Chicago for a Group of Ten, From Theater to Dance Floor

4.1 (1,425)

Wed – Fri, 16:00 – 00:00 (+1); Sat, 11:00 – 00:00 (+1); Sun, 10:00 – 00:00 (+1)

1059 W Addison St

Across from Wrigley Field, Cubby Bear combines a big open sports bar with live music or DJ sets that vary by day. Groups can settle in with bar food and play billiards. Its weekend opening starts at 11:00 AM, so it can work as an earlier stop before a later show.

4.7 (10,943)

Mon – Fri, 12:00 – 18:00

175 N State St

The Chicago Theatre is a 1921 downtown landmark with a famous vertical neon marquee, grand French Baroque architecture, a six-story lobby, and a majestic staircase. Its historic backstage signatures add a detail for architecture-minded groups. Listed weekday hours are 12:00 to 18:00, so check the current schedule and tour availability before planning a stop.

4.6 (1,123)

Tue – Fri, 12:00 – 16:00

2936 N. Southport Ave.

Inside a historic 1911 building in Lakeview, Athenaeum Center for Thought & Culture is Chicago's oldest continuously operating Off-Loop theatre. Its intimate, movie-house-style space includes balcony seating and a nook-style concession area with beer, wine, soda, and snacks. Groups can consider a concert for the room's exceptional acoustics, with an elevator available.

4.8 (4,323)

Mon, 08:30 – 08:00 (+1); Tue – Wed, 09:00 – 08:00 (+1); Thu, Sun, 08:30 – 09:00 (+1); Fri, 08:30 – 09:30 (+1); Sat, 08:00 – 09:30 (+1)

112 E. Wacker Drive

Chicago's First Lady Cruises runs the official Chicago Architecture Center River Cruise from the Riverwalk at 112 E. Wacker Drive. Docents guide groups past more than 50 buildings. Boats have an open-air upper deck and a climate-controlled lower cabin with refreshments. The 2026 cruising season ends November 22, so check sailing dates before adding it to a holiday-week plan.

4.7 (3,875)

Thu, 18:00 – 02:00 (+1); Fri – Sat, 21:00 – 04:00 (+1); Sun, 17:30 – 01:00 (+1)

2548 North Halsted Street

At Kingston Mines in Lincoln Park, bands alternate between two stages to keep live blues going late. Groups can move between the rooms as sets change. The club serves barbecue and pub food in a casual setting. Entry is restricted to ages 21 and older. Friday and Saturday nights run until 4:00 AM.

4.6 (89,369)

Mon – Thu, Sun, 11:00 – 20:00; Fri – Sat, 11:00 – 22:00

600 E Grand Ave, Chicago, IL 60611, USA

Navy Pier gives groups a free waterfront outing with Lake Michigan views, restaurants, shops, and carnival rides. Walk toward the end for open water and skyline scenery, or buy separate tickets for a boat cruise or the giant Ferris wheel. Listed hours run 11:00 to 20:00 Sunday through Thursday and to 22:00 Friday and Saturday, so check holiday-week schedules before going.

4.4 (2,909)

Mon – Fri, 12:00 – 18:00; Sat, 10:00 – 16:00

3145 N Sheffield Ave

Vic Theatre opened in 1912 as The Victoria Theater, presenting vaudeville and touring stage shows in Lakeview. The venue now hosts live music and comedy. Check each event's age limit before booking for a group. All ticket sales are final. Buying at the box office reduces convenience fees compared with online purchases.

3.7 (8,141)

520 S Michigan Ave, Chicago, IL 60605

Built in 1893 for visitors to the World's Columbian Exposition, Congress Plaza Hotel is a South Loop landmark on Michigan Avenue. Groups staying here can use large guest rooms, classic architecture, a lobby, sweeping lake views, and an onsite historic barbershop. A 24-hour front desk and walking access to downtown bars, restaurants, museums, and attractions make it a practical base.

4.5 (634)

Mon – Sun, 16:40 – 02:00 (+1)

2539 N. Kedzie Blvd.

Logan Square Auditorium fills a historic third-floor ballroom above Lula Café with high ceilings, moody lighting, ornate details, and a state-of-the-art sound system. It hosts live music, weddings, festivals, and community gatherings, making it a practical holiday-week option for groups. Plan for two flights of stairs, bring cash for the bar, and note that the venue is all ages.

Tue – Fri, 12:00 – 18:00

640 West Cermak Road

Radius Chicago fills a large industrial space in Pilsen with concerts, electronic acts, and popular DJs. Its state-of-the-art sound system, striking light shows, and clear sightlines make the room itself part of a group night out. During events, a small outdoor area has a couple of food trucks. Reviews praise the spacious layout, while staff experiences vary.