09/23/2011 05:28 pm ET Updated Dec 06, 2017

Chicago Weekend Plans: Puppies, Jazz And Sex Toys (9/23-9/25)

For Chicago, September is a month of ambiguities--we straddle the line between summer concert series and harvest festivals, the start of school and the end of summer vacation--and our city decides at random which season to cling to, as usual fluctuating only between two extremes. Capitalize on September's last hurrah with a rearview glimpse at the exploits of sunnier seasons. Soon the floral prints will be stashed and the last bottles of Summer Shandy drained as Chicago heads full-throttle into fall.

Hyde Park Jazz Festival
Celebrating its fifth anniversary, the annual Hyde Park Jazz Festival is extending to a weekend-long event this year. With showcases scattered across 13 Hyde Park venues, scene fixtures like the Don Byron New Gospel Quintet, Fareed Haque, Geof Bradfield and Paulinho Garcia will rock across the neighborhood Saturday, before bringing it in Sunday with an afternoon and evening of tunes at Midway Plaisance's Main Stage.
Where: Midway Plaisance Park, Chicago
When: 1 p.m. – 12 a.m., Saturday, 1 p.m. – 8 p.m. Sunday
Price: Free

Oktoberfest Chicago
As the "real" October looms on the horizon, the Chicago area is already getting Oktoberfest season underway. Celebrate the 11th annual revelry in all things Germanic at St. Alphonsus' Annual Oktoberfest in South Lakeview [PDF]. The three-day fest will be overflowing with beer, food and music from headliners like Bratwurst Brothers and the Polkaholics.
Where: 1429 W. Wellington Ave., Chicago
When: 5 p.m. - 11 p.m. Friday, 11 a.m. - 10 p.m. Saturday, 11 a.m. - 7 p.m. Sunday
Price: $5

Chicago Gourmet 2011
As one of the country's dining capitals, Chicago has no shortage of restaurants topping residents to-eat lists. Sample goodies from more than 100 hotspots at the Chicago Gourmet 2011 showcase. Celeb chefs like Rick Bayless, Graham Eliot and Carrie Nahabedian will host cooking demos, and tasting pavilions and wine sampling will draw even the most stove-phobic eaters.
Where: Millenium Park, Chicago
When: 6 p.m. – 9 p.m. Friday, 12 p.m. - 5 p.m. Saturday and Sunday
Price: Varies

Ladies Ring Shout
South Side cultural hub The Experimental Station will explore images and misrepresentations of the Black female in popular culture through spoken word, dance and music in "Ladies Ring Shout." Artists Felicia Holman, Abra Johnson and Meida McNeal dissect portrayals of domestic servants, sassy loudmouths and victims within pop culture through multimedia and lecture.
Where: Experimental Station, 6100 S Blackstone Ave., Chicago
When: 7 p.m. - 9 p.m. Friday
Price: Free

The Paper Machete
Nicknamed "a weekly salon in a Chicago saloon," The Paper Machete, a "live magazine," brings together comedians, journalists and performers for weekly showcases that are distributed as a podcast on WBEZ. They open the doors to their live taping this week, which includes performances by musician Bobby Conn and Katie Rich, from the Second City main stage, whose "Birth Control Ninja" video has been embraced by Planned Parenthood.
Where: Horseshoe, 4115 N Lincoln Ave., Chicago
When: 3 p.m. Saturday
Price: Free

Early to Bed Anniversary Party
Chicago's favorite female-friendly adult toy store Early to Bed is celebrating 10 years of sex positivity with an anniversary party and blowout sale. If the snacks, photo booths and cocktails made with the shop's signature aphrodisiac Love Potion No. 14 aren't enough to tickle your fancy, a 20 percent discount on all merchandise might sweeten the pot.
Where: 5232 N. Sheridan Rd., Edgewater
When: 6 p.m. - 9 p.m. Saturday
Price: Free

Zoo Run Run
Could you run run the Zoo Run Run? Although each year more species lose their race for survival and disappear from the wild, the race against extinction can be won--much like the Chicago Zoological Society Conservation Fund's annual 5k timed race through the Brookfield Zoo. Prove if you're a cheetah or a sloth and stay after the race to see the animals at a more leisurely pace.
Where: 3300 Golf Rd, Brookfield
When: 8:30 a.m. Sunday
Price: $35

Barkapalooza Walkathon
Let your pup help to save others at the 18th annual Barkapalooza Walkathon. Walkers and their dogs will be fundraising for the West Suburban Humane Society to help support care for homeless pets. Guests can enjoy a pet parade, scavenger hunt and a special appearance by the crime-fighting canine McGruff.
Where: 1825 Short St., Lisle
When: 10:00 a.m. - 2 p.m. Sunday
Price: Free

In anticipation of the release of Beirut's newest album, "The Rip Tide," frontman Zach Condon told HuffPost that after a full year break from touring, performing has "gotten easier." Take in Condon's maturing stage presence and the band's new pared-down sound at the Congress Theater Monday night with Laetitia Sadier.

Markethouse Demo And Tasting
Is your cookbook well-stocked with meat-free fare? October is Vegetarian Awareness Month, and Markethouse Executive Chef Scott Walton will preview the restaurant's monthlong vegetarian prix fixe menu by spotlighting a non-meat ingredient in a demo and tasting held at the restaurant's rooftop garden. Tomato lovers: this one's for you. While the eatery's urban mini-farm boasts a variety of herbs, root vegetables and lettuces, the heirloom tomatoes will be the star of this showcase.
Where: Markethouse, 611 N Fairbanks, Chicago
When: 6:30 p.m. Tuesday
Price: $35

Messing with a Friend
Tagged "a joyful, uncensored, and improvised romp through hell," Susan Messing continues her ongoing series "Messing with a Friend" that invites different Chicago comedians to improvise with her onstage. This week she's paired up with Second City alum Kevin Crowley, who has appeared on Drew Carey, Malcolm in the Middle and Boy Meets World.
Where: The Annoyance Theatre & Bar, 4830 N. Broadway, Chicago
When: 10:30 p.m. Thursday
Price: $5

Flickr photo by TheChanel.