Top activities
Top landmarks
Trip ideas
Nearby places
Port schedule

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!

Read More
Chicago Loop Self-Guided Audio Tour: Architecture & History Walk

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 …More

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...

120 to 150 minutes Free Cancellation
5.0 (4)
from
$10
Grafton History and Ghost Tales

Explore Grafton's chilling past on this one-hour walking tour, where history meets the supernatural. - One-hour walking tour focused on Grafton's history and ghost stories …More

Explore Grafton's chilling past on this one-hour walking tour, where history meets the supernatural. - One-hour walking tour focused on Grafton's history and ghost stories...

1 hour Free Cancellation
4.8 (4)
from
$25
Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

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 …More

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...

7 days Free Cancellation
5.0 (3)
from
$11
Guided Seasonal Hike

Discover Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock …More

Discover Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock...

4 hours Free Cancellation
5.0 (2)
from
$33
Chicago Gangster History Walking Tour of River North

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

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

2 hours Free Cancellation
4.8 (4)
from
$30
West Town Hot Spots Tour By Studio W.I.P.

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. …More

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....

90 to 105 minutes Free Cancellation
5.0 (3)
from
$27
Galena Self-Guided Audio Walking Tour of Historic Downtown

Walk through Galena, an unusually intact nineteenth-century town carved into a steep river valley, with a self-guided audio tour that plays automatically as you go. …More

Walk through Galena, an unusually intact nineteenth-century town carved into a steep river valley, with a self-guided audio tour that plays automatically as you go....

120 to 150 minutes Free Cancellation
4.6 (5)
from
$10
Chinatown Food Tour

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore …More

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore...

3 hours Free Cancellation
5.0 (1)
from
$98
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's Gold Coast Hidden History: A Self-Guided Audio Tour

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 …More

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...

50 minutes Free Cancellation
4.6 (8)
from
$9
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
Springfield Self-Guided Walking Audio Tour

See Abraham Lincoln as you’ve never seen him before with this self-guided walking tour of historic Springfield. Stroll through the 16th president’s old neighborhood, see …More

See Abraham Lincoln as you’ve never seen him before with this self-guided walking tour of historic Springfield. Stroll through the 16th president’s old neighborhood, see...

1 to 2 hours Free Cancellation
4.2 (6)
from
$13
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
Recent tour reviews
Activity name

Illinois Tours
Attractions
Guides
Calendar