Sky High in Lakeview: Unveiling Chicago’s Best Rooftop Bars with Breathtaking Vistas

Lakeview, a vibrant Chicago neighborhood pulsating with energy, offers more than just charming streets and bustling nightlife. For those seeking elevated experiences, its rooftops unveil a dazzling panorama of the Windy City, a tapestry of shimmering skyscrapers and twinkling lights spread beneath a vast expanse of sky. Whether you’re craving handcrafted cocktails under the stars, savoring delectable bites with a view, or simply soaking in the urban symphony, Lakeview’s rooftop bars cater to every desire.

Top Contenders for Sky-High Soirees:

  1. Rooftop on Addison: Perched atop the Godfrey Hotel, Rooftop on Addison is a chic oasis overlooking Lincoln Park and Lake Michigan. Sip on creative cocktails like the “Strawberry Fields Forever” or the “Spiced Pear Old Fashioned” while feasting on delectable small plates. Relax on plush lounge chairs, gather around fire pits on chilly nights, or dance under the moonlight at this trendy rooftop haven.
    Image of Rooftop on Addison, Chicago
  2. Cindy’s Rooftop Chicago: Located atop the Chicago Athletic Association, Cindy’s Rooftop is a sophisticated sanctuary boasting 360-degree views of the city skyline. Indulge in upscale pub fare like truffle mac and cheese and lobster rolls, paired with an extensive wine list and signature cocktails. Immerse yourself in the elegant ambiance, complete with vintage decor and lush greenery, making it ideal for romantic evenings or sophisticated gatherings.
    Image of Cindy's Rooftop Chicago
  3. Lula Rose: A hidden gem tucked away on the rooftop of the Robey Hotel, Lula Rose offers a laid-back atmosphere with stunning views of Lincoln Park and beyond. Vibrant murals adorn the walls, while string lights create a whimsical ambiance. Sip on seasonal cocktails crafted with fresh ingredients, savor wood-fired pizzas and shareable plates, and enjoy live music on Thursdays and Sundays.
    Image of Lula Rose Rooftop Chicago
  4. Untitled: Boasting unobstructed views of the iconic Wrigley Field, Untitled is a rooftop sports bar with a playful twist. Catch the game on one of the many TVs while indulging in gourmet burgers, tacos, and creative hot dogs. Enjoy refreshing cocktails like the “Wrigley Fizz” or the “Bleacher Bum,” and soak in the lively atmosphere during game days or weekend revelry.
    Image of Untitled Rooftop Chicago
  5. The Bad Apple: For a touch of speakeasy vibes, The Bad Apple takes you back to the roaring twenties with its hidden entrance and dim lighting. Sample artisanal cocktails with unique twists, like the “Bee’s Knees” or the “Rosemary Fizz,” and indulge in small plates like bacon deviled eggs and charcuterie boards. The intimate setting and vintage decor create a perfect escape for a special occasion or a sophisticated night out.
    Image of Bad Apple Rooftop Chicago

Beyond the Buzz: Experiencing Lakeview’s Rooftop Uniqueness:

While stunning views and vibrant atmospheres are a constant, each rooftop bar in Lakeview offers a distinct personality:

  • Family-Friendly Fun: Head to Skybar at Wrigleyville for panoramic views and a relaxed atmosphere, perfect for an afternoon outing with the kids. Enjoy live music, a dedicated kids’ menu, and plenty of space to run around.
  • Sunset Celebrations: The Rooftop at Wit Hotel provides front-row seats to breathtaking sunsets over Lake Michigan. Savor sunset-inspired cocktails, listen to live music, and watch the city transform into a twinkling sea of lights.
  • Craft Beer Haven: The Beer Garden at Wrigley Field Rooftop offers an extensive selection of local and international craft beers, paired with pub fare and stunning views of the ballpark. Catch a game on the big screen or simply relax with friends amidst the lively atmosphere.
  • Rooftop Fitness: Start your day with a yoga session at Upstairs at The Gwen, a rooftop fitness studio with breathtaking city views. Breathe in the fresh air, stretch your body, and enjoy a post-workout smoothie or coffee while soaking in the panorama.

Pro Tips for Your Rooftop Rendezvous:

  • Make reservations: Popular rooftop bars often fill up quickly, especially during peak season and weekends. Secure your spot beforehand to avoid disappointment.
  • Dress for the weather: Rooftop bars can be exposed to the elements. Dress accordingly, layering up for cooler evenings and bringing sunscreen for sunny days.
  • Mind the noise level: Be mindful of noise levels, especially when seated near other patrons. Keep conversations at a reasonable volume to respect the ambiance.
  • Tipping etiquette: Remember to tip your bartenders and servers appropriately for their service.
  • Responsible alcohol consumption: Enjoy your drinks responsibly and designate a driver or utilize public transportation if necessary.

From trendy cocktail havens to family-friendly spots and sunset celebrations, Lakeview’s rooftop bars offer an unparalleled experience. So, grab your friends, embrace the city’s vibrant energy, and prepare to be captivated by breathtaking views, delectable bites, and the intoxicating magic of Chicago’s skyline. Remember, responsible enjoyment and respect for the environment are key to ensuring a memorable experience for everyone. Now, step onto the rooftops, raise a toast to the Windy City, and let the sky be your limit!

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