Chicago, ILDeep dish, rooftop cocktails, and a hotel that used to be a gym.Updated 2026-03-08Must Go (3)Bars (3)Hotels (1)Restaurants (4)Must Go Spots(3)Chicago Athletic Association HotelMust GoHotelsGorgeous building right on Michigan Ave across from Millennium Park. Cindy's rooftop bar is here, and the lobby alone is worth a visit. One of the coolest hotel stays I've had.Cindy'sMust GoBarsRooftop bar on top of the Chicago Athletic Association hotel. Unreal views of Millennium Park and the lake. Great cocktails—go at sunset.RPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.All PlacesBub CityBarsBBQ, whiskey, and live honky-tonk. Big outdoor patio with a Nashville-in-Chicago vibe.Chicago Athletic Association HotelMust GoHotelsGorgeous building right on Michigan Ave across from Millennium Park. Cindy's rooftop bar is here, and the lobby alone is worth a visit. One of the coolest hotel stays I've had.Cindy'sMust GoBarsRooftop bar on top of the Chicago Athletic Association hotel. Unreal views of Millennium Park and the lake. Great cocktails—go at sunset.Parson's Chicken & FishRestaurantsFried chicken, negroni slushies, and ping pong. The patio is the move in summer.Ramen-sanRestaurantsSolid ramen in River North with a cool, dimly-lit atmosphere. Great for a quick, warming bowl.RPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.RPM SteakRestaurantsThree DotsBars
Chicago Athletic Association HotelMust GoHotelsGorgeous building right on Michigan Ave across from Millennium Park. Cindy's rooftop bar is here, and the lobby alone is worth a visit. One of the coolest hotel stays I've had.
Cindy'sMust GoBarsRooftop bar on top of the Chicago Athletic Association hotel. Unreal views of Millennium Park and the lake. Great cocktails—go at sunset.
RPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.
Chicago Athletic Association HotelMust GoHotelsGorgeous building right on Michigan Ave across from Millennium Park. Cindy's rooftop bar is here, and the lobby alone is worth a visit. One of the coolest hotel stays I've had.
Cindy'sMust GoBarsRooftop bar on top of the Chicago Athletic Association hotel. Unreal views of Millennium Park and the lake. Great cocktails—go at sunset.
Parson's Chicken & FishRestaurantsFried chicken, negroni slushies, and ping pong. The patio is the move in summer.
Ramen-sanRestaurantsSolid ramen in River North with a cool, dimly-lit atmosphere. Great for a quick, warming bowl.
RPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.