Chicago 101: A Detailed Beginner’s Guide to the Windy City

Chicago River architecture tour: Experience the city’s world-renowned skyline from the Chicago River as expert guides narrate the stories behind Chicago’s unique architecture. This river cruise offers an incredible vantage point to appreciate the diverse styles and engineering marvels that make Chicago an architectural capital.

Millennium Park: Visit the iconic Cloud Gate (“The Bean”) sculpture to capture the perfect selfie in the heart of this vibrant urban oasis. Enjoy stunning gardens and seasonal events at the city’s premier gathering spot.

Art Institute of Chicago: Consistently ranked among the top museums in the world, it houses the largest collection of Impressionist art outside of Paris. Fan of Ferris Bueller? His favorites were A Sunday on La Grande Jatte and American Gothic.

Navy Pier: A playground on the lake, Navy Pier features a towering Ferris wheel, live theater, and a variety of waterfront dining options. It is a family-friendly destination where you can catch a summer firework show or hop on a sightseeing cruise.

Michigan Avenue’s Magnificent Mile: Shop your way through over 450 luxury boutiques and flagship stores on Chicago’s most famous upscale thoroughfare. This bustling stretch perfectly blends high-end retail therapy with historic landmarks, world-class dining, and the Starbucks Reserve Roastery.

Lincoln Park Zoo and South Pond: It’s one of the last free zoos in the country nestled right in the middle of a massive park, providing a lush, green escape with incredible views of the skyline over the South Pond.

The Museum Campus: A 57-acre park along the city’s lakefront that includes the Field Museum, The Shedd Aquarium, Adler Planetarium, and Soldier Field.

The Chicago Riverwalk: This is a 1.25-mile pedestrian path below street level lined with wine bars, cafes, kayak rentals, and stunning views. It’s the best place to feel the energy of the city without the traffic.

Pequod’s Pizza: It’s ranked #1 for a reason. Try any kind of deep dish, but if you really want a taste of Chicago, get one topped with Italian beef and giardiniera.

Portillo’s: They’re known for their Chicago-style hot dogs, Italian Beef, and the chocolate cake shake!

Chicago Pizza & Oven Grinder Company: A cash-only restaurant with renowned pizza pot pies, Mediterranean bread, and the chef’s salad with a mix of garlic and poppyseed dressings.

MCCB: Located in the heart of Chinatown, it’s some of the best Chinese food in the city. It’s walk-in only, so be sure to put your name in and try some boba while you wait!

Kayao: It’s a beautifully designed space with a blend of Chinese, Japanese, and Peruvian fare. Since the food is so flavorful and unexpected, it’s my go-to for first-time visitors in the city.

Galit: A family-friendly Michelin-star Mediterranean restaurant with an impeccable menu co-owned by a James Beard Award winner Zachary Engel.

Cafe Yaya: Owned and operated by the same people that brought Galit, it is located right next door in Lincoln Park with incredibly unique pastries and amazing coffee.

Kasama: An iconic Filipino restaurant with two Michelin stars known for their breakfast sandwiches and pastries.

Momotaro: If you’re a fan of Japanese and sushi, this is a restaurant in Fulton Market that you cannot miss.

Au Cheval: Consistently named the best burger in the city for a reason.