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17 Of Our Favorite Events In Chicago This Weekend

By Michelle Meywes Kopeny in Arts & Entertainment on Jul 29, 2016 2:48PM

Party with Questlove on Sunday. Photo courtesy of Virgin Hotels Chicago.

Lollapalooza is in full swing in Grant Park, but there are still fun things to do all over the city this weekend.


LOLLAPALOOZA: The mother of all Chicago music festivals is already underway and continues through Sunday. Each summer for the last 12 years, Lollapalooza has taken over Grant Park, gobbling up more and more land every time. This year, the fest has grown from three days to four, so you have a whole extra day to take in hot bands, get fucked up and make bad decisions. Headliners include Radiohead, Red Hot Chili Peppers and LCD Soundsystem, but don’t miss out on those up-and-comers early on the schedule and on the side stages (check out some of our early picks here). Some local acts that made the bill are rapper Towkio, hip hop artist Vic Mensa and DJ duo Flosstradamus. GA tickets sold out immediately, but check those re-sale sites. VIP and Platinum packages are still for sale.

TALL SHIPS: Get your maritime hat on for the Tall Ships return to Navy Pier. Festivities continue through the weekend with opportunities to view, tour and even sail on the vintage vessels. Tickets start at $10.

JEFF FEST: Jefferson Park gets its own festival inside Jefferson Memorial Park this weekend. Food, art & craft vendors, fun for the kids and live music from the city’s hot cover bands will all be part of the northwest neighborhood fest. This year they’ve also added "Wine Tasting in the Park" on Saturday and Sunday from 3 to 6 p.m. Daily wine tasting passes are $20. Fest entry is a $5 gate donation benefiting the Jefferson Park Chamber of Commerce.

Photo courtesy of Newberry.

BOOK FAIR: Newberry’s 32nd Annual Book Fair is here and they’re selling more than 120,000 used books, vinyl records, and collectibles. Collectors can get their hands on that uncorrected proof of A Game of Thrones signed by author George R. R. Martin, first editions of F. Scott Fitzgerald or just pick up a quick read. The Book Fair goes all weekend, with the 30th anniversary of the "modern" Bughouse Square debates happening across the street in Washington Square Park on Saturday. Free.

BLOOMS + BORDEAUX + BEARS: Lincoln Park Zoo plays host to Bites, Blooms and Bordeaux from 6 to 9 p.m. The event, as titled, will have wine, horticulture conservation and gourmet snacks, plus live music. There’s also a VIP option that includes a wine-blending session with American Wine School. Tickets are $79 ($110 VIP).

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Photo via Fiesta del Sol's Facebook page by Alexandra Castro.

FIESTA DEL SOL: The largest Latino in the Midwest has carnival rides, live entertainment, local art and so much more in the Pilsen neighborhood this weekend. Fiesta del Sol also celebrates and gives back to the community with a Civil Rights of Immigrants Booth, College Fair, Health Booth and more. Admission is free.

PUNK4GOOD: Non-profit PUNK4GOOD hosts a party to support Everytown for Gun Safety at Township at 6 p.m. They’re calling it Drop Yr Weapons! and they’ll have live music from some local rock mainstays, plus raffle prizes and a silent art auction with works from David Yow, Jon Langford and many others. Performers include All Eyes West, Josh & Eli Caterer (The Smoking Popes), Tim Kinsella (Joan of Arc Band) and more. Tickets are $8.


WATER SLIDE CITY: A giant Slip-and-Slide hits Cricket Hill at Montrose Beach this Saturday from 9 a.m. to 6 p.m. Slide The City has two “wave times” for adventurers to take unlimited slides down the hill and party. Slide passes start at $25.

MICROBREW CRAWL: The website may be in retirement, but the spirit of Gapers Block is still alive and well, hosting a local Microbrewery Crawl this Saturday from 10:30 a.m. to 5:30 p.m. The crawl will stop at Lagunitas, Off Color Brewing, Dovetail and The Finch Kitchen, and includes tours at each brewery. They’ll also have food trucks along the way so you don’t overdo it on the brews. Tickets are $45.

RANDOLPH STREET MARKET: July’s Randolph Street Market has a “Tropical Punch” theme, and the usual suspects when it comes to vintage, antique and one-of-a kind vendors. They’ve also got live music, drinks from the Market Bar, and a fancy food market. The urban market takes place inside and outside Plumbers Hall from 10 a.m. to 5 p.m. Saturday and Sunday. Tickets are $8 in advance.

Photo courtesy of Simmer Brown Comedy.

STAND UP COMEDY: South Asian Comedy collective Simmer Brown continues to grow, adding two seasoned associate producers who will be performing at Saturday’s show at Bughouse Theater. The “New Faces” show will also feature performances from founders Sameena Mustafa and Prateek Srivastava, who recently appeared at the NBCUniversal Break Out Comedy Festival. 8 p.m. Tickets are $15.

MARGARITA FESTIVAL: A festival of margs? Count us in. The outdoor Chicago Margarita Festival at South Shore Cultural Center will have a beach vibe with tastings, live music and food trucks. Fest opens at noon Saturday and Sunday. Tickets start at $15 per day.

MIXOLOGY ACADEMY: Tiki drinks are all the rage, and at La Mez Agave Lounge’s Mixology Academy, you can construct your very own with the help of head mixologist Dylan Stewart. Learn the perfect proportions and a little bit of history while mixing up “Umbrella Drinks” inside Mercadito’s new downstairs lounge. 3 p.m. Cost is $45. RSVP by calling 312-329-9555.

FREE CHEESECAKE: Get a free Eli’s cheesecake sample for National Cheesecake Day at every Mariano’s location this Saturday. They’ll also have an opportunity to win cheesecake for a year.


Photo via Albany Park Theater Project's website.

REAL LIFE THEATER: Experience the real-life struggles of CPS students with Albany Park Theater Project’s new production, “Learning Curve,” opening Sunday. Partnered with Third Rail Projects and Goodman Theatre, the immersive performance takes place inside Ellen Gates Starr High School with a cast of 32 youth artists. Audience size is limited to 40 people per show to keep with the intimate experience. Runs through November 19. Tickets are $40.

LOLLA ROOFTOP PARTY: Continue the Lolla party outside the festival grounds and up on the Cerise rooftop bar at Virgin Hotels Chicago. Questlove will start your day with a DJ set starting at 2 p.m., and pop group Haim will close the night with a DJ set at 11 p.m. Free.

BACKYARD BBQ: It’s the second installment in bellyQ’s Backyard BBQ Series, and this month the guest chef is Michael Jordan’s Steak House’s Executive Chef Craig Couper. He’ll be grilling up Lobster, Sourdough Toasts with Country Ham, Sweet Corn and more, all with a special twist. 1 to 4 p.m. Tickets are $45.