Trips & Adventurous Activities in Chicago

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

2025 Chicago Winter Whiskey Tasting Festival (January 25) AE

 Sat Jan 25 2025 at 02:30 pm Downtown Chicago USD 20 to 89

Viceroy Chicago's Gingerbread Jubilee

 Sat Dec 07 2024 at 01:00 pm Viceroy Chicago 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

Chicago Ugly Sweater Bar Crawl

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

Old Town Presents: The Holiday Hop

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

Albany Park's 2nd Annual - Sip, Shop and Trolley Hop

 Thu Dec 12 2024 at 04:00 pm Albany Park Free

Grieg & Rachmaninov

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

Storytime with Olaf

 Sat Dec 21 2024 at 11:00 am Time Out Market Chicago Free

BAD HABITS DUO perform Classic Cinematic Soundtracks Live at FSC

 Tue Dec 10 2024 at 08:00 pm Fulton Street Collective Free

Mini-Fundraiser, Patio Bonfire, Live Music - Montrose Saloon

 Sun Dec 15 2024 at 04:30 pm Montrose Saloon Free

2025 Chicago Winter Whiskey Tasting Festival (January 25)

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

David Gray at Chicago Theatre

 Sun Feb 02 2025 at 07:30 pm Chicago Theatre

Chicago SantaCon 2024

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

Ferris Bueller Movie Tour at the Art Institute of Chicago

 Sat Dec 07 2024 at 11:30 am 159 E Monroe St USD 40

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

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

2025 Chicago Winter Tequila Tasting Festival (February 15)

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

Cozy Christmas Movie Night!

 Sat Dec 14 2024 at 07:00 pm 2134 W 18th St Free

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

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

Cre8tive Con 2025

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

Catalytic Sound Festival

 Fri Dec 06 2024 at 08:30 pm 3111 N Western Ave Chicago IL 60618

Celebrating Motown Soulful Music Holiday Lights Trolley

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

Portland Trail Blazers at Chicago Bulls at United Center

 Fri Apr 04 2025 United Center

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

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

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

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

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

DePaul Blue Demons vs. Marquette Golden Eagles

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

Holiday Blind Book Swap Party

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

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

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

Cherish the Ladies "A Celtic Christmas" Returns!

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

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

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

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! +21 BYOB

 Sat Dec 21 2024 at 06:00 pm The Insect Asylum USD 71

Owl Pellet Dissection / Jewelry Making Workshop

 Fri Dec 20 2024 at 03:00 pm The Insect Asylum USD 18 to 61

The Elfed Up Christmas Crawl

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

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

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

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

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

Old Town Presents... "The Holiday Hop"

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

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

 Sat Dec 21 2024 at 04:00 pm VU Rooftop

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

At NHM: Free Guided Tour

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

Crouching Tiger, Hidden Dragon - The Film with Orchestra

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

Opossum Paint and Sip Art Night! +21 BYOB

 Sat Dec 28 2024 at 06:00 pm The Insect Asylum USD 71

Yoga with Cats!

 Fri Jan 10 2025 at 07:00 pm 2914 N Elston Ave, Chicago, IL, United States, Illinois 60618

Owl Pellet Dissection / Jewelry Making Workshop

 Fri Dec 27 2024 at 03:00 pm The Insect Asylum USD 18 to 61

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

 Sat Jan 04 2025 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

St. Patrick's Day Lucky Charms Wrigleyville Bar Crawl

 Sat Mar 15 2025 at 10:00 am Wrigleyville USD 15 to 35

At NHM: Free Guided Tour

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

Open House: Humboldt Park 2BR Condos

 Sat Dec 14 2024 at 12:00 pm 1508 N Harding Ave Free

Film Screening: "Wreck-It Ralph"

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

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

 Sun Jan 05 2025 at 06:00 pm Recess USD 39

Chicago Bulls vs. Portland Trail Blazers

 Fri Apr 04 2025 at 07:00 pm United Center

Maria Bamford at The Den Theatre

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

Pink Martini featuring China Forbes: 30th Anniversary Tour

 Sat Mar 01 2025 at 07:30 pm Chicago Symphony Orchestra

BYOB Holiday Lights Trolley - Chicago

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

Jack Frost Christmas Pop-Up

Fri Nov 29 2024 at 12:00 am 170 N Green St

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

At NHM: Free Guided Tour

 Sat Dec 07 2024 at 01:00 pm National Hellenic Museum Free

Pigeons Playing Ping Pong

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

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

 Sat Jan 11 2025 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

Cumbia Dance Class

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

Chicago - Bulls Outing (Amigas Y Mas Co-ed)

 Fri Jan 10 2025 at 07:00 pm United Center USD 39

Girl Scout Information Night at Scottsdale Library- NEW Troops Starting

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

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

 Sat Jan 18 2025 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

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

 Thu Jan 16 2025 at 07:00 pm Untitled Supper Club USD 39

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

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

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

 Sun Jan 19 2025 at 06:00 pm Recess USD 39

At NHM: Free Guided Tours

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

An American Suite

 Sat May 31 2025 at 07:30 pm Chicago Symphony Orchestra

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

 Sun Jan 26 2025 at 06:00 pm Tabu USD 39

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

 Sat Jan 25 2025 at 07:30 pm WHIM Chicago @ Stage 773 USD 44

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

At NHM: Free Guided Tour

 Sun Dec 22 2024 at 01:00 pm National Hellenic Museum Free

At NHM: Free Guided Tour

 Sun Dec 22 2024 at 11:00 am National Hellenic Museum Free

Girl Scout Information Night at Little Village Library- NEW Troops Starting

 Sat Dec 21 2024 at 11:00 am Little Village Branch, Chicago Public Library Free

Globetrotter by Andrea Paone | Italian Comedy Show

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

Valentine's Tantra Speed Date® - Chicago! (Find Your Valentine!) Meet Singles Speed Dating

 Sat Feb 08 2025 at 05:30 pm Moksha Yoga Center USD 49 to 140

Swing Dance Class

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

YAC and YAM Chriskindlmarket

 Sun Dec 08 2024 at 01:00 pm Chriskindlemarket

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

Spice Up Your Winter: Pepper Soup Perfection Workshop

 Sun Jan 19 2025 at 04:30 pm 4410 N Milwaukee Ave USD 50 to 145

Camping In Alaska

 Thu Feb 20 2025 at 08:00 pm Subterranean

Story Luck! A Storytelling Potluck Show.

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

The 24th annual Midwest Awards Ball presents: Arcadia’s Paradise

 Sat Apr 19 2025 at 05:00 pm Chicago Theater Works

Sensory Seeking Sunday

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

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

Holiday Pop-Up Bar Hop in Wrigleyville Wonderland

 Fri Dec 06 2024 at 05:00 pm Wrigleyville Wonderland

No Wasted Time New Years Eve Party

 Tue Dec 31 2024 at 08:00 pm Everything Bar USD 55 to 92

Mezcal Winter Camp

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

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 36-48 | Chicago | Singles Night | SpeedChicago

 Sun Jan 12 2025 at 06:00 pm Tabu USD 39

Step by Step Drawing Animals

 Sun Dec 08 2024 at 01:00 pm 225 S Sangamon St, Chicago, IL, United States, Illinois 60607

Sensory Seeking Sunday

 Sun Dec 15 2024 at 01:30 pm The Insect Asylum USD 18 to 23

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

Kids Krampus Day! (crafts and D&D)

 Sat Dec 21 2024 at 12:00 pm 2849 W Belmont Ave, Chicago, IL

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

Art Institute Career Trek | Waldron Student-Alumni Connections Program

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

Sensory Seeking Sunday

 Sun Dec 22 2024 at 01:30 pm The Insect Asylum USD 18 to 23

VIP STADIUM TOUR

 Thu Jan 02 2025 at 03:00 pm Soldier Field

NIGHT SNOWTUBING CHI 2025

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