Arts & Entertainment in Streeterville

There is so much to experience here in Streeterville. Among the choices are beautiful rooftop restaurants and lounges, theaters and museum. Streeterville is a small city with plenty of exciting things to see and do, especially at night. The nights shine brightly in Streeterville and there is no shortage of after-hours entertainment. Whether your taste is for culture or cocktails, there are plenty of options to keep you entertained.

We have some of the best rooftop venues to enjoy during the beautiful summer months. Rooftop dining in Chicago reaches new heights at The Dec, adjacent to Deca restaurant on the 12th floor of the Ritz-Carlton. This newest addition is a chic rooftop bar perched 12 stories above Chicago’s famed Magnificent Mile, serving up hand-crafted cocktails, light bites and unparalleled views. Stop by the Deca Bar in the lobby for light bites and live music on Friday and Saturday nights.

The Dec at 160 E. Pearson St., (312) 573‑5160, will reopen for the season in May. Hours will be noon to 10 p.m. Sunday-Wednesday and noon to midnight Thursday-Saturday. Deca Bar hours are 3 p.m. to midnight Sunday-Thursday and 3 p.m. to 1 a.m. Friday-Saturday.

The lobby bar inside Loews Chicago is open from 7 p.m. to 4 a.m. During the summer months, Loews opens its breathtaking terrace, the largest in the downtown area.

Drumbar, 201 E. Delaware Pl., inside the Raefaello Hotel is a cocktail-focused rooftop bar off Michigan Avenue. The bar boasts an intimate indoor lounge area and a beautiful outdoor terrace with views of Lake Michigan and the Hancock Center. The inside features a dark wood bar stocked with caramel-colored spirits, an assortment of roomy nooks both inside and out, outdoor fire pits and greenery plus great acoustics.

Step off the elevator on the 18th floor and see the space transformed from the hotel’s former meeting space into 4,000 square feet of indoor space and 2,000 square feet of outdoor space. Drumbar is open 5 p.m. to midnight, Monday through Wednesday; 5 p.m. to 2 a.m., Thursday through Saturday and from 5 p.m. to midnight on Sunday. For information, call (312) 933‑4805.

If you’re looking for a relaxing evening, The Terrace at the Peninsula, 108 E. Superior St., and Shanghai Terrace showcase breathtaking views of Chicago. Hours are 11:30 a.m. to 10:30 p.m. For information, call (312) 337‑2888.

Looking for a place to unwind and dance? Kick up your heels beginning at 9:30 p.m. on Friday and Saturday
evenings at The Palm Court at the Drake Hotel, 140 E. Walton Pl. For information, call (312) 787‑2200.

Are you a Frank Sinatra fan looking for live entertainment? Stroll on over to the famous Ditka’s Restaurant, 100 E. Chestnut St., for a performance by locally-celebrated singer Johnny Vincent. He performs there from 7 to 11 p.m., Tuesday through Saturday. You never know who you may see at this iconic eatery named after legendary Bears Coach Mike Ditka. For more information, call (312) 587‑8989.

Another great venue for live music is Winter’s Jazz Club at 465 N. McClurg (promenade), overlooking the Ogden Slip. The club offers happy hours  with no cover and 25 percent off all drinks Tuesday-Saturday 5:30 to 7 p.m. (Live music begins at 7:30 and 9:30 p.m. six nights a week, with emphasis on vocalists. The club’s mission is simple: to perpetuate the joy of live jazz by presenting the best interpretations of the best arrangements of the best songs in the canon of classic jazz
(and slightly beyond).  For more information, call (312) 344‑1270 or visit

Love the theater? Chicago Shakespeare Theater, 800 E. Grand Ave., at Navy Pier attracts a wide array of clientele with selections from William Shakespeare’s 38 plays and new classical plays too. The beautiful theater seats 510 people on three levels around the courtyard theater’s thrust stage and attracts about 225,000 visitors annually. The lineup for this year includes “An Inspector Calls,” “Macbeth” and “Hamlet.” For information, call (312) 595‑5600 or visit

Broadway in Chicago, formed in 2000, has grown to be one of the largest commercial touring homes in the country. Its five theaters have entertain more than 1.7 million audience members annually with highly acclaimed musicals and plays. A night out at Broadway Playhouse at Water Tower, The Oriental Theatre, Bank of America Theatre or Cadillac Palace Theatre will put you in the middle of the excitement of this Chicago tourism hub. For more information, call (312) 977-1700.

Lookingglass Theatre Company in the Water Tower Works on Michigan Avenue has an outstanding lineup for this year including “Treasure Island” and “Blood Wedding.” The theater at 821 N. Michigan Ave. received the 2011 Tony Award for Outstanding Regional Theater. For more information, call (312) 337‑0665.

Goodman Theatre, established in 1925, has been a part of life in Chicago for years. Every season, the Goodman presents the work of extraordinary stage plays such as “A Christmas Carol,” “Rejoice,” “Two Trains,” “Little Foxes” and “Rapture.” For tickets, call (800) 775‑2000 or visit

Porchlight Music Theater, 1016 N. Dearborn St., is known for its bold, edgy and intimate music theater. The exciting 2019 lineup includes “A Chorus Line,” “Minnie’s Boys,” “A Gentleman Guide to Murder,” and  “New Faces Sing Broadway.”

For more than two decades, Porchlight has been the city’s leader in music theater featuring Chicago and Broadway’s brightest music theater talent. For more information, visit or call the box office at (773) 777‑9884.

The Arts Club of Chicago is a private club in Streeterville, exhibiting international contemporary art. It was founded in 1916, inspired by the success of the Art Institute of Chicago. The Arts Club collection is a combination of acquisitions from its exhibitions and donations from both members and artists.

The club offers three to four public exhibitions each year, a permanent collection including work by many modern and contemporary masters and a diverse calendar of programming offered to its membership and guests. Its collection was acquired from its exhibitions and donated by members and artists. Works in the collection are by modern masters including Georges Braque, Alexander Calder, Natalia Goncharova, Paul Klee, Henri Matisse, Joan Miró, Henry Moore, Isamu Noguchi, Francis Picabia and Pablo Picasso.

For additional information, call the Arts Club at (312) 222‑2222 or visit