Things To Do
606 Bloomingdale Trail Bridge
A 2.7‑mile elevated greenway perfect for biking, strolling, and public art spotting. Just steps away from our place - an awesome local option to explore before our backyard gathering.
Art Institute of Chicago
World-class collection of art. Featuring over 300,000 works across 11 curatorial departments - spanning 5,000 years and global traditions. The largest Impressionism and Post-Impressionism collection outside the Louvre! Home to classics like American Gothic by Grant Wood and The Old Guitarist by Picasso. Admission is $32/person.
Bungalow by Middle Brow
Serves as a café, bakery, brewery, pizzeria, and natural winery under one big skylit space. Has a lovely patio and is a neighborhood gem.
Chicago Cultural Center
Beautiful building with a Tiffany dome and rotating art exhibits. Drop in to enjoy historic architecture, cultural programming, and serene public space in the heart of Chicago. Free admission.
Chicago River Boat Architecture Tour
THE must-do boat tour. Throughout the 90-minute signature cruise, you will learn about more than 50 skyscrapers, bascule bridges, and historic sites. Calling all Art Deco design lovers - this one’s for you! Tours run daily. Admission starts at $49/person.
Garfield Park Conservatory
One of the largest and most stunning indoor gardens in the country. Features a truly breathtaking historic glasshouse with eight unique garden rooms as well as outdoor gardens and water features. About a 10-minute drive from our place. Admission is free for Chicago residents, with a suggested donation of $10/person for non-residents.
Navy Pier
Chicago’s iconic lakeside destination - a vibrant mix of history, entertainment, culture, and stunning views on Lake Michigan. Some highlights include: the Centennial Ferris Wheel, outdoor movies, deep-dish pizza, and fireworks. Be sure to check out the calendar on their website for events. There’s no cost to enter and explore the pier, though some rides, museums, and theater shows require tickets.
Millennium Park
Chicago’s vibrant urban centerpiece - a 24.5‑acre oasis of landscape design, public art, and cultural venues nestled within Grant Park. Including the iconic Bean! Tip: Visit mid‑morning or at dusk to experience iconic lighting on the Bean without peak crowds. Free admission.
Museum Of Contemporary Art Chicago
Edgy, engaging art in a modern space near Water Tower Place. Features artwork exploring minimalism, surrealism, pop art, and conceptual art, among others. The permanent collection includes icons like Jasper Johns, Andy Warhol, Cindy Sherman, and Alexander Calder. Admission is $22/person for non-residents.
Music Box Theatre
Historic art house and repertory theatre located in the Lakeview neighborhood. Chicago’s indie-film mecca - think first-run foreign films, cult classics, 70mm epics, even live-organ sing-alongs - all under a twinkling “night-sky” ceiling. Tip: Check out their website closer to September to see what they have in store that weekend.
Scofflaw Cocktail Bar
Gin-forward cocktail bar offering inventive cocktails and small plates. Bonus: has patio! Another bonus: another great neighborhood pick if you're looking for something to do before the backyard reception!
Skydeck Chicago
Soar 103 floors up in Willis Tower for 360° views of the city - and step out onto the sky with The Ledge, a glass balcony that lets you stand (literally) above Chicago. Fast elevator, interactive exhibits, and unbeatable photo ops. A thrill with a view. Admission starts at $32/person for non-residents.
Weegee's Lounge
An unpretentious, retro-style bar featuring classic cocktails, craft beers, shuffleboard, and a vintage photo booth. Beloved by locals (including us!) - and yet another perfect spot to grab a drink before our reception.
