If you only do one “Chicago” activity while you’re here — make it the architecture boat tour. It’s the perfect mix of skyline views, history, cocktails, and relaxing on the river. Most tours leave just a short walk or quick ride from The Gwen and the Cultural Center. Chicago is famous for its architecture, and the river tour is truly the best way to experience it. Each tour is 90 minutes just in time for cocktail hour!
Chicago rooftops in the summer are undefeated. A few favorites near the hotel: Upstairs at The Gwen — cocktails, fire pits, and skyline views right at the hotel Cindy's Rooftop — iconic views overlooking Millennium Park LH Rooftop — incredible river + city views The Gwen’s rooftop terrace is especially popular for happy hour and city views.
Need a caffeine boost? Here are a few nearby favorites: Blue Bottle Coffee — great coffee and an easy walk from The Gwen Intelligentsia Coffee — a Chicago classic near Millennium Park Happy Monday Coffee — cozy vibes and great pastries
A few easy nearby activities: Walk along the Chicago Riverwalk Visit Millennium Park & Cloud Gate (“The Bean”) Explore the Magnificent Mile Head to Lake Front Trail for some lake and beach views! The Gwen’s location makes it super walkable to many of Chicago’s best spots