Best Trips & Adventurous Activities in Chicago This Weekend | December 27 - 28

Q: What are the trending Trips & Adventurous Activities in Chicago?

Here are the trending events in Chicago: Joffrey Ballet: The Nutcracker, Chris Lake, Pier Pressure: Alison Wonderland & San Holo Wholseom Riddim Set - Night 2, Raheem Devaughn - 20 Lessons of Love at City Winery - Chicago, Raheem DeVaughn, Parking Joffrey Ballet - The Nutcracker

Trips & Adventurous Activities in Chicago this Weekend

Sat, 13 Dec Onwards

Joffrey Ballet: The Nutcracker

Lyric Opera House - IL

USD 132
Fri, 26 Dec, 2025 - 06:00 PM

Chris Lake

Radius - IL
Fri, 26 Dec, 2025 - 06:00 PM

Pier Pressure: Alison Wonderland & San Holo Wholseom Riddim Set - Night 2

Aon Grand Ballroom Navy Pier
Fri, 26 Dec, 2025 - 06:00 PM

Raheem Devaughn - 20 Lessons of Love at City Winery - Chicago

City Winery - Chicago
Sat, 27 Dec Onwards

Raheem DeVaughn

City Winery - Chicago
Fri, 26 Dec, 2025 - 08:00 PM

Parking Joffrey Ballet - The Nutcracker

Lyric Opera of Chicago
Fri, 26 Dec, 2025 - 10:00 PM

Chris Lorenzo at Radius Chicago

Radius Chicago
Sat, 27 Dec, 2025 - 01:00 AM

Parking Philadelphia 76ers at Chicago Bulls

United Center
Sat, 27 Dec, 2025 - 06:00 PM

Cloonee

Radius - IL
Fri, 26 Dec, 2025 - 06:00 PM

Matroda

Concord Music Hall
Sat, 27 Dec, 2025 - 11:59 PM

Pier Pressure - Saturday at Aon Grand Ballroom at Navy Pier

Aon Grand Ballroom at Navy Pier
Fri, 05 Dec Onwards

The Nasty Show: Tiny Thickemz

The Laugh Factory - Chicago
Fri, 26 Dec, 2025 - 07:00 PM

Its A Wonderful Life at Athenaeum Center

Athenaeum Center
Fri, 26 Dec, 2025 - 08:00 PM

Moon Taxi at Garcias Chicago

Garcias Chicago
Fri, 26 Dec, 2025 - 10:00 PM

Azzecca at Cermak Hall - Radius Chicago

Cermak Hall - Radius Chicago

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Day Trips in Chicago

4.8 (742)

Scavenger Hunts by Let's Roam

32 E Randolph St, Chicago, IL 60601, USA
5 (15)

Navy Pier Centennial Wheel

600 E Grand Ave, Chicago, IL 60611, USA
5 (14)

Chicago Flyover

60611
Scavenger Hunt Puzzle Adventure

20 E Randolph Street (Chicago)
Small-Group Sightseeing Boat Tour in Chicago

Blackhawk Boat Tours
Best of Chicago Small Group Tour

Skydeck Chicago

Boating in Chicago

4.9 (1.7k+)

Urban Kayaks

435 E, Chicago Riverwalk, Chicago, IL 60601, USA
4.7 (386)

Kayak Chicago

1220 W Le Moyne St, Chicago, IL 60642, USA
5 (248)

Next Wave Watersports

2601 N Cannon Dr I Dock, Chicago, IL 60614, USA
4.1 (130)

Jet Ski Chicago

1600 N Lake Shore Dr, Chicago, IL 60613, USA
4.7 (69)

River Canoe and Kayak at Clark Park

3400 N Rockwell St, Chicago, IL 60618, USA
Chicago River Architecture Tour on a Historic Yacht

465 N McClurg Ct

Trips & Adventurous Activities from nearby cities

Upcoming Trips & Adventurous Activities in Chicago

Date	Event	Venue
27 Dec 2025	Joffrey Ballet The Nutcracker	Lyric Opera House - IL, Chicago
27 Dec 2025	Raheem DeVaughn	City Winery - Chicago
27 Dec 2025	Parking Joffrey Ballet - The Nutcracker	Lyric Opera of Chicago
27 Dec 2025	Cloonee	Radius - IL, Chicago
27 Dec 2025	Pier Pressure - Saturday at Aon Grand Ballroom at Navy Pier	Aon Grand Ballroom at Navy Pier, Chicago
27 Dec 2025	Its A Wonderful Life at Athenaeum Center	Athenaeum Center, Chicago
27 Dec 2025	Moon Taxi at Garcias Chicago	Garcias Chicago
27 Dec 2025	Santas Secret - Chicago (18)	Pioneer Court - Chicago
27 Dec 2025	Mustard Plug	Bottom Lounge, Chicago
27 Dec 2025	AYYBO at Cermak Hall - Radius Chicago	Cermak Hall - Radius Chicago

Date

Event

Venue

27 Dec 2025

Joffrey Ballet The Nutcracker

Lyric Opera House - IL, Chicago

27 Dec 2025

Raheem DeVaughn

City Winery - Chicago

27 Dec 2025

Parking Joffrey Ballet - The Nutcracker

Lyric Opera of Chicago

27 Dec 2025

Cloonee

Radius - IL, Chicago

27 Dec 2025

Pier Pressure - Saturday at Aon Grand Ballroom at Navy Pier

Aon Grand Ballroom at Navy Pier, Chicago

27 Dec 2025

Its A Wonderful Life at Athenaeum Center

Athenaeum Center, Chicago

27 Dec 2025

Moon Taxi at Garcias Chicago

Garcias Chicago

27 Dec 2025

Santas Secret - Chicago (18)

Pioneer Court - Chicago

27 Dec 2025

Mustard Plug

Bottom Lounge, Chicago

27 Dec 2025

AYYBO at Cermak Hall - Radius Chicago

Cermak Hall - Radius Chicago

Frequently Asked Questions

Which Trips & Adventurous Activities can I attend in Chicago today?

Here are the best Trips & Adventurous Activities happening in Chicago today:

Joffrey Ballet: The Nutcracker is happening on 26 Dec 2025 from 6:00 PM onwards at Lyric Opera House - IL, Chicago
Chris Lake is happening on 26 Dec 2025 from 6:00 PM onwards at Radius - IL, Chicago
Pier Pressure: Alison Wonderland & San Holo Wholseom Riddim Set - Night 2 is happening on 26 Dec 2025 from 6:00 PM onwards at Aon Grand Ballroom Navy Pier, Chicago
Raheem Devaughn - 20 Lessons of Love at City Winery - Chicago is happening on 26 Dec 2025 from 6:00 PM onwards at City Winery - Chicago
Parking Joffrey Ballet - The Nutcracker is happening on 26 Dec 2025 from 8:00 PM onwards at Lyric Opera of Chicago
Chris Lorenzo at Radius Chicago is happening on 26 Dec 2025 from 10:00 PM onwards at Radius Chicago

Which Trips & Adventurous Activities can I attend in Chicago this weekend?

Here are the best Trips & Adventurous Activities happening in Chicago this weekend:

Raheem DeVaughn is happening on Sat 27 Dec 2025 from 6:00 PM onwards at City Winery - Chicago
Parking Philadelphia 76ers at Chicago Bulls is happening on Sat 27 Dec 2025 from 1:00 AM onwards at United Center, Chicago
Cloonee is happening on Sat 27 Dec 2025 from 6:00 PM onwards at Radius - IL, Chicago
Pier Pressure - Saturday at Aon Grand Ballroom at Navy Pier is happening on Sat 27 Dec 2025 from 11:59 PM onwards at Aon Grand Ballroom at Navy Pier, Chicago

What are the trending Trips & Adventurous Activities in Chicago?

Here are the trending Trips & Adventurous Activities in Chicago:

Joffrey Ballet: The Nutcracker is happening on Fri 26 Dec 2025 from 6:00 PM onwards at Lyric Opera House - IL, Chicago
Chris Lake is happening on Fri 26 Dec 2025 from 6:00 PM onwards at Radius - IL, Chicago
Pier Pressure: Alison Wonderland & San Holo Wholseom Riddim Set - Night 2 is happening on Fri 26 Dec 2025 from 6:00 PM onwards at Aon Grand Ballroom Navy Pier, Chicago
Raheem Devaughn - 20 Lessons of Love at City Winery - Chicago is happening on Fri 26 Dec 2025 from 6:00 PM onwards at City Winery - Chicago
Raheem DeVaughn is happening on Sat 27 Dec 2025 from 6:00 PM onwards at City Winery - Chicago
Parking Joffrey Ballet - The Nutcracker is happening on Fri 26 Dec 2025 from 8:00 PM onwards at Lyric Opera of Chicago

Trips & Adventurous Activities in Chicago this Weekend

Trips & Adventurous Activities in Chicago this Weekend

Trips & Adventurous Activities in Chicago this Weekend

Joffrey Ballet: The Nutcracker

Chris Lake

Pier Pressure: Alison Wonderland & San Holo Wholseom Riddim Set - Night 2

Raheem Devaughn - 20 Lessons of Love at City Winery - Chicago

Raheem DeVaughn

Parking Joffrey Ballet - The Nutcracker

Chris Lorenzo at Radius Chicago

Parking Philadelphia 76ers at Chicago Bulls

Cloonee

Matroda

Pier Pressure - Saturday at Aon Grand Ballroom at Navy Pier

The Nasty Show: Tiny Thickemz

Its A Wonderful Life at Athenaeum Center

Moon Taxi at Garcias Chicago

Azzecca at Cermak Hall - Radius Chicago

Explore events by date

Day Trips in Chicago

Scavenger Hunts by Let's Roam

Navy Pier Centennial Wheel

Chicago Flyover

Scavenger Hunt Puzzle Adventure

Small-Group Sightseeing Boat Tour in Chicago

Best of Chicago Small Group Tour

Boating in Chicago

Urban Kayaks

Kayak Chicago

Next Wave Watersports

Jet Ski Chicago

River Canoe and Kayak at Clark Park

Chicago River Architecture Tour on a Historic Yacht

Trips & Adventurous Activities from nearby cities

Explore Events around you

Chicago's Most-Loved

Upcoming Trips & Adventurous Activities in Chicago

Frequently Asked Questions

Here are the best Trips & Adventurous Activities happening in Chicago today:

Here are the best Trips & Adventurous Activities happening in Chicago this weekend:

Here are the trending Trips & Adventurous Activities in Chicago:

Places For Outdoor Adventures Activities Near Chicago

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