Did you know that Chicago boasts over 1,200 bars, each offering a unique experience? When planning your next bar crawl, you might want to mix it up with a blend of rooftop bars, historic pubs, and trendy lounges. Start at Cindy's to enjoy panoramic views, then make your way to The Green Door Tavern to soak in some Prohibition-era history. If you're a craft beer enthusiast, Revolution Brewing shouldn't be missed. There's more to uncover, from hidden gems to lively dance spots, so let's map out an unforgettable night in the Windy City.

Main Points

  • Explore River North's nightlife with stops at Three Dots and a Dash, The Underground, and Celeste.
  • Visit historic pubs like The Green Door Tavern and The Berghoff Restaurant for a dose of Prohibition-era charm.
  • Enjoy craft beer at local favorites like Revolution Brewing, Half Acre Beer Company, and Goose Island Brewery.
  • Elevate your experience with rooftop bars like Cindy's, J. Parker, and Raised for stunning city views.
  • Discover hidden gem bars such as DryHop Brewers, The Map Room, and Hopleaf Bar for unique atmospheres and rare brews.

Best Rooftop Bars

Chicago's rooftop bars offer stunning views and vibrant atmospheres that you won't want to miss. These elevated spots provide the best vantage points to appreciate the city's skyline and iconic landmarks.

One of the top choices is Cindy's, where you can enjoy breathtaking views of Millennium Park and Lake Michigan. It's a perfect blend of scenic beauty and lively ambiance.

Another standout is the J. Parker rooftop bar at Hotel Lincoln. Here, you'll find panoramic views of Lincoln Park and the city skyline, making it an ideal spot to unwind and take in the sights.

If you're looking for sophistication, Raised, an Urban Rooftop Bar, offers a chic setting with views of the Chicago River and downtown skyscrapers, perfect for a refined evening out.

LondonHouse Rooftop Bar is another must-visit, featuring a tri-level rooftop space with breathtaking views of the Chicago River and the city's iconic architecture.

The Godfrey Hotel's IO Godfrey Rooftop Lounge adds a trendy touch, offering a vibrant atmosphere with stunning city views, making it a popular spot for cocktails and socializing. These rooftop bars in Chicago truly offer some of the best experiences for both locals and visitors.

Historic Pubs Tour

On your Historic Pubs Tour, you'll appreciate the architectural charm and history of these storied establishments, each with unique designs and fascinating backgrounds.

Many of these pubs have hosted notable patrons, from famous writers to influential political figures, adding to their rich tapestry.

As you walk through each venue, you'll gain insights into Chicago's past and the enduring legacy of these iconic watering holes.

Architectural Charm and History

Amidst the bustling cityscape, you can explore a historic pubs tour that highlights Chicago's architectural charm and rich history. This Chicago bar crawl takes you through iconic bars, some dating back to the Prohibition era, where you can immerse yourself in the stories and legends behind the city's oldest drinking establishments.

Discover hidden gems and speakeasies that have stood the test of time, offering a unique blend of history, culture, and nightlife.

Here are some highlights to look forward to on your historic pubs tour:

  • The Green Door Tavern: Known for its Prohibition-era history, this bar offers a peek into the past with its hidden speakeasy.
  • The Berghoff Restaurant: Established in 1898, it's one of Chicago's oldest restaurants and bars, famous for its German beer and food.
  • The Old Town Ale House: A classic dive bar filled with eclectic artwork, it's been a favorite since the 1950s.
  • The Red Lion Pub: Modeled after a traditional British pub, it's been serving up pints and history in the Lincoln Park area for decades.
  • The Violet Hour: A modern speakeasy with a nod to the past, known for its craft cocktails and elegant ambiance.

This historic pubs tour offers a perfect mix of architectural charm, rich history, and vibrant nightlife.

Notable Past Patrons

As you step into these historic pubs, you'll follow in the footsteps of notable past patrons like Al Capone, Ernest Hemingway, and Frank Sinatra. These iconic figures once frequented these establishments, adding to the rich tapestry of Chicago history.

Each pub on the tour offers a glimpse into a bygone era where politicians, writers, and celebrities gathered to unwind and enjoy a drink.

At Al Capone's favorite haunts, you can almost imagine the infamous gangster plotting his next move. Hemingway's chosen spots offer a literary touch, making you feel as though you're part of his creative process. And with Sinatra's presence, the air is filled with timeless charm and sophistication.

The Historic Pubs Tour not only lets you walk where these patrons once stood but also dives deep into the cultural significance of each location. You'll hear captivating stories of the past, understanding how these pubs became integral to Chicago history.

As you sip your drink, you'll be connected to a legacy of remarkable individuals who once did the same. This tour is perfect for anyone looking to experience a slice of history while enjoying the vibrant atmosphere of Chicago's historic pubs.

River North Highlights

River North offers an electrifying mix of upscale bars, trendy nightclubs, and chic lounges perfect for your next bar crawl adventure. In this vibrant neighborhood, you'll find a variety of spots that cater to different tastes, making it an ideal destination for bar crawls.

The vibrant nightlife in River North means you'll never run out of places to explore, with every corner offering something unique. The area is renowned for its bustling atmosphere and diverse entertainment options. Whether you're in the mood for craft cocktails, live music, or stunning city views, River North has it all.

Here are some must-visit venues:

  • Three Dots and a Dash: A tropical tiki bar offering exotic cocktails and a lively ambiance.
  • The Underground: A trendy nightclub known for its energetic dance floor and stylish decor.
  • Celeste: Featuring a rooftop bar, Celeste is perfect for enjoying drinks with a view.
  • TAO Chicago: Combining a restaurant, lounge, and nightclub, TAO offers a comprehensive nightlife experience.
  • Bub City: A country-themed bar with live music and a great selection of whiskey.

With such a dynamic selection, River North ensures your bar crawl will be anything but ordinary.

Trendy Lounges

After exploring the vibrant energy of River North, you'll find that Chicago's trendy lounges offer a more sophisticated yet equally exciting experience. These lounges are perfect for those who appreciate stylish decor, craft cocktails, and an upscale ambiance. They're popular spots for socializing, networking, and enjoying a sophisticated night out in the city.

Many of these trendy lounges feature live music, DJ sets, and special events, creating a dynamic nightlife scene. You can expect attentive service and unique drink menus that add to the chic atmosphere. Whether you're looking to unwind after a long day or celebrate a special occasion, these venues cater to all your needs.

Here's a snapshot of what you can expect from Chicago's trendy lounges:

Feature Description Example Venue
Stylish Decor Modern, elegant interiors The Violet Hour
Craft Cocktails Unique, expertly-mixed drinks The Aviary
Upscale Ambiance Sophisticated, relaxed vibe Celeste
Live Music Bands or solo artists performing Untitled Supper Club
DJ Sets Energetic music from popular DJs Disco

Craft Beer Spots

When exploring Chicago's craft beer spots, you should start with local favorites like Revolution Brewing, Half Acre Beer Company, and Goose Island Brewery.

Don't miss out on the hidden gem bars scattered throughout the city that offer unique atmospheres and rare brews.

Keep an eye out for seasonal beer specials, as these breweries often release limited-edition brews that you won't want to miss.

Local Brewery Favorites

Chicago's craft beer scene is a must-explore with standout spots like Revolution Brewing, Half Acre Beer Company, and Goose Island Brewery. These local breweries offer a variety of unique and creative craft beers, from bold IPAs to rich stouts, tangy sours, and crisp lagers. If you're a fan of craft beer, Chicago's brewery tours are an excellent way to immerse yourself in the city's brewing culture.

Revolution Brewing, located in Logan Square, is well-known for its Anti-Hero IPA and offers an engaging brewery tour where you can learn about their brewing process.

Half Acre Beer Company, with its Lincoln Avenue and Balmoral locations, provides a cozy setting to enjoy their popular Daisy Cutter Pale Ale.

Goose Island Brewery, a pioneer in the craft beer movement, offers tastings and tours that showcase their innovative brewing techniques.

Here are some other must-visit local breweries:

  • Lagunitas Brewing Company: Known for its spacious taproom and live music events.
  • Metropolitan Brewing: Specializes in traditional German-style lagers.
  • Pipeworks Brewing Co.: Famous for their creative and bold beer flavors.
  • Off Color Brewing: Offers unique and experimental brews.
  • Dovetail Brewery: Focuses on classic European-style beers.

Explore these spots to get a true taste of Chicago's diverse and dynamic craft beer scene.

Hidden Gem Bars

Once you've explored Chicago's bustling breweries, it's time to check out some hidden gem bars that offer an equally impressive craft beer experience. DryHop Brewers is a standout, known for its innovative brews and cozy atmosphere. This spot is perfect if you're looking to discover something new and unique.

Another local favorite is The Map Room, which boasts a vast selection of craft beers from around the world. It's a must-visit for any beer enthusiast wanting to expand their palate.

For a taste of Belgium in Chicago, head over to Hopleaf Bar. With its extensive Belgian beer list and warm, inviting ambiance, it's an excellent place to unwind and explore flavorful brews.

Local Option is another hidden gem bar where you can enjoy a rotating selection of craft beers. Its laid-back vibe makes it a favorite among those who prefer a relaxed drinking experience.

Seasonal Beer Specials

During your Chicago bar crawl, you'll find an array of seasonal beer specials at top craft beer spots that cater to every palate. Chicago's craft beer scene is vibrant, with breweries and bars constantly updating their selections to offer unique and limited-edition brews.

Seasonal beers like pumpkin ales, winter stouts, summer IPAs, and spring saisons are available at various stops along your crawl, ensuring you get to sample a wide variety of flavors.

Popular craft beer spots in Chicago are known for their rotating taps, always bringing something new and exciting to the table. You'll discover fresh flavor profiles with each visit, making every stop an adventure in taste.

Here are a few spots you should definitely check out for their seasonal beer specials:

  • Revolution Brewing: Known for its creative seasonal brews.
  • Half Acre Beer Company: Offers a variety of limited-edition beers.
  • Goose Island Brewery: Famous for its seasonal craft beer selections.
  • Maplewood Brewery & Distillery: Combines craft beer with unique flavor twists.
  • Begyle Brewing: Frequently rotates its tap list with seasonal offerings.

Immerse yourself in the diverse world of craft beer in Chicago, savoring seasonal brews and making your bar crawl an unforgettable experience.

Speakeasy Adventures

Step into the clandestine world of Chicago's hidden speakeasies and uncover the secrets of these Prohibition-era gems. The allure of Chicago nightlife is amplified by its rich speakeasy culture, where hidden bars and secret entrances harken back to a time when alcohol was outlawed.

These spots, tucked away from the main streets, offer a unique experience that transports you to a different era.

One such hidden bar is Marge's Still, an authentic speakeasy that has stood the test of time. With roots in the Prohibition era, Marge's Still embodies the clandestine spirit of those times. As you enter through its discreet entrance, you're immediately immersed in a world that combines history with a sense of adventure.

The dim lighting, vintage décor, and intimate atmosphere make it a must-visit on your speakeasy bar crawl.

Exploring these hidden bars isn't just about enjoying a drink; it's about experiencing a piece of history. You'll find that each speakeasy has its own story, often shared by knowledgeable bartenders. It's a journey that combines the thrill of discovery with the enjoyment of finely crafted cocktails, making your night out in Chicago truly memorable.

Dance and Party Bars

For an electrifying night out in Chicago, head to dance and party bars that pulse with energy and diverse music scenes. You'll find places that cater to a wide range of tastes, from EDM beats to Latin rhythms. These spots are perfect for anyone looking to let loose and enjoy the city's vibrant nightlife.

Singles bars in Chicago offer a lively atmosphere where you can socialize, mingle, and maybe even meet someone new. They're packed with energy and provide a dynamic party experience that's hard to beat. As you hop from one bar to another, you'll encounter various music styles and different crowd vibes, ensuring a night full of variety.

A typical Chicago bar crawl might include stops at:

  • High-energy dance floors where you can dance the night away.
  • Rooftop bars offering stunning city views and a unique party atmosphere.
  • Singles bars that are ideal for meeting new people and enjoying the lively ambiance.
  • EDM clubs that keep the beat pumping and the crowd moving.
  • Latin dance spots where vibrant rhythms create an irresistible urge to dance.

Immerse yourself in Chicago's energetic nightlife, where every bar promises a unique and thrilling experience.

Neighborhood Gems

Exploring Chicago's neighborhood gems, you'll discover iconic spots like Billy Goat Tavern and Old Town Ale House that offer rich histories and unique charm. These local favorites are must-visits on your bar crawl, giving you a taste of Chicago's vibrant past and present.

Billy Goat Tavern, famous for its 'Cheezborger' and its ties to local journalism, provides an authentic Chicago experience. Meanwhile, Old Town Ale House, with its eclectic decor and storied past, offers a cozy, artistic vibe.

Don't miss out on Butch McGuires, a bar that's not only known for its lively atmosphere but also for facilitating numerous marriages over the years. It's a place where you can feel the love in the air. Marges Still, another local favorite, is a historic speakeasy that adds a unique charm to your pub crawl experience.

For more diverse venues, head to Kincades Bar & Grill or Glascotts Groggery. Kincades offers a sports-bar atmosphere perfect for catching a game, while Glascotts provides a laid-back, friendly setting. These neighborhood gems showcase Chicago's diverse nightlife, ensuring your bar crawl is filled with memorable stops.


You've now got a roadmap for an unforgettable Chicago bar crawl. Picture it like a well-crafted cocktail—each stop adds a unique flavor, from Cindy's breathtaking views to Butch McGuires' cozy charm.

Just as a perfect drink balances its ingredients, your night will blend history, craft beers, and vibrant nightlife seamlessly.

So grab your friends, follow this guide, and experience the best of Chicago's diverse bar scene, ensuring you make lasting memories with every sip.