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.12 S Michigan Ave, Chicago, IL 60603chicagoathletichotel.comCindy'sMust GoBarsRooftop bar on top of the Chicago Athletic Association hotel. Unreal views of Millennium Park and the lake. Great cocktails—go at sunset.12 S Michigan Ave, Chicago, IL 60603cindysrooftop.comRPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.52 W Illinois St, Chicago, IL 60654rpmrestaurants.comAll PlacesBub CityBarsBBQ, whiskey, and live honky-tonk. Big outdoor patio with a Nashville-in-Chicago vibe.435 N Clark St, Chicago, IL 60654bfrg.com/bub-cityChicago 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.12 S Michigan Ave, Chicago, IL 60603chicagoathletichotel.comCindy'sMust GoBarsRooftop bar on top of the Chicago Athletic Association hotel. Unreal views of Millennium Park and the lake. Great cocktails—go at sunset.12 S Michigan Ave, Chicago, IL 60603cindysrooftop.comParson's Chicken & FishRestaurantsFried chicken, negroni slushies, and ping pong. The patio is the move in summer.Logan Square: 2952 W Armitage Ave, Chicago, IL 60647Lincoln Park: 2407 N Milwaukee Ave, Chicago, IL 60647parsonschickenandfish.comOpen Logan Square in Google MapsOpen Lincoln Park in Google MapsRamen-sanRestaurantsSolid ramen in River North with a cool, dimly-lit atmosphere. Great for a quick, warming bowl.59 W Hubbard St, Chicago, IL 60654rfrg.com/ramen-sanRPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.52 W Illinois St, Chicago, IL 60654rpmrestaurants.comRPM SteakRestaurants66 W Kinzie St, Chicago, IL 60654Open in Google MapsThree DotsBars435 N Clark St, Chicago, IL 60654Open in Google Maps
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.12 S Michigan Ave, Chicago, IL 60603chicagoathletichotel.com
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.12 S Michigan Ave, Chicago, IL 60603cindysrooftop.com
RPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.52 W Illinois St, Chicago, IL 60654rpmrestaurants.com
Bub CityBarsBBQ, whiskey, and live honky-tonk. Big outdoor patio with a Nashville-in-Chicago vibe.435 N Clark St, Chicago, IL 60654bfrg.com/bub-city
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.12 S Michigan Ave, Chicago, IL 60603chicagoathletichotel.com
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.12 S Michigan Ave, Chicago, IL 60603cindysrooftop.com
Parson's Chicken & FishRestaurantsFried chicken, negroni slushies, and ping pong. The patio is the move in summer.Logan Square: 2952 W Armitage Ave, Chicago, IL 60647Lincoln Park: 2407 N Milwaukee Ave, Chicago, IL 60647parsonschickenandfish.comOpen Logan Square in Google MapsOpen Lincoln Park in Google Maps
Ramen-sanRestaurantsSolid ramen in River North with a cool, dimly-lit atmosphere. Great for a quick, warming bowl.59 W Hubbard St, Chicago, IL 60654rfrg.com/ramen-san
RPM ItalianMust GoRestaurantsThe Chicago flagship—stunning interior, incredible pasta, and one of those places where everything on the menu delivers. Reservations are a must.52 W Illinois St, Chicago, IL 60654rpmrestaurants.com