Chicago Holiday Rentals

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Holiday Rentals in Chicago

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street, Chicago, IL
The price is NZ$189 per night from 16 Nov. to 16 Nov.
Located in The Loop, this aparthotel is steps away from State Street and Grant Park. Columbia College Chicago and Roosevelt University are also within 15 minutes. ...
4.1/5 Very Good! (863 reviews)
"Great hotel. Clean. Great morning breakfast. Located nicely in downtown Chicago."

Reviewed on 17 Oct. 2021

Homewood Suites by Hilton Chicago Downtown South Loop
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

3 out of 5
110 West Huron St, Chicago, IL
The price is NZ$193 per night from 21 Nov. to 21 Nov.
Located in River North, this aparthotel is within 1 mi (2 km) of Chicago Theatre and Millennium Park. Art Institute of Chicago and Navy Pier are also within ...
4.3/5 Excellent! (796 reviews)
"The property was great… area / location is loud. Bed was dated.. as well as covers. I have stayed at other home 2 suites and the beds were very plush and the covers were very nice. Here not so much!!"

Reviewed on 19 Oct. 2021

Home2 Suites by Hilton Chicago River North
Homewood Suites by Hilton Chicago Downtown

Homewood Suites by Hilton Chicago Downtown

3 out of 5
40 East Grand Avenue, Chicago, IL
The price is NZ$169 per night from 21 Nov. to 21 Nov.
Located in River North, this aparthotel is steps away from State Street and Michigan Avenue. Wrigley Building and Chicago Riverwalk are also within 10 minutes. ...
4.3/5 Excellent! (1,024 reviews)
"Great location, room with a kitchen and staff!"

Reviewed on 16 Oct. 2021

Homewood Suites by Hilton Chicago Downtown
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Homewood Suites by Hilton Chicago Downtown West Loop

Homewood Suites by Hilton Chicago Downtown West Loop

3 out of 5
118 North Jefferson Street, Chicago, IL
The price is NZ$169 per night from 21 Nov. to 21 Nov.
Located in Near West Side, this aparthotel is within a 15-minute walk of Cadillac Palace Theatre, Chicago City Hall and Civic Opera House. Merchandise Mart and ...
4.6/5 Exceptional! (480 reviews)
"Quite, neat and great amenities. Close to downtown and other great food places."

Reviewed on 22 Oct. 2021

Homewood Suites by Hilton Chicago Downtown West Loop
The Chicago Hotel Collection - Millennium Park

The Chicago Hotel Collection - Millennium Park

2.5 out of 5
55 E Washington St., Chicago, IL
The price is NZ$195 per night from 25 Oct. to 25 Oct.
Located in The Loop, this aparthotel is steps away from Chicago Cultural Center, Michigan Avenue and State Street. Grant Park and Pritzker Pavilion are also ...
3.1/5 (1,266 reviews)
"The checkin/checkout system was simple. I had a little bit of trouble getting a key card at first, but that was eventually resolved. The room has a TV but it doesn't work. The blinds were missing panels. The shower water pressure was inconsistent, and very difficult to control hot and cold."

Reviewed on 12 Oct. 2021

The Chicago Hotel Collection - Millennium Park
Homewood Suites by Hilton Chicago - Schaumburg

Homewood Suites by Hilton Chicago - Schaumburg

3 out of 5
815 East American Lane, Schaumburg, IL
The price is NZ$145 per night from 21 Nov. to 21 Nov.
Situated in the business district, this aparthotel is within 3 miles (5 km) of Woodfield Mall, Ned Brown Forest Preserve and Legoland Discovery Center. Schaumburg ...
4.3/5 Excellent! (1,007 reviews)
"I loved the location and the price for what you get. It’s right by the mall and plenty of parks to take the kids or restaurants if you want to go out. Breakfast could use some work, but it wasn’t bad. They should hire a southerner for the kitchen and you might have something there."

Reviewed on 12 Sep. 2021

Homewood Suites by Hilton Chicago - Schaumburg
Home2 Suites by Hilton Chicago McCormick Place

Home2 Suites by Hilton Chicago McCormick Place

3 out of 5
123 E. CERMAK ROAD, Chicago, IL
The price is NZ$158 per night from 23 Nov. to 23 Nov.
Located in South Loop, this aparthotel is within a 10-minute walk of Wintrust Arena and McCormick Place. Soldier Field and Grant Park are also within 2 mi (3 ...
4.4/5 Wonderful! (181 reviews)
"Great place to stay and go around the city"

Reviewed on 6 Sep. 2021

Home2 Suites by Hilton Chicago McCormick Place
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

3 out of 5
152 E Huron St, Chicago, IL
The price is NZ$236 per night from 7 Nov. to 7 Nov.
Located in Near North Side, this aparthotel is steps away from Michigan Avenue, Northwestern Memorial Hospital and Museum of Contemporary Art. Chicago Water ...
4.3/5 Excellent! (1,008 reviews)
"Close to Lake-view from 33rd floor was amazing"

Reviewed on 23 Oct. 2021

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
Homewood Suites by Hilton Chicago-Lincolnshire

Homewood Suites by Hilton Chicago-Lincolnshire

3 out of 5
10 Westminster Way, Lincolnshire, IL
The price is NZ$169 per night from 31 Oct. to 31 Oct.
Situated in the suburbs, this aparthotel is within 9 mi (15 km) of Conway Farms Golf Club, Northwestern Lake Forest Hospital and Chicago Botanic Garden. Lake ...
4.5/5 Wonderful! (621 reviews)
"It was just an all-around pleasant surrounding staff were nice very helpful polite and courteous."

Reviewed on 21 Oct. 2021

Homewood Suites by Hilton Chicago-Lincolnshire
Home2 Suites by Hilton Lincolnshire Chicago

Home2 Suites by Hilton Lincolnshire Chicago

3 out of 5
350 Knightsbridge Pkwy, Lincolnshire, IL
The price is NZ$152 per night from 31 Oct. to 31 Oct.
Situated in Lincolnshire, this aparthotel is 3 mi (4.8 km) from Chevy Chase Country Club and within 6 miles (10 km) of Trinity International University and Raupp ...
4.4/5 Excellent! (11 reviews)
"Property is still very new. The staff were very accommodating and warm. The ambiance is pleasant and comfortable. Cleanliness in the room though isn't spot on. Either the beddings weren't thoroughly washed or wasn't completely changed."

Reviewed on 16 Oct. 2021

Home2 Suites by Hilton Lincolnshire Chicago
Home2 Suites by Hilton Chicago/Schaumburg, IL

Home2 Suites by Hilton Chicago/Schaumburg, IL

3 out of 5
1300 East American Lane, Schaumburg, IL
The price is NZ$162 per night from 1 Nov. to 1 Nov.
Situated in the business district, this aparthotel is within 2 miles (3 km) of Woodfield Mall, Legoland Discovery Center and Schaumburg Convention Center. Ned ...
4.4/5 Excellent! (490 reviews)
"Professional staff and complementary breakfast was great! Great location too!"

Reviewed on 14 Sep. 2021

Home2 Suites by Hilton Chicago/Schaumburg, IL
WoodSpring Suites Chicago Addison

WoodSpring Suites Chicago Addison

2.5 out of 5
991 E. Lake Street, Addison, IL
The price is NZ$138 per night from 25 Oct. to 25 Oct.
Located in the heart of Addison, this aparthotel is 3.1 mi (5 km) from Bloomingdale Golf Club and within 6 miles (10 km) of Odeum Sports and Expo Center and ...
3.1/5 (99 reviews)
"Nice fresh rooms but some staff members have a very hostile attitude."

Reviewed on 2 May 2021

WoodSpring Suites Chicago Addison
Homewood Suites by Hilton Aurora Naperville

Homewood Suites by Hilton Aurora Naperville

3 out of 5
4320 Meridian Pkwy, Aurora, IL
The price is NZ$206 per night from 18 Nov. to 18 Nov.
Situated in the business district, this aparthotel is 2.5 mi (4.1 km) from Nue Medical Solutions and within 6 miles (10 km) of Centennial Beach and Riverwalk ...
4/5 Very Good! (382 reviews)
"Love this hotel. Staff is so nice. The property is right on a pond which is so beautiful. Very dog friendly, my dog loved running around by the pond. Rooms are very clean & spacious. Would definitely recommend."

Reviewed on 19 Oct. 2021

Homewood Suites by Hilton Aurora Naperville
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street, Chicago, IL
The price is NZ$391 per night from 28 Oct. to 28 Oct.
This family-friendly Chicago aparthotel is located near the beach, within a 15-minute walk of State Street, Oak Street Beach and Michigan Avenue. 900 North Michigan ...
4.3/5 Excellent! (63 reviews)
"Nice clean, with lots of things to do. Pool, basketball, bocci, bbq are some of things avaliable. Easy walk to most necessities."

Reviewed on 28 Aug. 2021

Level Chicago – Old Town
Sonder | The Plymouth

Sonder | The Plymouth

3.5 out of 5
South Dearborn Street, Van Buren, Chicago, IL
Located in The Loop, this aparthotel is within a 5-minute walk of State Street and DePaul University-Loop Campus. Roosevelt University and Grant Park are also ...
4.3/5 Excellent! (15 reviews)
"Great location. Excellent, quick customers service resolution to a few issues, clean, modern, bright apartments. Very comfortable beds and large baths. Very impressed."

Reviewed on 5 Oct. 2021

Sonder | The Plymouth
Sonder | South Wabash

Sonder | South Wabash

3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
Located in South Loop, this aparthotel is within a 10-minute walk of State Street and Grant Park. Columbia College Chicago and Field Museum of Natural History ...
4.3/5 Excellent! (32 reviews)
"Good location and nicely laid out within the room."

Reviewed on 30 Sep. 2021

Sonder | South Wabash
Sonder | Jewelers Row

Sonder | Jewelers Row

3 out of 5
19 South Wabash Avenue, Chicago, IL
Located in The Loop, this aparthotel is steps away from Millennium Park and Chicago Cultural Center. State Street and Michigan Avenue are also within 5 minutes. ...
3.9/5 Very Good! (12 reviews)
"Really nice apt"

Reviewed on 30 Jun. 2021

Sonder | Jewelers Row
Kasa Chicago Old Town

Kasa Chicago Old Town

2.5 out of 5
808 N Wells St, Chicago, IL
Located in River North, this aparthotel is within a 10-minute walk of State Street and Holy Name Cathedral. Michigan Avenue and Chicago Water Tower are also ...
Kasa Chicago Old Town
Sonder at 820 South Michigan

Sonder at 820 South Michigan

3.5 out of 5
820 South Michigan Avenue, Chicago, IL
Located in The Loop, this aparthotel is within a 5-minute walk of Grant Park and State Street. Columbia College Chicago and Roosevelt University are also within ...
4/5 Very Good! (4 reviews)
"Everything was amazing and exactly as advertised"

Reviewed on 4 Oct. 2021

Sonder at 820 South Michigan
InTown Suites Extended Stay Chicago IL - Villa Park

InTown Suites Extended Stay Chicago IL - Villa Park

2.5 out of 5
350 East Roosevelt, Villa Park, IL
Situated near the airport, this aparthotel is within 3 miles (5 km) of Oakbrook Center Mall, Drury Lane Theater and Yorktown Shopping Center. York Woods County ...
4.3/5 Excellent! (4 reviews)
"No frills, but quiet, clean and excellent location, close to shopping, supermarkets and restaurants."

Reviewed on 24 Oct. 2021

InTown Suites Extended Stay Chicago IL - Villa Park
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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.

Other types of properties in Chicago you may be interested in

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$205 per night from 21 Nov. to 21 Nov.
DoubleTree by Hilton Chicago - Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$162 per night from 1 Nov. to 1 Nov.
Congress Plaza Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chicago holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chicago. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chicago. Seeing all the best attractions is bound to make you fall in love with Chicago. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chicago short-term rentals, that won’t be hard to do.

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