Trips & Adventurous Activities in Chicago

Check out happening trips & adventurous activities events all around Chicago, IL

2025 Chicago Top Shelf Tequila and Whiskey Tasting Festival (Sept 27) AE

 Sat, 27 Sep at 02:30 pm Downtown Chicago USD 25 to 89

Alice In Chicagoland Immersive Pop Up Show

 Sat, 18 Oct at 06:00 pm TBD USD 55 to 162

Jeopardy! at Chicago Theatre

 Fri, 12 Sep at 07:30 pm Chicago Theatre

Taste of Chicago Meet and Greet

 Fri, 05 Sep at 04:00 pm Chicago, Illinois, U.S.A.

Wine Crawl Chicago - Be a Tourist In Your Own Town

 Sat, 13 Sep at 01:00 pm TBD Free

2025 All Access Chicago Day Of The Dead Bar Crawl

 Sat, 01 Nov at 08:00 pm Lincoln Park, River North, Wicker Park Venues,Chicago,60654,US USD 0 to 22

The Office E.N.T & ClubMeet4More Presents Carnival Night Cabin Party

 Fri, 05 Sep at 05:00 pm Chicago, IL

Socks In The Frying Pan

 Sat, 06 Sep at 06:00 pm Old Town School of Folk Music

Mt. Joy at United Center

 Sat, 13 Sep at 07:30 pm United Center

Randy Johnson

 Sat, 06 Sep at 06:00 pm Buddy Guys Legends

Thanya Iyer

 Sat, 06 Sep at 06:00 pm The Empty Bottle

Joe Wortell and His Country Band

 Fri, 05 Sep at 06:00 pm Carol's Pub

Saturday Night (Ages 25-39) | Speed Dating in Chicago | Speed Chicago

 Sat, 27 Sep at 07:30 pm Time Out Market Chicago USD 44

Uncle Charlie's R&B Cookout: Charlie Wilson Babyface & K-Ci

 Fri, 05 Sep at 06:00 pm Huntington Bank Pavilion at Northerly Island

Art on the Farm with Chicago FarmWorks

 Fri, 19 Sep at 05:00 pm 407 N Albany Ave Free

The Chicago Big Bus Tour and Scavenger Hunt

 Sat, 06 Sep at 12:00 pm 20 S Clark St, Ste 200, Chicago, IL, United States, Illinois 60603

TWRP at Thalia Hall

 Fri, 05 Sep at 07:30 pm Thalia Hall

Chicago Cubs vs. Washington Nationals

 Thu, 04 Sep at 06:00 pm Wrigley Field USD 16 to 5,250

Atif Aslam Live In Concert

 Sun, 21 Sep at 12:00 am Arie Crown Theater

Le Sserafim at Wintrust Arena

 Fri, 05 Sep at 07:30 pm Wintrust Arena

Reaper at Concord Music Hall

 Fri, 03 Oct at 10:00 pm Concord Music Hall

B.o.B - Adventures of Bobby ray at House of Blues Chicago

 Fri, 12 Sep at 07:00 pm House of Blues Chicago

ASI 50th Anniversary Picnic 2025

 Sat, 20 Sep at 11:00 am Humboldt Park Boathouse Free

Fall Nature Fest

 Sat, 13 Sep at 12:00 pm LaBagh Woods Grove 2 Free

Wardruna at Auditorium Theatre Chicago

 Sat, 20 Sep Auditorium Theatre Chicago

Parking Washington Nationals at Chicago Cubs

 Fri, 05 Sep Wrigley Field

Candlelight - The Best of Hans Zimmer at Stan Mansion

 Fri, 26 Sep Stan Mansion

Laufey at United Center

 Fri, 10 Oct at 07:30 pm United Center

Bad Suns at House of Blues Chicago

 Sat, 04 Oct at 07:00 pm House of Blues Chicago

Chasen Wayne & Rachel Swain

 Fri, 03 Oct at 06:00 pm Carol's Pub

Chicago Oktoberfest 2025

 Sat, 27 Sep at 04:00 pm Chicago USD 7 to 31

MCR-T

 Fri, 05 Sep at 06:00 pm Smart Bar Chicago

Rico McFaland

 Fri, 26 Sep at 06:00 pm Buddy Guys Legends

Blessthefall at House of Blues Chicago

 Fri, 19 Sep at 06:30 pm House of Blues Chicago

Hamza Namira at Thalia Hall

 Sun, 14 Sep at 07:30 pm Thalia Hall

Saturday Night (Ages 25-39) | Chicago Speed Dating | Speed Chicago

 Sat, 20 Sep at 07:30 pm Tabu USD 44

Brandy and Monica at United Center

 Sat, 18 Oct at 08:00 pm United Center

Uncle Charlies R&B Cookout at Huntington Bank Pavilion at Northerly Island

 Sat, 06 Sep Huntington Bank Pavilion at Northerly Island

The High Hawks at Garcias Chicago

 Fri, 17 Oct at 08:00 pm Garcias Chicago

Gettin' Grown Podcast Live

 Sat, 06 Sep City Winery - Chicago

Satin Jackets at Subterranean - Upstairs

 Sat, 06 Sep at 09:00 pm Subterranean - Upstairs

Gary Gulman at Athenaeum Center

 Sat, 20 Sep at 07:30 pm Athenaeum Center

Adventure Club in Chicago

 Sat, 11 Oct at 09:30 pm Ramova Theatre

Big Wild at Salt Shed - Indoor Shed

 Fri, 19 Sep at 09:00 pm Salt Shed - Indoor Shed

The Disasters at Cubby Bear

 Fri, 10 Oct at 09:00 pm Cubby Bear

Unsubscribe Podcast at Riviera Theatre - IL

 Sun, 26 Oct at 07:00 pm Riviera Theatre - IL

Like Moths To Flames

 Sat, 25 Oct at 06:00 pm Bottom Lounge

Blitzkid at Bottom Lounge

 Fri, 26 Sep at 08:00 pm Bottom Lounge

Kamala Harris

 Fri, 10 Oct at 06:00 pm Auditorium Theatre - IL

Emo Prom Nite

 Thu, 11 Sep at 06:00 pm City Winery - Chicago

Bob Mould

 Fri, 03 Oct at 06:00 pm Gary & Laura Maurer Concert Hall at Old Town School of Folk Music

Saxsquatch at Bottom Lounge

 Sat, 11 Oct at 08:00 pm Bottom Lounge

Mirador at Metro Chicago

 Fri, 12 Sep at 07:30 pm Metro Chicago

Chris Rawlins and Marian Runk

 Fri, 05 Sep at 08:00 pm UncommonGround - Lakeview USD 15 to 18

Chicago Immigrant Orchestra

 Sat, 13 Sep at 06:00 pm Epiphany Hall at Epiphany Center for the Arts

California Honeydrops at Thalia Hall

 Sun, 28 Sep at 08:00 pm Thalia Hall

Quinn XCII at Huntington Bank Pavilion at Northerly Island

 Fri, 19 Sep at 08:00 pm Huntington Bank Pavilion at Northerly Island

Slow Crush at Reggies Chicago

 Fri, 12 Sep Reggies Chicago

Strict Scrutiny at Athenaeum Center

 Sat, 04 Oct at 08:00 pm Athenaeum Center

Riot Fest Late Night: Ovlov

 Thu, 18 Sep at 06:00 pm The Empty Bottle

Beach Bunny

 Sat, 06 Sep at 06:00 pm The Salt Shed Outdoors - Chicago

Sweetest Day Comedy Jam: Lavell Crawford Bill Bellamy & T.I. (TIP Harris)

 Fri, 17 Oct at 06:00 pm Wintrust Arena

Normal Gossip at Riviera Theatre - IL

 Fri, 26 Sep at 07:30 pm Riviera Theatre - IL

Jo Koy at United Center

 Fri, 07 Nov United Center

Southside Critical Mass Chicago Bicycle Ride

 Fri, 05 Sep at 05:45 pm 1300 E 55th St, Chicago, IL 60615-5302, United States

BNXN fka Buju

 Sat, 06 Sep at 06:00 pm Thalia Hall

Chris Distefano

 Sat, 06 Sep The Chicago Theatre

The Rapture at Riviera Theatre - IL

 Fri, 03 Oct at 07:30 pm Riviera Theatre - IL

Brent Cobb and The Fixins at Joes on W**d Street

 Sat, 27 Sep at 08:00 pm Joes on Weed Street

John Craigie at Garcias Chicago

 Sat, 27 Sep at 08:00 pm Garcias Chicago

Kid Congo Powers & The Pink Monkey Birds

 Sat, 13 Sep at 06:00 pm Beat Kitchen

George Janko

 Thu, 18 Sep at 06:00 pm Historic Main Stage at Athenaeum Center - IL

Swervedriver at Thalia Hall

 Sun, 05 Oct at 08:00 pm Thalia Hall

K Camp at Vic Theatre

 Thu, 04 Sep at 08:00 pm Vic Theatre

Blood Club at Bottom Lounge

 Fri, 10 Oct at 08:00 pm Bottom Lounge

Jeopardy - Chicago

 Sat, 13 Sep The Chicago Theatre

Chicago Bears vs. Dallas Cowboys

 Sat, 20 Sep at 06:00 pm Soldier Field

OUT OF THE PAST -- 35MM Screening at Noir City: Chicago!

 Sat, 06 Sep at 06:45 pm Music Box Theatre

Joffrey Ballet: The Nutcracker

 Thu, 04 Dec at 06:00 pm Lyric Opera House - IL USD 132 to 159

Dorothy & Eddie and The Getaway

 Tue, 16 Sep at 06:00 pm House Of Blues - Chicago

Turnstile at Huntington Bank Pavilion at Northerly Island

 Fri, 26 Sep at 07:00 pm Huntington Bank Pavilion at Northerly Island

Quinn XCII at Byline Bank Aragon Ballroom

 Fri, 19 Sep at 08:00 pm Byline Bank Aragon Ballroom

The Story So Far at Salt Shed - Outdoor Fairgrounds

 Thu, 11 Sep at 07:00 pm Salt Shed - Outdoor Fairgrounds

The Bouncing Souls

 Sat, 20 Sep Concord Music Hall

Parking Lorde with The Japanese House and Chanel Beads

 Sat, 20 Sep at 12:00 am United Center

Jimmy Dore

 Sat, 13 Sep Zanies Comedy Club - Chicago

Michelle Buteau

 Sat, 13 Sep at 12:30 am The Chicago Theatre

Speed Dating in Chicago (Ages 32-44) | Speed Chicago | Singles Events

 Sun, 14 Sep at 06:00 pm Recess USD 39

Quadeca at Thalia Hall

 Sun, 12 Oct at 07:30 pm Thalia Hall

Chris D'Elia at Chicago Theatre

 Sat, 15 Nov Chicago Theatre

Chicago Blues Allstars

 Fri, 05 Sep at 06:00 pm Buddy Guys Legends

Nikita Nichelle at City Winery - Chicago

 Thu, 11 Sep at 07:30 pm City Winery - Chicago

2026 Chicago All Access New Years Eve (NYE) Bar Crawl

 Wed, 31 Dec at 08:00 pm Downtown Chicago USD 0 to 77

Haim at United Center

 Fri, 12 Sep at 08:00 pm United Center

Ali Sethi at Vic Theatre

 Sat, 14 Jun at 08:00 pm Vic Theatre

Yousuke Yukimatsu at Ramova Theatre

 Fri, 12 Sep at 09:30 pm Ramova Theatre

World Series: Chicago Cubs vs. TBD - Home Game 4 (Date: TBD - If Necessary)

 Fri, 31 Oct Wrigley Field

Mojo Brookzz - Dyon Brooks at Chicago Theatre

 Sat, 13 Sep at 08:00 pm Chicago Theatre

Trash Panda at Beat Kitchen

 Wed, 15 Oct at 08:00 pm Beat Kitchen

Crown Rally South 2025

 Fri, 10 Oct at 01:00 pm Chicago, Illinois