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)
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
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
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
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
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)
50 E. Ida B. Wells Drive, Chicago
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)
418 Sheridan Road, Highland Park
Ravinia is the country’s oldest outdoor music festival, and a must-visit every summer.
Best Live Theater (City)
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
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)
325 Tudor Court, Glencoe
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)
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
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)
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.
Hotel Julian Chicago
168 N. Michigan Ave., Chicago
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
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
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
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)
Wrigley Field: 1060 W. Addison St., Chicago
You love rooting for the home team at Wrigley Field.
Best Sports Experience (Women’s Team)
Wintrust Arena: 200 E. Cermak Road, Chicago
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.