Judge James A. Shapiro

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.

If you want to escape from the hustle and bustle of the city, the Judy Istock Butterfly Haven is a perfect place to visit. Here, you can get up close and personal with over 40 exotic, free-flying butterflies and several stunning bird species from the Southern Hemisphere. The greenhouse, which spans 2,700 square feet, features serene pools of water, flowers, tropical trees, and over 1,000 butterflies, giving you the feeling of being in summer all year round. If you're interested in witnessing the life cycle of a butterfly from caterpillar to chrysalis to the very first flight, you should take advantage of the First Flight Butterfly Release. Moreover, they offer weekly Butterfly Haven Yoga sessions if you want to spend more time in the Butterfly Haven.

City Winery is a unique venue that offers live entertainment and a wide selection of wine in a warm and welcoming atmosphere. With a working winery on site, guests can enjoy up to 18 varieties of wine while being entertained. The venue can accommodate up to 300 guests, and each location offers a distinctive culinary and cultural experience for wine enthusiasts. City Winery has expanded to provide intimate concerts, food and wine seminars, private event spaces, upscale dining, and a fully functioning winery. Experience the charm of wine country with modern comfort and convenience in an urban setting. The performance venues are equipped with state-of-the-art acoustics provided by Meyer Sound. Before the concert, you can visit the tasting room to try a flight of wines. After the show, stop by the bar for more drinks. City Winery offers a range of functional spaces that can host a memorable night out for two or an unforgettable private event. There is something for everyone at City Winery, whether it's discovering new wines while enjoying an intimate concert or celebrating your wedding in the wine garden followed by an epic party.