Best of Chicago 2020: Arts & Entertainment

When it comes time to plan a fun day trip with the entire family or a night out with friends, these are the Chicago area museums, theaters, and more you love.

Best Art Gallery (City):
Catherine Edelman Gallery

1637 W Chicago Ave.

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A contemporary photography gallery that is hosting Keliy Anderson-Staley’s What Is Home? exhibit through October.

Best Art Gallery (Suburbs):
Anne Loucks Gallery

309 Park Ave., Glencoe

This multi-year winner highlights contemporary American paintings, sculptures and works on paper.

Best Comedy Venue (City):
The Second City

1616 N Wells St., 2nd Floor

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The infamous comedy club, theater and school is helping us laugh virtually from the safety of our homes.

Best Comedy Venue (Suburbs):

5437 Park Pl., Rosemont

A home for up-and-coming stand-up comedians, the venue is open for live shows at reduced capacity.

Best Museum (City):
The Art Institute of Chicago

111 S Michigan Ave.

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One of the world’s best art museums is right here in our own backyard, and it has reopened with safety measures in place, including a reservation system.

Best Museum (Suburbs):
Illinois Holocaust Museum & Education Center

9603 Woods Dr., Skokie

Remember the Past, Transform the Future. That’s the mission of this museum, and the work it’s doing is as important as ever. With online reservations, you can catch their Notorious RBG exhibit through January.

Best Children’s Museum (City):
Chicago Children’s Museum

700 E Grand Ave.

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This repeat winner, and much beloved museum at Navy Pier, is temporarily closed due to Covid-19. Connect with them on Instagram for fun at-home activities to do with the kids!

Best Children’s Museum (Suburbs):
Kohl Children’s Museum of Greater Chicago

2100 Patriot Blvd., Glenview

With an amazing selection of interactive exhibits and programs, the museum is offering guided play for small groups in their outdoor Habitat Park and V.I.P. (very important play) private rental options inside.

Best Children’s Theater (City):
Chicago Children’s Theatre

100 S Racine Ave.

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Inspiring children to lead lives of adventure, courage and curiosity, the theatre is offering a drive-in Beatrix Potter puppet show this October.

Best Children’s Theater (Suburbs):
Children’s Theatre of Winnetka

620 Lincoln Ave., Winnetka

This volunteer organization gives kids in grades 4-8 the chance to star both on stage and behind the scenes, and is offering socially distanced workshops this fall.

Best Live Music Venue (City):
Chicago Symphony Orchestra

220 S Michigan Ave.

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With performances canceled through December 23, you can connect with amazing musicians from home via online concerts and backstage interviews.

Best Live Music Venue (Suburbs): Tie

Ravinia Festival

418 Sheridan Rd., Highland Park

Ravinia is the country’s oldest outdoor music festival, and a must-visit every summer. With this season canceled, you can tune into Ravinia TV, a weekly variety show airing every Friday at 7p.m.


1245 Chicago Ave., Evanston

A small venue for live music, all shows at SPACE have been canceled through September. They are offering live music in their distanced Summer Stage, and even to-go concerts, on the North Shore. 

Best Band (City & Suburbs):
Arlen Music Productions

1415 Sherman Ave. #101, Evanston

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A perennial winner, this entertainment company knows how to get your guests moving with dance bands like Ken Arlen Evolution Orchestra and Indigo.

Best Live Theater (City):
Steppenwolf Theatre Company

1650 N Halsted St.

With all performances canceled this year, the 2021 season is planned to offer shows such as Good Night, and Good Luck and I Am Not Your Perfect Mexican Daughter. During the shutdown, consider donating to help their staff, or become a member.

Best Live Theater (Suburbs):
Writers Theatre

325 Tudor Ct., Glencoe

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The Wall Street Journal has called Writers the top regional theater in the country, and if you haven’t seen their gorgeous, state-of-the-art facility yet, you’ll want to visit when they reopen for performances in 2021. You can also help the theater give back to the community by dropping off supplies at their Donation Supply Drive.

Best Hotel (City):
Hotel Julian

168 N Michigan Ave.

A repeat winner, this Four Diamond hotel just steps from Millennium Park offers modern design and luxurious amenities.

Best Hotel (Suburbs):
Deer Path Inn

255 E Illinois Rd., Lake Forest

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Escape to this inn, where you can cozy up next to stone fireplaces, enjoy afternoon tea, stroll through the English garden, and more.

Best Staycation:
The Langham

330 N Wabash Ave.

Center your staycation in the heart of downtown at one of Chicago’s top luxury hotels. With amazing dining, a wellness spa, pool, modern health club, and breathtaking views, you don’t need to travel far to get away. 

Best Midwest Family Destination:
Door County, Wisconsin

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Jump in the car and spend some time in the upper Peninsula of Wisconsin. A beautiful fall destination, Door County is known for its shoreline, parks, fish boils and charming B&Bs.

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