🏙️ 🦒 🚶➡️ Just steps from the Chicago Athletic Association, Millennium Park is home to the city’s most famous landmark — Cloud Gate, affectionately known as The Bean. It’s a must-see for out-of-towners and a favorite photo stop for Chicagoans, too.
🦒 🚶➡️ A whimsical extension of Millennium Park, Maggie Daley Park is perfect for families and wanderers alike. Stroll its winding paths, cross the BP Bridge, or let kids explore the imaginative Play Garden.
🏙️ 🧱 🚶➡️ Just across the street from Millennium Park, the Chicago Cultural Center is one of the city’s most stunning (and free!) landmarks. Step inside to see its grand staircases, intricate mosaics, and the world’s largest Tiffany stained-glass dome. It’s a hidden gem of Beaux-Arts architecture.
🏙️ 🏛️ 🚶➡️ A place we both love to explore (and conveniently steps from our venue).
🏙️ 🚶➡️ Stretching along the Chicago River, the Riverwalk is a local favorite for scenic strolls, people-watching, and patio hopping. Grab a drink by the water, catch reflections of the skyline, and soak up the city’s energy from a whole new angle.
🧱 🦒 🚶➡️ A must-do for first-time visitors and locals alike, the Chicago Architecture River Tour is the most breathtaking way to see the city. Cruise along the Chicago River as expert guides share the stories behind its iconic skyline — from soaring Art Deco towers to sleek modern masterpieces. It’s the perfect blend of history, design, and city magic (and a favorite way to spend a sunny afternoon!).
🏙️ 🦒 🧱 🚶➡️ The Tribune Tower is a Gothic Revival gem on Michigan Avenue, built with stones from famous landmarks around the world — including the Parthenon and the Great Wall of China.
🧱 🚶➡️ An Art Deco icon of black granite and green terra cotta, the Carbide & Carbon Building is said to resemble a champagne bottle — a fitting symbol for our wedding weekend.
🏙️ 🧱 🦒 Atop the John Hancock building, 360 Chicago offers sweeping views of the city and lake. Thrill seekers can try TILT — a moving glass platform that leans you right over Michigan Avenue.
🏙️ 🧱 🦒 🚶➡️ With its glowing marquee and ornate 1920s interior, the Chicago Theatre is pure Art Deco magic. Catch a concert, comedy show, or simply stop for the photo-op — it’s one of the city’s most beloved landmarks.
🏙️ 🦒 A classic Chicago attraction, Navy Pier combines lakefront views, rides, dining, and year-round fun. Take a spin on the Centennial Wheel or grab a drink overlooking Lake Michigan — it’s nostalgia and skyline in one.
🏙️ 🧱 🦒 🚶➡️ Known as the “front yard of Chicago,” Grant Park is home to the iconic Buckingham Fountain, one of the largest in the world.
🏙️ 🧱 🦒 🚶➡️ Once the tallest building in the world, Willis Tower still reigns as a Chicago icon. Step onto The Ledge, a glass balcony 103 floors up, for unmatched views (and a little adrenaline).
💞 Located in the trendy West Loop, Puttery is a modern twist on mini golf — it also happens to be where Corey and Whitney had their second date! Reservations are recommended.
🏙️ 💞 The birthplace of modern improv, The Second City has launched some of comedy’s biggest names — from Bill Murray to Stephen Colbert. Grab a drink and settle in for a night of sharp sketches, spot-on satire, and that unmistakable Chicago humor.
🏛️ 🦒 Dive into the underwater world at the Shedd Aquarium, home to more than 30,000 animals — from belugas to penguins. Great for kids and adults alike.
🏛️ 🦒 Step back in time with Sue the T. rex, ancient artifacts, and world-class exhibits at the Field Museum — a Chicago treasure for science and history lovers.
🏛️ 🦒 The Adler Planetarium offers a cosmic experience with immersive shows and stunning lakefront views. It’s one of the best skyline photo spots in the city.
🏛️ 🦒 For something unexpected, visit the Federal Reserve Bank Money Museum — it’s free, fascinating, and you can even snap a photo with a million dollars in cash.
🏙️ 🧱 At the foot of LaSalle Street, the Chicago Board of Trade gleams with limestone grandeur and the famous statue of Ceres atop its peak — a favorite for architecture buffs.
🧱 💞 A Frank Lloyd Wright–renovated masterpiece, The Rookery blends ironwork, light, and glass in stunning form. Step inside the lobby for a jaw-dropping glimpse of Chicago’s architectural evolution.
🏙️ 🦒 🚶➡️ Right in the Loop, the Chicago Picasso is one of the city’s most recognizable public artworks.
🧱 💞 Designed by Frank Lloyd Wright, the Robie House is a Prairie-style masterpiece and a UNESCO World Heritage Site. A pilgrimage spot for architecture fans.
🏙️ 🦒 Baseball fan or not, Wrigley Field is pure Chicago charm — ivy-covered walls, old-school scoreboards, and all. Catch a game or just soak up the neighborhood vibe in Wrigleyville. Easily accessible by Red or Brown Line.
🏙️ 🦒 One of the few free zoos in the country, Lincoln Park Zoo sits within a beautiful park setting near the lakefront. A perfect outing for families (or anyone who loves giraffes).
🏙️ 🦒 💞 Located in Hyde Park, the Museum of Science and Industry is both playful and awe-inspiring — explore a captured WWII submarine, a tornado simulator, and so much more.
🦒 Step into a lush indoor oasis at the Garfield Park Conservatory, one of the largest and most stunning botanical conservatories in the country — perfect for a rainy afternoon or a peaceful retreat from the city bustle.
🧱 💞 Visit the Frank Lloyd Wright Home & Studio, where Wright developed his groundbreaking designs — and explore the nearby neighborhood of Wright-designed homes.
🦒 💞 A Chicago-area classic, Brookfield Zoo is expansive, educational, and filled with memories — it even hosted Corey and Whitney’s third date!
🍕 💞 🚶➡️ For a quintessential Chicago meal just steps from your hotel, visit The Gage — an upscale tavern serving inventive comfort food with a historic twist. It’s the kind of place where you can relax over a craft cocktail, watch the bustle of Michigan Avenue, and toast to the weekend.
🍕 🚶➡️ Family-owned and beloved, Pizano’s serves up classic Chicago deep dish (and thin crust!) in a cozy, old-school atmosphere. You can’t leave town without trying one.
💞 🚶➡️ A casual favorite for flavorful grilled chicken and sauces ranging from mild to fiery. Nando’s is a go-to for a quick, satisfying bite near downtown attractions.
🍕 💞 🚶➡️ Tucked inside the historic Pittsfield Building, this old-school café is one of Chicago’s hidden gems. Pop in for breakfast or a casual lunch amid Art Deco charm — it’s the perfect little pause between downtown adventures.
🍕 Steps from the Loop theaters, The Dearborn offers modern American fare in a stylish setting. Don't skip the fish and chips.
🍕 💞 A Chicago institution! Grab a Chicago-style hot dog, Italian beef sandwich, or slice of chocolate cake at Portillo’s — yum!
🍕 💞 Known for its caramelized crust and cult following, Pequod’s is the go-to for serious deep-dish lovers. If you don't make a reservation, expect a bit of a wait — it’s worth every minute.
🍸 💞 Where Corey and Whitney’s story began! First Draft in the South Loop boasts an amazing tap list, hearty pub food, and a laid-back atmosphere that makes everyone feel like a regular.
🍸 💞 Hidden behind an alley near River North, this tropical speakeasy is pure escapism. Three Dots and a Dash serves tiki cocktails in vintage mugs with plenty of island flair. Reservations recommended.
🍸 🚶➡️ Perched atop the Chicago Athletic Association, Cindy’s Rooftop offers sweeping views of Millennium Park, Lake Michigan, and the city skyline. It’s a favorite for brunch, cocktails, or a celebratory nightcap — especially when the sun sets over The Bean below.
🍸 Tucked away in the Gold Coast, Sparrow feels like a 1930s cocktail lounge lost in time. Expect elegant drinks, dim lighting, and just the right dose of glamour.
🍸 💞 Head up to Ravenswood for a tour or tasting at KOVAL Distillery, Chicago’s first distillery since Prohibition. Their organic whiskeys and liqueurs are handcrafted with care — and the cozy tasting room makes it easy to linger for “just one more.”
🍸 🍻 Equal parts brewery and distillery, Maplewood is known for its craft beers, house-made spirits, and stylish lounge setting. Order a flight, try their signature Charlatan Pale Ale, and enjoy the warm neighborhood vibe.
🍸 🍻 Community-driven and effortlessly friendly, Begyle Brewing is the kind of spot where you’ll instantly feel like a regular. Their lineup ranges from crisp lagers to creative seasonals — and it’s just a short stroll from Dovetail if you’re planning a brewery hop.
🍸 🍻 A love letter to traditional European brewing, Dovetail Brewery specializes in classic styles made with Old World techniques. Expect balanced lagers, open fermentation tanks, and a cozy taproom perfect for lingering on a lazy afternoon.