Name: Luxury Home Away From Your Home
Address: Chicago

Plan a trip to see Pleasant Home

Price found within the past 48 hours. Click for updated prices.

Pendry Chicago

Downtown Chicago

￥87,940

per person

Nov 27 - Nov 30

found 24 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

￥90,622

per person

Nov 27 - Nov 30

found 24 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Chicago (ORD)

9.4/10 Exceptional! (2,427 reviews)

Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

￥148,535

per person

Nov 27 - Nov 30

found 23 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

The best hotel in chicago

Reviewed on Oct 11, 2025

Browse tours and tickets to explore Pleasant Home

Tours & day trips

See all 147 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 22 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 9 activities

Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Unity Temple

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

Ernest Hemingway Museum and House

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

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.

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.

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 art scene in this vibrant area.

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 acclaimed art scene in this vibrant area.