Best of 2021: Arts & Entertainment

Best of 2021_ Arts & Entertainment Winners

Chicago has an incredibly vibrant arts community with a plethora of options for music, theatre, museums, and — of course — improv comedy. Here are your top picks for 2021!

Best Live Music Venue – City
Millennium Park 

201 E. Randolph St. Chicago

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The pride of Chicago’s downtown, this gorgeous park provides us with cultural events, special events, music, art, architecture, play space, and so much more. Did we mention The Bean?

Best Live Music Venue – Suburbs
Ravinia Festival

418 Sheridan Rd, Highland Park

Ravinia Festival 2021
Courtesy of Ravinia Festival

Nothing says summer like a night on the Ravinia lawn, surrounded by live music and friends, wine glass in hand and a picnic spread out before you.

Best Music Festival – City

Grant Park 337 E Randolph St

Our biggest outdoor music festival is back after a pandemic vacation, this year weighing in at four full days of music, merriment, mosh pits, and some of the best street food around.

Best Music Festival – Suburbs
Winnetka Music Festival 

Elm Street & Lincoln Avenue, Winnetka

Winnetka Music Festival

Usually found in downtown Winnetka, this year’s festival — titled “Valslist EMERGE Winnetka” — will take place on Sept. 11 at the Winnetka-Skokie Playfields with a great line up including Spencer Ludwig and Allen Stone.

Best Live Theater – City

1650 N. Halsted St.

This storied Chicago theatre, artistic home to some of our best-known actors, welcomes new generations of audiences back to live theatre with an expanded campus. The 400-seat round theater and state-of-the-art education center are due to open in November.

Best Live Theatre – Suburbs
Writers Theatre, Glencoe 

325 Tudor Court, Glencoe

For more than 25 years, this Glencoe theatre has entertained us with its inventive takes on classics and new work alike. The Jeanne Gang-designed theatre is truly special.

Best Children’s Theater 
Children’s Theatre of Winnetka

620 Lincoln Ave, Winnetka

Live performances at this nonprofit children’s theater return with “You’re a Good Man, Charlie Brown” in November, with kids both on stage and running stage crew.

Best Museum – City
The Art Institute of Chicago

111 S Michigan Ave

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This world-class art museum welcomed us back this year with some blockbuster exhibits, including the Obama Portraits and the Bisa Butler quilts.

Best Museum – Suburbs
IL Holocaust Museum and Education Center, Skokie

9603 Woods Drive, Skokie

IL Holocaust Museum and Education Center, Skokie

We must never forget the past — no matter how difficult the message — to move forward together into a brighter future. This is important work, and the Holocaust Museum does it with grace and dignity. 

Best Children’s Museum 
Kohl Children’s Museum, Glenview

2100 Patriot Blvd, Glenview

Indoor and outdoor exhibits here fuel the imaginations of kids from around the Chicago area. Early morning “members-only” hours make membership even more attractive!

Best Comedy Venue
The Second City

230 W. North Ave, 3rd Floor

Bringing all the funny for the last 60 years, with alumni ranging from John Belushi and Bill Murray to Stephen Colbert and Tina Fey. Legendary doesn’t begin to cover it.

1637 W. Chicago Ave

If you’re an art enthusiast, there’s no better place for contemporary fine-art photography than this beautiful West Town gallery. Currently by appointment only.

1717 Central Street Evanston

Art exhibits, in-person classes, tours, and important community partnerships to ensure that art is accessible to everyone… this Evanston art hub has it all.

Best Neighborhood Festival – City
Old Town Art Fair 

1763 N. North Park Avenue

This annual festival, with over 200 juried artists and an audience of 10,000 art lovers gathering in the heart of Old Town, is always a treat.

Best Neighborhood Festival – Suburbs
Bloody Mary Fest, Highwood 

17 Highwood Ave., Highwood

Bloody Mary Fest

It’s all about the outlandish garnishes at this wildly entertaining annual summer festival in Highwood. Don’t miss this year’s fest on Sunday, Sept. 19 from 10 a.m. – 5 p.m.

Best Family Outing – City
TIE Navy Pier and Shedd Aquarium    

Navy Pier: 600 E Grand Ave
Shedd Aquarium: 1200 S Lake Shore Dr

Navy Pier Summer

Long one of Chicago’s top tourist attractions, Navy Pier has special events, a ginormous Ferris wheel, dining, shopping, the Chicago Children’s Museum, and the Chicago Shakespeare Theatre. A little something for everyone!

Shedd Aquarium

Discover the wonder of the aquatic world and the animals that dwell within this marvel on Chicago’s Museum Campus. The cutest penguins, stingray feedings, beluga whales and more await at the Shedd.

Best Family Outing – Suburbs
Chicago Botanic Garden  

1000 Lake Cook Road, Glencoe

Chicago Botanic Gardens

Taking green space to a whole new level, this magnificent spot will connect you and your family with nature in beautiful ways. 

Best Chicago Sports Experience, Men’s Team
Chicago Cubs

Ian Happ. Photo courtesy of Chicago Cubs.

The Cubbies might not always win, but a visit to the ivied walls of Wrigley field is always a treat.

Best Chicago Sports Experience, Women’s Team
Chicago Sky

Hip hip hooray for Chicago’s amazingly talented WNBA team! Come watch a game and see them soar to new heights, led by superstar and Chicago-area native Candace Parker.

Category Sponsor
The Paige Dooley Team, Compass

Pandemic Pivot

“We have all had to adjust lives in so many ways during this pandemic. The definition and importance of home has become elevated for all of our clients. We have seen lots of our clients looking for ways to renovate their homes to create more home office spaces, more play spaces, more outdoor living. In addition to selling homes, much of our work is advising our current clients on how to add value to their homes and achieve their objectives for home space. Further, we have learned to host many more home searches with FaceTime. Many home transactions were effectively facilitated start (from staging) to fin- ish (final walk through) with Technology!” – Paige Dooley, Licensed Real Estate Broker

Paige’s Top 5 Arts & Entertainment Picks

Winnetka Music Fest pivots to Emerge Winnetka 2021
Skokie Playfields, 540 Hibbard Rd, Winnetka
Best very local, family friendly music festival bringing serious talent to the North Shore – top national and international emerging artists perform in a very intimate outdoor setting!

Wilmette Theatre
1122 Central Ave, Wilmette
Best locally supported cinema to see both latest and independent films plus live performances.

Writers Theatre
325 Tudor Ct, Glencoe
Highest caliber live theatre with top playwrights, directors and performers in a state of the art venue right in the center of Glencoe.

Botanic Garden
1000 Lake Cook Rd, Glencoe
Any time of year, this is one of the best events enjoy strolling the gardens any season or wander the breathtaking Lightscape show in the prime of winter!

Winnetka Historical Society
411 Linden St, Winnetka
Experience the settlement of Winnetka at the authentically restored and curated Log House, or enjoy the exhibits at the Winnetka Historical Society Museum at 411 Linden, or fascinating online programming.

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