Kick off your day at Wildberry Pancakes & Cafe, a bright and bustling diner with a modern feel. Embrace the family-friendly atmosphere and indulge in creative breakfast staples like the signature Berry Bliss Pancakes, loaded with mascarpone cream and fresh fruit. For something savory, try the slow-roast brisket hash or fried chicken and biscuits. Its convenient location near Millenium Park makes it the perfect spot to fuel up before exploring the local landmarks.

Head to Millennium Park—one of Chicago’s most famous outdoor hubs. Snap photos in front of iconic Chi-Town symbols like Cloud Gate (aka The Bean) and Crown Fountain. Stroll through serene paths surrounded by lush native plants in Lurie Garden and walk the BP Pedestrian Bridge for breathtaking skyline views. Visiting during winter? Don’t miss skating on the McCormick Tribune Ice Rink.

Take a short walk to the Art Institute of Chicago to discover one of the world’s finest art collections, with works by famed artists like Van Gogh and Monet. Explore fascinating exhibits like Arts of Africa, Sculpture Court, and Chicago Architectural Fragments. Stop by the Thorne Miniature Rooms for dollhouse-sized glimpses into various historical periods.

Step aboard Chicago’s First Lady for an architectural river cruise. Listen to stories about dozens of iconic buildings as you cruise by them, and find out how Chicago became the birthplace of modern architecture. Be sure to take plenty of pictures—this excursion is the only way to see many of these masterpieces from the water.

Step back in time with lunch at one of Chicago’s oldest restaurants. Dig into traditional German dishes like wiener schnitzel with creamed spinach and spätzle. Pair your meal with a frosty pint of house-brewed beer and bask in the old-world charm.

Make your way to the Chicago Cultural Center to marvel at the world’s largest Tiffany stained-glass dome. Once the city’s first public library, the Cultural Center now hosts rotating art exhibits, musical performances, and community events. Check out an eclectic mix of local and global art ranging from classic to contemporary. The best part? Admission is free.

For a striking blend of contemporary art and architecture, go to Wrightwood 659 next. Immerse yourself in thought-provoking exhibitions on social issues and global art in a space that’s a work of art itself. With exposed concrete walls and modern minimalist decor, this hidden gem is well worth a visit for any serious art lover.

Enjoy an upscale meal at Girl & The Goat, an industrial-chic restaurant helmed by Chef Stephanie Izard—the first woman to win Top Chef. Indulge in globally inspired small plates like goat empanadas or BBQ pork belly. Feeling adventurous? Try the roasted pig face, served with potato sticks and a sunny-side-up egg. Reservations are a must, so book your spot in advance.

Get your musical fix at Humboldt Park’s iconic California Clipper. Slide into a scarlet booth, grab drinks at the antique bar, and admire the 1930s-inspired decor of this retro cocktail lounge. Sip on a classic Sidecar or a modern Black Pearl while enjoying live music that ranges from jazz to indie, depending on the night. The drink list spans more than 70 libations, so you’re bound to find something that makes you feel right at home.

Take a short drive to the Chicago Botanic Garden, a serene oasis that’s free to visit and boasts 27 meticulously designed gardens. Embark on a peaceful self-guided walking tour through the English Walled Garden, the Malott Japanese Garden, and the Regenstein Fruit & Vegetable Garden. Before you go, check the schedule for seasonal farmer’s markets and cooking demonstrations with local chefs.