The Best Chicago Activities for Seniors and Over 50s – 10% Promo Code (November 2026)

Chicago, USA

Use promo code: WISDOM (must book on this website) and save 10% on the best tours, tickets, and things to do for seniors in Chicago. Pick your tour below and use code WISDOM (savings are shown at checkout). The WISDOM Promo Code discount cannot be used with other promotions, is only redeemable on City Sky Diving, and is a limited-time offer, so reserve your spot today while it lasts!

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Chicago Hauntings Original Ghost Walk through Old Chicago

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's …More

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's...

2 hours
5.0 (1)
from
$40
Welcome to Chicago: The Essential City Tour with photo stops

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history, …More

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history,...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$35
Chicago Photo Capture Your Adventure Walking Tour

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn …More

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$49
Private History and Architecture of Chicago Loop Walking Tour

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy …More

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$180
Chicago Chocolate Tour - An App-Guided Adventure

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and …More

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and...

2 hours Free Cancellation
3.0 (7)
from
$8
Chicago Jewish History Landmarks Private Guided Walking Tour

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and …More

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and...

2 hours Free Cancellation
3.0 (1)
from
$37
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the …More

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the...

45 to 60 minutes
from
$7
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