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!
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).
Barrel of Monkeys performs That’s Weird Grandma
When: Sundays at 2pm and Mondays at 8pm
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
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.
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
known for having some of the best jazz in Chicago.
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).