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.

A cozy living room with a brown leather sofa, a matching ottoman, a wooden side table with a lamp, and a wooden chair with a book.

A spacious living room with a fireplace, a piano, and a dining area with a table and chairs.

A neatly arranged bedroom with a large bed, bedside lamps, a nightstand, a dresser, and a built-in fireplace.

1. Harvey House Bed & Breakfast

1 km from Pleasant Home

Monica

HK$2,026

HK$2,248 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."

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

2. Carleton of Oak Park

0.2 km from Pleasant Home

Brad

HK$961

HK$1,066 total

includes taxes & fees

27 Oct - 28 Oct

A modern dining area with tables and chairs, a reception desk, and a large screen wall.

A modern hotel lobby with a sofa, chairs, a desk, and a map on the wall.

A hotel room with a bed, desk, chair, TV, and large windows with a city view.

A modern breakfast area with a counter displaying cereal and fruit options, a coffee machine, and a view of the city through large windows.

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

0.5 km from Pleasant Home

Heather

HK$1,279

HK$1,420 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

A dining area with a wooden table, four chairs, a sofa, and a lamp.

A living room with a sofa, a coffee table, and a TV mounted on the wall.

4. Classic Forest Park Foursquare < 1 Mi to Blue Line

1.2 km from Pleasant Home

HK$1,899

HK$3,727 total

includes taxes & fees

27 Oct - 28 Oct

A bathroom with a glass-tiled wall, a sink, and a shower area.

A cozy interior with a wooden staircase, a seating area with chairs and a table, and shelves with various items.

A patio with a grill, outdoor seating, and potted plants.

A room with wooden flooring, a bookshelf filled with books and decorative items, two chairs, and a table with various objects.

5. Ray's Bucktown B&B

10.5 km from Pleasant Home

Lora

HK$1,576

HK$1,780 total

includes taxes & fees

25 Oct - 26 Oct

A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

A kitchen with a large island, hanging kitchen tools, and a brick wall.

A modern hotel interior with a glass railing, a neon sign, a bar area, and a patterned rug.

A restaurant interior with wooden tables and chairs, a bar area with wine bottles, and a red booth.

6. The Publishing House B&B

11.9 km from Pleasant Home

Nobue

HK$1,787

HK$2,017 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a large bed, two bedside tables with lamps, a window with curtains, a wall-mounted air conditioner, and a colorful abstract painting.

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

A modern hotel room with a large bed, a desk, a chair, a TV, and a sliding door leading to a shower area.

A modern hotel with multiple floors, a covered entrance, and a parking lot.

7. Hampton Inn & Suites Chicago Medical District UIC

10.2 km from Pleasant Home

Bobby

HK$1,461

HK$1,737 total

includes taxes & fees

25 Oct - 26 Oct

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

A spacious hotel lobby with a large seating area, a bar, and a view of the city.

A modern living room with a fireplace, sofas, and a coffee table.

A hotel room with a bed, a desk, a chair, a shower, and a window with curtains.

8. Hampton Inn & Suites Rosemont Chicago O'Hare

12.9 km from Pleasant Home

Keerthika

HK$959

HK$1,093 total

includes taxes & fees

1 Nov - 2 Nov

A long, narrow hallway with a patterned carpet, recessed lighting, and doors on one side.

A modern interior with a wall-mounted fireplace and a decorative rock installation.

A modern bar area with a curved ceiling, wooden slats, and a bar counter with stools.

9. Loews Chicago O'Hare Hotel

11.2 km from Pleasant Home

Joshua Anthony

HK$1,719

HK$1,959 total

includes taxes & fees

23 Oct - 24 Oct

A modern lounge area with a fire feature, seating, and a bar.

A modern lounge area with a sectional sofa, red chairs, a glass coffee table, and a patterned rug.

A group of people seated at a table with drinks and a salad, in a modern indoor setting with large windows and a bar area.

An outdoor terrace with a fire feature, seating, and a city view.

10. Hyatt Place Chicago/Wicker Park

11.3 km from Pleasant Home

Tyler

HK$1,326

HK$1,557 total

includes taxes & fees

2 Nov - 3 Nov

An outdoor seating area with tables and chairs, a sofa, and a lamp post.

A spacious lobby with a reception desk, seating area, and a fire feature.

A modern living room with a sofa, a glass coffee table, and a pink armchair.

A modern hotel with a prominent neon sign, large windows, and a well-lit entrance area.

11. The Rose Chicago, Tapestry Collection by Hilton

11.5 km from Pleasant Home

melissa

HK$1,461

HK$1,665 total

includes taxes & fees

30 Oct - 31 Oct

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

A modern lobby with a sofa, a coffee table, and a vase of flowers.

A rooftop terrace with a view of a city skyline at dusk.

A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

12. Nobu Hotel Chicago

12.5 km from Pleasant Home

Abhay

HK$3,569

HK$4,439 total

includes taxes & fees

15 Nov - 16 Nov

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

A spacious dining area with a long wooden table, ornate chairs, and a chandelier.

A room with a wooden table, a coffee machine, a clock, and a framed sign on the wall.

A courtyard with brick arches, outdoor seating, and potted plants.

13. Villa D' Citta

13.2 km from Pleasant Home

Hernando

HK$1,977

HK$2,320 total

includes taxes & fees

26 Oct - 27 Oct

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

A reception desk with a "Welcome to the Prairie State" sign, a Hilton Honors sign, and a wooden wall with a herringbone pattern.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

14. Hampton Inn Chicago-O'Hare International Airport

10.1 km from Pleasant Home

Jennifer

HK$973

HK$1,119 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern kitchen with a central island, built-in appliances, and a dining area with a sofa and chairs.

A spacious lobby with a grand staircase, modern seating, and a large window providing natural light.

A modern hotel lobby with a long bar, seating area, and large windows.

15. Hyatt House Chicago Medical/University District

10.6 km from Pleasant Home

Andrea

HK$1,797

HK$2,137 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel room with a sofa, a flat-screen TV, a fireplace, and a dining area.

A modern living room with a fireplace, a flat-screen TV, a pool table, and a chess table.

An outdoor patio area with seating, tables, and string lights.

16. DoubleTree by Hilton Chicago Midway Airport

13.3 km from Pleasant Home

Kelly

HK$1,155

HK$1,357 total

includes taxes & fees

31 Oct - 1 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.

A bar area with a circular bar, stools, and a well-stocked shelf of bottles.

A building facade with a dark entrance, two wall-mounted lights, and a sign reading "The Robey Chicago".

A modern interior with a bar area, seating, and large windows offering a city view.

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

10.5 km from Pleasant Home

Patricia

HK$1,601

HK$2,073 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

A spacious indoor area with seating arrangements, large windows, and indoor plants.

A modern lounge area with a sofa, chairs, and a large potted plant.

A window with a view of a cityscape, a wooden desk with a radio, and a small window ledge.

18. The Emily Hotel

12.3 km from Pleasant Home

Lori

HK$1,843

HK$2,191 total

includes taxes & fees

1 Nov - 2 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.

A bedroom with a large window overlooking a cityscape.

A balcony with a city view, a table, and two chairs.

A rooftop patio with outdoor seating, a fire pit, and a city view.

19. Level Chicago - River North

13.4 km from Pleasant Home

Sergio

HK$1,892

HK$2,415 total

includes taxes & fees

1 Nov - 2 Nov

A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.

A spacious lobby with a fireplace, comfortable seating, and a modern chandelier.

A bar with multiple shelves of bottles, a long counter, and several stools.

A cozy reading area with a dark blue sofa, multiple bookshelves, and a small table with a drink and a glass.

20. The Hoxton, Chicago

12.5 km from Pleasant Home

Jordan

HK$2,033

HK$2,647 total

includes taxes & fees

1 Nov - 2 Nov

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Top Pleasant Home Hotel Reviews

Super 8 by Wyndham Chicago/Rosemont/O'Hare/SE

10/10 Excellent

"Stayed for the weekend to relax and decompress. I needed this time to myself It was quiet and clean I had no issues."

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

10/10 Excellent

"All in All Good Place To Stay"

Luxury Home Away From Your Home

10/10 Excellent

"The house was good. We had 3 rooms plus the couch became a bed. Super spacious kitchen and we had 2 bathrooms. We used the train and we were like two blocks away so we will always walk to the station. And then it was like 9 stops or 10 to go to downtown. We had a good time."

Holiday Inn Express and Suites Chicago West Oak Park by IHG

10/10 Excellent

"Great location, friendly staff, clean rooms and comfortable beds!"

Chicago Avenue Inn

8/10 Good

"This is an affordable and comfortable option that's proximate and easy to access. The immediate area is a lil rough but it's blocks away from main avenues that connect you to many of the choice neighborhoods in Chicago. Christine is the onsite house manager and is sweet and helpful. They even had a lil business center which was handy and great. I'd stay there again and recommend it if you're going for a solid budget option."

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. ❤️"

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

8/10 Good

"Overall this was a decent property. Property does need a little TLC however. The sink in the 2nd bathroom was not working and the sink itself was damaged. It was raining while we were there and we woke up to water dripping from the ceiling of the upstairs bathroom and standing water in the basement. We ended up leaving a day early."

Spacious 5-bedroom house with movie room, game room and more!

10/10 Excellent

"X"

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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Mills Park

7.2/10 (7 reviews)

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 theatre scene in this vibrant area.

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Oak Park Visitors Center

7.8/10 (8 reviews)

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 galleries in this vibrant area.

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Downtown Oak Park

Downtown Oak Park is just one of the places to see in Oak Park, so why not enjoy the other things to explore during your travels? Visit the shops and top-notch restaurants in this walkable area.

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Tre Sorelle Ristorante

Tre Sorelle Ristorante is just one of the places to see in Oak Park, so why not enjoy the other things to explore during your travels? Visit the shops and top-notch restaurants in this walkable area.

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Labyrinth

Enjoy an outing to Labyrinth during your stay in Oak Park. Visit the shops and top-notch restaurants in this family-friendly area.

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Oak Park Public Library

You can take time to visit Oak Park Public Library during your travels to Oak Park. Visit the shops and top-notch restaurants in this walkable area.

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Madison Street Theatre

7.0/10 (6 reviews)

You can get tickets for a performance at Madison Street Theatre during your trip to Oak Park. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

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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

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Star rating

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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. Classic Forest Park Foursquare < 1 Mi to Blue Line

5. Ray's Bucktown B&B

6. The Publishing House B&B

7. Hampton Inn & Suites Chicago Medical District UIC

8. Hampton Inn & Suites Rosemont Chicago O'Hare

9. Loews Chicago O'Hare Hotel

10. Hyatt Place Chicago/Wicker Park

11. The Rose Chicago, Tapestry Collection by Hilton

12. Nobu Hotel Chicago

13. Villa D' Citta

14. Hampton Inn Chicago-O'Hare International Airport

15. Hyatt House Chicago Medical/University District

16. DoubleTree by Hilton Chicago Midway Airport

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

18. The Emily Hotel

19. Level Chicago - River North

20. The Hoxton, Chicago

Top Pleasant Home Hotel Reviews

Super 8 by Wyndham Chicago/Rosemont/O'Hare/SE

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

Luxury Home Away From Your Home

Holiday Inn Express and Suites Chicago West Oak Park by IHG

Chicago Avenue Inn

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

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

Spacious 5-bedroom house with movie room, game room and more!

Other attractions near Pleasant Home

Unity Temple

Mills Park

Oak Park Visitors Center

Downtown Oak Park

Tre Sorelle Ristorante

Labyrinth

Oak Park Public Library

Madison Street Theatre

Frequently asked questions