Chicago: Food, Views & Vibes

Walk the Lakefront Trail: One of the best ways to experience Chicago is on foot along Lake Michigan, especially around sunrise or golden hour. It’s scenic, peaceful, and gives you the most iconic and breathtaking views.

Take the Chicago Architecture Boat Tour: This is the #1 must-do in Chicago. Seeing and learning about the city’s architecture from the river is unforgettable, and it’s the perfect first-day activity.

Visit the Starbucks Reserve Roastery: A fun and essential stop for coffee lovers. The space is huge, beautiful, and feels like a coffee experience rather than just a cafe.

Explore the Field Museum: One of the best museums in the country, with exhibits that are genuinely impressive even if you’re not a museum person. Plan a few hours here—it’s massive and worth it.

See the Shedd Aquarium: A classic Chicago experience right on Museum Campus, especially great for a cozy afternoon plan. It’s one of the most iconic aquariums in the US for a reason.

Catch a show at the Chicago Theatre: The marquee alone is worth seeing, but the inside is just as stunning. It’s a perfect nighttime activity for a more elevated, old-school Chicago vibe.

Stroll the Magnificent Mile (and shop around): Even if you’re not a big shopper, this walk feels very “Chicago” and is great for people-watching. You’ll find everything from luxury stores to classic city staples.

Visit Pilsen: One of the most vibrant neighborhoods in the city, known for its murals, local shops, and incredible Mexican food. It’s a must if you want Chicago beyond the tourist areas.

Visit Chinatown: A fun neighborhood to explore for food, bakeries, bubble tea, and cultural spots. It’s one of my favorite places to go when I want a more local, casual day.

Take in the skyline from Millennium Park: Stop by “The Bean” in Millenium Park and walk through the park for classic Chicago photo moments. It’s central, easy to fit into any itinerary, and beautiful in every season.

Lou Malnati’s: A Chicago classic and one of the best spots to try iconic deep-dish pizza.

Portillo’s: A Chicago staple for classic fast-casual eats like Italian beef and Chicago-style hot dogs. It’s iconic and a must-have if you are visiting.

Jumping Bean Cafe: A cozy, small neighborhood café with great coffee, warm vibes, and the perfect stop while exploring Pilsen.

Pittsfield Cafe: A hidden gem tucked inside the historic Pittsfield Building, this cozy old-school café feels like stepping into a classic Chicago time capsule. It’s the perfect spot for an affordable breakfast or lunch downtown.

Crying Tiger: A trendy Thai restaurant known for bold flavors, shareable plates, and some of the best cocktails in the city. It’s extremely popular, so make your reservation well in advance.

Beatrix: A go-to for brunch, coffee, and healthy-ish comfort food. It’s the kind of place that works for literally any time of day.

Girl & The Goat: One of Chicago’s most famous restaurants for a reason: creative dishes, bold flavors, and a great vibe. Book ahead because it fills up fast.

Pizzeria Portofino: A gorgeous riverside Italian spot known for its thin-crust pizza, pastas, and breezy coastal vibe. It’s perfect for a fun dinner downtown, especially in warmer months when the patio is open, but you still have an amazing view in the wintertime.