Pleasant Home Tours and Activities

Plan a trip to see Pleasant Home

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,775, price is now CA $1,041 per person
CA $1,041
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Great place, everyone was wonderful!

Reviewed on Aug. 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,441, price is now CA $1,974 per person
CA $1,974
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,444, price is now CA $1,439 per person
CA $1,439
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Tours & day trips

See all 158 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.6 out of 10 with 1443 reviews
Free cancellation available
Price is CA $68 per adult
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Food, drink & nightlife

See all 31 activities
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Activity duration is 1 hour and 30 minutes
8.8 out of 10 with 17 reviews
Free cancellation available
Price is CA $58 per adult
Chicago: Architecture Boat Tour with DrinksOpens in new tab

Private & custom tours

See all 25 activities
Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

Activity duration is 1 hour and 35 minutes
Free cancellation available
The previous price was CA $17 and current price is CA $14 per adult*
Eastside Chicago The Heist Exploration Game and TourOpens in new tab

Attractions

See all 14 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 658 reviews
Free cancellation available
Price is CA $42 per adult
360 CHICAGO Observation DeckOpens in new tab

Adventure & outdoor

See all 9 activities
Rosemont: Two Flight Indoor Skydiving Experience

Rosemont: Two Flight Indoor Skydiving Experience

Activity duration is 1 hour
6.6 out of 10 with 7 reviews
Free cancellation available
Price is CA $135 per traveller
Rosemont: Two Flight Indoor Skydiving ExperienceOpens in new tab

Popular places to visit

Unity Temple featuring religious aspects, a temple or place of worship and a city

Unity Temple

This was Frank Lloyd Wright’s first major public building and is still considered one of his greatest achievements.

Unity Temple
Ernest Hemingway Museum and House featuring interior views and food

Ernest Hemingway Museum and House

Peek into the early life of one America’s best-loved writers.

Ernest Hemingway Museum and House
Frank Lloyd Wright Historic District

Frank Lloyd Wright Historic District

Visit the birthplace of modern architecture to explore the world's largest collections of homes and buildings designed by Frank Lloyd Wright.

Frank Lloyd Wright Historic District

Mills Park

Mills Park is just one of the places to see in Oak Park, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Mills Park

Oak Park Visitors Center

After visiting Oak Park Visitors Center, make a plan to see the other sights and activities in Oak Park. Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.

Oak Park Visitors Center

Madison Street Theatre

You can make plans for a show at Madison Street Theatre during your trip to Oak Park. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Madison Street Theatre

Best Lodging Options Near Pleasant Home

Carleton of Oak Park

Carleton of Oak Park

3 out of 5
1110 Pleasant St, Oak Park, IL
Carleton of Oak Park
Oak Park Queen

Oak Park Queen

Oak Park
Oak Park Queen
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4 out of 5
107 South Scoville Avenue, Oak Park, IL
Harvey House Bed & Breakfast
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Travel Inn

Travel Inn

2.5 out of 5
1150 Roosevelt Rd, Broadview, IL
Travel Inn
The Shamrock

The Shamrock

2.5 out of 5
1212 S Cicero Ave, Cicero, IL
The Shamrock
Cindy Lyn Motel

Cindy Lyn Motel

2 out of 5
5029 Ogden Ave, Cicero, IL
Cindy Lyn Motel
Zoo Holiday Retreat beautiful home with parking, near train into Chicago.

Zoo Holiday Retreat beautiful home with parking, near train into Chicago.

Brookfield
Zoo Holiday Retreat beautiful home with parking, near train into Chicago.
VIBE INN - WHIRLPOOL SUITES

VIBE INN - WHIRLPOOL SUITES

2.5 out of 5
7307 Ogden Ave, Lyons, IL
VIBE INN - WHIRLPOOL SUITES
See all 4,375 properties in Pleasant Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.