Your Chicago Curated Weekend: 5/25 and Beyond

It’s another fun week in Chicago and the temps are rising again (hopefully for the rest of summer)! So let’s enjoy the spring vibes with some incredible markets, movies, a heaping offering of festivals, and more on this weekend’s calendar.

While it feels like the pandemic is behind us, you still need to be mindful when you go out this weekend and beyond. The winter season has seen a lot of colds, flu, RSV, and of course bouts of COVID. It’s better to be safe and wear a mask when you go out to big events. And if you’re still a little hesitant to go out, there are many events and things to do from home. So whether you’re staying in or going out, keep safe and stay healthy!

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


Chicago Humanities Festival Spring 2023: 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. Be on the lookout for updates to the upcoming season as their website is constantly updated with new talks.  Here is a taste of what’s coming up!

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

FRIDAY – SUNDAY, MAY 26th – 28th(& BEYOND)

Festival Mole de Mayo 2023 @ Pilsen on 18th St. Between Ashland & Blue Island, 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 Los Gallos, Dos Santos, 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.

Belmont-Sheffield Music Festival @ Sheffield from Belmont Ave. to Roscoe St., 3200 N. Sheffield Ave., 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!

Mayfestiversary 2022 @ Dovetail Brewery, 1800 W Belle Plaine Ave, Saturday Noon – 10:00pm, Sunday Noon – 9:00pm
WHAT: Mayfestiversary returns!
SO WHAT: Begyle Brewing and Dovetail Brewery are teaming up again for two days of amazing beer, live music, 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!

Randolph Street Market Festival @ 1341 W Randolph St., 10:00am – 5:00pm
WHAT: This fun street market is back after a few years away!
SO WHAT: Celebrate the return of the Randolph Street Market Festival where you can experience over 200 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!

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! With plenty of COVID precautions in place, you’ll be able to enjoy the funny, disgusting, profound, terrifying, irreverent, and downright entertaining show with friends!
NOW WHAT: Join the Neo-Futurists this weekend for $15! Head over to their website to see all they have planned now that in-person audiences are a thing again! If you’re still a little anxious about going out, The Infinite Wrench Goes Viral will be continuing til February (and possibly beyond) over at their Patreon


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 !

SATURDAY & SUNDAY, MAY 27th & 28th

Sueños: El Festival Latino @ Grant Park, 337 E Randolph St, Noon – 10:00pm, 18+
The second 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 Grupo Firme Wisin y Yandel. Other notable names on the lineup include Feid, Nicky Jam, Becky G, Arcangel. and many more!
NOW WHAT: Single day general admission passes are $199 & 2-day passes are $299 , VIP are $379/$599, and El Sueño passes are $1499!


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 $33 per car for these movies, so bring the family for a safe movie watching experience

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!

Back on the Big Screen and Virtual Cinema @ Music Box Theatre, 3733 N Southport Ave and at your home, any time you want to watch a movie
A great way to support a great local theater
SO WHAT: The Music Box Theatre is really to fill that art house need in you with some excellent movies including with Blackberry, L’Immensita, You Hurt My Feelings, The Claim, Paris, Texas, a midnight screenings of Coyote Ugly and Footprints on the Moon and more! But if you want to watch some first-run movies at home, you can still watch great movies and support them online! They are currently screening films via their The Music Box Direct series! There are also tons of select titles available on their new platform!
NOW WHAT: Digital subscription is $4.99 a month, $49.99 a year, in person screenings vary, so sit back and enjoy!

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 Balfa Toujours, Donka & Nikolay Kolev, Juan Rivera, Henry Barnes & Conner Vlietstra, Po’ Ramblin’ Boys, Jerron Paxton; Tim Britton, John Williams and Katie Grennan!
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!

Masque of the Red Coronavirus! @ Black Button Eyes Productions, Any time on your computer or mobile device. For 18+.
WHAT: Written by Black Button Eyes Productions producing artistic director Ed Rutherford, this short satirical piece is available online free as a combined script-and-video experience.
SO WHAT: In addition to reading the play, you will see various Chicago artists act out portions of the script on video, recorded remotely. The event includes puppets, burlesque, original music, fire dancing and more in a brief, darkly comedic confection.
With the Red Coronavirus running rampant across the countryside and a vaccine still months away, what’s a Prince to do? Lock himself in a secure bunker in an undisclosed location along with a cohort of his top donors, of course. To prevent him and his rich supporters from becoming bored, the Prince has also brought a few artists into the bunker to entertain the crowd. But as the hour grows later and the night grows weirder, it’s clear that something else has also invaded the party.
NOW WHAT: Settle down for an evening of this great story!

Julian Ramirez
Julian Ramirez