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Monday Nights in Chicago

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Wondering how to spend your Monday night while in the Windy City?  There are countless delicious restaurants and bars to choose from, of course, but what about after dinner?  Most theatres are dark on Monday nights- meaning the lights are quite literally off and “dark” since there aren’t any shows.  Luckily, there are plenty of fun, MONDAY specific things to do in Chicago.

Check out our Chicago Visitors Guide, with budget advice, travel guides, and information about local Chicago attractions

Here are a few of our favorite theatre performances, comedy shows, live music, and even painting activities!


Drink and Paint!

When: Every day- But Mondays are $5 off!

Where: Bottle and Bottega, 2900 N. Lincoln Ave

Nearest Public Transit: Brown line Diversey

Cost: $30- which includes the class and the painting

Bring your inner artist to Bottle and Bottega for an evening of painting!  They provide the paint, brushes, and canvas for your evening of channeling Monet.  Bottle and Bottega is B.Y.O.B. so you can bring your own wine or alcoholic beverage.  They have glasses and will uncork your bottles for you.  Each night a paint instructor will lead you through a different work of art that is on the calendar.  Every Monday is their “happy hour” where there class is $5 off.  Also, good news:  They will ship your painting for you (for an additional cost).

Bottle and Bottega
Looks like these folks are having a great time at Bottle and Bottega.


Barrel of Monkeys performs That’s Weird Grandma

When: Sundays at 2pm and Mondays at 8pm

Barrel of Monkeys
Barrel of Monkeys company members Elisa  Carlson, Jejf Trainor and Linsey Falls and the cast of THAT’S WEIRD, GRANDMA perform “Super Agent Max Jones,” directed by Geoff Rice. Photo by Beth Bullock.

Where: The Neo-Futurist Theater, 5133 N. Ashland

Nearest Public Transit: Red line Berwyn or Bus #22, #36

Cost: Tickets are $6 for kids and $12 for adults

Barrel of Monkey’s is a unique theatre company that works with Chicago public school elementary kids.  That’s Weird Grandma is a hilarious and often very touching collection of the stories and sketches inspired and written by the  kids in the theatre programs.  Their tagline is “written by kids. Performed by grownups. Enjoyed by humans.”  You can catch this show on Sunday and Monday nights at the Neo Futurarium. Best part?  This show is truly fun for all ages. Fun fact: That’s Weird, Grandma celebrates its 15th anniversary at the Neo-Futurist Theater in April 2016!


Second City presents Best of Second City

When: Mondays at 8:00pm

Where: 1616 N. Wells

Nearest Public Transit: Brown line to Sedgewick

Second City has grown to include several theatres; including a comedy club and many spaces to take classes.  There is always something to laugh about.  Mondays are great because the Touring company presents a compilation of the best sketches, songs, and improv! Tickets range from $17-$21.  You can really eat, drink, and be merry because the bar is always open!

Cost: Tickets are $17-$25


ioSee a show at i.O.

When: All Days; including Mondays shows at 8pm, 8:30pm, 10pm, 10:30pm

Where: 1501 N. Kingsbury St.

Nearest Public Transit: Red Line to North/Clyborn

Cost: Tickets range from FREE to $20

i.O. has four stages and every stage has a Monday night line up!  There are literally 7 different shows to choose from that vary in cost and style.  i.O. is known for improv and that is certainly what you will get any day that you visit.  People are literally making it all up.  Their new space has a great bar with food, too!


Live music at Petterino’s

When: Monday’s from 7:30pm-9:30pm

Where: Petterino’s, 150 N. Dearborn

Nearest Public Transit: Red/Brown/Pink/Orange/Blue Line Lake

Cost: The entertainment is free with a meal or drink.

Looking for a delicious Italian meal, a dessert with coffee, and possible a nightcap while being entertained?  Every Monday night, Petterino’s offers a live musical performance. They don’t typically tell you who will be performing unless you are their facebook fan.  You can see sneak peaks of the “impromptu” guests here.


Jazz at the Green Mill

When: Most Days; including Mondays from 9pm-1am

Where: 4802 N. Broadway Ave. Chicago, IL 60640

Nearest Public Transit: Red line Lawrence

Cost: Cover charge that ranges from $4 to $15

The Green Mill is known for two things: history and jazz.  This club used to have connections to Chicago mob history in the 20’s and is famed for being partly owned by an associate of Al Capone during prohibition.  Al Capone’s favorite booth is still found at the west end of the bar.  Nowadays, you can visit the Green Mill any night of the week for fantastic music and a cocktail.  They are

The Green Mill marquee in Chicago.
The Green Mill marquee in Chicago.

known for having some of the best jazz in Chicago.


Davenport’s Piano Bar

When: Open Mic (or entertainment) on Monday nights only

Where: 1383 N. Milwaukee

Nearest Public Transit: Blue Line to Division

Cost: Cover charge that ranges from $5-$10 with a 2 drink minimum

Davenport’s is a lively piano bar that features cabaret style music and comedy.  On Monday nights- you can take the stage during the open mic night from 7:30pm-10:30pm.  The pianist can play just about anything but bring sheet music if it isn’t a known song (just in case).  Well drinks are $3.50 on Mondays too.  This might be to loosen up the performers (you).  Some Mondays there are fabulous entertainers instead of open mic so always be sure to check the calendar first!


Monday Night Trivia

When: Mondays at 6pm

Where: Sidebar Grille at 221 N. La Salle Street

Nearest Public Transit: Brown/Green/Pink/Orange line Clark/Lake or Red line Lake

Cost: Free to play with purchase of food or a drink

Sidebar Grille has an excellent free trivia night where you can enjoy a bite and a beverage while testing your knowledge.  They typically have great food and drink specials that rotate like $4 craft beers, $1 hamburger sliders, and $15 pitchers.  They also love to give out prizes (T-shirts, shots, appetizers for your next visit, etc).

About The Author

Canden Arciniega

Canden is a historian and tour guide in Washington DC with 4 published books about the city. She has written for HuffPost Travel and has been featured in the Washington Post, WTOP, and numerous other DC papers. She's also been interviewed by the BBC, NPR, Travel Channel and Discovery Family Channel. Canden is the producer of our podcast, Tour Guide Tell All With a M.A. in History from University College London and a B.A. in History from Elon University, she is an authority on D.C. history, and has led tours in the city for over 10 years. She currently resides in DC, but has also lived in London and South Korea, and has travelled to 28 countries. Her two children (both under the age of 4) have their passports and own frequent flier accounts.
Updated: September 26th, 2021
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