Welcome to October, Chicago

BEST DATE NEWS

Oct. 2, 2025: Best Date News Volume #146

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about the Cubs win or go home game today, The Original Rainbow Cone, Lincoln Square Apple Fest, the album release of The Life of a Showgirl, a ton of festivals taking place this weekend and more!

Oct. 2: National Holidays

• National Smarties Day

• National Name Your Car Day

• National Fried Scallops Day

• National Custodian Day

• National Produce Misting Day

Sponsored by our friends at Oak Brook Artisan Market

Free Outdoor Market this Weekend

• Oak Brook Artisan Market: The twice-a-year Oak Brook Artisan Market returns this weekend for their fall market. This massive two-day, outdoor market is free to attend, kid and dog friendly and has free parking.

• What makes this market incredibly unique is that it takes place right in the heart of Oakbrook Center! Where else can you explore a local market of this size that supports small businesses, while also shopping all the iconic brands you know and love?!

• The fall market brings together 110+ talented local and Midwest artisans specializing in categories like art, jewelry, woodworking, food, handbags, clothing, sauces and spices, ceramics, dog items and more.

• Oak Brook Artisan Market takes place within Oakbrook Center on Saturday, Oct. 4 from 10 a.m. to 6 p.m. and Sunday, Oct. 5 from 11 a.m. to 6 p.m. There will be multiple large collections of white tents set up on and around the lawn of the shopping center. RSVP for free if you want to let them know you’re coming.

Chicago News

• Chicago Cubs: It all comes down to a do-or-die Game 3 in the Wild Card Series as the Cubs take on the San Diego Padres this afternoon at Wrigley Field. If the Cubs win, they advance. If they lose, their season is over. After a 3-0 loss in Game 2 yesterday, the Cubs will look to bounce back and close out the series at home to advance to the National League Division Series. First pitch is set for 4:08 p.m. CT. Watch on ESPN or get tickets.

• The Original Rainbow Cone: Chicago’s iconic ice cream shop The Original Rainbow Cone opened a new downtown location on Monday at 163 North Michigan Avenue, bringing its signature five-flavor slice closer to the Loop. To celebrate spooky season, they’re also serving a limited-time Spooky Sliced Creation with chocolate ice cream, orange sherbet and chocolate sprinkles, available through Nov. 2.

• Vintage CTA: To celebrate its 78th anniversary yesterday, the CTA rolled out 1920s era train cars for a special ride through the Loop. The vintage cars ran for two hours, making regular stops just like today’s trains, with normal fares applying for anyone lucky enough to hop aboard. Weren’t able to catch it? Don’t worry, we have you covered.

• Andersonville Arts Weekend: From Friday, Oct. 3 through Sunday, Oct. 5, Andersonville hosts its 21st annual Andersonville Arts Weekend. More than 30 local businesses will showcase artists from across Chicago, beginning with opening parties and receptions on Friday evening. Guests can explore self-guided art walk locations throughout the neighborhood, then cap off the weekend with the Andersonville Fall Wine Walk on Sunday.

• Ear Taxi Festival: The month-long Ear Taxi Festival 2025, themed The Composer’s Voice, kicks off tomorrow, Friday, Oct. 3, and runs through Nov. 2 across Chicago. The festival is a landmark celebration of contemporary concert music, featuring more than 700 artists in 60+ hours of programming, from large-scale anchor performances to intimate showcases, chamber ensembles, operas and experimental works happening citywide.

Just For Fun

• The Life of a Showgirl: It’s a big night for Swifties as Taylor Swift’s new album The Life of a Showgirl drops tonight at 11 p.m. CT. If you are looking to celebrate in Chicago, there are multiple opportunities including The Official Release Party of a Showgirl in theaters this weekend only (Oct. 3–5), a listening party at Paradise Park tonight, another one tomorrow at Stolen Saddle (that features a Travis Kelce look-alike contest) and The Life of a Burlesque Girl: A Taylor Swift Cabaret at The Newport Theater on Saturday.

• Oktoberfest on Division: Prost in the Gold Coast this weekend as Division Street transforms into a lively Oktoberfest celebration. Oktoberfest on Division Street runs Friday, Oct. 3 from 3 to 10 p.m. and Saturday, Oct. 4 from 11 a.m. to 10 p.m., with stein holding contests, festive games and live music from Maggie Speaks, 7th Heaven, Polka Confetti and more. Saturday also brings college football viewing on jumbo street screens, making this two-day party a true mix of Bavarian tradition and Chicago fun.

• Southport Fall Jam: Southport Avenue turns festive on Sunday, Oct. 5 from 2 to 4 p.m. with the Southport Fall Jam. Guests can enjoy complimentary bites from Itoko, Little Goat Diner and GG’s Chicken Shop, along with drink specials, sidewalk art, face painting and games. It’s free to attend and the perfect excuse to gather friends, family and pups for an afternoon of cozy autumn fun.

• STEAM-Powered Saturday: Harold Washington Library hosts a fun STEAM-Powered Saturday family event on Saturday, Oct. 4 from 11 a.m. to 3 p.m. Kids ages 3 to 11 can make glow-in-the-dark slime, try LEGO challenges, meet live animals and explore hands-on STEM activities with partners like the Shedd Aquarium and Museum of Science and Industry. The event is free, but registration is required.

• Fall Fest on the Riverwalk: If you’re looking for those fall pumpkin patch vibes in the heart of the city, check out Island Party Hut Fall Fest on the Chicago Riverwalk. Taking place every Saturday in October, you’ll find hayrides on the river, pumpkin patches, live music, fall cocktails, beer and apple cider donuts.

Sponsored by our friends at High Stakes Productions

Clued In: Where There’s a Will, There’s a Way

• Murder Mystery Improv: Welcome to Clued In: Where There’s a Will, There’s a Way, the new improvised mystery that proves that revenge is an estate of mind. Tonight is opening night of a month-long run at The Second City leading up to Halloween.

• Inspired by Agatha Christie, seven improvisers will weave together a made-up murder mystery, sparked by the audience’s suggestion of an unusual inherited object. Your job is to figure out who did it while enjoying plenty of laughs during this 90-minute, fully-improvised show.

• This fast-paced and wildly clever experience is brought to life by High Stakes Productions through an immersive and interactive pre-show, specialty cocktails, mysterious menus, and an estate-like atmosphere at The Second City’s UP Comedy Club.

• Clued In: Where There’s a Will, There’s a Way happens Thursdays at 7 p.m. and Sundays at 4 p.m. from Oct. 2 to 26, with a bonus show on Halloween night at 8 p.m. Tickets are $30 general admission, with seating assigned upon arrival.

Weekend Festivals

• Lincoln Square Apple Fest: The Lincoln Square Ravenswood Apple Fest is back this weekend for its 38th year, lining Lincoln Avenue with the flavors of fall such as apple pies, cider, donuts, caramel treats and other seasonal bites from local vendors. Beyond the food, the fest offers live music, family friendly activities and a lively neighborhood atmosphere. Hours are Friday, Oct. 3 from 3 to 7 p.m., and Saturday, Oct. 4 and Sunday, Oct. 5 from 9 a.m. to 6 p.m. A $5 donation is suggested.

• Moon Festival Chicago: Chicago’s Chinatown comes alive on Saturday, Oct. 4 from 2 to 9 p.m. at Chinatown Square (2130 S Archer Ave) for the Mid-Autumn Festival, one of the most significant cultural celebrations after Lunar New Year. This year’s Moon Festival Chicago will feature glowing lanterns, live performances of music, dance and martial arts, and a high-energy K-Pop competition. Guests can enjoy mooncakes, sip chrysanthemum tea and take in the festive atmosphere under the full moon. Free and open to the public.

• Lincoln Park Wine Fest: The 9th annual Lincoln Park Wine Fest returns to Jonquil Park this weekend, Oct. 3–5, transforming the space into an open-air wine garden with tastings from around the world. General admission tickets include twelve tasting pours and a commemorative glass, while VIP passes add specialty wines, extra tastings and private seating. Sessions run in two-hour blocks throughout the weekend, with food vendors, live music and a market rounding out the experience. Tickets start at $30.

• Taste of Northalsted: Northalsted’s neighborhood tasting crawl is back on Saturday, Oct. 4 from 1 to 5 p.m. as Taste of Northalsted Fall takes over the neighborhood with more than 20 locations offering bites, beer, spirits and cocktails. Tickets are $30 and include samples at every stop, from local restaurants and cafes to bars, breweries and shops. With six different check-in spots and an extra hour added this year, it’s an affordable way to explore the flavors of Northalsted in one afternoon.

• Chicago Beer Fest: The Field Museum hosts the Chicago Beer Festival on Saturday, Oct. 4 from 7 to 11 p.m., featuring more than 65 breweries pouring seasonal favorites. Guests can sip their way through 40 tasting vouchers while also exploring select museum exhibits after hours. General admission is $69, with an $87 early admission option that includes entry at 7 p.m. and specialty beers during the first hour.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter, we asked which of the two lobster roll styles you preferred. 69% preferred Connecticut Style (warm with melted butter) compared to 31% who preferred Maine Style (chilled and tossed with mayo).

Sunrise & Sunset in Chicago

Here is today’s outlook in Chicago (compared to last week):

• Sunrise: 6:48 a.m. (7 minutes later)

• Sunset: 6:29 p.m. (12 minutes earlier)

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