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 Key West Private Charters, and is a limited-time offer, so reserve your spot today while it lasts!
The Best Chicago Activities for Seniors and Over 50s – 10% Promo Code (November 2026)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed...
$508

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for...
$5

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...
$6

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...
$6

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the...
$7

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's...
$7

You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided...
$7

The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of...
$7

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...
$8

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must...
$9

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on...
$10

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers...
$10

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent...
$11

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer...
$13

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start...
$13

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once...
$15

Step inside a unique and fascinating journey through Chicago’s premier indoor mushroom farm, as seen on FX/Hulu’s acclaimed series "The Bear," where our mushrooms were...
$20

Frank Lloyd Wright Robie House Admission
The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture....
$27

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art....
$27

This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike...
$30

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets....
$30

