Name: Live Music at Boleo Chicago
Start: 2026-05-20T18:00:00-05:00
Location: Boleo

Boleo

Boleo Chicago is turning up the rooftop vibes this season with live music performances paired with skyline views and Latin-inspired flavors. Guests can enjoy live sets from Spanish guitarist David Chiriboga every Wednesday through Friday, along with soulful Saturday performances by Patrick Jasper on the 2nd and 4th Saturdays of each month from 5–8 p.m. With vibrant music, craft cocktails, and a lively rooftop atmosphere, Boleo is the perfect spot to soak in summer nights in downtown Chicago.

Local Event: Live Music at Boleo Chicago

Chicago

Cook County

Chicago Metropolitan Area

Illinois

Live Music at Boleo Chicago

Boleo Chicago is turning up the rooftop vibes this season with live music performances paired with skyline views and...

Mariano's

Mariano’s Northbrook 
Tuesday, May 19 
4:00 PM – 6:00 PM
Join us for an exclusive in-store wine experience featuring Elizabeth Vianna, acclaimed winemaker of Chimney Rock Winery. Discover the story behind one of Napa Valley’s most celebrated wineries while tasting exceptional wines and connecting directly with the visionary behind them.
Featured Wines: 
• Elevage Blanc – Proprietary White Blend 
• Stags Leap District – Cabernet Sauvignon 
• Elevage – Proprietary Red Blend 
• Tomahawk Vineyard – Cabernet Sauvignon
Event Highlights: 
• Learn about the artistry, passion, and winemaking process directly from Elizabeth 
• Enjoy tastings of Chimney Rock wines 
• Exclusive bottle signing with purchase 
• Discover new favorites and expand your wine knowledge
Whether you’re a seasoned wine enthusiast or simply looking for a fun and engaging evening, this is an experience you won’t want to miss. We hope to see you there.
Meet Elizabeth Vianna: 
Elizabeth Vianna, a native of São Paulo, Brazil, discovered her passion for winemaking after an inspiring tasting experience shifted her path from pre-med studies at Vassar College to pursuing enology at University of California, Davis. She began her journey with Chimney Rock Winery as a harvest intern in 1999 and rose to head winemaker in 2005, later becoming General Manager in 2011. With more than two decades at the winery, Elizabeth is celebrated for crafting highly acclaimed wines and for her deep commitment to the Stags Leap District, where she has also served as President of the Winegrowers Association.

Local Event: Meet the Winemaker: Elizabeth Vianna of Chimney Rock Winery at Mariano's!

Meet the Winemaker: Elizabeth Vianna of Chimney...

Mariano’s Northbrook 
Tuesday, May 19 
4:00 PM – 6:00 PM
Join us for an exclusive in-store wine experience featuring Elizabeth...

Meet the Winemaker: Elizabeth Vianna of Chimney Rock Winery at Mariano's!

Mama Delia

Get ready, Chicago, patio season is calling! Join us in Wicker Park this Tuesday, May 19 for the 4th Annual Patio Palooza, where we’ll take over Division Street for an unforgettable evening of outdoor dining and neighborhood exploration. Stroll from patio to patio and savor delicious small bites and signature appetizers from top local restaurants.
This popular crawl is a true celebration of Wicker Park’s vibrant food &amp; patio scene and it sells out every year, so don’t wait! Check-in runs from 5:30-7:00 p.m.

Local Event: Wicker Park Bucktown Patio Palooza

Wicker Park Bucktown Patio Palooza

Get ready, Chicago, patio season is calling! Join us in Wicker Park this Tuesday, May 19 for the 4th Annual Patio Palooza,...

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago celebrates the season with its annual LH Rooftop Opening Party on Tuesday, May 19. Guests can enjoy 25 percent off lunch, Veuve Clicquot specials, grab bags and live DJs, all set against sweeping views of the Chicago River and skyline. <a href="https://www.exploretock.com/lhrooftop" rel="nofollow noopener" target="_blank"></a>

Local Event: LH Rooftop Official Summer Launch Party

LH Rooftop Official Summer Launch Party

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On Wednesday, May 20, all Pop’s Beef locations will offer a discounted 6” Italian beef sandwich for $5.99. With every purchase, guests will also receive a bounce-back card redeemable during the month of June for one discounted 6” beef sandwich at $5.99.

Local Event: Pop's Beef Celebrates National Italian Beef Day

Pop's Beef Celebrates National Italian Beef Day

On Wednesday, May 20, all Pop’s Beef locations will offer a discounted 6” Italian beef sandwich for $5.99. With every purchase,...

Presented in commemoration of the 80th Anniversary of the Weber&nbsp;Siblings’ arrival in America!&nbsp;***Now streaming on Netflix***
UnBroken&nbsp;is the true story of the seven Weber siblings, ages 6 to 18, who evaded capture and death and&nbsp;ultimately escaped&nbsp;Nazi Germany following their mother’s incarceration and murder at Auschwitz. Hidden in a laundry hut by a German farmer, the children spent two years on their own in war-torn Germany, emboldened by their father’s mandate that they always stay together. Separated from their father, the siblings were forced to declare themselves orphans&nbsp;in order to&nbsp;escape to a new life in America. That salvation would become what finally tore them apart. They would not be reunited for another 40 years.&nbsp;
Directed by&nbsp;Beth Lane, daughter of the youngest Weber sibling, the film builds its story from the voices of the surviving siblings themselves, recorded in their eighties and nineties, alongside Lane’s own journey retracing the family’s path across Germany. She walks the roads they walked. She stands in the village where they&nbsp;hid. She asks the questions her family spent a lifetime learning not to ask. The result is a work of deep personal excavation that also functions as a piece of historical urgency. The film won Best Documentary Premiere at the Heartland International Film Festival, became Oscar-qualified in February 2025, and has been seen by more than 1.5 million viewers since its Netflix debut on Yom HaShoah.&nbsp;Legendary film critic and former co-host of At the Movies with Roger Ebert, Richard Roeper will lead a conversation with Holocaust Survivor Ginger Lane, the youngest of the Weber siblings whose story anchors the film, and her daughters, Jen Lane Landolt, Executive Producer and Treasurer of the Weber Family Arts Foundation, and the film’s Director, Producer and Writer, and President of The Weber Family Arts Foundation, Beth Lane, marking the anniversary of the siblings' arrival and resettlement in the United States. After emigrating in 1946, Alfons, Senta, Ruth, Judith, Renee, Gertrude, and Bela Weber established their lives in Hyde Park on Chicago's South Side, with the sponsorship of the Chicago Jewish Children's Bureau.

Free to the public.
Reservations&nbsp;required.&nbsp;

Local Event: Sold Out - Film Screening & Discussion: UnBroken (now streaming on Netflix)

Sold Out - Film Screening & Discussion:...

Presented in commemoration of the 80th Anniversary of the Weber Siblings’ arrival in America! ***Now streaming on...

Sold Out - Film Screening & Discussion: UnBroken (now streaming on Netflix)

The Lincoln Lodge

Get the late night talk show experience without heading to NYC or LA.

The Not That Late Show is a POC- and queer-led late-night talk show hosted by Justin Swinson, featuring an ensemble of Chicago comedians debuting brand-new material each month. NTLS is just like the late night talk shows you would see on TV (Colbert, The Daily Show, Last Week Tonight, etc.), but with a Chicago focus. Taking place every third Wednesday at The Lincoln Lodge, the show blends sketch comedy, sharp interviews, and live music from emerging local artists. Past guests have included Mayor Brandon Johnson; Writer and Educator Dr. Eve L. Ewing; Viral Chicago Attorney, Rachel Cohen; and Medea Benjamin of CODEPINK among others.

This month's guest is Leftist political commentator, Lily Eagla.

Local Event: Leftist political commentator Lily Eagla joins Chicago’s Late Night Talk Show

Leftist political commentator Lily Eagla joins...

Get the late night talk show experience without heading to NYC or LA.

The Not That Late Show is a POC- and queer-led...

Leftist political commentator Lily Eagla joins Chicago’s Late Night Talk Show

NOTICE: Join the Chicago Astronomer at Horner Park - Thursday 21 May 2026 - 7:30 pm to 9:30 pm. We will enjoy the conjunction line-up of Jupiter, Venus and the Moon. If you have one, bring your telescope and join the crew as we explore the skies and engage in astro chat. Be there with the cool kids...you know you want to.Astro Joe

Local Event: The Chicago Astronomer at Horner Park

The Chicago Astronomer at Horner Park

NOTICE: Join the Chicago Astronomer at Horner Park - Thursday 21 May 2026 - 7:30 pm to 9:30 pm. We will enjoy the conjunction...

Lincoln Park

Bucktown-Wicker Park

Lakeview

North Center-Roscoe Village

Hyde Park

West Side

Lorraine Swanson

South Side

Lincoln Square

Oak Park-River Forest

Forest Park

British International School of Chicago, South Loop

Our school is dedicated to shaping a generation of successful, creative, and resilient global citizens. Our inclusive community and personalized international curriculum combine the best of both worlds, giving our Preschool, Primary, Middle School and High School students a truly global outlook rooted in Chicago’s rich heritage.

British International School of Chicago, South...

Our school is dedicated to shaping a generation of successful, creative, and resilient global citizens. Our inclusive community and personalized...

Trusted Chicago Real Estate Investment Company since 2011

Braddock Investment Group Inc

Braddock Investment Group Inc is a Chicago-based real estate investment and consulting firm specializing in helping homeowners sell their houses fast and without stress. Serving Chicago homeowners since 2008. Incorporated in 2011, Braddock has worked with property owners across Chicago and surrounding suburbs to provide straightforward, as-is home sale solutions with fair cash offers and flexible closing timelines. As professional cash home buyers in Chicago, Braddock purchases houses in any condition — no repairs, no agent commissions, and no hidden fees. Whether a property needs significant updates, has tenant complications, or has been inherited through probate, the company offers a simple process designed to eliminate uncertainty and delays. Braddock Investment Group works with homeowners facing foreclosure, inherited property situations, divorce transitions, landlord fatigue, major repairs, or unexpected life changes. The team understands that selling a home quickly is often about more than just price — it’s about clarity, timing, and reducing stress during challenging moments. With deep knowledge of the Chicago real estate market, Braddock provides transparent evaluations and straightforward offers backed by local experience. The company has successfully completed hundreds of property transactions throughout Chicago neighborhoods and nearby communities, helping homeowners move forward confidently. Beyond property acquisition, Braddock is committed to improving local housing stock by revitalizing properties and contributing to neighborhood stability. Their approach combines efficiency with integrity, offering Chicago homeowners a reliable alternative to the traditional listing process. Homeowners searching for a trusted Chicago company that buys houses for cash can connect directly with Braddock Investment Group to explore options and receive a no-obligation offer tailored to their timeline and goals.

Braddock Investment Group Inc is a Chicago-based real estate investment and consulting firm specializing in helping homeowners sell their houses...

Chicagoland Firearm Training

We have been around for 30+ years, so you get a lot of experience from the owner Mr. Don Haworth that is a Certified USCCA Instructor. Also, he is a Marine Corp. vet You don't stay in business for 30+ years if you don't know what you are doing.

We have been around for 30+ years, so you get a lot of experience from the owner Mr. Don Haworth that is a Certified USCCA Instructor. Also, he is...

Custom Home Care - Personalized care that feels like family

Custom Home Care

Custom Home Care, LLC is a licensed Home Services Agency and Home Nursing Agency based in Chicago, Illinois. Founded in 1994 by Registered Nurse Tamara Jackson, the company has been helping seniors across the greater Chicagoland area live safely and independently at home for more than 30 years. Guided by a nurse-managed approach, Custom Home Care carefully matches dependable, qualified caregivers with each client to deliver compassionate, professional support. Today, the family-owned agency is recognized as one of Chicago’s most trusted providers of senior care, employing more than 300 care professionals and serving over 10,000 clients since its founding.

Custom Home Care, LLC is a licensed Home Services Agency and Home Nursing Agency based in Chicago, Illinois. Founded in 1994 by Registered Nurse...

Gold Coast Sounds Good Choir

Chicagoland's largest no-audition choral program for adults "55 and better" has nine choirs throughout Chicago and the suburbs, including the Gold Coast. Conducted by Jonathan Miller, the choir rehearses and performs at the beautiful, historic Fourth Presbyterian Church on Chicago's Magnificent Mile, 126 E. Chestnut Ave. Three sessions a year are offered -- two 15-week sessions in the fall and spring, and one 8-week session in the summer). All sessions include: a weekly 90-minute rehearsal with an additional (optional) online Friday rehearsal; guidance and instruction by professional conductors and accompanists; licensed sheet music; accessible rehearsal and performance venues; and free, public performances by each choir. Registered singers are also free to rehearse and perform with as many of the nine choirs as they wish for just one registration fee per session. Scholarships are readily available -- call the Sounds Good office at 630.395.9542 to apply. Sounds Good Choir also offers the only choir in Illinois for adults with early-stage dementia and their care partners. The Good Memories program is specifically designed to provide a safe, welcoming community in which to sing, socialize, and have fun. For more information about either program, to register for a choir, or to learn about upcoming concerts, please visit soundsgoodchoir.org.

Chicagoland's largest no-audition choral program for adults "55 and better" has nine choirs throughout Chicago and the suburbs, including the Gold...

Best House Cleaning Services in Chicagoland Area

House Keep Up Chicago

House Keep Up Chicago offers cleaning services in Chicago, Illinois. Serving many happy clients and offering high-quality cleaning in the Chicagoland area. From one time standard deep cleaning, to recurring move-in and move out services. We offer a great selection and add-on options to serve every needs of our clients. We pride ourselves on making sure all of our maids and cleaners are paid and honest, living wage, ensuring your home is cleaned by the best professionals we can find.

House Keep Up Chicago offers cleaning services in Chicago, Illinois. Serving many happy clients and offering high-quality cleaning in the...

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Live Music at Boleo Chicago

Event Details

More Upcoming Events

Meet the Winemaker: Elizabeth Vianna of Chimney Rock Winery at Mariano's!

MAY

19

4:00 PM

Mariano's, 784 Skokie Blvd, Northbrook, IL

Wicker Park Bucktown Patio Palooza

MAY

19

5:30 PM

Mama Delia, 1721 W Division St, Chicago, IL

LH Rooftop Official Summer Launch Party

MAY

20

12:00 AM

LondonHouse Chicago, Curio Collection by Hilton, 85 E Wacker Dr, Chicago, IL

Pop's Beef Celebrates National Italian Beef Day

MAY

20

11:00 AM

7301 183rd St, Tinley Park, IL

Sold Out - Film Screening & Discussion: UnBroken (now streaming on Netflix)

MAY

20

6:30 PM

1850 2nd St, Highland Park, IL