Best of Chicago 2019: Arts & Entertainment

Better: Best of 2019

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 visit.

Best Art Gallery (City)

Weinberg/Newton Gallery

688 N. Milwaukee Ave., Chicago

The mission of this gallery is “to collaborate with nonprofit organizations and artists to educate and engage the public on social justice issues.” Upcoming exhibit The Way the Mystic Sees opens Sept. 6.

Best Art Gallery (Suburbs)

Anne Loucks Gallery

309 Park Ave., Glencoe

This multi-year winner highlights contemporary American works. The current exhibit, Photography 2019: In Focus, which features photos by David Burdeny and Joshua Jensen-Nagle, closes Aug. 15.

Best Comedy Venue

The Second City


When you could just use a really fun night out, turn to The Second City and one of their many hilarious shows.

Best Museum (City)

The Art Institute of Chicago

111 S. Michigan Ave., Chicago

Best of 2019: The Art Institute of Chicago
The Art Institute of Chicago. Michigan Avenue Entrance. Courtesy of the Art Institute of Chicago. Edward Kemeys, Lions. Bronze with Green patina. Gift of Mrs. Henry Field, 1898.1a-b. The Art Institute of Chicago. The lions are the registered trademarks of the Art Institute of Chicago.

One of the world’s best art museums is right here in our own backyard. Make plans to see Manet and Modern Beauty before it closes Sept. 8, and don’t miss Andy Warhol—From A to B and Back Again, opening Oct. 20. 

Best Museum (Suburbs)

Illinois Holocaust Museum & Education Center

9603 Woods Drive, 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. Save the date for special exhibit Notorious RBG: The Life and Times of Ruth Bader Ginsburg, opening Feb. 9, 2020.

Best Children’s Museum (City)

Chicago Children’s Museum

700 E. Grand Ave., Chicago 

Your kiddos will love exploring exhibits like Dinosaur Expedition, Tinkering Lab, Treehouse Trails, WaterWays, and the new Sound Playground. 

Best Children’s Museum (Suburbs)

Kohl Children’s Museum of Greater Chicago

2100 Patriot Blvd., Glenview

Best of 2019: Kohl Children's Museum
Photo courtesy of Kohl Children’s Museum.

All of the 17 interactive exhibits and programs at this museum align with Illinois State Learning Standards and set children up for a lifetime of learning.

Best Children’s Theater (City)

Chicago Children’s Theatre

100 S. Racine Ave., Chicago

Don’t miss upcoming shows “The Very Hungry Caterpillar Show,” opening Sept. 28, and “The Beatrix Potter Holiday Tea Party,” opening Dec. 7.

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 off with productions in the fall and spring. This year’s fall show is “Beauty and the Beast.” 

Best Family Outing (City)

Blue Man Group

Briar Street Theatre: 3133 N. Halsted St., Chicago

Best of 2019: Blue Man Group, Chicago
Photo by Caroline Talbot.

Blue Man Group Chicago has entertained 35 million people over the past 21 years.

Best Family Outing (Suburbs)

Chicago Botanic Garden

1000 Lake Cook Road, Glencoe 

Best of 2019: Chicago Botanic Garden
Photo courtesy of Chicago Botanic Garden.

With 27 gardens and four natural areas on 385 acres, plus a variety of family and youth programs and events, there’s so much to explore here.

Best Live Music Venue (City)

Auditorium Theatre

50 E. Ida B. Wells Drive, Chicago

Best of 2019: Auditorium Theatre
Photo by Karl Solano.

You have good taste — this theater also recently received the League of Historic American Theatre’s Outstanding Historic Theatre Award.

Best Live Music Venue (Suburbs)

Ravinia Festival

418 Sheridan Road, Highland Park

Best of 2019: Ravinia Festival
Photo courtesy of Ravinia.

Ravinia is the country’s oldest outdoor music festival, and a must-visit every summer.

Best Live Theater (City)

Goodman Theatre

170 N. Dearborn St., Chicago

Goodman is the city’s oldest and largest not-for-profit theater. “The Music Man” continues through Aug. 18, and the annual production of “A Christmas Carol” returns Nov. 16.

Steppenwolf Theatre Company

1650 N. Halsted St., Chicago

Best of 2019: Steppenwolf Theatre Company
Photo by Kyle Flubacker.

This theater’s accolades include the National Medal of Arts and 12 Tony Awards. “True West” runs through Aug. 25, and the 2019/20 season begins with “The Great Leap” on Sept. 5. 

Best Live Theater (Suburbs)

Writers Theatre

325 Tudor Court, Glencoe

Best of 2019: Writers Theatre
Photo by Steve Hall © Hedrich Blessing.

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 must.

Best Music Festival (City)


Best of 2019: Lollapalooza
Photo by Charles Reagan Hackleman/Lollapalooza 2018.

Lolla returns Aug. 1-4 with The Strokes, The Chainsmokers, Childish Gambino, Tame Impala, Twenty One Pilots, J Balvin, and many more. 

Best Music Festival (Suburbs) | Best Neighborhood Festival (Suburbs)

Winnetka Music Festival

Best of 2019: Winnetka Music Festival
DOROTHY at the 2019 Winnetka Music Festival (Photo by Emily Stone.)

This music festival celebrated its third year in June (see some amazing photos from the event) and is already one of the best ways to discover new artists. 

Best Neighborhood Festival (City)

Andersonville Midsommarfest

This summer event features music, kids’ entertainment, food, artists, and more throughout Chicago’s Andersonville neighborhood.

Old Town Art Fair

In 2020, this event will feature 250 artists from around the country, plus a garden walk, music, food court, and children’s corner.

Best Hotel

Hotel Julian Chicago

168 N. Michigan Ave., Chicago

Best of 2019: Hotel Julian
Photo by Daniel Kelleghan.

This Four Diamond hotel, just steps from Millennium Park, opened late last year and offers modern design and luxurious amenities.

Grand Geneva Resort & Spa

7036 Grand Geneva Way, Lake Geneva, Wisconsin 

Best of 2019: Grand Geneva Resort & Spa
Photo courtesy of Grand Geneva.

This hotel is great for a getaway thanks to two championship golf courses, spa services, horseback riding, skiing and snowboarding, and more.

Best Hotel | Best Staycation (Suburbs)

Deer Path Inn

255 E. Illinois Road, Lake Forest

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 (City)


85 E. Wacker Drive, Chicago

Best of 2019: LondonHouse
Photo by Nicholas James Photography.

Center your staycation in the heart of downtown, at the corner of Michigan Avenue and Wacker Drive, at this luxury lifestyle hotel that offers personalized service and incredible views of the city. 

Best Staycation (Suburbs)


Set aside plenty of time to explore this village, where you can catch a show at Allstate Arena or Rosemont Theatre, cheer on the Chicago Dogs, shop at the Fashion Outlets of Chicago, dine and play at the Parkway Bank Park entertainment district, and more. 

Best Midwest Destination


Sure, we might be a little biased, but with so many museums, restaurants, theaters, sports, shopping, neighborhoods, and more to explore, there’s a lot to love.

Best Midwest Family Destination

Lake Geneva, Wisconsin

Best of 2019: Lake Geneva, Wisconsin
Photo courtesy of Lake Geneva Cruise Line.

Jump in the car and spend some time at the lake. You’ll be making memories in no time. 

Best Sports Experience (Men’s Team)

Chicago Cubs

Wrigley Field: 1060 W. Addison St., Chicago

You love rooting for the home team at Wrigley Field. 

Best Sports Experience (Women’s Team)

Chicago Sky

Wintrust Arena: 200 E. Cermak Road, Chicago

Best of 2019: Chicago Sky
Photo courtesy of Chicago Sky.

Cheer on the Sky as they take on the New York Liberty on Aug. 7, Los Angeles Sparks on Aug. 16, or the Washington Mystics on Aug. 23.

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