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-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided …More

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided...

3 hours Free Cancellation
5.0 (77)
from
$85
The Deep Pockets Of Graceland Cemetery Walking Tour

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting …More

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting...

1 hour 30 minutes Free Cancellation
4.9 (13)
from
$45
Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic …More

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic...

120 to 150 minutes Free Cancellation
5.0 (22)
from
$71
A Woman's Place: The Chicago Women's History Walking Tour

Forget the history you learned in school—Chicago’s story looks very different when told through the women who helped shape it. On this captivating 2-hour walking …More

Likely to Sell Out
Likely to Sell Out

Forget the history you learned in school—Chicago’s story looks very different when told through the women who helped shape it. On this captivating 2-hour walking...

2 hours Free Cancellation
5.0 (4)
from
$35
Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. …More

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists....

2 hours Free Cancellation
4.9 (56)
from
$60
Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking …More

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking...

2 hours Free Cancellation
5.0 (7)
from
$50
Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary …More

Likely to Sell Out
Likely to Sell Out

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary...

5 hours Free Cancellation
5.0 (3)
from
$99
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock …More

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock...

3 hours Free Cancellation
5.0 (3)
from
$109
Private Vacation Photoshoot with Photographer in Chicago

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing …More

Likely to Sell Out
Likely to Sell Out

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing...

1 hour Free Cancellation
4.0 (4)
from
$135
Haunted Chicago: Lincoln Park Ghost & History Walking Tour

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 …More

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...

1 hour 30 minutes Free Cancellation
4.3 (13)
from
$30
The Art Institute in Chicago Highlights Tour & Photoshoot

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & …More

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included &...

1 hour 15 minutes Free Cancellation
5.0 (5)
from
$101
Explore the Historic Old Post Office in Chicago

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 …More

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...

1 hour 30 minutes Free Cancellation
5.0 (27)
from
$15
Prairie Avenue Haunted History Tour and Ghost Hunt

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this …More

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this...

2 hours 20 minutes
5.0 (12)
from
$44
Explore Chicago Black Culinary Heritage

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s …More

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s...

2 hours 45 minutes Free Cancellation
5.0 (6)
from
$75
Chicago Architecture Gilded Interiors Walking Tour

Visit the most beautiful interiors in Chicago with a local guide bringing their stories to life. Step into stunning centuries-old architecture on a guided walking …More

Visit the most beautiful interiors in Chicago with a local guide bringing their stories to life. Step into stunning centuries-old architecture on a guided walking...

1 hour 30 minutes Free Cancellation
5.0 (4)
from
$28
Private Chicago Foodie Tour

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, …More

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza,...

4 hours Free Cancellation
5.0 (6)
from
$288
Private Chicago Architecture Walking Tour

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some …More

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some...

3 hours Free Cancellation
4.8 (6)
from
$211
Chicago Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used …More

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used...

1 hour 30 minutes Free Cancellation
5.0 (4)
from
$53
Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This …More

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This...

2 hours 30 minutes Free Cancellation
5.0 (5)
from
$43
Cocktail Adventure Tour 21+

Sipping Our Way Through History Visit some of the best cocktail bars and tavern that line the streets of Galena. Galena once boasted over 60 …More

Sipping Our Way Through History Visit some of the best cocktail bars and tavern that line the streets of Galena. Galena once boasted over 60...

1 hour 30 minutes
4.9 (13)
from
$71
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