Food & Drink in Chicago

Monday, Oct 5

Late Night Concert Series w/Andrew Toombs

Andy's Jazz Club & Restaurant

Enjoy a late-night concert featuring Andrew Toombs in a cozy jazz club. Ideal for jazz lovers and night owls.

Monday, Oct 5

Jeremy Bell

Redhead Piano Bar

Experience an exciting night with Jeremy Bell at the Redhead Piano Bar, perfect for late-night entertainment.

Monday, Oct 5

Monday Drink Special: $7 22oz Fatpours

Hopsmith Chicago

Enjoy $7 draft beers in 22oz mugs every Monday at Hopsmith. A great way to kick off your week.

Monday, Oct 5

Happy Hour in Gold Coast at Hopsmith

Hopsmith Chicago

Enjoy daily drink specials and happy hour at Hopsmith Chicago, known for its friendly staff and vibrant atmosphere.

Monday, Oct 5

Happy Hour

Woodie's Flat

Enjoy drink and food specials during Happy Hour at Woodie's Flat. A great spot to unwind after work.

Monday, Oct 5

1st Set With The Blueshift Big Band

Andy's Jazz Club & Restaurant

Enjoy live jazz music with The Blueshift Big Band at Andy's Jazz Club. A perfect night for jazz lovers in Chicago.

Monday, Oct 5

Injustice Watch : Check Your Judges

The California Clipper

Attend the Check Your Judges Election Guide event with music and free drink tickets. Ideal for community engagement.

Tuesday, Oct 6

Trivia at Fatpour Wicker Park

Fatpour McCormick: Ultimate Chicago Sports Bar

Join us for General Knowledge trivia at Fatpour Wicker Park. A fun night for trivia fans and friends looking to compete.

Wednesday, Oct 7

De Aquí Y De Allá : Ulises

The California Clipper

Celebrate Hispanic Heritage Month with specialty cocktails at De Aquí Y De Allá: Ulises in Chicago.

Thursday, Oct 8

The Judgment of Paris Wine Dinner

Mastro's Steakhouse

Join us for a wine dinner featuring iconic wines at Mastro's Steakhouse. Perfect for wine enthusiasts.

Friday, Oct 9

2000's Party (Chicago)

Howl at the Moon Chicago

Join the 2000's Party at Howl at the Moon for a night of Y2K music and drink specials. A fun night for nostalgia lovers.

Saturday, Oct 10

Chicago Spritz Fest - Bubbly Cocktail Tasting

IO Godfrey Rooftop Lounge

Enjoy four hours of bubbly cocktails at this unique tasting event. Ideal for cocktail lovers and social drinkers in Chicago.

Saturday, Oct 10

Chicago Fire FC vs. New York City FC

Fatpour McCormick: Ultimate Chicago Sports Bar

Watch Chicago Fire FC take on New York City FC at Soldier Field. A great match for soccer fans.

Monday, Oct 12

The Metalliques - Live

Skylark

Enjoy a free live performance by The Metalliques at Skylark in Chicago. A vibrant night for music lovers.

Tuesday, Oct 13

1st Set With Henry Johnson %26 Charles %26#8216;Rick’ Heath

Andy's Jazz Club & Restaurant

Experience live jazz with Henry Johnson and Charles 'Rick' Heath at Andy's Jazz Club & Restaurant.

Tuesday, Oct 13

October Member Meeting

CHAOS Brew Club

Meet club members and tour the brewhouse at the October Member Meeting. An inviting event for beer enthusiasts.

Thursday, Oct 15

2026 Sam Adams Stein Hoisting Contest!

Timothy O'Toole's Pub Chicago

Join the fun at the Sam Adams Stein Hoisting Contest at Timothy O'Toole's Pub. Compete for prizes in a spirited atmosphere.

Saturday, Oct 17

SATURDAY OCTOBER 17: COMEDY BRUNCH! FEATURING BAD MOMZ OF COMEDY

The Comedy Bar

Enjoy a hilarious brunch with Orly K.G.'s Bad Momz of Comedy at The Comedy Bar. A fun event full of stand-up and laughs.

Monday, Oct 19

Sips x Z Bar - October 19

Z Bar

Join Sips at Z Bar for a curated cocktail evening. Ideal for cocktail enthusiasts and social gatherings.

Wednesday, Oct 21

Ghouls Night Out Paint & Sip!

Timothy O'Toole's Pub Chicago

Enjoy a fun paint and sip night with art supplies included and themed drinks. A great evening for friends or date night.

Wednesday, Oct 21

A Chillingly Chic Pumpkin Paint Night

ERIS Brewery and Cider House

Join us for a fun pumpkin painting night at ERIS Brewery and Cider House. A creative evening with friends awaits.

Saturday, Oct 24

Timmy's Tailgate For A Cause! With Noon Whistle & Sun Cruiser

Timothy O'Toole's Pub Chicago

Join Timmy's Tailgate for a Cause benefiting cancer research. Enjoy food and drinks while supporting a great cause in Chicago.

Sunday, Oct 25

John Primer & The Real Deal Blues Band

Rosa's Lounge

Join us for a night of blues with John Primer & The Real Deal at Rosa's Lounge. Perfect for blues enthusiasts and late-night music lovers.

Sunday, Oct 25

John Primer & The Real Deal Blues Band

Rosa's Lounge

Enjoy a night of blues music with John Primer and his band at Rosa's Lounge. Ideal for blues lovers and late-night music fans.

Sunday, Oct 25

Sunday Brunch Stand Up Comedy

Laugh Factory

Enjoy a fun Sunday brunch with stand up comedy at Laugh Factory. Ideal for comedy lovers.

Wednesday, Oct 28

Halloween Singo - Music Bingo!

Timothy O'Toole's Pub Chicago

Join Halloween SINGO Music Bingo at Timothy O'Toole's Pub for a fun twist on bingo. A festive night for music lovers and bingo fans.

Thursday, Oct 29

Noir at the Bar

ERIS Brewery and Cider House

Join local authors for a thrilling night of crime novels at ERIS Brewery and Cider House. A unique literary experience.

Thursday, Oct 29

From Lava to Vine: A Volcanic Wine Dinner

The Village

Explore volcanic wines with a curated dinner at The Village. Perfect for wine enthusiasts and food lovers.

Friday, Oct 30

Halloween Party at Howl at the Moon Chicago

Howl at the Moon Chicago

Celebrate Halloween with live music and a costume contest at Howl at the Moon Chicago. A lively night for party-goers.

Saturday, Nov 14

Godfrey Wine Fest - Wine Tasting at I|O Godfrey Rooftop in Chicago

IO Godfrey Rooftop Lounge

Sample a variety of wines at the Godfrey Wine Fest in Chicago. A unique experience for wine lovers at a rooftop venue.