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Chicago Vacation Rentals and Hotels

Tour the Windy City—All from Discount Chicago Accommodations

HotStays.com will introduce you to discount Chicago hotel rooms with views of the city’s breathtaking skyline or near the city’s wide array of museums and cultural hangouts. No matter what your reason for visiting, you can browse for the best Chicago vacation rentals through HotStays.com. Whether jazz and blues clubs are your thing or the rock scene gets your heart pumping, we have a hotel close to it.

Are sports your favorite pastime? Book a cheap Chicago condo reservation near Wrigley Field. Like to eat? Try making a cheap Chicago resort reservation close to one of the city’s fine dining establishments.

Whether you’re going for a business meeting or traveling there for a family getaway, HotStays.com lists Chicago luxury villas with tons of amenities and nearby attractions. That’s why you need to book your Chicago bed and breakfast reservations through HotStays.com. Book now!

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We have over 600 properties in the Chicago, Illinois area.
Please browse our top 30 properties below

Vacation Rentals in the Chicago area.

	Furnished Downtown Rental - Near Magnificent Mile #2329				From $185/night
	1 Beds	1 Baths	Sleeps 2	Apartment
These Vacation Rentals are located in the New East Side, a mixed-use neighborhood east of Michigan Avenue that includes apartments, homes, businesses and retailers surrounded by magnificent parks that are framed by the Chicago River to the North, Buckingham Fountain to the South, Michigan Avenue to the ...


	Lincoln Park, Lake Michigan, the Chicago Skyline! #2323				From $185/night
	1 Beds	1 Baths	Sleeps 1-3	Condo
Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside service, premier gym, wireless internet lounge, and much more. Overlooking 1,200 acres of glorious Lincoln Park greenery and offering panoramic views of Lake Michigan, our Vacation ...


	Affordable Hotel Alternatives - PRATT SHORE #2330				From $60/night
	1 Beds	1 Baths	Sleeps 2	Apartment
Pratt Shore another great Chicago Hotel Alternative, extended stay - temporary housing solution 8 story midrise near the lake, beach, tennis court, park. Living with beach and university close at hand Beaches, parks, vintage apartments -- these features and more make Rogers Park a desirable Chicago ...


Hotels in the Chicago area.

	Amalfi Hotel Chicago				From $119.00/nt 4 Star Hotel
	Overview \| Map \|			Hotel
The Amalfi Hotel Chicago is situated two blocks from the Magnificent Mile and the Theater District, approximately 13 miles from Midway Airport, and 17


	Club Quarters Central Loop				From $79.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Experience peace and calm in a members-only, club-like atmosphere in Chicago's Central Loop.


	Club Quarters Wacker At Michigan Chicago				From $79.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Club Quarters is an exclusive and club-like hotel that ensures privacy and tranquility.


	Amalfi Hotel Chicago				From $119.00/nt 4 Star Hotel
	Overview \| Map \|			Hotel
The Amalfi Hotel Chicago is situated two blocks from the Magnificent Mile and the Theater District, approximately 13 miles from Midway Airport, and 17


	Homewood Chicago Downtown				From $135.16/nt 3 Star Hotel
	Overview \| Map \|			Hotel
The Homewood Suites by Hilton Chicago Downtown is located 15 miles from the Chicago O?Hare International Airport.


	Super 8 Chicago Il				From $79.99/nt 2 Star Hotel
	Overview \| Map \|			Hotel
The Super 8 Chicago Loyola University is located 1 block from Lake Michigan beaches where you can enjoy a evening stroll or a morning jog along the beautiful


	Chicago Hotel 71				From $125.10/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Immerse yourself in the convenient location and urban sophistication of Hotel 71-a quiet haven in the heart of downtown Chicago only steps from The Magnificent


	Four Points by Sheraton Chicago Downtown Magnificent Mile				From $115.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Whether checking out Magnificent Mile shops or seeking an indoor rest by the pool, Four Points Chicago has it all, High Speed Internet and Free Bottled


	Crowne Plaza Metro Downtown Chicago				From $109.00/nt 4 Star Hotel
	Overview \| Map \|			Hotel
The Crowne Plaza Hotel Chicago Metro is located in the trendy West Loop neighborhood, blocks from the Financial District, and approximately 18 miles from


	Hampton Inn - Majestic Chicago Theatre District				From $84.16/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Relax at a unique boutique-style hotel atop the newly renovated Bank of America Theatre in the downtown Theater District.


	Springhill Suites Marriott Downtown				From $130.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Experience an exciting innovation in Chicago lodging at the Residence Inn/SpringHill Suites Downtown Chicago.


	Residence Inn Marriott River North Chicago				From $140.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Experience the comforts of home in the Windy City at the Residence Inn Chicago Downtown/Magnificent Mile Hotel located in the posh Gold Coast district


	La Quinta Inn & Suites Chicago Downtown				From $236,032.91/nt 3 Star Hotel
	Overview \| Map \|			Hotel
The property features a contemporary design that is both functional and environmentally friendly. Shopping, dining, and entertainment venues are within


	Dana Hotel And Spa Chicago				From $169.00/nt 4 Star Hotel
	Overview \| Map \|			Hotel
The sleek exterior facade, designed by Chicago's Eckenhoff Saunders Architects, will feature a stunning 28 foot high clear glass curtain wall offering


	Holiday Inn Midway Airport Chicago				From $105.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
Holiday Inn Chicago - Midway Airport is located just ten miles from downtown Chicago and offers complimentary 24 hour airport shuttle service to and from


	Hotel Felix Chicago				From $139.00/nt 4 Star Hotel
	Overview \| Map \|			Hotel
The Hotel Felix Chicago is situated near area attractions like Adler Planetarium, Art Institute of Chicago, Comiskey Park, John Hancock Observatory, Lincoln


	Chicago Central Loop Hotel				From $79.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
The Central Loop Hotel is located at the corner of Adams and Clark Streets in the center of the Loop, Chicago's business and cultural district, making


	Thewit Chicago - A Doubletree by Hilton Hotel				From $175.00/nt 4 Star Hotel
	Overview \| Map \|			Hotel
Chicago's newest hotel, theWit Chicago - a DoubleTree by Hilton Hotel has several great restaurants and a new room format that is sure to change your expectations.


	River Hotel Chicago				From $79.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
The River Hotel is located in the center of downtown Chicago, overlooking the famous Chicago River, Tribune Tower and Wrigley Building. Just one block


	Chicago South Loop Hotel				From $99.00/nt 3 Star Hotel
	Overview \| Map \|			Hotel
The Chicago South Loop Hotel is located near McCormick Place, IIT, and Chinatown. The property offers free parking, a fitness center, meeting space, business


	Chicago Carlton Inn Midway				From $89.00/nt 3 Star Hotel
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Centrally located 2 miles from Midway Airport and right around the corner from the Orange Line elevated train, the Carlton Inn Midway guest rooms express


	Chicago Ohare Garden Inn				From $37.00/nt 1 Star Hotel
	Overview \| Map \|			Hotel
The Chicago O'Hare Garden Hotel offers a complimentary welcome drink upon arrival. A free airport shuttle from O'hare is available as well as free wireless


	Hotel Palomar Chicago				From $158.54/nt 4 Star Hotel
	Overview \| Map \|			Hotel
The sparkling new Hotel Palomar Chicago is located on State Street, north of the Chicago River, in the heart of the Streeterville neighborhood.


	Ohio House Motel Chicago				From $109.00/nt 2 Star Hotel
	Overview \| Map \|			Hotel
The Ohio House Motel is a quaint treasure located in the heart of Chicago that offers a great value with an even greater location. This landmark motel


	China Doll Guest House				2 Star Hotel
	Overview \| Map \|			Hotel
In Chicagos Lincoln Park neighborhood, China Doll offers three complete self-contained apartment suites with private entrances. All have fireplaces, two-person


	House 5863 Chicago				From $129.01/nt 2 Star Hotel
	Overview \| Map \|			Hotel
All rooms feature contemporary furnishings and a hip design. Free wireless Internet access is available throughout the property


	Chicago The Wicker Park Inn				From $99.01/nt 2 Star Hotel
	Overview \| Map \|			Hotel
The Wicker Park Inn offers high quality yet affordable accommodations in Chicago's trendy Wicker Park neighborhood just minutes from Downtown.

We have over 600 properties in the Chicago, Illinois area.
Please continue your search by clicking "Search Now".

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Chicago Vacation Rentals | Hotels