Chicago Pleasant Home Hotels: 2026 Limited-Time Hotel Deals @Expedia

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Our top choices for Pleasant Home hotels

A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

1. Harvey House Bed & Breakfast

1 km from Pleasant Home

Monica

HK$2,247 total

includes taxes & fees

5 Nov - 6 Nov

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

2. Carleton of Oak Park

0.2 km from Pleasant Home

Johnny

HK$1,066 total

includes taxes & fees

11 Nov - 12 Nov

A modern hotel room with a large bed, a desk, and a view of the city through a window.

3. Holiday Inn Express and Suites Chicago West Oak Park by IHG

0.5 km from Pleasant Home

Daniel

HK$1,175 total

includes taxes & fees

22 Nov - 23 Nov

A compact bedroom with a bed, a desk, a chair, a dresser, a TV, and a window with curtains.

4. Ray's Bucktown B&B

10.5 km from Pleasant Home

Lora

HK$1,731 total

includes taxes & fees

2 Nov - 3 Nov

A modern indoor pool area with lounge chairs, a wooden table, and large windows.

5. Hampton Inn & Suites Chicago Medical District UIC

10.2 km from Pleasant Home

Eduin

HK$1,102 total

includes taxes & fees

22 Nov - 23 Nov

A modern hotel with a prominent 'Zachary' sign, multiple floors, and a well-lit facade.

6. Hotel Zachary Chicago, a Tribute Portfolio Hotel

13.7 km from Pleasant Home

Andrew

HK$1,815 total

includes taxes & fees

22 Nov - 23 Nov

A rooftop terrace with outdoor seating, a fire feature, and a modern building with large windows.

7. Hyatt Place Chicago/Wicker Park

11.3 km from Pleasant Home

Tasha L

HK$1,372 total

includes taxes & fees

22 Nov - 23 Nov

A hotel with a stone facade, multiple windows, and a well-lit entrance.

8. Hampton Inn & Suites Rosemont Chicago O'Hare

12.9 km from Pleasant Home

Brigid

HK$1,092 total

includes taxes & fees

24 Nov - 25 Nov

A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

9. Nobu Hotel Chicago

12.5 km from Pleasant Home

"Very disappointing — Luxury prices, substandard service. Having enjoyed a previous stay at one of the Nobu Hotel Chicago suites, I was shocked by the decline in service during our recent visit. 1. Credit card charge: At check-in, staff explicitly confirmed I could pay in cash at checkout, yet the hotel charged my card against our agreement, without my consent. 2. Disregard for privacy: Housekeeping repeatedly knocked insistently despite our privacy indicator being activated. 3. Poor...

DANIEL FERNANDO CRUZ

HK$3,359 total

includes taxes & fees

22 Nov - 23 Nov

A spacious lobby with a long bar area, red curtains, and a patterned carpet.

10. Canopy by Hilton Chicago Central Loop

13.7 km from Pleasant Home

Michael

HK$1,419 total

includes taxes & fees

22 Nov - 23 Nov

A grand foyer with a wooden staircase, a chandelier, and a large window.

11. Villa D' Citta

13.2 km from Pleasant Home

Hernando

HK$1,896 total

includes taxes & fees

1 Dec - 2 Dec

A modern hotel lobby with a seating area, a bar, and a kitchen.

12. DoubleTree by Hilton Chicago Midway Airport

13.3 km from Pleasant Home

Kelly

HK$1,353 total

includes taxes & fees

22 Nov - 23 Nov

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

13. Hampton Inn Chicago-O'Hare International Airport

10.1 km from Pleasant Home

Jaime

HK$1,028 total

includes taxes & fees

24 Nov - 25 Nov

A grand hotel facade with classical architecture, featuring tall columns, ornate detailing, and a prominent entrance with a marquee.

14. Hyatt House Chicago Medical/University District

10.6 km from Pleasant Home

lieneke

HK$1,203 total

includes taxes & fees

22 Nov - 23 Nov

A breakfast setting with a plate of toast, a bowl of fruit, a cup of coffee, and a newspaper on a table by a window with a city view.

15. The Robey, Chicago, a Member of Design Hotels

10.5 km from Pleasant Home

Renee

HK$1,759 total

includes taxes & fees

23 Nov - 24 Nov

A modern lobby with a sofa, coffee table, and potted plants.

16. The Emily Hotel

12.3 km from Pleasant Home

Veronica

HK$1,790 total

includes taxes & fees

22 Nov - 23 Nov

A modern living room with a large TV, a sofa, a coffee table, and a chair. There is a large window with a city view.

17. Level Chicago - River North

13.4 km from Pleasant Home

Veronica

HK$1,832 total

includes taxes & fees

24 Nov - 25 Nov

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

18. Hampton Inn Chicago West Loop Fulton Market Area

13 km from Pleasant Home

Peggy.

HK$1,377 total

includes taxes & fees

25 Nov - 26 Nov

A rooftop pool area with lounge chairs and a view of the city skyline.

19. The Hoxton, Chicago

12.5 km from Pleasant Home

Kyla

HK$1,901 total

includes taxes & fees

24 Nov - 25 Nov

A rooftop terrace with outdoor seating, a pergola, and a view of surrounding high-rise buildings.

20. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

13 km from Pleasant Home

Danielle

HK$1,260 total

includes taxes & fees

22 Nov - 23 Nov

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Compare popular hotels close to Pleasant Home

Property	Property class	Guest rating
Harvey House Bed & Breakfast	4.0 star property	9.8 Exceptional 137 reviews	View
Carleton of Oak Park	3.0 star property	9.2 Wonderful 1,208 reviews	View
Holiday Inn Express and Suites Chicago West Oak Park by IHG	2.5 star property	8.4 Very good 106 reviews	View
Ray's Bucktown B&B	3.5 star property	9.8 Exceptional 423 reviews	View
Hampton Inn & Suites Chicago Medical District UIC	2.5 star property	9.6 Exceptional 847 reviews	View

Top Pleasant Home Hotel Reviews

Carleton of Oak Park

8/10 Good

"Very nice efficient charming old hotel. I would stay again and I would try the restaurants for dinner and breakfast."

Luxury Home Away From Your Home

10/10 Excellent

"Ms. Linnie was an exceptional host! She was very easy to communicate with and helpful when I couldn't figure out how to open the gate. :) The entire house was spotless. There were 8 of us in my group and we were all very pleased with our accommodations. We easily found parking right in front of the house and just stayed parked there. The location was perfect it was only 10 minutes from the venue where the wedding we were attending was located. We would definitely stay there again."

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

8/10 Good

"Clean property. Host was very easy to work with. We did not use parking area but seemed to be ample area. Kitchen worked fairly well. The pilot lights on the stove were a bit finicky at times. Very little closet space (only on bedroom) and the king size bed was in a room far too small for a king bed especially with the enormous bed frame and gigantic TV. A bit of a work in progress with some plugs pulling out from the wall. Nice to have a large washer and dryer."

Theater • Game Room • Gym • Firepit • 4BR Home

10/10 Excellent

"We had a wonderful and relaxing stay, and we were able to get some much-needed rest. The place was beautiful, clean, and comfortable. The only thing I noticed is that it takes a while for the shower to get hot, and the hot water runs out pretty quickly. But overall, it was a great stay. We only wish we could have stayed longer to enjoy it even more! We’d definitely love to come back for a longer stay next time. ❤️"

Other attractions near Pleasant Home

Unity Temple

8.8/10 (11 reviews)

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

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Frequently asked questions

What's the area like around Pleasant Home?

Pleasant Home is located in a vibrant area of Oak Park known for its array of dining options and stunning architecture. If you're looking for a convenient place to stay, take a look at the 101 hotels and other accommodation options you'll find within a mile.

What's the best hotel to stay close to Pleasant Home?

Adjacent to Pleasant Home, Carleton of Oak Park is one of the top choices for your stay based on our traveller data, and this hotel offers 2 restaurants and 2 bars. Other good choices close by include Holiday Inn Express and Suites Chicago West Oak Park by IHG and Harvey House Bed & Breakfast.

How many hotels are there close to Pleasant Home?

Expedia has 101 hotels and other accommodation options within a mile from Pleasant Home.

If I need to cancel the hotel reservation for my stay near Pleasant Home, will I receive a refund?

Yes, the majority of hotel room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within a 24-hour period of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to view the best deals available near Pleasant Home.

What can I see and do near Pleasant Home?

Study the collections at Ernest Hemingway Museum and House, Frank Lloyd Wright Home and Studio or Trailside Museum of Natural History. While you're exploring, swing by Frank Lloyd Wright Historic District, Walt Disney House and Unity Temple to learn a bit about the area. You can enjoy live performances at Madison Street Theatre and Distro Music Hall.

Chicago Pleasant Home Hotels

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Our top choices for Pleasant Home hotels

1. Harvey House Bed & Breakfast

2. Carleton of Oak Park

3. Holiday Inn Express and Suites Chicago West Oak Park by IHG

4. Ray's Bucktown B&B

5. Hampton Inn & Suites Chicago Medical District UIC

6. Hotel Zachary Chicago, a Tribute Portfolio Hotel

7. Hyatt Place Chicago/Wicker Park

8. Hampton Inn & Suites Rosemont Chicago O'Hare

9. Nobu Hotel Chicago

10. Canopy by Hilton Chicago Central Loop

11. Villa D' Citta

12. DoubleTree by Hilton Chicago Midway Airport

13. Hampton Inn Chicago-O'Hare International Airport

14. Hyatt House Chicago Medical/University District

15. The Robey, Chicago, a Member of Design Hotels

16. The Emily Hotel

17. Level Chicago - River North

18. Hampton Inn Chicago West Loop Fulton Market Area

19. The Hoxton, Chicago

20. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Compare popular hotels close to Pleasant Home

Top Pleasant Home Hotel Reviews

Carleton of Oak Park

Other attractions near Pleasant Home

Unity Temple

Frequently asked questions