Best Trips & Adventurous Activities in Chicago December 2026

Q: Which kind of events are trending in Chicago?

Here are the top trending events in ChicagoFestivals, Carnivals, 🌮 Cinco de Mayo, Free Events, Live Music, Car Shows

Trips & Adventurous Activities in Chicago in December

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Places For Outdoor Adventures Activities Near Chicago

All you travel enthusiasts, we have got you covered for some exciting options & places for adventure sports and fun day trips from Chicago.
Top places for adventurous things to do in Chicago:

The Chakra Shoppe

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

Sun, 19 Apr Onwards

Picnic: Couple Date Night (Self-Guided) - Gurnee Area!

Viking Park West - 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 Onwards

Carol Stream Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

USD 10
Sun, 19 Apr Onwards

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

Northside 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 Onwards

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

Timber Ridge 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 Onwards

Pop-Up Park Picnic: Couple Date Night (Self-Guided) - Schaumburg Area

Volkening 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 Onwards

Pop-Up Park Picnic: Couple Date Night (Self-Guided) - Glen Ellyn Area

Panfish 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 Onwards

Picnic: Couple Date Night (Self-Guided) - Orland Park Area!

Turtlehead Lake, 13600 S Harlem Ave - 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 Onwards

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

Wing 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 Onwards

Pop-Up Park Picnic: Couple Date Night (Self-Guided) - Gurnee Area!

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

USD 10