Best Trips & Adventurous Activities in Chicago This Weekend | April 18 - 19

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

Here are the trending events in Chicago: Dave - Rapper, Chicago Cubs vs. Philadelphia Phillies, New York Mets at Chicago Cubs at Wrigley Field, Chicago Cubs vs. New York Mets, LANY at Credit Union 1 Arena at UIC, CamelPhat at Salt Shed - Indoor Shed

Trips & Adventurous Activities in Chicago this Weekend

Sun, 19 Apr, 2026 - 06:00 PM

Dave - Rapper

The Salt Shed Indoors - Chicago
Sun, 19 Apr Onwards

Chicago Cubs vs. Philadelphia Phillies

Wrigley Field

USD 57
Fri, 17 Apr Onwards

New York Mets at Chicago Cubs at Wrigley Field

Wrigley Field
Thu, 16 Apr Onwards

Chicago Cubs vs. New York Mets

Wrigley Field

USD 70
Fri, 17 Apr, 2026 - 07:00 PM

LANY at Credit Union 1 Arena at UIC

Credit Union 1 Arena at UIC
Fri, 17 Apr, 2026 - 09:00 PM

CamelPhat at Salt Shed - Indoor Shed

Salt Shed - Indoor Shed
Sat, 18 Apr, 2026 - 05:00 PM

Regina Belle at City Winery - Chicago

City Winery - Chicago
Fri, 17 Apr, 2026 - 06:00 PM

Regina Belle

City Winery - Chicago
Sat, 18 Apr, 2026 - 06:00 PM

Crazy Ex-Girlfriend

The Chicago Theatre
Thu, 16 Apr Onwards

Chicago Area - Pop Up Picnic Park Date for Couples! (Self-Guided)

Robert Taylor Park - Recommended Park Venue or another park choice (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

USD 10
Sun, 19 Apr, 2026 - 12:00 AM

Dance Hall Crashers

House of Blues Chicago
Sat, 18 Apr, 2026 - 07:00 PM

Odumodublvck at Concord Music Hall

Concord Music Hall
Sun, 19 Apr, 2026 - 11:00 PM

Josh Garrels

House of Blues Chicago
Thu, 16 Apr Onwards

Chicago Architecture Center River Cruise at Chicagos First Lady

Chicagos First Lady
Sat, 18 Apr, 2026 - 07:00 PM

Lily Rose at Joes on W**d Street

Joes on Weed Street

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Pick Range

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
4.4 (13)

Kayak at Chicago Montrose Beach

200 W Montrose Harbor Dr, Chicago, IL 60640, USA

Trips & Adventurous Activities from nearby cities

Upcoming Trips & Adventurous Activities in Chicago

Date	Event	Venue
19 Apr 2026	Dave - Rapper	The Salt Shed Indoors - Chicago
19 Apr 2026	Chicago Cubs vs. Philadelphia Phillies	Wrigley Field, Chicago
18 Apr 2026	New York Mets at Chicago Cubs at Wrigley Field	Wrigley Field, Chicago
18 Apr 2026	Chicago Cubs vs. New York Mets	Wrigley Field, Chicago
18 Apr 2026	Regina Belle at City Winery - Chicago	City Winery - Chicago
19 Apr 2026	Chicago Area - Pop Up Picnic Park Date for Couples (Self-Guided)	Robert Taylor Park - Recommended Park Venue or another park choice (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED), Chicago
19 Apr 2026	Dance Hall Crashers	House of Blues Chicago
18 Apr 2026	Odumodublvck at Concord Music Hall	Concord Music Hall, Chicago
19 Apr 2026	Josh Garrels	House of Blues Chicago
18 Apr 2026	Lily Rose at Joes on Wd Street	Joes on Weed Street, Chicago

Date

Event

Venue

19 Apr 2026

Dave - Rapper

The Salt Shed Indoors - Chicago

19 Apr 2026

Chicago Cubs vs. Philadelphia Phillies

Wrigley Field, Chicago

18 Apr 2026

New York Mets at Chicago Cubs at Wrigley Field

Wrigley Field, Chicago

18 Apr 2026

Chicago Cubs vs. New York Mets

Wrigley Field, Chicago

18 Apr 2026

Regina Belle at City Winery - Chicago

City Winery - Chicago

19 Apr 2026

Chicago Area - Pop Up Picnic Park Date for Couples (Self-Guided)

Robert Taylor Park - Recommended Park Venue or another park choice (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED), Chicago

19 Apr 2026

Dance Hall Crashers

House of Blues Chicago

18 Apr 2026

Odumodublvck at Concord Music Hall

Concord Music Hall, Chicago

19 Apr 2026

Josh Garrels

House of Blues Chicago

18 Apr 2026

Lily Rose at Joes on Wd Street

Joes on Weed Street, 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:

New York Mets at Chicago Cubs at Wrigley Field is happening on 17 Apr 2026 from 11:59 PM onwards at Wrigley Field, Chicago
Chicago Cubs vs. New York Mets is happening on 17 Apr 2026 from 6:00 PM onwards at Wrigley Field, Chicago
LANY at Credit Union 1 Arena at UIC is happening on 17 Apr 2026 from 7:00 PM onwards at Credit Union 1 Arena at UIC, Chicago
CamelPhat at Salt Shed - Indoor Shed is happening on 17 Apr 2026 from 9:00 PM onwards at Salt Shed - Indoor Shed, Chicago
Regina Belle is happening on 17 Apr 2026 from 6:00 PM onwards at City Winery - Chicago
Chicago Architecture Center River Cruise at Chicagos First Lady is happening on 17 Apr 2026 from 11:59 PM onwards at Chicagos First Lady

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

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

Dave - Rapper is happening on Sun 19 Apr 2026 from 6:00 PM onwards at The Salt Shed Indoors - Chicago
Chicago Cubs vs. Philadelphia Phillies is happening on Sun 19 Apr 2026 from 6:00 PM onwards at Wrigley Field, Chicago
Regina Belle at City Winery - Chicago is happening on Sat 18 Apr 2026 from 5:00 PM onwards at City Winery - Chicago
Chicago Area - Pop Up Picnic Park Date for Couples! (Self-Guided) is happening on Sat 18 Apr 2026 from 1:00 PM onwards at Robert Taylor Park - Recommended Park Venue or another park choice (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED), Chicago
Dance Hall Crashers is happening on Sun 19 Apr 2026 from 12:00 AM onwards at House of Blues Chicago
Odumodublvck at Concord Music Hall is happening on Sat 18 Apr 2026 from 7:00 PM onwards at Concord Music Hall, Chicago

What are the trending Trips & Adventurous Activities in Chicago?

Here are the trending Trips & Adventurous Activities in Chicago:

Dave - Rapper is happening on Sun 19 Apr 2026 from 6:00 PM onwards at The Salt Shed Indoors - Chicago
Chicago Cubs vs. Philadelphia Phillies is happening on Sun 19 Apr 2026 from 6:00 PM onwards at Wrigley Field, Chicago
New York Mets at Chicago Cubs at Wrigley Field is happening on Fri 17 Apr 2026 from 11:59 PM onwards at Wrigley Field, Chicago
Chicago Cubs vs. New York Mets is happening on Fri 17 Apr 2026 from 6:00 PM onwards at Wrigley Field, Chicago
LANY at Credit Union 1 Arena at UIC is happening on Fri 17 Apr 2026 from 7:00 PM onwards at Credit Union 1 Arena at UIC, Chicago
CamelPhat at Salt Shed - Indoor Shed is happening on Fri 17 Apr 2026 from 9:00 PM onwards at Salt Shed - Indoor Shed, Chicago

Trips & Adventurous Activities in Chicago this Weekend

Trips & Adventurous Activities in Chicago this Weekend

Trips & Adventurous Activities in Chicago this Weekend

Dave - Rapper

Chicago Cubs vs. Philadelphia Phillies

New York Mets at Chicago Cubs at Wrigley Field

Chicago Cubs vs. New York Mets

LANY at Credit Union 1 Arena at UIC

CamelPhat at Salt Shed - Indoor Shed

Regina Belle at City Winery - Chicago

Regina Belle

Crazy Ex-Girlfriend

Chicago Area - Pop Up Picnic Park Date for Couples! (Self-Guided)

Dance Hall Crashers

Odumodublvck at Concord Music Hall

Josh Garrels

Chicago Architecture Center River Cruise at Chicagos First Lady

Lily Rose at Joes on W**d Street

Explore events by date

Boating in Chicago

Urban Kayaks

Kayak Chicago

Next Wave Watersports

Jet Ski Chicago

River Canoe and Kayak at Clark Park

Kayak at Chicago Montrose Beach

Trips & Adventurous Activities from nearby cities

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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Trips & Adventurous Activities from nearby cities