Chicago Halloween Night With Symphony Hall and a Late Deli

4.4 (4,262)

Tue, Fri, 11:00 – 18:00

200 E Cermak Road

Wintrust Arena brings Chicago Sky and DePaul Blue Demons basketball, major concerts, family shows, and 10,387 seats to the Near South Side. A skybridge connects the arena with McCormick Place and nearby hotels. Reviews praise the clean setting, sightlines, and audio, while bag checks, long lines, and high drink prices call for extra planning. Guaranteed parking costs 40 USD per day by advance order.

4.5 (4,764)

Mon, Sun, 08:00 – 15:30; Tue – Sat, 08:00 – 20:00

1141 South Jefferson Street

Manny's Cafeteria & Delicatessen has served Chicago since 1942, with a cafeteria line for classic Jewish deli fare and traditional comfort food. Order a substantial pastrami or corned beef sandwich, then settle into the huge dining area. The deli can be busy and pricey, so check current details before making it your holiday-week food stop.

4.5 (1,375)

Mon – Fri, 12:00 – 17:00

322 W. Armitage

Park West is a Lincoln Park live music venue in a 1916 building originally made for movies and vaudeville. Its rare diamond-shaped auditorium gives the intimate room direct sightlines, and reviews praise its audio mixing. Multiple bars serve drinks. Plan for cashless payment, and note that the box office opens at 2pm on show days only.

4.7 (24,683)

Mon – Sat, 11:00 – 17:00

1901 W Madison St

United Center brings professional basketball, hockey, major concerts, and large-scale entertainment to the Near West Side. Look up for championship banners and team history, then use the organized concourse for food options and staff help. Regular hours are 11 a.m. to 5 p.m. Monday through Saturday. Parking costs 40 to 50 dollars, or up to 60 dollars for concerts.

4.8 (135)

Mon – Sat, 10:00 – 17:00

220 S. Michigan Ave.

At 220 S. Michigan Ave., Symphony Center is the historic Loop home of the Chicago Symphony Orchestra. The hall presents orchestral performances, chamber music, recitals, film-accompaniment concerts, and an annual jazz series, with exceptional acoustics. For a holiday-week evening, plan around a performance. The box office runs noon to 6 p.m. Monday through Saturday and on concert-day Sundays from noon to 4 p.m.

4.2 (30)

Thu, Sat – Sun, 17:30 – 02:00 (+1)

1357 N Elston Avenue

Three Top Lounge sits atop The Salt Shed at 1357 N Elston Avenue, with an indoor-outdoor space, sweeping city views, and a lounge-style interior for groups. Order pre-batched craft cocktails with chicken katsu sando, sliders, or taquitos. Reviewers praise the staff and drinks, while noting higher prices. For a holiday-week stop, check the concert calendar because hours and access vary.

4.7 (191)

6525 N Sheridan Rd

Joseph J. Gentile Arena on Loyola University Chicago's campus hosts Ramblers basketball and volleyball, with close-to-the-floor seating that suits a compact college sports outing. Concessions offer a wide selection of food and drinks. Some sections use continuous bench rows, and reviews mention occasional sound issues in upper areas, so check seating details before choosing a game.

4.6 (45)

Mon – Fri, 04:00 – 19:00; Sat – Sun, 10:00 – 19:00

820 W Jackson Blvd, Chicago, IL 60607, USA

Chicago Red Stars brings National Women’s Soccer League matches, gritty play, and a dedicated fanbase to a holiday-week sports plan. Professional women’s soccer gives this stop a focused live event option, and paid admission is required. Reviews average 4.6/5 across 45 platform ratings. Check the current match schedule and admission details before traveling.

4.8 (28)

Mon – Fri, 07:00 – 19:00

4120 W Diversey Ave

The Fields Studios turns a former Marshall Field’s warehouse at 4120 W Diversey Avenue into a 23-acre film and television production campus. Nine sound stages use silent HVAC systems and high-grid ceilings, with production offices, retail, dining, and residential lofts across the grounds. Public entry and ticketing vary by hosted exhibition, so check weekday event details before going.

4.7 (949)

Tue – Sat, 12:00 – 16:00

1331 N Milwaukee Ave

The Den Theatre at 1331 N Milwaukee Ave in Wicker Park packs multiple stages into a labyrinthine venue for stand-up comedy, podcasts, theater, and live music. Its intimate venue has an elegant feel, and table QR codes support in-seat drink ordering during shows. For holiday-week planning, the box office is open Tuesday through Saturday, noon to 4 p.m.