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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 Cool Shore Excursions, and is a limited-time offer, so reserve your spot today while it lasts!

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Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects …More

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects...

2 hours Free Cancellation
5.0 (1)
from
$349
Chicago Self-Guided Audio Tour

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your …More

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your...

3 to 9 hours
4.1 (7)
from
$6
Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores; stand beside the Berlin Wall; take in ghastly …More

Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores; stand beside the Berlin Wall; take in ghastly...

110 to 140 minutes Free Cancellation
4.5 (2)
from
$6
Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are …More

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are...

2 hours Free Cancellation
5.0 (1)
from
$469
Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the …More

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the...

1 hour Free Cancellation
5.0 (1)
from
$59
Wicker Park Walking Tour History Trivia and Local Flavors

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour …More

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour...

90 to 120 minutes Free Cancellation
5.0 (1)
from
$40
2-Hour Chicago's Chinatown History and Culture Tour

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by experienced local …More

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by experienced local...

2 hours Free Cancellation
3.8 (5)
from
$30
Chicago Highlights Private Walking Tour with a Guide

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey …More

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey...

2 hours Free Cancellation
5.0 (1)
from
$46
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
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’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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