Trips & Adventurous Activities in Chicago

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

Portland Trail Blazers at Chicago Bulls at United Center

 Fri Apr 04 2025 at 07:00 pm United Center

Holidy Express 2 (Magnificent Mile lights Parade)

 Sat Nov 23 2024 at 04:15 pm North Michigan Avenue Free

At NHM: Free Guided Tour

 Sat Nov 23 2024 at 11:00 am National Hellenic Museum Free

Cycling in the City 101

 Fri Nov 22 2024 at 05:00 pm 4600 W Palmer St Free

ILEAD Field Trip - Shedd Aquarium

 Tue Nov 26 2024 at 11:00 am Shedd Aquarium Free

Robinson Woods Walk

 Tue Nov 26 2024 at 01:00 pm Robinson Woods-South Free

Chicago Bulls vs. Portland Trail Blazers

 Fri Apr 04 2025 at 07:00 pm United Center

At NHM: Free Guided Tour

 Sat Dec 14 2024 at 11:00 am National Hellenic Museum Free

At NHM: Free Guided Tours

 Sun Dec 15 2024 at 11:00 am National Hellenic Museum Free

Girl Scout Information Night at Beverly Library- NEW Troops Starting

 Mon Nov 25 2024 at 06:30 pm Beverly Branch Library Free

CHICAGO JOSELINES CABARET TOUR DAMELO

 Fri Nov 22 2024 at 07:00 pm 1645 N Cicero Ave USD 72 to 589

Chicago Ugly Sweater Bar Crawl

 Sat Dec 21 2024 at 04:00 pm Chicago USD 0 to 25

Girl Scout Information Night at Mt Greenwood Library- NEW Troops Starting

 Tue Dec 10 2024 at 05:00 pm Mount Greenwood Branch, Chicago Public Library Free

Romansia: A La Orient Romantic Dinner and Show

 Sun Nov 24 2024 at 05:00 pm 1240 W Randolph Street USD 34 to 55

Tales by the Fire: Fall Festivities

 Mon Nov 25 2024 at 04:00 pm 1201 W 63rd St Free

Van Trip to Jasper-Pulaski Park and Sandhill Cranes

 Fri Nov 22 2024 at 01:30 pm South Loop Jewel Osco Parking Lot Free

HEAVY TRIP / HEAVIER TRIP Double Feature

 Wed Nov 27 2024 at 07:00 pm Music Box Theatre

S'More Time Together: A Camping-Themed Family Event at Bennett Day School

 Sat Dec 14 2024 at 02:00 pm Bennett Day School Free

Old Town Presents... "The Holiday Hop"

 Sat Dec 07 2024 at 01:00 pm Old Town USD 17

Storytime with Captain America

 Sat Nov 23 2024 at 11:00 am Time Out Market Chicago Free

Girl Scout Information Night at West Lawn Library- NEW Troops Starting

 Mon Jan 06 2025 at 06:00 pm West Lawn Branch, Chicago Public Library Free

Girl Scout Information Night at Chicago Lawn Library- NEW Troops Starting

 Tue Jan 07 2025 at 06:00 pm Chicago Public Library (Chicago Lawn Branch) Free

Life Time Turkey Trot Chicago 2024 5K & 8K

 Thu Nov 28 2024 at 08:00 am North Cannon Drive

Speed Dating | Ages 24-36 | Singles Event | Chicago | SpeedChicago

 Thu Dec 05 2024 at 07:00 pm Untitled Supper Club USD 39

Chicago SantaCon 2024

 Sat Dec 21 2024 at 04:00 pm Chicago USD 0 to 31

Old Town Presents: The Holiday Hop

 Sat Dec 07 2024 at 01:00 pm 1610 N Wells St, Chicago, IL 60614, United States

Wicker Park Bucktown Winter Wonderland

 Thu Dec 26 2024 at 10:00 am Wicker Park Bucktown Free

Grieg & Rachmaninov

 Thu Dec 05 2024 at 07:30 pm Chicago Symphony Orchestra

At NHM: Free Guided Tour

 Sat Dec 07 2024 at 11:00 am National Hellenic Museum Free

MARVIN STUMBLES

 Fri Nov 22 2024 at 07:00 pm Lemon USD 13

Girl Scout Information Night at Lozano Library- NEW Troops Starting

 Tue Dec 03 2024 at 06:00 pm Lozano Branch, Chicago Public Library Free

2025 Chicago Winter Whiskey Tasting Festival (January 25)

 Sat Jan 25 2025 at 02:30 pm Downtown Chicago USD 0 to 400

Girl Scout Information Night at Brainerd Library- NEW Troops Starting

 Sat Nov 30 2024 at 11:00 am Brainerd Branch, Chicago Public Library Free

Speed Dating | Ages 25-39 | Chicago | Saturday Event | SpeedChicago

 Sat Dec 21 2024 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

Holiday Blind Book Swap Party

 Sat Dec 14 2024 at 07:00 pm The Last Chapter Book Shop USD 22

Girl Scout Information Night at Vodak East Side Library-NEW Troops Starting

 Mon Dec 02 2024 at 06:00 pm Vodak-East Side Branch, Chicago Public Library Free

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

 Sat Dec 07 2024 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

Mezcal Winter Camp

 Sat Dec 14 2024 at 03:00 pm CH Distillery Bar & Table

Girl Scout Information Night at Scottsdale Library- NEW Troops Starting

 Sat Dec 07 2024 at 11:00 am Scottsdale Branch, Chicago Public Library Free

YAC and YAM Chriskindlmarket

 Sun Dec 08 2024 at 01:00 pm Chriskindlemarket

LO Great Lakes x Escala Chicago | Indoor Rock Climbing at Movement

 Fri Dec 06 2024 at 06:30 pm Movement Lincoln Park Free

Art Institute Career Trek | Waldron Student-Alumni Connections Program

 Thu Dec 05 2024 at 11:00 am The Art Institute of Chicago Free

VIP STADIUM TOUR

 Mon Nov 25 2024 at 01:00 pm Soldier Field

VIP STADIUM TOUR

 Mon Nov 25 2024 at 11:00 am Soldier Field

2025 Chicago Winter Tequila Tasting Festival (February 15)

 Sat Feb 15 2025 at 02:30 pm Downtown Chicago USD 0 to 400

The Windy City Witches present: HERITAGE

 Sat Nov 30 2024 at 03:00 pm The Newport Theater USD 23 to 39

Film Screening: "Wreck-It Ralph"

 Sun Dec 08 2024 at 03:00 pm American Writers Museum USD 0 to 7

BABY ON BOARD: Infant Car Seat Safety - WEISSBLUTH PEDIATRICS (SOUTH LOOP)

 Thu Dec 19 2024 at 06:00 pm Weissbluth Pediatrics Free

Celebrating Motown Soulful Music Holiday Lights Trolley

 Fri Dec 06 2024 at 06:30 pm 230 W North Ave, (Inside Lobby) Next to Parking Garage USD 73

The Elfed Up Christmas Crawl

 Sat Dec 14 2024 at 02:00 pm Headquarters Beercade USD 10 to 25

BABY ON BOARD: Infant Car Seat Safety - WEISSBLUTH PEDIATRICS (BUCKTOWN)

 Thu Feb 27 2025 at 06:00 pm Weissbluth Pediatrics Free

Speed Dating | Ages 36-48 | Chicago Singles Night | SpeedChicago

 Sun Nov 24 2024 at 06:00 pm Tabu USD 39

Speed Dating in Chicago | Ages 24-38 | Saturday Event | SpeedChicago

 Sat Nov 23 2024 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

Floral Bar Workshop @ Mott St

 Sun Nov 24 2024 at 01:00 pm Mott St USD 40 to 157

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

 Sat Nov 30 2024 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

Owl Pellet Dissection / Jewelry Making Workshop

 Sat Nov 23 2024 at 03:00 pm The Insect Asylum USD 18 to 61

Celebrating Motown Soulful Music Holiday Lights Trolley

 Sat Dec 14 2024 at 05:00 pm 230 W North Ave, (Inside Lobby) Next to Parking Garage USD 73

The Chosen Few Djs Holiday Party at Vu Rooftop. House Music in 2 Rooms.

 Sat Dec 21 2024 at 04:00 pm VU Rooftop. 22nd Floor USD 18 to 194

Celebrating Motown Soulful Music Holiday Lights Trolley

 Fri Dec 13 2024 at 06:30 pm 230 W North Ave (inside Lobby) USD 73

Chicago Speed Dating | Ages 32-44 | Singles Night | SpeedChicago

 Sun Dec 08 2024 at 06:00 pm Recess USD 39

Sensory Seeking Sunday

 Sun Nov 24 2024 at 01:30 pm The Insect Asylum USD 17 to 23

New Moon Yoga Series: Expansion & Vision

 Sun Dec 01 2024 at 06:00 pm 936 W Randolph St USD 34

Cre8tive Con 2025

 Fri Feb 21 2025 at 05:00 pm InterContinental Chicago Magnificent Mile, an IHG Hotel USD 268

Toys For Tots Motorcycle Parade Viewing Party

 Sun Dec 01 2024 at 08:30 am 1901 S Western Ave, Chicago, IL, United States, Illinois 60608

Lessons From Abroad Chicago 2025 Conference

 Sat Feb 01 2025 at 09:30 am DePaul University - Lincoln Park Student Center USD 29 to 34

Foxtrot & Foxxy Dance Class

 Sat Nov 23 2024 at 07:15 pm Ballroom College USD 29

Tiny Moving Parts, Action/Adventure, Greywind in Chicago

 Sat Nov 23 2024 at 08:00 pm Bottom Lounge Chicago

Sensory Seeking Sunday

 Sun Dec 01 2024 at 01:30 pm The Insect Asylum USD 18 to 23

Speed Dating | Ages 24-38 | Saturday Night in Chicago | SpeedChicago

 Sat Dec 14 2024 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

Chicago Speed Dating | Ages 32-44 | Singles Event | SpeedChicago

 Sun Dec 22 2024 at 06:00 pm Recess USD 39

Opossum Paint and Sip Art Night! BYOB @ The Insect Asylum

 Fri Nov 22 2024 at 06:00 pm The Insect Asylum USD 71

Opossum Paint and Sip Art Night! BYOB @ The Insect Asylum

 Sat Nov 23 2024 at 06:00 pm The Insect Asylum USD 71

Maria Bamford at The Den Theatre

 Thu Dec 12 2024 at 07:15 pm 1331 N Milwaukee Ave, Chicago, IL, United States, Illinois 60622

Terry Hunter * Dj Heather * Duane Powell

 Fri Nov 22 2024 at 10:00 pm Smartbar

Sensory Seeking Sunday

 Sun Dec 08 2024 at 01:30 pm The Insect Asylum USD 18 to 23

BYOB Holiday Lights Trolley - Chicago

 Fri Nov 29 2024 at 03:00 pm Matilda & BabyAtlas

Speed Dating | Ages 24-36 | Singles Night | Chicago | SpeedChicago

 Thu Dec 19 2024 at 07:00 pm Untitled Supper Club USD 39

XFA Presents Watch The Throne

 Fri Nov 29 2024 at 08:00 am X - Fat Azz Cycling & Fitness Studio USD 39

PREMIER ONE DANCE CONSERVATORY presents The MADNESS Before Christmas

 Sun Dec 15 2024 at 05:30 pm Morgan Park Academy USD 34

Speed Dating | Ages 24-38 | Saturday Event in Chicago | SpeedChicago

 Sat Dec 28 2024 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

Cherish the Ladies "A Celtic Christmas" Returns!

 Fri Dec 13 2024 at 07:00 pm Mayfair Theatre USD 30 to 40

DePaul Blue Demons vs. Marquette Golden Eagles

 Tue Jan 14 2025 at 06:00 pm USD 29 to 512

Olaf's Frozen Adventure

 Sun Dec 22 2024 at 02:30 pm Dr. Martin Luther King, Jr. Roller Skating and Bowling Center USD 15 to 19

Dave Koz and Friends Christmas Tour 2024

 Thu Dec 12 2024 at 07:30 pm 50 E Ida B Wells Dr, Chicago, IL, United States, Illinois 60605

Pigeons Playing Ping Pong

 Fri Apr 25 2025 at 08:00 pm The Vic Theatre

2024 Turkey Trot

 Fri Nov 29 2024 at 08:00 am The Bean

Sensory Seeking Sunday

 Sun Dec 29 2024 at 01:30 pm The Insect Asylum USD 18 to 23

Crouching Tiger, Hidden Dragon - The Film with Orchestra

 Fri Jan 10 2025 at 07:30 pm Chicago Symphony Orchestra

Holiday Winter Dash Beer Run | 2024 Illinois Brewery Running Series

 Sun Dec 08 2024 at 12:00 pm Goose Island Beer Co. & Midwest Coast Brewing USD 35 to 50

Santa Cycle Rampage 2024

 Sat Dec 14 2024 at 12:00 pm Twisted Spoke

Homeschool Field Trip - STEM Trip to iFLY Lincoln Park!

 Fri Jan 10 2025 at 09:30 am iFLY Indoor Skydiving - Chicago Lincoln Park USD 64

Swing Dance Class

 Sat Feb 22 2025 at 07:15 pm Ballroom College USD 20

Chicago Bulls vs. Portland Trail Blazers

 Fri Apr 04 2025 at 07:00 pm United Center

Bites & Vines: Food & Wine Pairing Series Featuring Gloria Ferrer and Tapas Menu

 Fri Dec 06 2024 at 06:00 pm 521 North Rush Street, Chicago, IL, United States, Illinois 60611

Globetrotter by Andrea Paone | Italian Comedy Show

 Sat Mar 29 2025 at 06:00 pm The Lincoln Lodge USD 18

NIGHT SNOWTUBING CHI 2025

 Sat Jan 25 2025 at 03:00 pm Long Room Chicago USD 139

Story Luck! A Storytelling Potluck Show.

 Sun Feb 02 2025 at 06:30 pm Theater Wit USD 5 to 23

St. Patrick's Day Lucky Charms West Loop Bar Crawl.

 Sun Mar 16 2025 at 12:00 pm West Loop USD 10 to 35

Cumbia Dance Class

 Sat Jan 25 2025 at 07:15 pm Ballroom College USD 20

St. Patrick's Day Lucky Charms West Loop Bar Crawl

 Sat Mar 15 2025 at 12:00 pm West Loop USD 15 to 40