Tourists often stick to the well-trodden paths of downtown Chicago, but venturing into its vibrant neighborhoods offers a fresh perspective and a wealth of experiences. Whether you’re a local looking to play tourist or a visitor eager to explore, this perfect weekend itinerary will help you make the most of your time in downtown Chicago.
Where to Stay
Viceroy Chicago
Located in the Gold Coast, Viceroy Chicago offers a rooftop pool with views of Lake Michigan through the skyscrapers. It’s an ideal spot to relax and unwind.
InterContinental Chicago Magnificent Mile
This hotel places you right in the heart of downtown action, perfect for those wanting to be close to everything.
Virgin Hotels Chicago
Known for its quaint charm and free happy hour for loyalty program members, Virgin Hotels Chicago offers a unique stay experience.
St. Regis Chicago
For those looking to splurge, the St. Regis Chicago boasts stunning waterfront views, two excellent restaurants, a nightly champagne sabering, and the city’s only Forbes 5-star spa.
Friday Evening: Happy Hour and Dinner
Tre Dita Bar
Start your evening with a drink and a bite at Tre Dita Bar inside the St. Regis Chicago. Enjoy a Negroni and fluffy pancakes glazed with rosemary and sea salt.
Tzuco
Head to Tzuco on the Gold Coast, where celebrity chef Carlos Gaytan offers Mexican dishes with French techniques. Try the whole red snapper or cochinita pibil on their gorgeous covered patio.
Ummo
In River North, Ummo serves up delicate house-made ricotta tortellini in lamb ragu, perfectly cooked New York strip steaks, and creative desserts.
Kyuramen
For a casual option, Kyuramen specializes in ramen and fluffy omelets layered with fried rice.
Saturday: Coffee, Pastries, and a Walk Through the Park
Somerset at Viceroy
Grab a La Colombe nitro coffee and a fresh kouign-amann or a warm, gooey chocolate-filled croissant from Somerset.
Paris Baguette
With multiple downtown locations, Paris Baguette offers traditional French pastries and Asian-inspired snacks like choux pastry and mochi doughnuts.
Tary Bakery
Try Kazakh cuisine and pastries at the new Tary Bakery.
Millennium Park
Visit Millennium Park early to avoid the rush. Snap a photo at Cloud Gate (The Bean), smell the flowers at Lurie Park, and join free exercise classes on the Great Lawn.
Double Clutch Brewery
For lunch, head to Double Clutch Brewery for brunch and a free mimosa with your meal. Alternatively, explore Maggie Daley Park before stopping at The Berghoff for bratwurst and Bavarian pretzels.
Visit the Museum
Art Institute of Chicago
Explore masterpieces by Van Gogh, Rivera, Hopper, and O’Keeffe, along with ancient sculptures.
Field Museum
Discover a massive collection of fossils, including the largest dinosaur ever discovered.
Shedd Aquarium
See marine life from the Great Lakes and around the world, including sharks, seahorses, and otters.
Saturday Evening: Dinner and Entertainment
Avec
Featured in “The Bear,” Avec offers Mediterranean-inspired small plates like sausage-stuffed dates and hummus with stovetop pita bread.
Kindling
Inside Willis Tower, Kindling serves live-fired dishes from James Beard Award-winning chef Jonathan Sawyer.
Broadway in Chicago
Catch a musical like “Six” or “The Book of Mormon” in the Chicago Theater District.
Goodman Theater
Experience eclectic entertainment including long-form improv, spoken word, and magic shows.
Gene Siskel Film Center
Watch films from around the world at this renowned film center.
Brando’s Speakeasy
For post-show fun, head to Brando’s Speakeasy for raucous karaoke.
Sunday: Breakfast and Water Activities
Planta Queen
Enjoy endless brunch cocktails and plant-based dishes like scallion and broccoli pancakes and sesame peanut noodles.
Alpana
For a more traditional breakfast, Alpana offers endless mimosas, crab cakes, and steak and eggs.
Chicago River Cruise
Take a relaxing 90-minute Chicago Architectural Tour or a 45-minute cruise from Wendella to learn about Chicago’s dramatic skyline.
Urban Kayaks
Opt for an active outing with Urban Kayaks, offering introductory lessons and historical tours.
Sunday Afternoon: Interactive Museums and One Last Dinner
Museum of Ice Cream
Ride a bright pink L train, play mini-golf, and try the ice cream version of a Chicago hot dog.
BomboBar
Visit this Instagram-famous spot for gelato and Italian cake.
Tamu
End your weekend with sushi at Tamu in the West Loop. Enjoy affordable omakase or sit-down dining for rolls and quesendons.
Gaijin
Specializing in grill-smooth okonomiyaki and kakigori cocktails, Gaijin offers a unique dining experience.
Girl & The Goat
Stephanie Izard’s acclaimed restaurant serves a la carte or four-course menus featuring global street food.
CH Distillery
Finish with a drink at CH Distillery, known for Jeppson’s Malört, before heading back to your hotel to collect your bags.
This perfect weekend itinerary in downtown Chicago ensures you’ll experience the best the city has to offer, from world-class attractions and dining to vibrant nightlife and relaxing activities.
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