Building showcases early 20th century architecture with historic character and beautiful views. Atmosphere blends classy, elegant charm with modern exclusivity, creating a harmonious and inviting setting. Amenities include squash courts, gym, library, and bar, supporting both relaxation and active pursuits.
Offers a very nice bar with a great view and a bar area connected to a game room. Amenities include first-class bars alongside restaurants and other facilities.
Historic character shines through the stunning architecture and thoughtful design. The library holds a large selection of historical volumes on topics like religion and government.
"The views of Lake Michigan from the club are great."
"This historic building is fascinating and stunning."
"The bar's historic character combines with modern ambience."
Good to know
The club hosts various events, including weddings and corporate gatherings.
Expect high costs for events, with weddings starting around $50,000.
Reservations are recommended for dining, especially during peak hours.
Cozy dive bar with historic wooden interiors and a hidden speakeasy downstairs creates a unique old-school vibe. Social and friendly atmosphere fills the space with nostalgic memorabilia and warm energy. Regulars enjoy spinning a shot wheel and relaxing with good music and sports on TV.
An old school dive bar with a cozy vibe and historic appeal. Bartenders offer great service and the spot has hooks for bags, making it easy to hang out with friends.
Walls hold rich history and the upstairs displays many historical items. The place feels like a cozy dive bar full of historic appeal and speakeasy charm.
Good to know
Reservations are recommended for the downstairs speakeasy to ensure entry.
The hidden bar opens later in the evening, providing a unique experience.
Happy hour offers late night food and drink specials.
Old apothecary setting preserves historic charm with original features from a century ago. Atmosphere feels cozy and jazzy, blending eclectic warmth with a speakeasy vibe. Small space attracts those seeking an intimate spot for craft cocktails and quiet conversation.
An intimate bar with original century-old features offers a cozy spot for friendly conversations. The attentive bartender crafts some of the best cocktails in a relaxed neighborhood setting.
Building shows strong historic character throughout. Space feels chill yet deeply rooted in history.
Good to know
Cocktails cost $15 each.
A Jazz Trio plays on Thursday nights.
The space is not large, so it is not suitable for large groups.
Historic church converted into an event venue offers intimate acoustics and rotating art displays. The atmosphere blends inviting neighborhood vibe with diverse live music, including jazz and DJ sets. Outdoor terrace and garden spaces complement the indoor bar and dance floor areas.
A lively bar sits inside a historic old cathedral with a great happy hour. Full bars serve drinks including their own brand of gin, vodka, and bourbon.
A former church restored into a historic venue filled with galleries and alcoves. The space holds deep history and elegance visible in its architecture and design.
Good to know
Happy hour runs from 4-7pm in the main bar with discounted drinks.
Free or low-cost events are available all weekend long.
Parking is limited; nearby street and garage options are available.
Pub offers European-style handcrafted wooden interiors filled with WWI and WWII memorabilia and historical artifacts. Atmosphere feels like a cozy British and Irish pub with a quiet, inviting vibe. Regulars enjoy traditional British ales and hearty pub food in a setting rich with history.
Feels like stepping into an old British pub with warm, inviting atmosphere and European-style handcrafted wooden interiors. Offers fast, friendly service and serves drinks and pub food true to traditional British style.
Walls display World War I and II memorabilia including a katana, Prussian helmet, and seppuku knife. The owner shares detailed stories about his Dad's military service and the historical artifacts throughout the pub.
Good to know
Reservations are required for dining, especially during peak hours.
Happy hour offers good deals on drinks and appetizers from 4-6pm.
Expect a 1 hour and 40 minute limit on table reservations.
Sports bar with historic baseball decor and electric game day energy draws a lively crowd of fans. Indoor and outdoor seating offer bird's-eye views and ample space despite crowds. Atmosphere captures classic ballpark vibe and deep ties to local baseball culture.
Known for its strong ties to Chicago baseball lore, this bar stands out as a top pre-game spot around Wrigley. It offers a fun atmosphere that draws crowds even outside baseball season.
Decades of deep history and cultural significance shape the atmosphere here. The place feels like a living tribute to the city's sports passion.
Good to know
Expect long wait times during Cubs games.
Reservations are recommended for winter eve dinners.
The bar accepts credit cards and mobile payments.
Neighborhood bar with pool tables, dartboards, and multiple TVs streaming sports creates a casual, relaxed vibe. Friendly crowd and a sense of rich history make it feel like a familiar gathering spot. Bold, spooky decorations add unique character to the space.
A classic dive bar with a rich history and friendly service. It offers good prices and a relaxed, casual vibe perfect for kid-free nights.
Rich history fills the walls of this well-maintained dive bar. Guests get snacks and stories about Chicago's past, making it a spot full of historical charm.
Good to know
You can rent the side room for very cheap for events.
The Levee accepts cash only, but there is an ATM on site for convenience.
The Levee will have been a bar for 100 years in 2028.
Elegant edifice with dark wood, marble, and gold fixtures creates a historic American atmosphere. Ambiance blends old-world charm with a relaxing yet professional vibe. Amenities include a library, multi-story gym, pool, and co-working spaces that support both leisure and business.
An indoor bar offers a secluded spot for quiet moments and lively pre-dinner drinks. The bar downstairs gets lively during games, creating a great vibe alongside the event room on the second floor.
Elegant venue with rich history and impressively preserved features. Combines historic charm with luxury in a beautiful, old building.
Good to know
Expect to pay an extra $50 per night if you are a non-member.
Parking costs $68 for same-day in-and-out access.
The venue hosts monthly birthday parties for members with dinner included.
Hotel offers an industrial chic vibe with luxurious, soulful ambiance and phenomenal rooftop views. Multiple bars and a café create a lively, celebratory atmosphere. Location near transit and neighborhood shops adds convenience and local flavor.
Two rooftop bars offer unique views of downtown Chicago and a great rooftop ambiance. The second floor bar features city views and games for a lively atmosphere.
Rooms reflect the historic building vibe with good size and quality. The building itself feels stunning and neat, carrying a strong sense of history.
Good to know
The Cabana Club is open to the public from 4-6 PM for happy hour.
Happy hour features discounted drinks and appetizers at The Robey.
Story hour at the Clever Coyote takes place every Sunday.
Wood-paneled sports bar with a large warm wood bar and historic vibes creates a welcoming, laid-back atmosphere. Polka music and live performances add a German Beer Hall feel, while televisions offer casual entertainment. The place stays relaxed during mid-afternoon and grows lively later in the day.
A large, warm wood bar creates a welcoming atmosphere with lots of draught beer selections including German styled drafts. The bar offers great service and full access to the historic restaurant next door.
History dates back to 1870 with ties to the Chicago World Fair. The place offers a strong historic ambiance and shares fascinating stories about its past.
Good to know
Expect busy times during holidays; reservations are not required.
Pickpocketing incidents have been reported, so keep personal items secure.
Credit cards and mobile payments are accepted for purchases.
Historic opera house converted into a modern music venue offers intimate concerts with great acoustics and vintage architecture. Spacious layout includes a balcony and multiple bars, creating a cool atmosphere with excellent views from all angles.
Three bars spread across an old opera house offer vintage architecture and quick service. A bar on the main level provides easy access for drinks before shows.
Unbelievably beautiful with historic charm and pleasing acoustics, this concert hall blends cozy ambiance with a rich story and history.
Good to know
Parking in the area can be rough; add time for street parking.
The coat check costs $5.
Food is reasonably priced, with popcorn at $4 and hot dogs at $5.
Restored brownstone with early 1900s decor and photos of local celebrities creates a traditional steakhouse atmosphere. Live piano music plays softly, adding to the luxurious and old-fashioned vibe. Comfortable seating and personalized touches enhance a refined dining experience.
Bartenders like Derrick and Julio craft amazing cocktails and help pick drinks that match your meal. The bar area works well for celebrations and offers drinks like a stellar Old Fashioned.
Old, historic pictures and memorabilia create a cool atmosphere. The setting has offered this experience for over 40 years, adding to its special, historical vibe.
Good to know
During the 40th anniversary, all food ordered was 40% off.
Valentine’s Day celebrations offer special menu items.
Reservations are recommended, especially during holidays.
U-shaped bar made from reclaimed local wood creates a communal vibe in a sleek, modern space with indoor and outdoor seating. Atmosphere feels laid-back and playful, attracting people who enjoy quality beer and relaxed socializing. Specialty brews and exclusive offerings add a unique touch to the experience.
Attentive and knowledgeable bar staff create a welcoming atmosphere. The laid-back vibe centers around a U-shaped bar made from reclaimed local wood, adding authentic character.
Tours include a quick history lesson on brewing and the area's past. Guides share fun anecdotes and detailed knowledge about Bourbon County and local history.
Good to know
The brewery tour costs $15 per person and lasts over an hour.
Bingo events are held regularly, providing a fun community experience.
Participate in March Madness promotions for a chance to win prizes.
Intimate jazz club with historic décor and excellent acoustics creates a cozy, relaxed atmosphere. Live performances feature talented musicians playing in a setting that honors jazz legends. Dim lighting and comfortable seating offer a balanced sound experience ideal for soaking in pure jazz.
A cozy, authentic jazz bar with a long history as the second oldest in the US. The bar serves a solid selection of drinks at reasonable prices, and the staff adds to the memorable atmosphere.
A historic jazz venue since 1947, it offers a cozy, intimate atmosphere with a rich sense of history. The Dearborn Station room adds an old-school vibe that highlights its deep roots.
Good to know
Admission is $20 per person for entry.
Jazz Showcase does not serve food but allows patrons to bring their own.
It is advisable to buy tickets in advance as shows often sell out.
Small, intimate theater with eclectic underground decor and classic elegance creates a cozy yet sophisticated atmosphere. Two levels with bars and diverse seating support a welcoming environment. Performances feel immersive due to the close proximity and detailed staging.
Small bar offers drinks before shows and during intermission. Staff is friendly and cool, creating a funky vibe in the lobby.
A historic building with a rich history gives the theatre a unique charm. It feels like a cute indie theatre with deep roots in its community.
Good to know
Parking around the theatre can be challenging, but there is street parking available.
Open seating means arriving early is recommended for larger groups.
Shows can be edgy and may not be suitable for young children.
Huge building with castle-like architecture hosts multiple events across four floors including a pub with live Celtic music and a theater with excellent sound quality. Atmosphere feels cozy and laid back, with a lively bar scene reminiscent of an Irish pub. Spaces offer intimate settings for gatherings, blending cultural heritage with social energy.
Cozy atmosphere defines the pub with libraries converted into bars adding unique charm. The great bar scene includes a pub serving amazing pub food and a bar manager who is very accommodating.
A well-preserved building holds a rich history dating back to 1254 with Irish, Welsh, Anglican, Norman, and Celtic influences. Inside, it features historical items and hosts regular events that highlight Irish American heritage.
Good to know
Parking is free on-site, with a large paved lot available.
The center is open Thursday through Saturday only.
The venue is handicap accessible with ramps and an elevator.
Historic building hosts a French bistro with European charm and elegant design. Live jazz music creates a relaxing atmosphere complemented by a skilled bar offering standout cocktails. The space feels cozy and stylish, attracting those seeking a refined dining experience.
Cozy atmosphere with skilled bartenders crafting drinks. Offers wines by the glass and bottle at reasonable prices compared to other spots.
A restored historic building anchors the space with architectural beauty. The atmosphere and design bring an elegant, stylish feel that fits the building's history.
Good to know
Reservations are recommended, especially on weekends, to avoid being turned away.
Happy hour runs from 4-6pm on weekdays with discounted drinks and appetizers.
Expect a $10 charge for each cheese on the charcuterie board.
Classic dive bar with a fishing theme and historic charm updated through thoughtful renovations. Atmosphere stays relaxed and cozy, attracting an older crowd who share stories in a lively yet low-key setting. Features include outdoor seating, multiple TVs, and a jukebox system, with music leaning toward pop country and hip-hop rather than punk or metal.
An old school dive bar with a historic neighborhood vibe and friendly, experienced bartenders. It hosts pop-up food events and captures the feel of a classic Chicago tavern.
Historic neighborhood bar with recent renovations done carefully. Updates follow guidance from prior owners and longtime regulars.
Good to know
Lunch is served from 11 AM to 2 PM on weekdays.
They host a Monday Night Foodball pop-up event.
Expect a rotating selection of local cooks at food pop-ups.