Chicago September 2015 Weekend Guide Photo: Amanda Elliott

Chicago Summer: September 2015 Weekend Guide

This summer is almost over. If you want to squeeze in all of the sunshine that Chicago has left to spare, there’s a lot to do this weekend.

Drink: Windy City Wine Festival

The main event downtown, to every wine lover, is the Windy City Wine Festival.

The event begins Friday, September 11, 2015  from 4:00 pm to 10:00 pm and runs until September 12, 2015 from 2:30 pm to 8:00 pm at Buckingham Fountain downtown.

Sample wines sourced from over 300 countries. If you love wine, but don’t know anything about it, there are seminars. Each ticket comes with a souvenir wine glass, 12 tastings, one pint of any beer, seminars, musical entertainment, and a special discount on wine bottles.

And if you are driving to the festival, you can get a special designated driver ticket. In any other city, I would understand, but with the CTA and Uber and Lyft and taxis and with all of your friends who stay downtown, I would rethink that option. Simply because the wine is going to be that good. But if you must, smell the wine and enjoy the live entertainment.

Find ticket information here. 21+ or one adult (21+) may accompany a youth.

Shop: Andersonville City Made Fest

The Third Annual Andersonville City Made Fest  celebrates local vendors craftsmanship. The marketplace will be setup on Clark Street between Argyle and Carmen. Activities include all of the essential festival components including one of a kind products, live music, and savory food. The event runs Saturday September 12, 2015 from 12:00 pm to 9:00 pm and Sunday, September 13, 2014 from 12:00 pm to 7:00 pm.

Explore Oak Park: Frank Lloyd Wright Home and Studio Free Admission

Oak Park is quite lovely. While part of Chicago and reachable via the Green Line west to the Oak Park stop, Oak Park is its own suburbia. On Saturday, September 12, 2015, enjoy free admission to one of the most acclaimed and must-see places in Oak Park—Frank Lloyd Wright’s Home and Studio. For more information, and to see other attractions that will also be free in River Forest and Oak Park, please visit the open house page.

Crawl: Lakeview Bar Crawls

On Saturday, September 12, 2015 you can drink your way through the day. Day drinking is still in (in Lakeview).

The first pub crawl is country themed. The Country Crawl begins at 11:00 am to 6:00 pm, but you can drop-in throughout the day. Be sure to wear your cowboy boots and flannel because this is Chicago and we do like to get dressed up. Click here for ticket information. P.S. If you were wondering why a lot of people were in jeans and flannel on Friday, September 11, 2015 in Wrigleyville, now you know.

The First Annual Bridesmaid’s Bar Crawl in Lakeview is your opportunity to wear the ugly lime green dress your best friend made you buy and wear in front of all of those people. If you haven’t been a bridesmaid because you have no best friends, you can still wear that sales dress you bought and never wore.  Note that proceeds from the bar crawl will directly benefit the homeless dogs and cats at PAWS Chicago. The goal of this event is to raise $3,000, which will save the lives of 9 animals. Purchase tickets here.

Learn: Edgewater Learnapalooza

Learnapalooza is a day long event to learn new skills in your neighborhood. They hold events in Lakeview, Logan Square, Wicker Park, and more recently, Edgewater.

On Saturday, September 12, 2015 enjoy classes in Edgewater. Classes include: Online Marketing for Small BusinessesMake Your Mark: Logo Basics,  and Excel for Everybody. There are also non-academic classes such as The Feng Shui of Relationships and Bow Ties Are Cool!. Most of the events will be taking place at the Edgewater Library.

To register for classes and for more information, visit Learnapalooza. Walk-ins are welcome as well!

Sports: Watch Chicago Bears at Soldier Field

This Sunday, September 13, 2015, the Chicago Bears will be playing the Green Bay Packer’s at Soldier Field. Even if you don’t have tickets, you can go to the hundreds of Chicago sports bars, wear your Bears’ Jersey and make an afternoon of it. Suggested sports bars include: Jimmy Green’s and Wabash Tap in the South Loop,

Share Your Weekend Updates

These afternoon showers that turn the sky black are just a glimpse into what we have to prepare for the next few months. Enjoy the outdoors this weekend and let me know which neighborhood you explored on Instagram, Twitter, or Facebook with the #windycitycosmo.

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