Search Hotels Near Pleasant Home, Chicago

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26 Dec - 27 Dec
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27 Dec - 28 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Pleasant Home hotels

Exterior detail
Carleton of Oak Park

Carleton of Oak Park

Carleton of Oak Park
3.0 star property
0.3 km from Pleasant Home
9.2 out of 10, Wonderful, (1007)
"Beautiful historical hotel!"
United States
Cheryl
Carleton of Oak Park
Free daily buffet breakfast
Holiday Inn Express and Suites Chicago West Oak Park by IHG

Holiday Inn Express and Suites Chicago West Oak Park by IHG

Holiday Inn Express and Suites Chicago West Oak Park by IHG
2.5 star property
0.5 km from Pleasant Home
The price is ฿3,604
฿4,000 total
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Inn Express and Suites Chicago West Oak Park by IHG
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
1.2 km from Pleasant Home
The price is ฿4,910
฿12,817 total
includes taxes & fees
4 Jan - 5 Jan 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
10.5 km from Pleasant Home
9.8 out of 10, Exceptional, (383)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is ฿4,899
฿5,531 total
includes taxes & fees
28 Dec - 29 Dec
Ray's Bucktown B&B
Business centre
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC
2.5 star property
10.2 km from Pleasant Home
9.6 out of 10, Exceptional, (385)
"Easy check in/out process and good breakfast:)"
United States
Belle
The price is ฿2,746
฿3,223 total
includes taxes & fees
30 Dec - 31 Dec
Hampton Inn & Suites Chicago Medical District UIC
Breakfast and dinner served
Hyatt Place Chicago/Wicker Park

Hyatt Place Chicago/Wicker Park

Hyatt Place Chicago/Wicker Park
3.0 star property
11.3 km from Pleasant Home
9.4 out of 10, Exceptional, (1001)
"Absolutely wonderful and we will definitely be staying here again☺️"
United States
Victoria
The price is ฿3,418
฿4,012 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt Place Chicago/Wicker Park
Premium bedding, in-room safe, individually decorated
The Rose Chicago, Tapestry Collection by Hilton

The Rose Chicago, Tapestry Collection by Hilton

The Rose Chicago, Tapestry Collection by Hilton
4.0 star property
11.5 km from Pleasant Home
9.4 out of 10, Exceptional, (1000)
"Such a hospitable team. Loved my stay. "
United States
Isabel
The price is ฿4,357
฿4,966 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Rose Chicago, Tapestry Collection by Hilton
Exterior
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
10.1 km from Pleasant Home
9.2 out of 10, Wonderful, (2132)
"very nice hotel "
United States
emily
The price is ฿2,703
฿3,081 total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn Chicago-O'Hare International Airport
3 bars/lounges, cocktail bar, rooftop bar, rooftop bar
The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels
3.5 star property
10.5 km from Pleasant Home
9.2 out of 10, Wonderful, (999)
"Good location, great staff!"
United States
Veronica
The price is ฿3,962
฿5,417 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Robey, Chicago, a Member of Design Hotels
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
12.5 km from Pleasant Home
9.4 out of 10, Exceptional, (764)
"Staff was amazing, room was spotless and the whole vibe of the hotel is relaxing. Celebrated our anniversary and it was intimate and perfect. "
United States
Filjelaine
The price is ฿9,905
฿11,627 total
includes taxes & fees
4 Jan - 5 Jan 2026
Nobu Hotel Chicago
Exterior
Hampton Inn & Suites Rosemont Chicago O'Hare

Hampton Inn & Suites Rosemont Chicago O'Hare

Hampton Inn & Suites Rosemont Chicago O'Hare
2.5 star property
12.9 km from Pleasant Home
9.4 out of 10, Exceptional, (1018)
"All around, great stay. "
United States
Eric
The price is ฿3,414
฿3,892 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hampton Inn & Suites Rosemont Chicago O'Hare
Exterior
The Emily Hotel

The Emily Hotel

The Emily Hotel
4.0 star property
12.3 km from Pleasant Home
9.2 out of 10, Wonderful, (1288)
"Clean rooms & courteous staff"
United States
Allyson
The price is ฿7,163
฿8,408 total
includes taxes & fees
20 Jan - 21 Jan 2026
The Emily Hotel
Exterior
Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District
3.5 star property
10.6 km from Pleasant Home
9.0 out of 10, Wonderful, (1278)
"Clean room, nice staff, great location "
United States
Kati
The price is ฿2,890
฿3,392 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hyatt House Chicago Medical/University District
Property entrance
Wicker Park Inn

Wicker Park Inn

Wicker Park Inn
3.5 star property
10.8 km from Pleasant Home
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Executive lounge
Level Chicago Fulton Market

Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
12.7 km from Pleasant Home
9.2 out of 10, Wonderful, (364)
"Great spot for a quick work trip! I loved the space and kitchen and location. "
United States
Marie
Level Chicago Fulton Market
Lobby
Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District
3.0 star property
10.6 km from Pleasant Home
9.0 out of 10, Wonderful, (1426)
"Clean room and friendly staff."
United States
Kevin
The price is ฿2,734
฿3,210 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt Place Chicago Medical/University District
Exterior
The Hotel at Midtown

The Hotel at Midtown

The Hotel at Midtown
4.0 star property
11 km from Pleasant Home
9.0 out of 10, Wonderful, (835)
"Clean room. Great gym and convenient parking."
United States
Daniel
The Hotel at Midtown
Terrace/patio
Hyatt House Chicago Oak Brook

Hyatt House Chicago Oak Brook

Hyatt House Chicago Oak Brook
3.0 star property
11.2 km from Pleasant Home
9.0 out of 10, Wonderful, (1000)
"Nice staff, clean rooms and good hot breakfast."
United States
Patrick
The price is ฿4,319
฿4,707 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hyatt House Chicago Oak Brook
Terrace/patio
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
13 km from Pleasant Home
9.2 out of 10, Wonderful, (1001)
"Good place to stay in."
United States
Joan
The price is ฿4,051
฿4,756 total
includes taxes & fees
2 Jan - 3 Jan 2026
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Exterior
DoubleTree by Hilton Chicago Midway Airport

DoubleTree by Hilton Chicago Midway Airport

DoubleTree by Hilton Chicago Midway Airport
4.0 star property
13.3 km from Pleasant Home
9.2 out of 10, Wonderful, (1001)
"Clean room, friendly staff, great food at coaches! "
United States
Edward Harte
The price is ฿4,306
฿5,059 total
includes taxes & fees
2 Jan - 3 Jan 2026
DoubleTree by Hilton Chicago Midway Airport
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.
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Top Pleasant Home Hotel Reviews

MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside

10/10 Excellent
"good"
yusef 2-night trip
Posted 1 month ago
MainStay Suites Chicago Hillside

Hotels near other Pleasant Home attractions

#franklloydwright #house #architecture #interior
Photo by Krystalvation
Open Photo by Krystalvation

Unity Temple

4.0/5 (5 reviews)
This was Frank Lloyd Wright’s first major public building and is still considered one of his greatest achievements.
See properties
Ernest Hemingway Museum and House featuring heritage elements

Ernest Hemingway Museum and House

3.6/5 (5 reviews)
Peek into the early life of one America’s best-loved writers.
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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 79 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 79 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?
You'll want to browse the exhibits at Ernest Hemingway Museum and House and 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. Local parks like Garfield Park, Garfield Park Conservatory and Oak Park Conservatory are peaceful spots to stop and take in some fresh air.