Best Rooftop Restaurants In Lake Forest, IL

There’s nothing more exceptional than enjoying delicious food and drinks with a stunning view. Here in Lake Forest, Illinois, we have access to some of the best rooftop restaurants in the state. With Chicago just a short distance away, many of these rooftops offer dazzling sights of the city skyline. 

However, a nice view doesn’t always go hand in hand with quality food and drinks. Luckily for you, we’ve gathered a list of some of the best rooftop restaurants, bars, and lounges in the area. We at Pasquesi Sheppard love a good time and can’t wait to share our favorite spots with you. 


raw meat with spices on green ceramic plate
Image by Taylor Grote is licensed with Unsplash Licenseraw meat with spices on green ceramic plate

Delectable South American fusion food overlooking the tranquil Lake Michigan — what more could you ask for? Longitud315 is the perfect restaurant to try exotic flavors from Peru, Brazil, Venezuela, Argentina, and Brazil. Head Chef Tony Castillo’s passion for cooking South American dishes grew from his childhood in Venezuela, where he made his favorite dishes alongside his beloved grandmother. He loves to share his culture, and he promises that this flavorful food will liven up your dining experience.

Longitud315 serves a wide variety of South American dishes, with steak and seafood entrees taking center stage. Every piece of meat is cooked in an open flame grill and served with their signature chimichurri sauce and hand-crafted bread. Longitud315 has an extensive small plate menu with delicious offerings, such as empanadas, arepas, yuca, ceviche, plantains, and much more. They even offer vegetarian and vegan options for many of their dishes. Next time you’re craving a taste of South America, check out Longitud315 and make sure to sit on their cozy rooftop patio. 

  • Location: 315 Waukegan Ave., Highwood
  • Hours: Closed Monday, 4:30 p.m. to 9:30 p.m. Tuesday through Thursday, 2 p.m. to 10 p.m. Friday and Saturday, 2 p.m. to 8 p.m. Sunday

Strawberry Moon

The quaint space of Strawberry Moon offers a variety of beverages and food, all with a unique Wauconda flavor. They provide the perfect blend of sweet and savory drinks alongside live music, indulgent small bites, and good vibes. If you’re searching for a place where you can have fun and enjoy a lavish night out, look no further than Strawberry Moon. 

“Strawberry Moon” is the Native American name for the first full moon of June, when they would begin the strawberry harvest. Fittingly, there are many delectable moon-themed drinks on the menu. Their signature drink, the Strawberry Moon, includes Stoli Strawberry, Bicerin white chocolate liqueur, and strawberry puree. Another favorite is the Full Moon Martini, a special martini created for each moon phase. If you’re hungry, we highly recommend their cheese and wine fondue, made with gruyere cheese and served with French bread and fresh apples for dipping. Strawberry Moon is the ideal location for a lavish night out.

  • Location: 204 S. Main St., Wauconda
  • Hours: Closed Sunday and Monday, 4 p.m. to 9 p.m. Tuesday and Wednesday, 4 p.m. to 10 p.m. Thursday, 4 p.m. to 11 p.m. Friday and Saturday

Tavern on the Point

Tavern on the Point is your ultimate rooftop bar with an industrial-inspired interior and views of the spectacular Chicago skyline. This dynamic rooftop bar is conveniently located near Edison Park in the northwest tip of Chicago. The area is known for its historic neighborhood and is the perfect place to catch up with friends and enjoy a great meal. Despite its size and location, the pub has a warm feel, especially during the winter season. They even have a heated tent on the upper deck, so you can still enjoy the patio during the winter months. 

Tavern on the Point features an extensive selection of American comfort food, craft beer, specialty whiskeys, and quality bourbons. Their drink menu also includes a variety of seasonal and classic drinks, as well as an impressive wine list. One of their most popular food items is the Point Fried Chicken, a pan-fried chicken with mashed potatoes and garlic-infused green beans doused in a hearty country gravy. You won’t want to miss their weekday happy hour or weekend brunch, where you can try even more enticing comfort foods.

  • Location: 6724 N. Northwest Highway, Chicago
  • Hours: 11:30 a.m. to 11:30 p.m. Monday through Thursday, 11:30 a.m. to 1 a.m. (next day) Friday, 11 a.m. to 1 a.m. (next day) Saturday, 11 a.m. to 11 p.m. Sunday

Five & Dime

If you view a patio as a playground, then Five & Dime is the perfect place to grab a drink and play some fun games. The bar is located above its sister establishments, Taco Diablo, The Blue Horse Tavern, and LuLu’s in downtown Evanston.

During the summer season, the outdoor rooftop deck offers a stellar view of Chicago and Lake Michigan. There’s also a game room on the second floor where you can play a variety of games, such as backgammon or scrabble. There’s even a giant towering Jenga or bag toss if you want to compete with your friends. 

Five & Dime’s interior is designed to provide a tranquil environment where you can relax and enjoy some of life’s simple pleasures. The menu features a variety of curated wines and signature cocktails. If you’re hungry, you can choose from various dishes on their small plate menu, such as the prime rib sandwich, which consists of shaved roasted prime rib, caramelized onions, and roasted garlic aioli on a toasted telera. The BBQ ribs are also to die for. Five & Dime supplies the perfect vibe for a fun time filled with games, laughter, and lively libations. 

  • Location: 1026 Davis St., Evanston
  • Hours: Closed Monday and Tuesday, 4 p.m. to 10 p.m. Wednesday through Saturday, 4 p.m. to 9 p.m. Sunday

Next time you want to relax and enjoy the outdoors over exceptional food, make sure to check out some of the locations on our list. Know of any amazing rooftop restaurants that we missed in Lake Forest? Contact our team at Pasquesi Sheppard so we can update our list. If you’re looking to unwind and take a break, our helpful team of accountants and consultants  would love to help you with any of your financial needs. We also offer a variety of online tools to help you take hold of your financial future.