From world-class museums and iconic architecture to epic food tours and indulgent dining experiences, the Windy City has something for everyone. Whether you’re an art enthusiast or a foodie on a mission, here are two unforgettable ways to make the most of your time in Chicago.
Day 1: Must-See Art & Cultural Attractions
Morning
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.
Next, 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.
End your morning 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.
Afternoon
Step back in time with lunch at one of Chicago’s oldest restaurants. The Berghoff is a family-run gem steeped in German-American heritage, from the wood-paneled walls to the stained-glass windows. 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.
After lunch, 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.
Evening
Enjoy an upscale dinner 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.
Wrap up your evening with a world-class performance by the Chicago Symphony Orchestra at the Symphony Center. Soak up the sophisticated ambiance and listen to the sounds of one of the country’s “Big Five” orchestras. Pro tip: Check the schedule for special-themed concerts or collaborations with contemporary artists.
For a more laid-back vibe, 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.
Day 2: Chi-Town Foodie Adventures
Morning
Begin your adventure at Lou Mitchell’s, a vintage diner that’s been a Route 66 icon for over a century. The local legend is known for pairing hearty breakfast classics with a dose of nostalgia. Choose from the expansive omelet menu, or indulge in staples like corned beef hash and eggs benedict. Don’t be surprised when your waiter drops off complimentary prunes—it’s a nod to old-school dining traditions that they’ve maintained over the years.
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.
Head back to the city to snack your way through the Chicago French Market. Explore more than 30 international food stalls, from Lito’s Empanadas to Saigon Sisters to Barangaroo’s Aussie. As a microcosm of Chicago’s culinary diversity, stopping here means your palate can travel the world without leaving the building. If you’re up for a late-morning picnic, pack up your treats and enjoy them along the nearby Riverwalk.
Afternoon
No foodie trip to Chicago is complete without trying the legendary burger at Au Cheval. This cozy, speakeasy-style hotspot is famous for serving up what’s been called the best burger in America. Chow down on their signature burger topped with a fried egg, thick-cut bacon, and Mornay sauce. They don’t take reservations so the wait can be long, but it’s worth every minute.
Next up, dive into a whimsical world of sweet treats at the Museum of Ice Cream. Float in the giant sprinkle pool, marvel at larger-than-life ice cream sculptures, and snap Instagram pictures inside interactive exhibits like the Sprink-L Train and the Jelly Bean room. Savor delectable tastings throughout the museum, including locally inspired flavors like Chicago-style popcorn ice cream. Book your tickets in advance—this spot is a favorite for locals and tourists alike.
Quench your thirst with Barrel Run on a boozy tour of Chicago’s best breweries. Step inside a prohibition era-themed barrel on wheels to immerse yourself in the area’s vibrant brewing scene and rich gangster history. Taste craft beer samples at three breweries and tour a production facility to see where the magic happens. Book a spot on a public tour or rent out your own bus for a private tour with your crew.
Evening
Turn dinner into an experience at Alinea, the only 3-Michelin-starred restaurant in town. The dim lighting and understated decor let the food take center stage, with molecular gastronomy as the star of the show. Expect 12-20 courses that change with the seasons, from helium-filled green apple balloons to edible canvases where you paint the meal. Don’t be surprised if the decor or even your table changes its appearance with each course—it’s all part of the show.
For dessert, satisfy your sweet tooth at the original Margie’s Candies on Western & Armitage. The iconic ice cream parlor looks just like it did when it opened in 1921, from old-school diner booths to tabletop jukeboxes and nostalgic decor. Indulge in an extra-thick milkshake or order a sundae in a vintage clamshell dish. Visiting with a group? Try The Royal George, but don’t be surprised if you can’t finish the enormous bowl of ice cream.
Prefer a boozy dessert? Head to JoJo’s Shake Bar for over-the-top milkshakes, cookie flights, and candy cocktails. Shoot fruity vodka out of a Fruity Pebbles shot glass, sip liquor-infused shakes like the Gold Digger or Chocolate Nirvana, and play 80s-inspired arcade games. Don’t worry, they have zero-proof drinkable desserts for the kids, too!
