The Guesthouse Hotel is located at the crossroads of Chicago’s most popular destination neighborhoods—Andersonville, Lincoln Square and Uptown. While each has its own distinct personality, they all offer some of the best options for entertainment in Chicago—and most venues are within walking distance of The Guesthouse Hotel!


Aragon Ballroom - 1106 West Lawrence Ave
Originally built in 1926, Aragon Ballroom’s interior was designed to mimic a Spanish village. It was a popular destination spot for swing dancing, roller skating, and hosted an hour long radio show. Today, some of music’s biggest entertainers pack the house with a variety of music from pop to punk to Latin.  Located just off the CTA Red Line, it is major part of the historic Uptown district.

The Riviera 4746 N Racine Ave
Completed in 1917, The Riviera was originally built as a movie theater.  In the mid 80’s, it was turned into a private club and has hosted many amazing artists over the years. Hundreds of musicians – from Billy Idol to Fall Out Boy – have graced the stage making “The Riv” one of Chicago’s most popular concert venues. 

The Green Mill 4802 N Broadway
A Chicago institution and one of Al Capone’s favorite watering holes! The Green Mill is sophisticated informality, warm glowing atmosphere steeped in the heady sounds of the early ’30s and ’40s jazz. Uniquely comfortable to all audiences from the sequined Saturday night date to the progressively dressed offbeat student, the magic of the Mill is an audience that commingles in its mutual respect for music.

Old Town School of Folk Music 4544 N Lincoln Ave
Old Town School of Folk Music is one of the largest independent community arts schools in the United States. In addition to teaching various instruments and cultural dances, they host hundreds of artists, musicians and dancers for concerts and workshops throughout the year. 



Uptown Underground 4707 N Broadway
Hosting a different show every night, it’s a mix of hilarious hosts, quirky musicians, awe-inspiring variety performers and beautiful burlesque dancers! Running every Friday night, they have been named Chicago’s Best Cabaret by The Chicago Reader.

Black Ensemble Theater 4450 N Clark St
A leader and innovator in the African-American and mainstream arts communities, Black Ensemble Theater is recognized as one of the most diverse theaters in the country, producing excellent musical theater. Located on Clark Street, just 4 blocks south of The Guesthouse Hotel, the theater’s popular productions have included ‘The Jackie Wilson Story’, ‘The Other Cinderella’, and ‘At Last: A Tribute to Etta James’.

pH Comedy Club 1515 W. Berwyn Ave
As one of the newest additions to the Andersonville theater scene, pH Comedy Theater is here to make you laugh.  Every night of the week you will find a different show – from stand up to improv to musicals. Fancy yourself a comedian? You’d have your shot at the weekly open mic night!

Neo-Futurists 5153 N Ashland Ave
Since 1988, the Neo-Futurists have been performing the show Too Much Light Makes the Baby Go Blind: 30 Plays in 60 Minutes making it the longest running show in Chicago. An ever changing show, the plays are wildly eclectic, touching on all genres and tones all touching on current events.

Raven Theatre 6157 N Clark St
Raven Theatre boasts an ambitious line up of actors that have performed many critically acclaimed revivals. This non profit theater has produced shows from the likes of Tennessee Williams and Arthur Miler. 

Mary’s Attic 5400 N Clark Street
Hamburger Mary’s: where you can grab a burger in the restaurant, a beer at her Brewery next door or a show in the Attic! From burlesque and karaoke to one act plays and musicals, there’s always something going on in this little slice of Andersonville.


Winter Brew - January
Local breweries from around Chicago set up shop on the 5th floor ballroom and 6th floor skyline lounge of Lincoln Square’s historic Dank Haus to showcase what great beers Chicago has to offer.  Past participants include Begyle, Half Acre, Finch's, Metropolitan and Revolution. Visit for more information.

Lincoln Square Ravenswood Wine Stroll - Late April and Early November
The streets of Lincoln Square and Ravenswood are transformed into Chicago's very own wine country during this popular Wine Stroll held each Spring and Fall. Businesses throughout the neighborhood market themselves to wine strollers as they stop by for tastings of wine and complimentary hors d' oeuvres.

Andersonville Wine Walk  - Mid May
How to make your shopping trip even better? Add wine! With a ticket to the Andersonville Wine Walk, participants receive a wine glass and a map of the neighborhood marking all of the local shops and restaurants serving tastings of various wines. Set in mid May, there is no better time to wander up and down Clark Street sipping wine and enjoying the spring air.

Celebrating Andersonville’s Swedish heritage for 50 years, Midsommarfest brings the traditional Swedish celebration to Chicago. Located along Clark Street, Chicago’s biggest street festival combines 3 days of music, food and entertainment for the whole family! Grab a Glogg slushy while dancing around the Maypole or catch 16 Candles playing while enjoying a beer from one of our local brewers.

Windy City RibFest July
Fourth of July Weekend is the perfect time to get out and enjoy the best of Chicago’s BBQ. Held at the corner of Lawrence and Broadway in Uptown’s Historic District, this fest serves up amazing ribs, live music, beer, wine and a kids area. Don’t be afraid to get messy!

AppleFest  Mid-September
Apple Fest is a long-standing tradition in Lincoln Square bringing the community together to celebrate the beginning of fall. Pick up a fresh baked apple pie, a bushel of locally grown apples, hot apple cider, or even an apple pizza. Bring the kids along and hang out in the Kid Zone where children's activities will occur throughout the weekend. There's sure to be something for everyone at Apple Fest!

Andersonville Art and Design WeekendMid October
Over the weekend, dozens of local shops and restaurants (including The Guesthouse Hotel!) showcase local artists, live shows and performances. Andersonville’s artistic community has kept this weekend buzzing into it’s 15th year! And kicking it off is the Friday night event, Night of 100 pARTies! – an evening of receptions up and down Clark Street.