The leaves aren't the only thing changing in Chicago right now. Michigan Avenue is preparing for the opening of a flagship Apple store, and we're all planning out which identities we'll assume for Halloween festivities ahead of October 31. It finally feels as though we're settling into the brisker weather, so we're glad so many of this weekend's events are cozy, indoor ventures. 


Open House Chicago
October 14-15 // Free admission

Chicago Board of Trade Building

Wake up early and catch some of the best views of the city. From 9 a.m. to 5 p.m. on both Saturday and Sunday, more than 200 buildings that are usually closed to the public will open their doors for behind-the-scenes access. From gems tucked away in neighborhoods to the top of the Loop’s skyscrapers, make sure you take advantage of the 48-hour window.


Chicago Riverwalk Oktoberfest
October 13 // Free admission

Friday Night Flights full beer

The Chicago Riverwalk will be activated with a variety of events and activities in the spirit of OKTOBERFEST from 3 - 8 pm, culminating at 7:30 pm with a PYROTECHNIC WATERFALL DISPLAY on the LaSalle, Clark, Dearborn and State bridges (west side). Raise a glass with Revolution Brewing’s Oktoberfest being served up at Island Party Hut and O’Brien’s, plus there's Tiny Cider and specialty fall beers from Tiny Tapp. Live music, boat cruise tours and kayak tours are also on the schedule.

For another fall seasonal celebration, the 3rd annual Harvest Fest transforms the rooftop terrace of Loews Chicago Hotel. The October 14 event is complete with a pumpkin patch, carnival games, entertainment, and biergärten.


Old Town School of Folk Music Open House
October 13 // Free admission

Old Town School of Folk Music

For 60 years, the Old Town School of Folk Music has provided a range of music classes for Chicago residents, and its Friday night Open House will be a showcase of the talent that’s cultivated here. Stop by for performances and sing-alongs, as well as free go-go dancing lessons, a barn dance and bluegrass jams.


Bizarre Wicker Park Tour
October 14 // $20

Some strange things have gone on in Chicago, and the Bizarre Wicker Park Tour is more than happy to point out the oddities of this artistic neighborhood. The tours are limited to 12 people, and you’ll hear about radicals, beer barons and other tycoons who shaped the neighborhood. Although this week’s installments of the Bizarre Bucktown tour are sold out, check in over the next few weeks for a great tour that’s timely for Halloween in Chicago.  


Wine Riot
October 13-14 // $65

Treat yourself this weekend at Wine Riot, hosted in the Fulton Market District. Try wine samples from across the world and learn about your favorite red, white or rose. Thirty-minute crash courses and interactive tasting sessions will help you navigate your palette.


Andersonville Arts Week
Through October 15 // Free admission


Focusing on nine genres of art, the Andersonville Arts Week is wrapping up its nod to visual, theatre, dance, music, culinary, handmade, family and public arts. Previously only a weekend long, the 15-year festival is expanded to a week this year after it became so popular, and more than 70 businesses and 200 artists will showcase work alongside free activities. On Sunday, catch the reveal of the neighborhood’s latest public art installation as a way to pay tribute to Chicago’s Year of Public Art.

As another option, heads up it's also opening weekend for the 12th Annual Folk Art Festival, free at the National Museum of Mexican Art.


Chicago International Film Festival
Through October 26 // $8+

Chicago International Film Festival

Given the forecast, we wouldn’t blame you if you just wanted to kick back with a great film. Luckily, the Chicago International Film Festival kicks off this weekend. In the festival’s opening days, catch films created in Japan, South Korea, Germany, France, Denmark and more in venues across the city.


Logan Center Bluesfest
October 13-15 // Most events are free

Billy Branch

Make your way to the South Side for concerts, workshops, film, food and more that all honor the legacy of the Blues. The headlining double-bill concert features Elvin Bishop’s Big Fun Trio, Wee Willie Walker, winner of two 2016 Living Blues Music Awards and Critic’s Poll Comeback Artist of the Year, and more.


Need more ideas? Use this weekend as a perfect excuse to check out Chicago's incredible theater scene. With more than 200 theaters throughout town, you'll find big productions, Broadway hits and underground companies. Click here to learn about some of the key players in town. It should also be a perfect weekend to visit a museum. Whether you prefer the big names at Museum Campus and Museum Campus South or love hidden gems, make sure you do some exploring  in Chicago.