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Music & Comedy, Theatre & Performing Arts
moonwatchers
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
Thursday, April 30th
8:00 p.m. – Sunday, May 17th
2:30 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueMusic & Comedy, Theatre & Performing Arts
moonwatchers
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
Friday, May 1st
8:00 p.m. – Monday, May 18th
2:30 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueMusic & Comedy
Stargazers Adventure Club
Blast off with Stargazers Adventure Club in Planetary Games, an interactive space spectacular where imagination fuels the fun! You’ll learn planetary facts from out-of-this-world host,…
Saturday, May 2nd
10:00 a.m. – 11:30 a.m.Stars & Garters Theater
3914 N. Clark St.Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Music & Comedy, Tours & Attractions
Kentucky Derby Party at Utopian Tailgate: Down & Derby
Enjoy a Kentucky Derby watch party in perfect form at Utopian Tailgate; Old Town’s premier rooftop and high-energy party landscape. Saturday, May 2nd * 3pm to…
Saturday, May 2nd
3:00 p.m. – 6:00 p.m.Utopian Tailgate
1608 North Wells StreetFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Music & Comedy, Tours & Attractions
Kentucky Derby Party at The J. Parker: Running of the Roses Party
Enjoy the Kentucky Derby with no stakes and high limits at The J. Parker Rooftop. This Lincoln park attraction is sure to impress with its indoor/outdoor…
Saturday, May 2nd
3:00 p.m. – 6:00 p.m.The J. Parker
1816 North Clark StreetFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Music & Comedy, Tours & Attractions
Kentucky Derby Party at Parlay: Welcome To The Infield
Enjoy the Kentucky Derby with all the right style at Parlay (Lincoln Park). Dress up and throw down at one of the city’s finest indoor/outdoor…
Saturday, May 2nd
3:00 p.m. – 6:00 p.m.Parlay Lincoln Park
950 W Wrightwood AveFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Music & Comedy, Tours & Attractions
Kentucky Derby Party at Joy District: Welcome To The Grandstands
Enjoy the Kentucky Derby with a “Grand Stand” experience at the Rooftop of JOY District. This picture-perfect setting is sure to deliver a high-roller’s party scene…
Saturday, May 2nd
3:00 p.m. – 6:00 p.m.Joy District
112 West Hubbard StreetFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Music & Comedy, Tours & Attractions
Kentucky Derby Party at Paradise Park
Get ready for a day of big hats, cold drinks, and horse racing! Paradise Park is turning Wicker Park into your Derby Day destination with…
Saturday, May 2nd
3:00 p.m. – 6:00 p.m.Paradise Park
1913 W North AveFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Music & Comedy, Tours & Attractions
Kentucky Derby Party at ROOF on theWit: Derby Disco
Watch the Kentucky Derby 27 stories above Chicago at one of the top-rated rooftop bars in the world. ROOF on theWit puts a disco spin…
Saturday, May 2nd
3:00 p.m. – 6:00 p.m.ROOF on TheWit
201 N State St 27th FloorMusic & Comedy
McLuhan and Friends Celebrate Kentucky Derby Day
McLuhan & Friends: 4:00-5:30 pm Watch the Derby and Raffles (prizes): 5:40-6:10 pm Esmerelda’s Boys: 6:15-7:00 pm Happy Birthday to McLuhan band leader Neal Rosner!
Saturday, May 2nd
4:00 p.m. – 7:00 p.m.Phyllis’ Musical Inn
1800 W. Division StMusic & Comedy, Theatre & Performing Arts
You Win Some, You Dim Sum: an uplifting comedy show
We don’t celebrate our wins enough — so we made a comedy show where you can watch stand-up, win dim sum treats, and celebrate each…
Saturday, May 2nd
6:00 p.m. – 7:30 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Saturday, May 2nd
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Music & Comedy
Aurie Styla at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Aurie Styla is an award-winning comedian,…
Saturday, May 2nd
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
Matteo Lane – We Gotta Catch Up! Tour
Matteo Lane is bringing his much‑anticipated “We Gotta Catch Up!” comedy tour to Chicago, performing at the historic The Chicago Theatre on May 2, 2026 at 7:00 PM. Hailing from the Chicago area,…
Saturday, May 2nd
7:00 p.m. – 9:00 p.m.The Chicago Theatre
175 N. StateMusic & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Saturday, May 2nd
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy, Theatre & Performing Arts
Improvised Jane Austen
Improvised Jane Austen Improvised Jane Austen continues its entirely improvised tales of love and laughter. Audiences will enjoy an evening with wit and heart in…
Music & Comedy
Saturday Night’s Alright For Improv
Saturday Night’s Alright for Improv and Corn Productions is the best place to see it! Two Saturdays, two amazing line-ups, one great host. Hosted by…
Music & Comedy, Theatre & Performing Arts
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…
Music & Comedy
The Head and The Heart at Auditorium Theatre
Alternative music reigns over North America this 2026 because The Head And The Heart just plotted the North American dates and will be touring many…
Saturday, May 2nd
8:00 p.m. – 10:00 p.m.Auditorium
50 East Ida B. Wells DriveMusic & Comedy
The Head and The Heart at Auditorium Theatre
Alternative music reigns over North America this 2026 because The Head And The Heart just plotted the North American dates and will be touring many…
Saturday, May 2nd
8:00 p.m. – 10:00 p.m.Auditorium
50 East Ida B. Wells DriveMusic & Comedy
Katt Williams – Heaven On Earth Tour
On the heels of his explosive Netflix comedy special, WOKE FOKE, critically acclaimed comedian Katt Williams announces the HEAVEN ON EARTH TOUR. The upcoming tour…
Saturday, May 2nd
8:00 p.m. – 11:00 p.m.United Center
1901 W Madison St,Music & Comedy
Il Volo: North American 2026 Tour
Renowned Italian vocal trio IL Volo will perform live at Rosemont Theatre on May 2, 2026.
Saturday, May 2nd
8:00 p.m. – 11:00 p.m.Rosemont TheatreMusic & Comedy
They Might Be Giants – The Bigger Show Tour
They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…

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