September 2025

• The best late-night bars in Chicago that are open until 4am—or later
• The best places to see fall colors in Chicago
• Streeter's Tavern
• The hottest nightclub in Chicago is hiding in a Polish dive bar
• The Sticks
• Opheli-YASS!: Taylor Swift 'The Life of a Showgirl' Listening Party
• Rooftop Cinema Club
• The 12 most romantic hotels in Chicago for 2025
• The Hangge-Uppe
• Ravens
• Old Town Ale House
• Zarella Pizzeria & Taverna
• Ice Skating at Rosemont's Parkway Bank Park
• Cheer at the Pier!
• Festival of Wood and Barrel-Aged Beers
• ZooLights
• Block Club Chicago Block Party
• The best December 2025 events in Chicago
• Chicago’s coolest neighborhood officially has a new No. 1 restaurant
• The Nutcracker: Duke It Out!
• Rooftop Silent Disco with HUSH
• The 20 best restaurants in Avondale
• Anelya
• I had dinner with strangers at Chicago’s hottest supper club. Here’s how I fared.
• Into the Feral
• Two Chicago restaurants officially rank among the 50 best in North America
• Streeterville Social is hosting the ultimate Taylor Swift album release party—and you could win a free hotel stay
• The Balloon Museum’s wildly photogenic exhibition, EmotionAir: Art You Can Feel, is floating into Chicago
• Chicago’s biggest country bar is throwing a Taylor Swift-themed bash, complete with a Travis Kelce lookalike contest
• John Mulaney makes Chicago history as first comedian to headline Wrigley Field—what to know about the upcoming show
• JUST IN: This Chicago bar has been named on the World’s 50 Best Bars longlist
• Start your engines! Drag Race: The Experience, an immersive RuPaul’s Drag Race fan pop-up, is coming to Chicago this fall
• New Apple TV+ docuseries spotlights a Chicago restaurant’s dramatic journey to earning a Michelin star
• I’ve lived in Avondale for 10 years—here’s why it’s the coolest neighborhood in Chicago
• Chicago just got a brand-new classical music venue—and it’s inside a former 7-Eleven
• Bar Mar
• Shaw’s Crab House
• A Negroni-drinking challenge is taking over this Fulton Market bar
• A new report crowned these four Illinois universities among the best in the U.S.—see who made the cut
• Rainbow Cone brings its gigantic five-flavor ice cream to Millennium Park
• A River North bar gets the NYC treatment, courtesy of the team behind Pete Davidson, Nicholas Braun and Justin Theroux’s legendary bars
• Avondalia Art Show: In Chorus & Cohesion
• Take Time Out’s survey on city life in Chicago—and you could win a $500 Amazon gift card
• This Chicago neighborhood was named one of the coolest in the world, ranking higher than New York, Miami and Austin
• Chicagoans can help revitalize a new green space in the world’s first-ever floating eco-park this weekend
• Meet Me On Milwaukee
• Calumet Fisheries
• Block to Block Chicago + Urban Rivers
• After a two-year closure, Chicagoans can visit this beloved landmark again
• Iconic Chicago chef Grant Achatz is collabing with Milk Bar on an intergalactic new sundae—and you can get it now
• Reuse-a-Palooza at The Plant
• Autumn Boozy Tea
• All Seasons Apple Orchard
• Chicago Ceramics Crawl
• The Palmer House Hilton
• The 23 best ramen shops in Chicago
• The 15 best hotels in Chicago for 2025
• Dorothy's First Annual Homo Homecoming
• Witch Crafts Market
• Bramble Arts Loft
• High Five Ramen
• Hokkaido Ramen Santouka
• HGTV just named the most beautiful garden in Illinois—and you probably won’t guess it
• The 10 best spa hotels in Chicago for 2025
• The best day trips from Chicago for an exciting adventure
• The best art galleries in Chicago
• Florasonic
• It's official: one of the best burgers in the world is in Chicago
• Chicago Asian American Jazz Festival
• Ithaki Estiatorio
• Chicago Underground Film Festival
• Five iconic landmarks you’ll be able to access for free during Open House Chicago 2025
• The 14 best bars in Avondale
• A new Nordic-Japanese restaurant is coming to West Town—with a familiar face at the helm
• This horror franchise will haunt Chicago Shakespeare Theatre this October with help from the creator of Sleep No More
• I found the prettiest smoothie in Chicago—and it’s not from Chicago Health Foods
• Virgin Hotels Chicago
• The Guesthouse Hotel
• This farm-to-table Chicago fine-diner was just named one of America’s best new restaurants of 2025
• Free pet-friendly Barktoberfest returns to the Chicago Riverwalk this week
• Central Park Bar
• The Midwest’s largest VR experience is coming to Rosemont, and it’ll transport you right to the Great Pyramids of Egypt
• The best November 2025 events in Chicago
• The No. 1 bar in the world is popping up at the Mile High Cocktail Club this fall
• Santa Baby Christmas Bar
• Holiday Magic at Brookfield Zoo
• Turkey Trot Chicago
• The LaSalle Chicago, Autograph Collection
• Barktoberfest
• Hotel EMC2, Autograph Collection
• The 24 best hot dogs in Chicago, according to locals
• Music Box of Horrors: Dead and Loving It!
• Ravenswood Costume Crawl
• Forest Park Casket Races
• Schaumburg Halloween Carnival
• Curse of the Nile
• Nightmare on Wacker Drive: Dia De Los Muertos
• Boo! at the Zoo
• Stolen Saddle
• The Brewed Halloween Block Party
• La Carrera de los Muertos
• Benito Juarez Community Academy
• Trick or Treat on Southport
• SkyRise Chicago
• Hot Chocolate Run
• Christmas Around the World
• Randolph Street Holiday Market
• Redhot Ranch
• Haunted Halloween Ball
• Jim's Original
• theWit Chicago, a Hilton Hotel
• Slow & Low: Chicago Lowrider Festival
• Arts in the Dark Upside Down Parade
• The Wiener's Circle
• Sandía & Soul Day Party & Market
• Hoste
• Byron's Hot Dogs
• Chicago’s Dog House
• Labubu Land
• Rosehill Cemetery Crypt 5K Run & Walk
• Adults Night Out: Howl-O-Ween
• SAUCED Night Market
• Taste of Northalsted 2025
• SpaDerma | Lincoln Park
• Christkindlmarket Wrigleyville
• Christkindlmarket
• Magnificent Mile Lights Festival
• This study proves why Chicagoans should be grateful the Bears are leaving Soldier Field
• Haunted House Party at the Shedd
• Olio | Lincoln Park
• Renaissance Chicago’s Hispanic Heritage Market
• Where to celebrate Oktoberfest in Chicago
• Sounds of the Riverwalk
• The 24 best deep dish pizzas in Chicago
• Paranormal Activity
• Jack's Pumpkin Pop-up
• Jack's Pumpkin Pop-Up
• Teen Lit Night: Unbound
• Tortoise with Chicago Philharmonic
• Ariana Grande is playing two nights in Chicago: dates, tickets and everything you need to know about the 2026 Eternal Sunshine Tour
• Pequod’s Pizza
• George's Deep Dish
• Milly's Pizza in the Pan
• Good grief! A ‘Peanuts’ exhibit is debuting at this Chicago museum on Saturday—here’s a first look inside
• 9 Malört cocktails to try in Chicago right now
• This 130-year-old garden in Chicago is the No. 1 proposal spot in the world
• Two Chicago spots were just ranked among the 50 best restaurants in the U.S.
• This Illinois park was just named the No. 4 most visited state park in the U.S.—and it has a dark history
• Chicago is officially home to one of the top 50 pizzerias in the world—again
• The 26 best sushi restaurants in Chicago
• Lincoln Park Uncorked Wine Stroll
• Inside the Chicago Architecture Biennial: A first-timer’s guide to North America’s largest architecture exhibition
• Empty Bottle 33 ⅓rd Anniversary Concerts
• It’s the Great Pumpkin, Charlie Brown!: A Guitar for Guaraldi Tribute
• The Rocky Horror Picture Show: The 50th Anniversary Spectacular Tour!
• Is Chicago actually the 'murder capital of the world'? Here’s what the latest crime data says
• Miru
• Sushi-san
• Hallo-Queen!
• Hokus Pokus Live!
• Andrew Bird's Gezelligheid Holiday Concert Series
• ‘Twas the Night Before… by Cirque du Soleil
• Amadeus at Steppenwolf
• Chicago Market for Makers
• 15 reasons fall in Chicago truly stands out—from someone who’s lived it
• Casa Madai
• Watch chefs break down a whole 300-pound bluefin tuna at Miru
• The best chocolate shops and candy stores in Chicago
• Outset
• The best pumpkin patches near Chicago to visit this fall
• Jack O’Lantern World
• Taste of Chicago 2025: Everything you need to know
• Little Lark
• Chicago Canine Rescue Barktoberfest
• FEAT with Cameron Esposito
• These Chicago vending machines sell local art and unexpected treasures—all for under $20
• Illinois Holocaust Museum Experience360
• This West Loop rooftop party has an espresso martini ice luge and free tequila
• Two iconic Chicago restaurateurs are teaming up with the Pope for a new Vatican restaurant
• Love Isn't Blind
• Printers Row Lit Fest returns for 40th year with headliner Sandra Cisneros and 250 more authors
• The 20 best things to do in Logan Square, Chicago
• Chicago’s iconic karaoke bar Hidden Cove to shutter this month, after three decades of lively, late-night singing
• This map can tell you when fall foliage will peak in Chicago
• The Joffrey Ballet presents The Nutcracker
• Halfway to St. Patrick’s Day
• Drunk Dracula
• Riverwalk Oktoberfest Pub Crawl
• Haymarket Oktoberfest
• A 1,000-plus person scavenger hunt is coming to Chicago—with a $4,000 grand prize
• You only have a few months to visit these four Chicago museums for free
• Three Dots and a Dash
• The best free museum days in Chicago
• This powerhouse hospitality team strikes again with new Avondale eatery
• This Chicago landmark is home to America's best hotel bar, says new ranking
• The best August 2026 events in Chicago
• The best January 2026 events in Chicago
• The best February 2026 events in Chicago
• The best March 2026 events in Chicago
• The best May 2026 events in Chicago
• The best July 2026 events in Chicago
• April 2026 events calendar for Chicago
• June 2026 events calendar for Chicago
• Open Books, Logan Square
• Chicago Billiard Cafe
• The Magic Gateway: A Magic Show for the Family
• WONDRA