Your Chicago Curated Weekend: 5/23 and Beyond

Memorial Day Weekend crept up on us this year! As did all the amazing street festivals that are always a staple of Chicago summers. Plus add to that all the amazing concerts at our favorite venues, great movies throughout the city, markets, art exhibitions, and so much more just waiting for you! Don't let these fantastic events pass you by; start planning your perfect weekend in Chicago!

Now, let's get on with your Chicago Curated Weekend!




ChiTown Movies @ Pilsen Neighborhood, 2343 S. Throop St, Various Times, All Ages
An old school experience for the modern age
SO WHAT: Take a trip back in time and head out to a drive-in movie with ChiTown Movies. Ever since the pandemic started and shut down traditional movie screening, a few pop up drive-ins have arrived and ChiTown Movies has persevered, offering up modern movies in this retro setting. Check out their lineup below for showings this weekend and in the future!

NOW WHAT: Tickets are $35 per car for these movies, so bring the family for a safe movie watching experience

Belmont-Sheffield Music Festival @ Sheffield from Belmont Ave. to Roscoe St., 3200 N. Sheffield Ave., Friday 5pm-10pm, Saturday and Sunday 11:00am – 10:00pm, all ages
WHAT: The annual Belmont-Sheffield Music Festival!
SO WHAT: Spend your weekend at the Belmont-Sheffield Music Festival and catch some fun local tribute bands on the main stage (near Roscoe), great eats, a few drinks (beer and wine) and pick up some cool items from some incredible artisans. There will also be an eclectic “community” entertainment stage (near Belmont) featuring fun neighborhood music acts, DJs, and other performers. Check out the lineups at their event page!
NOW WHAT: Head out and enjoy the Northside festival!

Festival Mole de Mayo 2023 @ Pilsen on 18th St. Between Halsted and Morgan, Friday & Saturday Noon – 10:00pm, Sunday Noon – 9:00pm, All Ages
Mole, a staple of Mexican dishes, is delicious. That alone should be enough to convince you to go.
SO WHAT: Mole De Mayo is an excellent three-day event showcasing the wonderful dish mole and pitting local chefs and restaurants against one another to find out whose version of the Mexican staple is best. Two awards will be up for grabs: Mole de Mayo’s Best Mole Award & People’s Choice Award. There will also be live music the whole weekend including Dos Santos; Galli Lucha Libre (that’s some good old fashioned wrastlin’) on Saturday and Sunday 3pm-5pm, an open-air Mercado/Market with plenty of merchants and artisans, amazing food vendors, and a whole bunch of other cool stuff in Chicago’s epicenter of Mexican culture. Check out the rest of the festivities at their event page!
NOW WHAT: There’s a $5 suggested donation for individuals and $10 for families at the gate.

The Neo-Futurists’ The Infinite Wrench @ The Neo-Futurist Theater, 5153 N Ashland, Friday and Saturday 10:30pm, Sunday 7:00pm, 16+
WHAT: Quick plays live and online!
SO WHAT: The Neo-Futurists are back! Their Infinite Wrench is an  ongoing, ever-changing attempt to perform 30 plays in 60 minutes for a live audience. Now it’s actually a live audience that will be enjoying the performance in person!
NOW WHAT: Join the Neo-Futurists this weekend for $20!  The Infinite Wrench Goes Viral will be continuing til February (and possibly beyond) over at their Patreon


Mayfestiversary 2024 @ Dovetail Brewery & Begyle Brewing, 1800 W Cuyler Ave, Saturday 11am– 10:00pm, Sunday 11am– 9:00pm
WHAT: Mayfestiversary returns!
SO WHAT: Begyle Brewing and Dovetail Brewery are teaming up again for two days of amazing beer, live music, and the finest food trucks this city has to offer! Check out the full lineup of music and food over at their event page.
NOW WHAT: Entry is free! The suggested donation of $5 goes to The Friendship Center and their mission of fostering hope and dignity through access to food, vital resources, and critical social services in the community!

Sueños Music Festival @ Grant Park, 337 E Randolph St, Noon – 10:00pm, 18+
Another edition of the Latin Music festival Sueños !
SO WHAT: Sueños is the perfect festival for Latin music fans!  This brand new 18+ fest will be taking over Grant Park with tons of talented Reggaeton and Latin artists for an unforgettable weekend. Dance your weekend away with headliners like Peso Pluma, Ivan Cornejo, Rauw Alejandro, Maluma and many more!
NOW WHAT: Two-day passes are $535 , VIP are $1488, and El Sueños passes are $1920!

Randolph Street Market Festival @ 1341 W Randolph St., 10:00am – 5:00pm
WHAT: This fun street market is back for another great year!
SO WHAT: Celebrate the Randolph Street Market Festival where you can experience over tons of vendors with a wide variety of items perfect for the summer season! Shop for vintage and antique items while enjoying a drink and the live music playing throughout the market!
NOW WHAT: Tickets start at $12, which are good for both days and go up with a nice selection of tiers including drink packages, totes, and more!

Wingout Chicago @ Gallagher Way, 3635 N Clark St, Noon – 9:00pm
WHAT: Some delicious wings for your weekend
SO WHAT:WingOut Chicago is an outdoor, chicken wing block party, offering all-you-can-eat wings from the top vendors in the city.  Beyond the delicious treats, there will be a live music stage, a la carte food items for order, shopping, and cold beverages.
NOW WHAT: Pre-sold tickers are sold out, but walk up tickets may be available after 5pm!


Summer Fireworks @ Navy Pier, 600 E. Grand Avenue, 10:00pm – 10:10pm
WHAT: Enjoy the spectacle of fireworks all summer long
SO WHAT: Take a trip to Navy Pier and check out their dazzling display of fireworks! Each show features dramatic and popular music soundtracks with some special occasion soundtracks sprinkled throughout the season. It’s the first fireworks show of the year so kick off summer with this explosive tradition.
NOW WHAT: It’s free!  Just make your way to Navy Pier, find a spot, and enjoy the show !


Weekend Shows @ Lincoln Hall & Schubas, 2424 N Lincoln Ave & 3159 N Southport Ave, various times, 18+
WHAT: A full weekend of amazing shows at Schubas and Lincoln Hall!
SO WHAT: Lincoln Hall and Schubas are some of our favorite venues in the city and they always have something great going on. Check out what's going this weekend at these great venues

NOW WHAT: Head out to Schubas & Lincoln Hall and enjoy this great lineup of shows!

Movies on the Big Screen and Home @ Music Box Theatre, 3733 N Southport Ave, various times
A great way to support a great local theater
SO WHAT: The Music Box Theatre is ready to fill that art house need in you with some excellent movies like Babes, Wildcat, Songs of Earth, From Here to Eternity, First Blood, Midnight screenings of The Room & Stop Making Sense and more!
NOW WHAT: Sit back and enjoy a new film at one of our favorite movie theatres in the city!

Chicago Humanities: New Talks and Video Archives @ Various Locations & Chicago Humanities Festival YouTube channel, your favorite browser or YouTube app, any time you want some inspiration, All Ages
WHAT: Interesting conversations with interesting people!
SO WHAT: Chicago Humanities Festival always brings some of the best ideas to the surface with entertaining programming that captures your imagination. Their year may be over, but certainly be on the lookout for updates for next year's season as their website is constantly updated with new talks. 

NOW WHAT: Head over to take a look at their past events here! You should also sign up for their email list to get updates on upcoming talks in 2023

University of Chicago Folk Festival @ Your favorite spot in your home, All Ages
WHAT: A fantastic folk festival
SO WHAT: University of Chicago Folk Festival might have come and gone but their digital presence is still around, making sure the wonderful music reaches as many people as possible! You can check out the past few years of performances on their Facebook page and their YouTube channel any time you want! This past year's performers included The Price Sisters, Brian Conway, Jerron "Blind Boy" Paxton, Ruby John, Sean "Mack" McDonald, and many more!
NOW WHAT: Head over to their Facebook page and their YouTube channel and enjoy the show! We highly encourage you to donate to help support this fantastic folk festival!

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Julian Ramirez