AI Travel Planner LogoAI Planner
This Week

Chicago This Week

Oct 27 - Nov 2, 2025

Exciting events and experiences happening this week in Chicago.

Showing 1-20 of 100 events • Page 1 of 5
Chicago Architecture Center River Cruise Aboard First Lady
entertainment

Chicago Architecture Center River Cruise Aboard First Lady

Mon, Oct 27
Chicago Architecture Center - First Lady

Ticket Information

Check venue for pricing

Bubble Test
entertainment

Bubble Test

Mon, Oct 27 at 11:00 AM
TBA

Event Information

Test

Ticket Information

Check venue for pricing

Weed Passport Tours: North Michigan Ave Experience
entertainment

Weed Passport Tours: North Michigan Ave Experience

Mon, Oct 27 at 12:00 PM
TBA

Event Information

  Weed Passport Tours: Chicago 🌆🍃 Walk. Chill. Explore. Discover Chicago’s vibrant North Michigan Ave like never before — through the lens of cannabis culture, art, and relaxation. Our guided Weed Passport Tour takes you on a scenic walk through iconic stops including premium dispensaries, local art landmarks, the Chicago Riverwalk, and chill zones by the lake.  ✅ Exclusive dispensary discounts ✅ Local art + culture highlights ✅ Meet fellow cannabis travelers ✅ Perfect for tourists and locals alike 🎟️ Get your Weed Passport, explore the Magnificent Mile, and unlock a new kind of high-end Chicago experience. 📍 Start Location: Cookies Chicago, 215 N Clinton St, Chicago, IL 60661 (Outside Store) (“Exact meet-up instructions sent after booking.”) 🕒 Tour Time: Approx. 1.5 hours walking 🎫 Book your tour today #WeedPassportTours #ChicagoCannabis #WeedCulture #NorthMichiganAve #420Friendly #ChicagoTours #CannabisTravel

Ticket Information

Check venue for pricing

Jacks Pumpkin Pop Up Chicago
entertainment

Jacks Pumpkin Pop Up Chicago

Mon, Oct 27 at 5:30 PM
Jack's Pumpkin Pop Up Chicago

Event Information

  Jack's Pumpkin Pop-Up | Open Sept 18 until Nov 2nd, 2025  Jack’s Pumpkin Pop-Up is Chicago’s ultimate all ages fall destination - an immersive festival experience packed with seasonal cocktails, carnival games, axe throwing, a giant corn maze, and endless photo moments surrounded by thousands of pumpkins. It’s all ages, all the time: picture-perfect days for families and kids, then after dark the lights kick in, the energy turns BOO-zy, and the whole place transforms into a fall festival party. From sipping drinks under the lights to getting lost in the maze with your crew, every corner is designed for big laughs, good vibes, and the kind of nights you’ll want to relive all season. It’s part festival, part party, and all fall- Chicago’s go-to spot when you’re ready to turn autumn all the way up. Jack's Pumpkin Pop-Up | September 18th until Nov 2nd, 2025  The time on your ticket (ex 5 PM) is your entry window. You can arrive up to 30 minutes before or after that time. Once inside, you’re welcome to stay as long as you’d like. All Ages Welcome | 21+ to Drink | 18+ Axe Throwing   

Ticket Information

Check venue for pricing

Lovejoy - One Simple Tour
music

Lovejoy - One Simple Tour

Mon, Oct 27 at 6:00 PM
House of Blues Chicago

Event Information

Doors open at 6PM. Performance begins at 7PM. This show is for ALL AGES. House of Blues Chicago is a standing room only venue, all tickets are General Admission unless otherwise stated. *All support acts are subject to change without notice.* Upgrade Your Experience: https://www.sevenrooms.com/events/hobchicago/hobwebsite

Accessibility Information

Accessible Tickets House of Blues Chicago has requested that all accessible seating ticket accomodations be solicited only through their representatives. Those in need of accessible seating need to first purchase a General Admission ticket, then contact the venue Box Office to reserve accomodations. The box office cannot take phone orders. You may purchase tickets online or call (800) 745-3000.

Ticket Information

Check venue for pricing

Between the Buried and Me with Hail the Sun
music

Between the Buried and Me with Hail the Sun

Mon, Oct 27 at 6:30 PM
Vic Theater

Ticket Information

Check venue for pricing

Chicago Bulls vs. Atlanta Hawks
sports

Chicago Bulls vs. Atlanta Hawks

Mon, Oct 27 at 7:00 PM
United Center

Accessibility Information

ADA seating for patrons with wheelchairs, or hearing imparied and their companions is available for all Chicago Bulls events. Guests may purchase one accessible seat and one companion seat. If you have questions or desire further information, please contact the Box Office at (312)455-4655.

Ticket Information

Check venue for pricing

Midnight Til Morning with Adrian Lyles
music

Midnight Til Morning with Adrian Lyles

Mon, Oct 27 at 8:00 PM
Thalia Hall

Event Information

$1 from each ticket sold will support Save the Music. Entry VIP PackageIncludes One GA standing Ticket, Early Access, Acoustic session, Q&A, & Commemorative VIP Laminate and LanyardPremium VIP PackageIncludes One GA Standing Ticket, Early Access, Acoustic session, Q&A, Commemorative VIP Laminate and Lanyard, + 1 Item of Merch exclusively designed by favorite band memberSuper Fan VIP PackageIncludes One GA Standing Ticket, Early Access, Acoustic session, Q&A, Commemorative VIP Laminate and Lanyard + One (1) Exclusive Midnight Til Morning Gift Pack with Four Exclusive Merchandise Items (One Designed By Each Band Member), and a Signed Tour Poster.Package Details and Instructions: All VIP Package purchasers will be contacted by email (to the email address submitted at the time of purchase) approximately five (5) days before the concert. If you do not receive communication three (3) days prior, please double check your junk email folder. If you cannot locate any VIP communications by three (3) days prior, please email info@chuggmusic.comIf you have questions or concerns regarding the delivery, collection, or contents, of your VIP Package inclusions, please email info@chuggmusic.comMidnight Til Morning Live on TourLaunched from the global Netflix hit Building the Band, Midnight Til Morning are a breakout four-piece blending powerhouse vocals, emotional vulnerability, and undeniable onstage chemistry. Their debut single Bye co-written with hitmakers behind artists like Benson Boone, Harry Styles, and Shawn Mendes introduced a soaring, bittersweet sound thats both cinematic and deeply personal. With a creative team spanning Grammy-nominated producers and acclaimed video directors, every part of their artistry is built to connect. From viral moments to streaming buzz, theyve quickly captured a global audience drawn to their harmonies, heart, and brotherhood. Now, Midnight Til Morning are stepping off the screen and onto stages worldwide with a live show that promises raw energy, rich storytelling, and unforgettable moments.

Ticket Information

Check venue for pricing

UIC Flames Women's Basketball v Eastern Illinois
sports

UIC Flames Women's Basketball v Eastern Illinois

Tue, Oct 28 at 6:30 PM
Credit Union 1 Arena at UIC

Accessibility Information

ADA seating for patrons and their companions is available for all UIC Pavilion events. Accessible seating locations will vary per event. Accessible seating is limited and is sold on a first come first served basis. There is a ticket limit of four per purchase for all ADA and companion seating. If you have questions or desire further information, please contact the Box Office at 312-413-5740.

Ticket Information

Check venue for pricing

The Sound of Music (Chicago)
arts

The Sound of Music (Chicago)

Tue, Oct 28 at 7:00 PM
James M. Nederlander Theatre

Accessibility Information

Wheelchair and companion seating available. For more information please call (312) 977-1701 ext. 1259.

Ticket Information

Check venue for pricing

Loyola Ramblers Mens Basketball vs. St. Francis Cougars Mens Basketball
sports

Loyola Ramblers Mens Basketball vs. St. Francis Cougars Mens Basketball

Tue, Oct 28 at 7:00 PM
Gentile Arena

Ticket Information

Check venue for pricing

Odeal: The Shows That Saved Me Tour (17+)
music

Odeal: The Shows That Saved Me Tour (17+)

Tue, Oct 28 at 7:00 PM
House of Blues Chicago

Event Information

Doors open at 7PM. Performance begins at 8PM. This show is for AGES 17 AND OLDER. Valid Photo ID is required for age restricted shows. Forms of valid ID are current and non-expired Driver's License, State ID, or Passport. House of Blues Chicago is a standing room only venue, all tickets are General Admission unless otherwise stated. *All support acts are subject to change without notice.* Upgrade Your Experience: https://www.sevenrooms.com/events/hobchicago/hobwebsite

Accessibility Information

Accessible Tickets House of Blues Chicago has requested that all accessible seating ticket accomodations be solicited only through their representatives. Those in need of accessible seating need to first purchase a General Admission ticket, then contact the venue Box Office to reserve accomodations. The box office cannot take phone orders. You may purchase tickets online or call (800) 745-3000.

Ticket Information

Check venue for pricing

Paranormal Activity
entertainment

Paranormal Activity

Tue, Oct 28 at 7:00 PM
Chicago Shakespeare Theater

Ticket Information

Check venue for pricing

YOB with mr.phylzzz
music

YOB with mr.phylzzz

Tue, Oct 28 at 7:30 PM
Thalia Hall

Event Information

Slow is fast, says Mike Scheidt, singer, guitarist, and creative nucleus of the Oregon-based doom metal trio YOB. Its a concept that speaks to both the immense propulsion of their megalithic compositions and the way their artistry has patiently unfurled across their 25-year tenure. Change and revelation take time. You cant snap yourself into epiphany and you cant force yourself into another shape. You have to trudge. It doesnt mean youre failing. You persevere through the muck or you stop and you sink. There is no third way.YOBs music spreads across a plain where vast weather systems converge. Since sharing their first demo in 2000, the band has slowly, graciously gathered a devoted audience into their planetary orbit. Together with bassist Aaron Rieseberg and drummer Dave French, Scheidt tethers pendulous riffs to sky-flung vocals, sinking deep into the trenches and then cresting through the clouds. From the stoner rock ripples of their 2002 debut Elaborations of Carbon through the cavernous echoes of 2018s Our Raw Heart, YOB wield their totalizing gravity to bore into the light that hides in everything.Scheidt was reared on punk and metal in the eighties and nineties: parallel outsider ecosystems that lent language and dimension to deep feelings of unbelonging. Music became for me what I think it is for everybody: an anchor, he says. Its something that soothes; its something that lets you feel the intensity of anger without the damage of anger. He turned toward doom after seeing Cathedral perform in Portland in the early nineties. I was hanging out in the back. Then Cathedral started playing and it took maybe ten minutes for me to go from the back of the room to wedging myself against the front of the stage, Scheidt remembers. It changed my life. Before then I was in punk bands. After that, I started to play slower and lower.Toward the end of the nineties, Scheidt started writing songs in the stoner doom tradition of Black Sabbath and Sleep. He dubbed his new project YOB and submitted its first demo to stonerrock.com, one of many online musical communities that sprung up during the explosion of home internet service at the end of the millennium. At the time, Scheidt was busy parenting his three young children and didnt expect the recording to lead to much. I just submitted the demo because I wanted to be a part of the community, says Scheidt. There was no idea of anything beyond that. Life was very busy and I had other priorities. Everything that came afterwards was surprise after surprise after surprise.

Ticket Information

Check venue for pricing

Oktoberfest Nation | Chicago 2025
entertainment

Oktoberfest Nation | Chicago 2025

Tue, Oct 28 at 7:30 PM
Fulton Market

Event Information

🍻THE ULTIMATE OKTOBERFEST PARTY STRAIGHT FROM HOFBRAÜ MÜNCHEN IS TAKING OVER FULTON MARKET🍻  📍 Chicago – Fulton Market📅 September 18th – October 19th The time on your ticket (ex 5 PM) is your entry window. You can arrive up to 30 minutes before or after that time. Once inside, you’re welcome to stay as long as you’d like. About the event: Get ready to raise a stein at Chicago’s biggest Oktoberfest — right in the heart of Fulton Market. We’re pouring official Hofbräu München brews straight from Germany, serving up giant pretzels and juicy brats, and packing in non-stop Oktoberfest energy. Throw on your dirndl or lederhosen (or snag one on-site), then dive into stein-holding contests, carnival games, Oompah bands, and DJs.  This year, the party’s got some serious pedigree—Munich’s biggest beer traditions are being brought to life by the original mastermind behind Hofbräuhaus Chicago, Mike Matushka, who’s back to raise the bar once again. It all kicks off this September 18th for a limited time only, so grab your crew, throw on your dirndl or lederhosen, and be part of the party everyone will be talking about. 🍺 Beer Exclusively from Hofbräu München The legendary Munich brewery behind the official Oktoberfest—Prost to the real deal. This isn’t just some themed brew. It’s actual Hofbräu München beer, brewed in Munich, shipped straight to us, and poured by the liter. If you know, you know. 🌭 Brats, Bites & Bavarian Vibes Jumbo pretzels, grilled bratwursts, classic sausages, and enough snackable bites to fuel your next round. Yes, it’s all made to pair perfectly with whatever’s in your stein. 🍹 Full Bars & Festive Sips Not a beer person? We got you. From spiced apple cider mules to Prost Punch and cinnamon schnapps, our cocktail game is just as strong. 🎲 Gaudi Games Think Oktoberfest Olympics—with a Bavarian twist. From stein-carrying races and barrel rolls to brat tosses and more, these high-energy games are made for big laughs, fierce competition, and unforgettable photo ops. 🎶 Straight from Munich: A Live German Band Experience Grab a stein and hit the Hofbräu Stage for nonstop music, dancing, and next-level Oktoberfest vibes. This legit oompah band is flying in straight from Munich’s iconic Hofbräu München to turn Fulton Market into the ultimate Bavarian beer hall. Think pounding drums, wild toasts, and the kind of Oktoberfest energy you usually have to cross an ocean for. 🎡 The Devil’s Wheel A beloved fest tradition! Grab your crew and get ready to spin, slide, and laugh your way through this Oktoberfest crowd favorite. It’s fast, it’s wild, and it’s all in good fun. 👗 Lederhosen & Dirndl Pop-Up No outfit? No problem. Shop traditional Oktoberfest looks right onsite and get fest-ready in minutes. So grab your crew, pick a weekend (or five), and get ready to Prost like you mean it. This is Oktoberfest—Fulton Market style. And it’s going to be a blast. All sales are final. No refunds or exchanges.

Ticket Information

Check venue for pricing

Chicago Blackhawks vs. Ottawa Senators
sports

Chicago Blackhawks vs. Ottawa Senators

Tue, Oct 28 at 7:45 PM
United Center

Accessibility Information

ADA seating for patrons with wheelchairs and their companions is available for all Chicago Blackhawks events. Guests may purchase one wheelchair accessible seat and one companion seat. If you have questions or desire further information, please contact the Box Office at (312)455-4655.

Ticket Information

Check venue for pricing

An Evening With David Byrne - Who is the Sky Tour
music

An Evening With David Byrne - Who is the Sky Tour

Tue, Oct 28 at 8:00 PM
The Auditorium

Event Information

For current health safety information please visit www.auditoriumtheatre.org for details.

Accessibility Information

Accessible seating is available. For more information, please call: 312.341.2300

Ticket Information

Check venue for pricing

Bassvictim
music

Bassvictim

Wed, Oct 29 at 6:30 PM
Outset

Event Information

This is an ALL AGES event. Outset is a standing room only venue, all tickets are General Admission unless otherwise stated. There is NO re-entry.

Ticket Information

Check venue for pricing

Chicago Bulls vs. Sacramento Kings
sports

Chicago Bulls vs. Sacramento Kings

Wed, Oct 29 at 7:00 PM
United Center

Accessibility Information

ADA seating for patrons with wheelchairs, or hearing imparied and their companions is available for all Chicago Bulls events. Guests may purchase one accessible seat and one companion seat. If you have questions or desire further information, please contact the Box Office at (312)455-4655.

Ticket Information

Check venue for pricing

Maddie Zahm w/ Mercer Henderson
music

Maddie Zahm w/ Mercer Henderson

Wed, Oct 29 at 7:00 PM
Metro

Ticket Information

Check venue for pricing

Ready to Experience Chicago?

Plan your perfect itinerary around these amazing events

Create a personalized Chicago itinerary with our AI planner. Get recommendations for hotels, restaurants, and activities that complement these events. Our intelligent trip planner considers your preferences, budget, and travel dates to create the perfect Chicago travel plan.

Explore Events in Other Cities
contact@aiplanner.ai
AboutPrivacy PolicyTerms of Use
© 2025 AI Planner. All rights reserved.