettable mix of culture, entertainment, and history. Here are five must-do experiences to make the most of your Chicago adventure.
1. River Cruise Architecture Tour
Chicago’s architecture tour is a must for anyone wanting to dive into the city’s rich design legacy. Cruising along the Chicago River, you'll hear the stories behind the towering skyscrapers, historic buildings, and bold innovations that define the skyline. It's equal parts relaxing and fascinating—a perfect introduction to the city's soul.
2. Explore Millennium Park
Millennium Park is the heart of downtown Chicago, where art, architecture, and nature come together. Home to the iconic Cloud Gate (aka "The Bean"), splash-worthy Crown Fountain, and stunning Jay Pritzker Pavilion, it’s a vibrant gathering place perfect for photos, picnics, and people-watching.
3. Wander the Navy Pier
Chicago’s Navy Pier is a lakefront playground packed with fun for all ages. From the towering Centennial Wheel to boat cruises, restaurants, shops, and seasonal events, it’s the perfect spot for waterfront entertainment and unbeatable skyline views.
4. Stroll the Magnificent Mile
The Magnificent Mile is Chicago’s premier shopping and dining destination, stretching along Michigan Avenue with iconic retailers, luxury boutiques, and delicious eats. Lined with historic buildings and sparkling city lights, it’s a vibrant hub for fashion, food, and fun in the heart of the city.
5. Discover History at the Field Museum
The Field Museum is a treasure trove of natural history, where you can come face-to-face with Sue, the world’s most complete T. rex, and explore exhibits on ancient cultures, gems, and the wonders of our planet. It’s an awe-inspiring stop for curious minds of all ages.
Beyond the top five, Chicago is full of hidden gems worth exploring. Here are a few extra recommendations that I just couldn’t leave off.
Wrigley Field - Whether you're a Cubs fan or just love a lively atmosphere, a day at historic Wrigley Field is a classic Chicago experience
Deep Dish Pizza - No trip to Chicago is complete without indulging in its legendary deep-dish pizza. Giordano’s, Lou Malnati’s, and Pequod’s are all local favorites
Lakefront Trail - This 18-mile path along Lake Michigan offers stunning views, perfect for a walk, jog, or bike ride on a sunny day
Skydeck - Head to the top of Willis Tower and step out onto the glass ledge for an unforgettable look over the city from 1,353 feet up
