Portage Grounds Coffee & Tea

If you're looking for a romantic date spot in Chicago, consider ROOF on theWit. This lounge within the Wit Hotel offers a breathtaking city view from its outdoor patio and hangover space. Whether you're in the mood for steak or pizza, their dinner menu offers a wide range of delicious entrees. ROOF is a luxurious retreat that can be found on the 27th floor, offering unique hand-crafted cocktails, delectable cuisine, stunning views of the skyline, and vibrant design and entertainment. It has been crowned Hotel Bar of the Year by the Nightclub & Bar Awards and recognized by Travel+Leisure as one of the top 3 rooftop bars in the world. Guests can indulge in the finest acoustic music series, world-class DJs, and live runway shows.

Naper Settlement is an outdoor museum showcasing downtown Naperville's rich history. Spread over 13 acres, it offers visitors a unique opportunity to connect with the area's cultural heritage and foster a sense of community. The museum's vision is to encourage conversations, enrich educational opportunities, and provide engaging experiences for visitors, businesses, and the local community. Naper Settlement is an excellent place for families to visit as it offers interactive learning opportunities for people of all ages. The site boasts 30 historic buildings that visitors can explore to learn about the connections between the past and present. Additionally, the museum hosts special events, programs, and on-site activities throughout the year, giving visitors a unique chance to engage with the area's rich cultural heritage.

Experience the rich history, art, and architecture of Glessner House by taking a journey back in time. The cultural center and museum are renowned for their innovative design and offer a unique collection of cultural arts from the late 1800s to the present. It is home to original artifacts and is steeped in family history, making it a one-of-a-kind experience. Engage in immersive tours, educational programs, and engaging events that take you through the past, connecting you to the power of design and cultural arts. Explore one of the most innovative residences built in the 19th Century. Discover the restored rooms and their original furnishings. Additionally, Glessner House offers rental opportunities, making it an ideal venue for corporate events and memorable gatherings.

The Empty Bottle sounds like an excellent spot to catch some live music. They offer affordable drinks, reasonable cover, and a fun crowd. It's interesting to note that the bar started as a cat-filled hole-in-the-wall in 1992 but later moved two blocks up the street to a slightly larger and better-equipped venue. They've been putting on great shows for the past 20 years and have managed to maintain their success thanks to their low prices, lack of attitude, and loyal customer base.