Hop on a Wendella architecture boat tour (our favorite!) for iconic skyline views, or stroll the Riverwalk on foot. Back on land, snap a photo at The Bean, grab a cocktail at Cindy's Rooftop, or brave the glass ledges atop Willis Tower's Skydeck.
Don't miss the Chicago Cultural Center, home to the world's largest Tiffany dome (and free!). The Art Institute is just down the street, and the Museum Campus packs the Field Museum, Shedd Aquarium, and Adler Planetarium into one lakefront stretch.
Stroll or bike the Lakefront Trail for skyline views, visit the free Lincoln Park Zoo and Conservatory, or post up at one of the lakefront beaches. September weather makes it the perfect time to be outdoors in Chicago.
A few favorites: Mott St, Mindy's Bakery, and Wolf & Co. in Wicker Park, Bird's Nest in Lincoln Park (our favorite wings!), Wilde and Pingpong in Lakeview, Pizza Portofino in River North, and Trivoli Tavern, Aba, or Duck Duck Goat in West Loop. Don't leave without trying Pequod's caramelized-crust deep dish in Lincoln Park.
Chicago's craft beer scene is packed with great patios and beer gardens. Goose Island Taproom at the Salt Shed sits right on the river, Revolution Brewing and Maplewood are in Logan Square, and Half Acre, Dovetail, and Begyle are all just a short ride north.
Our wedding weekend overlaps with Riot Fest 2026 in Douglass Park—three days of punk, rock, and hip-hop legends if that's your scene. For something low-key, catch jazz at the Green Mill, an indie show at Empty Bottle, or whoever's headlining the Salt Shed.
Catch improv at Second City, iO Theater, or Annoyance Theater, or stand-up at Zanies, The Laugh Factory, or Lincoln Lodge. Chicago is where countless comedy legends got their start, so you're in good hands.