City Winery on the Riverwalk 

By Trent Modglin

If you haven’t experienced the Chicago Riverwalk yet, let’s just say you’re definitely overdue. Completed back in 2016, it’s a winding, open-air pathway more than a mile long that blends the energy of the city with a sense of outdoor living.

Spanning from Lake Shore Drive to Lake Street, it’s filled with several dining and drinking possibilities (City Winery, Tiny Tapp, O’Brien’s and the Chicago Brewhouse are personal favorites), as well as fun activities like kayaks and boat rentals, tours, etc. It’s a gorgeous space to relax with your significant other and take in the sights of the city above — all at a unique river level.

Lurie Garden in Millennium Park

Obviously, we all know the bean in Millennium Park, officially known as Cloud Gate, is a popular spot for tourists, but just a bit to the south is Lurie Garden, a tree-lined oasis of sorts that provides relaxing, flower-filled photo ops of the skyline away from a lot of the crowds. And did we mention what it looks like during the fall colors?

With splendid views of Millennium Park, Lake Michigan and the skyline, Cindy’s specialty cocktails, all-season terrace and delicious seasonal cuisine make it a dynamic summer or fall destination.

Cindy’s Rooftop

The Chicago Athletic Association is a historic 1890s building that, several years ago, was transformed into an impeccable Chicago boutique hotel with splendid views of Millennium Park, Lake Michigan and the skyline from Cindy’s Rooftop, a glass atrium-covered restaurant on the 13th floor of the hotel. Now add in some specialty cocktails, an all-season terrace and delicious seasonal cuisine (not to mention an entire game room inside), and you can see why Cindy’s is a dynamic summer or fall destination, perfect for spending quality time and a drink or two with a loved one. It’s also a solid location for weekend brunch.

The LondonHouse hotel rooftop venue — appropriately called LH Rooftop — is located just off the Chicago River in the Loop and offers up some sweeping city views, re-imagined American dishes and a quality cocktail list. Reservations are recommended, since the terrace does tend to be busy, especially for early dinners.

LH Rooftop