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

Illinois, 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 Illinois. 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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Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago’s …More

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago’s...

2 hours Free Cancellation
5.0 (95)
from
$70
Chicago Art Deco Madness Walking Tour

Chicago’s Loop is home to some of the city’s most perfectly preserved Art Deco architecture designed during the Roaring 20s. See 7 stunning Art Deco …More

Likely to Sell Out
Likely to Sell Out

Chicago’s Loop is home to some of the city’s most perfectly preserved Art Deco architecture designed during the Roaring 20s. See 7 stunning Art Deco...

1 hour 30 minutes Free Cancellation
4.9 (33)
from
$45
Private Magnificent Mile Architecture Tour and 360 Chicago Ticket

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers. …More

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers....

2 hours Free Cancellation
4.9 (80)
from
$99
Chicago: Gangsters and Food Tasting Walking Tour

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine …More

Likely to Sell Out
Likely to Sell Out

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine...

2 hours Free Cancellation
4.7 (49)
from
$80
Chicago Haunts and Hooligans Tour

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a …More

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a...

1 hour 30 minutes Free Cancellation
5.0 (42)
from
$35
Chicago Walking Tour: Historic Skyscrapers

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build …More

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build...

1 hour 30 minutes Free Cancellation
4.8 (73)
from
$35
River North Food Walking Tour

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor …More

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor...

3 hours Free Cancellation
4.6 (96)
from
$89
Chicago Walking Tour: Modern Architecture

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) …More

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM)...

1 hour 30 minutes Free Cancellation
4.9 (69)
from
$35
Lincoln Park Hauntings Ghost Investigation Tour

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator. …More

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator....

2 hours 15 minutes Free Cancellation
4.9 (47)
from
$44
Chicago Walking Tour: The Magnificent Mile

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier …More

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier...

1 hour 30 minutes Free Cancellation
4.9 (51)
from
$35
Lincoln Park Zoo & Nature Museum Private Tour

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At …More

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At...

2 hours Free Cancellation
5.0 (29)
from
$275
Chicago Walking Tour: Connecting Past and Present

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying …More

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying...

1 hour 45 minutes Free Cancellation
5.0 (43)
from
$35
Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a …More

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a...

2 to 8 hours Hotel pickup offered Free Cancellation
4.8 (41)
from
$199
Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life …More

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life...

2 hours Free Cancellation
5.0 (27)
from
$59
Chicago Photo Walk to Bean and Landmarks

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, …More

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together,...

1 hour Free Cancellation
5.0 (32)
from
$169
Intro to Chicago Architecture

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired …More

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired...

1 hour 45 minutes Free Cancellation
5.0 (26)
from
$35
History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became …More

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became...

2 hours Free Cancellation
5.0 (31)
from
$33
Historic Homes and Cottages of Wicker Park Walking Tour

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, …More

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty,...

1 hour 30 minutes
5.0 (53)
from
$45
Downtown Galena Food and Drink Tour

Welcome to our one-of-a-kind food tour in historic Galena! Our mission is to let visitors discover Galena's vibrant Main Street while immersing themselves in its …More

Welcome to our one-of-a-kind food tour in historic Galena! Our mission is to let visitors discover Galena's vibrant Main Street while immersing themselves in its...

2 hours 30 minutes
4.9 (64)
from
$87
Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how …More

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how...

2 hours Free Cancellation
5.0 (12)
from
$35
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