Summertime CHI Edition: Hot Cool and Dope Picks

SummerTime Chi 2016: Hot Cool and Dope Picks of Summer

Mary L. Datcher

Arts & Entertainment Editor

3464721462301193353 Hot Cool & Dope

In the summer, Chicago is a favorite international travel destination, but for residents and our suburban neighbors — summertime in the ‘Chi’ can sometimes feel like a vacation while at home.

Here’s some of our top picks from neighborhood festivals, outdoor and rooftop dining to ‘must-see’ concerts and programs.  

If you love the energy of catching a movie in the park with the family or patronizing a wonderful neighborhood business, we will be premiering various hot spots and programs throughout the summer.

In May, the The Chicago Park District will hold festivities for the Great Migration that will launch from May 27-October 6, marking the Great Migration Centennial, a long term movement of African Americans from the rural South to the urban North that transformed Chicago between 1916 and 1970. Programs will include; Lucy Smith’s Chicago Bound: The Great Migration of the Blues, Classic Black’s One Way Ticket along with performances and workshops by Live the Spirit Residency’s young jazz musicians and much more.

Here’s just a sneak peek at the Chicago Defender’s top choices to get you started. 

Hot Summer Hangouts

 Pier Thirty-One

Located at 31 Street Beach, this has become a great hangout to grab a cocktail while people-watching at the same time. Wednesdays are jam packed with urban professionals enjoying the sounds of classic House music.

Raised-One West Wacker Drive

Recently opened in early May, Raised has panoramic view of the downtown skyline with a great dining experience along with cocktails.

The Betty-839 W. Fulton

This low-key lounge is one of Chicago’s best-kept secrets, located in the heart of the meatpacking district. A great place to get some of the best well-crafted cocktails, a light meal and funky R&B tunes playing in the background. Add this to your list for indoor and outdoor dining with a budget.

Roof on The Wit-201 S. State St.

We never get tired of the The Wit’s rooftop — it has become a summertime Chicago stable where business people meet night time club goers for afterwork views and brews.  

The Godfrey Hotel Chicago indoor/outdoor rooftop lounge.

The Godfrey Indoor Outdoor Rooftop-127 W. Huron  

One of the hippest indoor/outdoor rooftop lounges that offer a variety of live dj music, creative cocktails and top fine dining in a chic way.  

Norm’s Bistro –1003 E. 43rd St.

In the heart of Bronzeville, owner Norman Bolden opens up the patio for patrons to enjoy the summertime breeze while enjoying the neighborhood scenery, eats and live music.

 Yusho –1301 E. 53rd St.

A Hyde Park favorite food spot with tasty Japanese dishes from noodles, buns, ramen and other creative eats. The restaurant’s outdoor patio is an added treat.

Flavor Restaurant –Richton Park/Hazel Crest

With two locations under their belt, mother and son team — Cassandra Kemp and Jerome Kemp gives you the upscale fine dining experience of Flavor in Richton Park and the casual brunch location in Hazel Crest. Great soul food with a twist.

 Mr. Brown’s Lounge –2301 W. Chicago Ave.

The original Mr. Brown’s Lounge is where the hipsters, rastas and residents of Ukrainian Village hang out for good traditional beer brands, Jamaican rum punch and the best jerk dinner meals on the Northwest side. Live music and DJs almost every night. Great outdoor patio for summer nights.

 The Promontory –5311 S. Lake St.

This two-story facility sports more than a live performance venue, the restaurant on the first level is cool dining experience with the combination of great date night for couples or a small dinner party for a girls’ night out. The outdoor patio on both levels are fit for summer nights while enjoying the venue’s live music concerts.

 90 Miles Cuban Café- 2540 W. Armitage90-miles-cuban-cafe

If you’ve never traveled to Cuba, this place serves the best in Cuban street food. Reasonable price, they have three locations on the North and West Side. With outdoor dining, it is almost always packed out with diners waiting on their Cuban and steak sandwiches.

Reggie’s Rock Club –2109 S. State St.

The three-level venue houses a casual restaurant, a live performance venue, a cool record store that still sells vinyl and an intimate rooftop with a citywide view. Every night they showcase a variety of music and shows catering to both 18+ and 21+ patrons.

 Cool Fests


 26th Annual Comedy Festival

June 1-5

Featuring Tracy Morgan on June 1.

 31st Chicago Gospel Festival

June 3-4

Millennium Park

Performances include Hezekiah Walker and the Love Fellowship Choir, Travis Greene, Shirley Caesar and many more.

FREE Admission

Attendees enjoy the beers at the Hyde Park Brew Festival.

3rd Annual Hyde Park Brew Fest

June 4-5


 57th Street Art Fair

June 4-5


Chicago Blues Festival

June 10-12

The largest Blues Festival in the world will feature heavy hitters, Shemekia Copeland, Fred Wesley & The New JBs, Wee Willie Walker & We “R”, and tribute to Otis Rush.

 America’s Cup World Series

June 10-12

Ribfest Chicago

June 10-12 

Spring Awakening Music Festival

June 10-12

10th Annual Latin Jazz Festival

June 10-August 19

Humboldt Park Boathouse -1140 N. Sacramento

Jazz Cabaret: Paul Marinaro Trio 

Columbus Park’s Refectory – 5701 W. Jackson Ave. and Seward Park – 375 W. Elm St. 

Pilsen Food Truck Social

June 11-12

Movies in the Parks

June 13-September 5

The Chicago Park District will bring big-screen entertainment to local parks for the 16th year of Movies in the Parks. There will be a variety of films with something for everyone to enjoy including Back to the Future, The Color Purple, Jurassic World, Star Wars, Captain America, The Avengers and Ferris Bueller’s Day Off.

Puerto Rican Festival & Parade

June 16-19

Taste of Randolph St.

June 17-19 

Real Men Cook Chicago

June 19

This year on Father’s Day, RMC will expand to various communities including Englewood, Bronzeville, Hyde Park, South Shore, Hyde Park, the South Suburbs and more.

Dew Tour at Grant Park Skate Park

June 20-21

Make Music Chicago

June 21

There will be 16 hours of music, 80 locations across Chicago featuring 250 live performances and over 1,500 musicians. Check site for listings.

Millennium Park Summer Film Series

June 21- August 30

Chicago-SummerDance_Grant-ParkChicago SummerDance

June 24-September 11

This is the kick-off to the City of Chicago’s weekly program of live outdoor music programming featuring Chicago DJs and dance instructors in Grant Park. 

Vegan Food and Drink Festival

June 25

Randolph Street Market Festival

June 25-26

Chicago Pride Fest

June 26


African Caribbean International Festival of Life

July 1-4

Union Park

3464721462300966872Chosen Few Picnic House Music Festival

July 2-4

Jackson Park

The 26th Chosen Few DJ House Picnic will feature two days of non-stop House and Soul music featuring musical guests Roy Ayers, Cheryl Lynn, DJ Spinna, Joe Claussell, Josh Milan, Monique Bingham and more.

Windy City RibFest Uptown

July 2-4

Fourth of July Fireworks at Navy Pier

July 4

Taste of Chicagotasteofchicago2016

July 6-10

This year’s biggest food and music festival will showcase The Roots, Billy Idol, The Isley Brothers, Sheila E. KONGOS among other talent.

Mamby On the Beach

July 2-3

Roscoe Village Burger Fest

July 9-10

Dance in the Parks

July 15-August 7

Dance in the Parks brings free, professional, outdoor dance concerts to Chicago’s parks. The all-ages performances feature works created and performed by professional Chicago dance artists.

Windy City Smokeout

July 15-17

560 W. Grand Ave.

Pitchfork Music Festival

July 15-17

Union Park

Considered the summer’s best outdoor music festival alternative to Lollapalooza, Pitch Fork features a diverse line up of indie and major artists in underground Rock, EDM, Hip Hop and alternative Soul music. This year’s talent features BJ the Chicago Kid, Digable Planets, Miguel, Jeremih and many more.

Chicago Hot Sauce Fest

July 23-24

Wicker Park Fest

July 23-24

Fiesta del Sol

July 28-31


July 28-31

The 25th Lolla will be one of the biggest music festivals to date, a week early this year. Some of the featured artists include Red Hot Chili Peppers, Disclosure, Vic Mensa, J. Cole, Future and much more.

Black Chicago Eats Week

July 29 – August 12

The week-long program will highlight some of Chicago’s best restaurants and chefs that are also Black owned and operated. for listings.

Chicago Margarita Festival

July 30-31


Chicago Hot Dog Fest

August 5-7

Clark and LaSalle St.

The Art of Rap

August 5

Tinley Park

The tour will feature Hip Hop’s finest and architects of the craft with a stellar line-up featuring Public Enemy, Naughty By Nature, Ice-T, MC Lyte, EPMD, Mobb Depp and Kurtis Blow.

Queens of House Picnic

August 6


Chicago Park District Calumet -9801 S. Avenue G.

This all-day House picnic will feature some of the best and leading women DJs in the House music community. Featuring DJ Solkat, First Lady, Anji Stone, Deejay Alicia, Celeste The DJ Alexander, Erica Kane, Queen B., Mz. Nicky and Lady Alicia

Taste of Lincoln Ave.

August 6-7

Festival Cubano

August 12-13

Riis Park

Reggae Fest Chicago

August 13

Medill Park

Northalsted Market Days

August 13-14

westsidemusicfestWestside Music Festival

August 20

Douglas Park


South Shore Summer Festival

August 21


Chicago Air & Water Show

August 21-21

Country Club Hills Jazz Festival

August 27

Feat. Norman Brown, Kirk Whalum, Rick Braun and Nick Colionne


Great American Lobster Fest

September 2-3

Navy Pier 

Chicago Jazz Festival

September 1-4

North Coast Music Festival

September 2-4

Union Park

African Festival of the Arts

September 2-5

Washington Park

Midnight Circus in the Parks

September 3 – October 16

Midnight Circus will present the 10 year of a true “Big Top” tent extravaganza in eight parks citywide, celebrating community and rebuilding parks one circus at a time.

17th Chicago’s Best Summer WingFest

September 5

Bailey Auditorium

Windy City Wine Festival

September 5

Grant Park

World Music Festivalheadway-imported-image-33

September 9-25

Various Locations 

Venetian Night at Navy Pier

September 10

Sam Adams’ Lakeview Taco Fest

September 17-18

riot-fest-chicagoRiot Rest & Carnival

September 16-18

This year’s non-stop 3-day festival will feature a great deal of rock music, metal and sprinkled with hip hop. This year’s highlight will be a performance by Redman and Method. More are being added to the carnival festivities.

Chicago Gourmet

September 23-25

Grant Park

Dope Picks

This summer is by far one of the best concert line-ups we’ve had in a long while. The choices are endless. So, get your credit card out and consider if the need to travel to the Essence Music Fest in NOLA or Cincinnati’s Music Festival is necessary. The live music shows around the Chicagoland area will keep music lovers busy.

Our top recommendations for a great guide of Jazz, Soul, Hip Hop and classics.


May 27-28

Soldier Field

E.Z. Mo Breezy Presents: Grits & Biscuits

May 27-28

House of Blues Chicago 

harpercourt_instagram1080x1080_2Harpercourt Summer Music Series

May 25, June 29, August 31

Blues, Jazz, Steppers, Latin Music & Afro-Beats



Pete Rock

May 28

The Promontory

thebeanhosuepartyChicago House Party at Millennium Park

May 28


Celebrate House music, born in Chicago 35+ years ago. The House Legacy Project will perform and Robert Williams will be recognized for his contributions to House Music with a mayoral proclamation. Performances featured: Steve ‘Miggedy’ Maestro, Jerry C. King, Byron Stingily, Dajae, Lidell Townsell, Faith Howard, Paris Brightledge, First Lady, Peven Everett Trio, Vick Lavender Ensemble, Superjane’s DJ Heather, Lady D and much more.

The Foreign Exchange

May 31


June 4

The Promontory

WGCI Summer Jam 2016

June 17

Live concert featuring Fetty Wap, Young Jeezy, 2 Chainz, T.I. Migos, Lil Durk and Migos

Rachelle Ferrell, Robert Glasper & Avery Sunshine

June 18

Country Club Hills Theatre

Patti LaBelle & The Commodores

June 23


Duran Duran with Chic feat. Nile Rogers

July 8


nikkigiovannaNikki Giovanni & Morris Gearring

Oscar Brown, Jr. Celebration

July 10

The Promontory 

Will Downing and Peabo Bryson

July 16

Country Club Hills Theatre

Diana Ross

July 27


Kindred The Family Soul

August 4-5

The Promontory

commonjillJill Scott and Common

August 5

Horseshoe Casino/Hammond, IN

Bud Biliken Day Parade

August 13

39th and Martin Luther King Drive to Washington Park

Patti Austin and Lalah Hathaway

August 13

Country Club Hills Theatre

10th Annual Global Mixx Music & Film Forum

August 20-21

SAE Institute Chicago

A two-day conference that hosts an array of panels, workshops, showcases and mentoring sessions for established professionals and aspiring talent seeking a career in film, music, marketing, journalism and creative media.

Lauryn Hilllauryn hill pic

September 1


No matter how many times Ms. Hill is delayed during her concerts, her loyal fanbase continues to come out to sold out venues waiting to hear her hits from The Fugees, to the Miseducation masterpiece and her latest musical works. This is a ‘must-see’ and ‘don’t-to-miss’ show.

Stay tuned throughout the summer for the latest events, festivals, neighborhood programs and social gatherings around our beautiful city.

Have a hot restaurant, cool event, dope find? Make sure to email us your event:

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