Trips & Adventurous Activities in Chicago

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

2025 Chicago Summer Whiskey Tasting Festival (August 23) AE

 Sat, 23 Aug at 12:00 am Galeria Chicago USD 20 to 89

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

Saturday Night Fireworks Booze Cruise!

 Sat, 16 Aug at 08:30 pm Summer Of George USD 49 to 107

Atif Aslam at Arie Crown Theater

 Sat, 20 Sep at 07:00 pm Arie Crown Theater

Alice In Chicagoland Immersive Pop Up Show

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

Purple Madness - A Tribute To Prince

 Sat, 16 Aug at 06:00 pm City Winery - Chicago

Benson Boone at United Center

 Sat, 23 Aug at 08:00 pm United Center

Flight Facilities, Mindchatter in Chicago

 Fri, 15 Aug at 05:00 pm Chicago Plumbers Union Hall Parking Lot

2025 Air & Water Show Viewing Party - The Lakefront Green - Sunday 8/17

 Sun, 17 Aug at 11:00 am The Lakefront Green at Theater on the Lake USD 55 to 130

Wine Crawl Chicago - Be a Tourist In Your Own Town

 Sat, 13 Sep at 01:00 pm TBD Free

Chicago Cubs vs. Milwaukee Brewers

 Sun, 17 Aug at 06:00 pm Wrigley Field USD 27 to 5,250

35TH ANNUAL AFRICAN FESTIVAL OF THE ARTS

 Sat, 30 Aug at 10:00 am Washington Park

Chicago Sky vs. Las Vegas Aces

 Sun, 24 Aug at 06:00 pm Wintrust Arena USD 52 to 361

Le Dîner en Blanc Chicago

 Thu, 21 Aug at 07:00 pm Chicago

Taste of Chicago Meet and Greet

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

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

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

Haim at United Center

 Fri, 12 Sep at 08:00 pm United Center

Air & Water Show Yacht Cruise (Anita Dee 1) Chicago

 Sun, 17 Aug at 11:30 am Anita Dee Yacht Charters USD 82 to 535

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

Wicker Park Walking Tour

 Sun, 17 Aug at 03:00 pm Damen Blue Line USD 0 to 45

Back To School Block Party

 Sat, 23 Aug at 08:30 am Rainbow PUSH Headquarters

Feature Fridays | M (1930s Cinema Appreciation Week)

 Fri, 22 Aug at 08:30 pm Parkway Ballroom Free

The Chainsmokers at Aon Grand Ballroom

 Sat, 16 Aug at 07:00 pm Aon Grand Ballroom

Jessie Murph at Byline Bank Aragon Ballroom

 Sat, 16 Aug Byline Bank Aragon Ballroom

Perfume Making Class - Create Your Own Personal Scent

 Sat, 20 Jul at 01:00 pm Reggie Hathorn Candles and Home Fragrances | Candle Making Classes USD 93

Joffrey Ballet: The Nutcracker

 Fri, 05 Dec at 06:00 pm Lyric Opera House - IL USD 132 to 159

Mannheim Steamroller Christmas at Nederlander Theatre Chicago

 Sat, 20 Dec at 03:00 pm Nederlander Theatre Chicago

Chicago Cubs vs. Washington Nationals

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

Mana at United Center

 Fri, 26 Sep at 08:30 pm United Center

City Cruises Chicago Offers City's Best Seats For 2025 Chicago Air & Water Show

 Fri, 15 Aug at 10:30 am City Cruises

The Starting Line at Vic Theatre

 Fri, 29 Aug at 07:30 pm Vic Theatre

2025 Air & Water Show Viewing Party - The Lakefront Green - Saturday 8/16

 Sat, 16 Aug at 11:00 am The Lakefront Green at Theater on the Lake USD 55 to 130

Getter at Ramova Theatre

 Sat, 16 Aug at 09:30 pm Ramova Theatre

Atif Aslam Live In Concert

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

Singles Events Ages 32-44 | Chicago Speed Dating | Speed Chicago

 Sun, 17 Aug at 06:00 pm Recess USD 39

Brandy and Monica at United Center

 Sat, 18 Oct at 08:00 pm United Center

US99 Presents: Low Dough Show with George Birge

 Wed, 27 Aug at 07:30 pm Joe's on Weed St.

Above and Beyond at Huntington Bank Pavilion at Northerly Island

 Fri, 22 Aug Huntington Bank Pavilion at Northerly Island

Chicago Oktoberfest 2025

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

N.Flying at Riviera Theatre - IL

 Sun, 24 Aug at 07:30 pm Riviera Theatre - IL

Walking Tour | Historic Prairie Avenue

 Sun, 31 Aug at 12:00 pm Glessner House

The Third Mind at Garcias Chicago

 Fri, 10 Oct at 08:00 pm Garcias Chicago

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

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

Runner and Bobby

 Wed, 13 Aug at 06:00 pm Reggie's Music Joint

Laufey at United Center

 Fri, 10 Oct at 07:30 pm United Center

Ryan Ellis

 Sat, 16 Aug at 06:00 pm Subterranean

EST Gee at Vic Theatre

 Sun, 24 Aug at 07:00 pm Vic Theatre

The Twenty-Sided Tavern at Broadway Playhouse at Water Tower Place

 Sat, 23 Aug at 07:30 pm Broadway Playhouse at Water Tower Place

SPARK Art Fair at Mozart Park

 Fri, 15 Aug at 04:00 pm Mozart (Amadeus) Park Free

ShadowGrass at Garcias Chicago

 Fri, 29 Aug at 08:00 pm Garcias Chicago

Gary Gulman at Athenaeum Center

 Sat, 20 Sep at 07:30 pm Athenaeum Center

Hamza Namira at Thalia Hall

 Sun, 14 Sep at 07:30 pm Thalia Hall

Blue Heaven at Black Ensemble Theater

 Sat, 06 Sep at 08:00 pm Black Ensemble Theater

Adventure Club in Chicago

 Sat, 11 Oct at 09:30 pm Ramova Theatre

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

 Sat, 06 Sep Huntington Bank Pavilion at Northerly Island

Packages & Hospitality: Benson Boone

 Fri, 22 Aug at 06:00 pm United Center

Marcus Bailey

 Fri, 15 Aug at 06:00 pm Cubby Bear

Reba Meyers

 Fri, 15 Aug at 06:00 pm Cobra Lounge

Ali Sethi at Vic Theatre

 Sat, 14 Jun at 08:00 pm Vic Theatre

An Inconceivable Evening With Cary Elwes

 Sat, 27 Sep at 11:00 am 50 E Ida B Wells Dr, Chicago, IL, United States, Illinois 60605

We Came As Romans at Byline Bank Aragon Ballroom

 Fri, 22 Aug at 06:00 pm Byline Bank Aragon Ballroom

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

 Sat, 16 Aug at 07:30 pm Time Out Market Chicago USD 44

An Evening of Yacht Rock at City Winery - Chicago

 Mon, 01 Sep at 07:30 pm City Winery - Chicago

Andrew Callaghan at Riviera Theatre - IL

 Thu, 16 Oct at 07:30 pm Riviera Theatre - IL

Le Sserafim at Wintrust Arena

 Fri, 05 Sep at 07:30 pm Wintrust Arena

Quinn XCII at Huntington Bank Pavilion at Northerly Island

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

Strict Scrutiny at Athenaeum Center

 Sat, 04 Oct at 08:00 pm Athenaeum Center

Delta Sleep in Chicago

 Fri, 19 Sep at 11:00 pm Sleeping Village

Silverada at Thalia Hall

 Wed, 13 Aug at 08:00 pm Thalia Hall

Wardruna at Auditorium Theatre Chicago

 Sat, 20 Sep Auditorium Theatre Chicago

Mt. Joy at United Center

 Sat, 13 Sep at 07:30 pm United Center

Jo Koy at United Center

 Fri, 07 Nov United Center

B.o.B - Adventures of Bobby Ray 15th Anniversary Tour

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

Turnstile at Huntington Bank Pavilion at Northerly Island

 Fri, 26 Sep Huntington Bank Pavilion at Northerly Island

Xoth

 Fri, 19 Sep at 06:00 pm Reggie's Music Joint

Dorothy & Eddie and The Getaway

 Tue, 16 Sep House Of Blues - Chicago

Lucius at Salt Shed - Indoor Shed

 Sat, 18 Oct at 07:30 pm Salt Shed - Indoor Shed

Queer Outdoor Movie Night

 Sat, 23 Aug at 07:00 pm Kathy Osterman Beach Free

Boston Bruins at Chicago Blackhawks at United Center

 Sat, 17 Jan at 07:00 pm United Center

CMAT at Park West

 Sat, 13 Sep at 08:00 pm Park West

Beach Bunny

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

Matteo Lane

 Sun, 17 Aug at 06:00 pm Zanies Comedy Club - Chicago

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

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

Ken Carson at Credit Union 1 Arena at UIC

 Sat, 16 Aug at 08:00 pm Credit Union 1 Arena at UIC

Borgeous at Sound Bar - Chicago

 Sat, 23 Aug Sound Bar - Chicago

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

 Sat, 23 Aug at 07:30 pm Tabu USD 44

Story Time with Dr. Kay!

 Sat, 16 Aug at 11:00 am Call & Response Books USD 0 to 25

Lyfe Jennings at City Winery - Chicago

 Thu, 14 Aug at 07:30 pm City Winery - Chicago

Blue Oyster Cult

 Sat, 16 Aug at 12:30 am Riviera Theatre - Chicago

Yuno

 Sat, 16 Aug at 06:00 pm Schubas

Anaheim Ducks at Chicago Blackhawks at United Center

 Sun, 19 Oct at 06:00 pm United Center

Children's Storytime: HILWA'S GIFTS by Safa Suleiman

 Sat, 13 Sep at 10:30 am Women & Children First Free

Bad Planning

 Sat, 06 Sep Bottom Lounge

Summer Saturdays - Naples

 Sat, 16 Aug at 02:00 pm Eataly Chicago USD 43 to 188

K Camp at Vic Theatre

 Thu, 04 Sep at 08:00 pm Vic Theatre

Mars FM

 Fri, 22 Aug at 08:00 pm UncommonGround - Lakeview USD 15 to 18

Blue Oyster Cult at Riviera Theatre - IL

 Fri, 15 Aug at 07:30 pm Riviera Theatre - IL

Stockyards Industrial Walking Tour

 Sat, 23 Aug at 11:00 am South Halsted Street & West Exchange Avenue (SW Corner) USD 0 to 45

Jerrys Middle Finger at Garcias Chicago

 Fri, 19 Sep at 08:00 pm Garcias Chicago

Violent Femmes at Salt Shed - Indoor Shed

 Fri, 17 Oct at 08:00 pm Salt Shed - Indoor Shed