The Best Hotels Closest to Pleasant Home in Chicago - 2026 Updated Prices

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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 modern kitchen with wooden cabinets, a stainless steel refrigerator, and a red coffee machine.

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.

1. Harvey House Bed & Breakfast

0.6 mi from Pleasant Home

Monica

£245

includes taxes & fees

12 Oct - 13 Oct

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

A residential street with a sidewalk, houses, and greenery.

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

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 mi from Pleasant Home

Brad

£94

includes taxes & fees

25 Oct - 26 Oct

A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

A two-story house with a steeply pitched roof, a chimney, and a well-maintained garden with various shrubs and a tall coniferous tree.

A modern kitchen with white cabinets, a stainless steel stove, and a large window.

A room with a bed, a chair, a fireplace, a door leading to another room, and a painting on the wall.

3. Historic Oak Park Home

0.6 mi from Pleasant Home

Janette

£223

includes taxes & fees

27 Oct - 28 Oct

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

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

0.3 mi from Pleasant Home

Donna

£133

includes taxes & fees

29 Oct - 30 Oct

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

A modern kitchen with white cabinets, a stainless steel dishwasher, and a wooden countertop.

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

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

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

0.7 mi from Pleasant Home

£359

includes taxes & fees

1 Oct - 2 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 room with wooden flooring, a bookshelf filled with books and decorative items, two chairs, and a table with various objects.

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

6. Ray's Bucktown B&B

6.5 mi from Pleasant Home

Susan

£158

includes taxes & fees

1 Oct - 2 Oct

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden dining table with benches.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden dining table.

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

7. The Sono Chicago

8.3 mi from Pleasant Home

Christie

£226

includes taxes & fees

1 Oct - 2 Oct

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

A hotel reception area with a counter displaying pastries and coffee, a coffee machine, and a golden clock.

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.

8. Hampton Inn & Suites Chicago Medical District UIC

6.3 mi from Pleasant Home

Bobby

£182

includes taxes & fees

31 Oct - 1 Nov

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.

An outdoor patio with wicker furniture, a pergola, and a view of the cityscape.

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

9. Hampton Inn & Suites Rosemont Chicago O'Hare

8 mi from Pleasant Home

Richard Joseph

£127

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

10. Hampton Inn Chicago-O'Hare International Airport

6.2 mi from Pleasant Home

karen

£122

includes taxes & fees

30 Oct - 31 Oct

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

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.

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

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

11. Hyatt Place Chicago/Wicker Park

7 mi from Pleasant Home

Tyler

£203

includes taxes & fees

25 Oct - 26 Oct

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.

12. The Rose Chicago, Tapestry Collection by Hilton

7.1 mi from Pleasant Home

MILAN

£155

includes taxes & fees

30 Oct - 31 Oct

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

8.2 mi from Pleasant Home

Jeffrey

£224

includes taxes & fees

7 Oct - 8 Oct

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

A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.

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

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

14. Nobu Hotel Chicago

7.7 mi from Pleasant Home

Abhay

£431

includes taxes & fees

4 Oct - 5 Oct

A modern building with a glass facade, surrounded by a parking lot and greenery.

A modern balcony with a city view, a cushioned chair, a small table, and potted plants.

A modern living room with a grey sofa, a round coffee table, and a large window offering a view of a building.

A modern living room with a large window, a white sofa, a grey sofa, and a dining area with a white table and chairs.

15. ENVITAE Hotel 4 Bedroom Luxury Apartments

7.9 mi from Pleasant Home

Karthik

£403

includes taxes & fees

14 Oct - 15 Oct

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

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

A DoubleTree by Hilton hotel with a modern design, a covered entrance, and well-maintained landscaping.

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

16. DoubleTree by Hilton Chicago Midway Airport

8.3 mi from Pleasant Home

Jessica

£130

includes taxes & fees

31 Oct - 1 Nov

A spacious lobby with a modern design, featuring a large seating area with sofas and chairs, a coffee table, and a dining table with chairs. Large windows provide a view of the outdoors.

A bar area with wooden walls, bar stools, and a bar counter.

A modern hotel lobby with a reception desk, a seating area, and a view of the lobby leading to the business center.

A hotel entrance with a prominent sign reading "The Westin."

17. The Westin O'Hare

7.8 mi from Pleasant Home

Makayla

£162

includes taxes & fees

16 Oct - 17 Oct

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

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

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

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

18. The Emily Hotel

7.6 mi from Pleasant Home

Leslie

£208

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

6.5 mi from Pleasant Home

BRIAN

£218

includes taxes & fees

4 Oct - 5 Oct

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

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.

A spacious living area with a pool table, comfortable seating, a fireplace, and large windows.

20. Hyatt House Chicago Medical/University District

6.6 mi from Pleasant Home

Enrique

£233

includes taxes & fees

25 Oct - 26 Oct

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Top Pleasant Home Hotel Reviews

The Shamrock

8/10 Good

"For its price, it was worth the cost and was better than I expected. The ac worked well, and the room was very spacious. Only real complaints were a faint smell of smoke that may just be lingering from years of use and wasnt very quiet. You could easily hear the noise of the neighborhood and a mysterious hum/ring that would arise sporadically. Parking was limited, but many of the spots were taped off for work. They were free before the weekend was over."

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

8/10 Good

"Staff was very helpful. Location was convenient. Parking lot was safe"

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. ❤️"

Luxury Home Away From Your Home

10/10 Excellent

"Another very nice stay at Ms Linnie’s place. The new couch and seat in the living room are great!"

VIBE INN - WHIRLPOOL SUITES

10/10 Excellent

"Hell of a deal, huge hot tub, nice staff 24/7, quiet, comfy, et al"

Experience Chicago living near United Center

8/10 Good

"House was overall clean but had a musty cat smell. Host responded quickly when we didn’t receive check-in instructions. Parking was street parking so could get full in the evenings. Very nice kitchen! Lots of space for the price!"

Harvey House Bed & Breakfast

8/10 Good

"Beautiful clean spacious and really nice staff"

Cindy Lyn Motel

10/10 Excellent

"I didn't like where the out let's are not near not stand one can't use cpap. Has to bring extra cords the rooms could use fixing up needs paint dont like mirror across from bed . The staff was very helpful like I ccan get free coffees"

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

10/10 Excellent

"The apartment was excellent. Clean and well stocked for our stay. Everything we could have needed was already there. Close enough to the city but in a residential area that was safe and quiet. We will definitely keep this one bookmarked for the future."

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.

Search Hotels Near Pleasant Home, Chicago

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Be picky

Check prices for these dates

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Our top choices for Pleasant Home hotels

1. Harvey House Bed & Breakfast

2. Carleton of Oak Park

3. Historic Oak Park Home

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

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

6. Ray's Bucktown B&B

7. The Sono Chicago

8. Hampton Inn & Suites Chicago Medical District UIC

9. Hampton Inn & Suites Rosemont Chicago O'Hare

10. Hampton Inn Chicago-O'Hare International Airport

11. Hyatt Place Chicago/Wicker Park

12. The Rose Chicago, Tapestry Collection by Hilton

13. Villa D' Citta

14. Nobu Hotel Chicago

15. ENVITAE Hotel 4 Bedroom Luxury Apartments

16. DoubleTree by Hilton Chicago Midway Airport

17. The Westin O'Hare

18. The Emily Hotel

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

20. Hyatt House Chicago Medical/University District

Top Pleasant Home Hotel Reviews

The Shamrock

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

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

Luxury Home Away From Your Home

VIBE INN - WHIRLPOOL SUITES

Experience Chicago living near United Center

Harvey House Bed & Breakfast

Cindy Lyn Motel

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

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