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The Loop Holiday Rentals

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All 34 Rentals in The Loop
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From
$382
Per Night
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1 / 27
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$793
Per Week
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1 / 40
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The Loop
Studio, 1 Bathroom, Sleeps 2
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Details Reviews (6) Make Enquiry
From
$302
Per Night
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1 / 10
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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From
$381
Per Night
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1 / 34
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to Chicago -- far from your typical Chicago rental. The building offers unparalleled amenities, upscale stylish accommodations, and floor-to-ceiling dynamic views of the Chicago skyline. This property is unlike any other in its class and the experience is definitely one-of-a-kind.... View all property information
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5 of 5 stars Reviewed 22 October 2014
El departamento está mucho mejor de lo que se ven en las fotos y vale la pena cada centavo que pagamos por él. Además de la excelente ubicación (está a una cuadra de la avenida...
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From
$95
Per Night
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1 / 18
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The Loop
Studio, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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4 of 5 stars Reviewed 21 August 2014
Tr`es bien situé, propre et bien équipé. Personnel de l'immeuble bien chaleureux. Pitsfield's café `a ne pas manqué au rez-de-chaussée. Calme , bien insonorisé...`a l'exeption de...
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From
$401
Per Night
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1 / 32
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Take me to the Penthouse! Stay in our Penthouse Condo on the 50th Floor! A true Penthouse, stunning views of the lake and city. Walk to everything downtown. Upgraded everything. Granite kitchen counter tops, stainless steal appliances, marble in the bathrooms, king size beds, floor to ceiling... View all property information
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5 of 5 stars Reviewed 30 June 2014
Can't sat enough good things about this place. Excellent host, great amenities, perfect location. Top shelf stay.
5 of 5 stars Reviewed 16 August 2011
Was a bit nervous booking the condo vs. a traditional hotel for a group of co-workers. Fantastic accommodations, great view, clean, convenient location. We already re-booked with...
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From
$637
Per Night
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1 / 24
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Beautiful B & B Boatel Yacht - Pier Gold offers Chicago visitors a great alternative to regular hotel stays. Located at Chicago's most sought after harbor in the heart of our city waterfront; at Burnham Harbor you will enjoy waking up at your floating waterfront boatel at our harbor with stunning... View all property information
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4 of 5 stars Reviewed 31 July 2014
This was absolutely a great choice for a buddy and I to hang out in Chicago for a long weekend. The location was incredible and fortunately for so was the weather. Having done...
5 of 5 stars Reviewed 9 August 2013
A short walk (about a block) from the museums you find yourself in the quiet Burnham Harbor and on you very own Yacht! Two very private cabins, a comfortable living area with...
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From
$350
Per Night
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1 / 14
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Tides is a great way to experience life and culture in the heart of Chicago! Featuring a modern contemporary feel, the short term rentals at The Tides offer dramatic finishes including tiled entries, granite islands and cherry cabinetry, open floor plans with captivating views from the... View all property information
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4 of 5 stars Reviewed 6 February 2015
This apartment is located in a modern, somewhat glitzy group of buildings which form their own mini-village. It is located east of Michigan Ave., almost across the street from...
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From
$401
Per Night
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1 / 12
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (9) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Walk to Everything Downtown! Enjoy Stunning Views of the City Skyline and Grant Park! ONE OF FEW 3BD/2.5BA UNITS RIGHT IN THE MIDDLE OF DOWNTOWN CHICAGO. Very affordable! ***WALK TO EVERYTHING ***YES, THESE ARE THE VIEWS! ***BREATHTAKING VIEWS OF THE CITY SKYLINE AND GRANT PARK ***3... View all property information
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4 of 5 stars Reviewed 31 October 2014
This is a superb place to stay. Warm, comfortable with stunning views of downtown and Grant Park. We booked with stepstoeverything and their communications were top class...
5 of 5 stars Reviewed 19 July 2014
Pretty close to downtown parking is across the street Reservation and service are with phone communication, quick and helpful. Keyless entry Recent renovated with quality...
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From
$318
Per Night
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1 / 10
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
**LOCATION **LOCATION **LOCATION! ***CAN'T BEAT IT! ***Views Views Views! Breathtaking Lake and City Views!!*** Looks Like Hawaii Up There!*** Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep of... View all property information
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5 of 5 stars Reviewed 3 September 2014
We're home from our trip and back to reality! We loved your City and will definitely be back, next time could you arrange a bit better weather please!! But, as Brits we're used to...
5 of 5 stars Reviewed 23 July 2014
We booked through Steps From Everything and they were very easy to work with. The price was very reasonable and the location was great. We could walk two blocks to the Metro...
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From
$113
Per Night
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1 / 6
The Loop
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
These Vacation Rentals are located in the Chicago LOOP, a mixed-use neighborhood west 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... View all property information
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4 of 5 stars Reviewed 17 September 2014
Upon arrival we were greeted with a sign on the door saying we could not use the kitchen sink. Room had no iron, dish towels, kitchen utensils, hangers, missing a light bulb in...
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From
$559
Per Night
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1 / 32
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (26) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Brand new luxury 2 bedroom 2 bathroom corporate housing suite with panoramic views in a building unlike anything in Chicago!! The Resort is located in Chicago's high end neighborhood, Lakeshore East, where the Chicago River meets Lake Michigan. You will enjoy exclusive access to two full-floors... View all property information
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5 of 5 stars Reviewed 3 September 2013
We arrived to a great welcome from Nadiya - everything was very straightforward and well organised. The apartment is superb, with terrific lakeside views and is very well...
5 of 5 stars Reviewed 15 March 2013
The suite was beautiful... from the furnishings, the view, the amenities, and a few surprise items! Underground free parking was a big plus. Location was perfect. Walking...
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From
$8,403
Per Month
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1 / 21
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
This building just opened up in July of 2014 and is the most modern building you can find in the Chicago Loop area. From the state of the art amenities to the amazing and helpful staff, you will love staying at this apartment. Located in the Loop you have access to all the tourist attractions as... View all property information
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From
$1,775
Per Night
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1 / 4
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The Loop
5 Bedrooms, 1 Bathroom, Sleeps 8
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Amenities & Details
  • Ocean Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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From
$1,528
Per Night
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1 / 7
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The Loop
2 Bedrooms, 4 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Amazing penthouse available with city views. This unit is like no other available and can accommodate a variety of guests, you have the flexibility of separating the unit into a 1 bed 1.5 baths unit and a studio or the entire unit for a 2 bed 2.5 bath property. The unit is conveniently located by... View all property information
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From
$223
Per Night
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1 / 22
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy all that Chicago has to offer and then come home and relax on the huge (20 x20) deck with the best skyline views in the city. This is a charming Condo in the perfect location. Have the neighborhood feel with dozens of great places to go for a bite to eat within a couple blocks, and also... View all property information
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From
$298
Per Night
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1 / 13
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This two queen room overlooks the city. The pillowtop bed and blackout drapes/curtains help ensure a restful night. The private bathroom has complimentary toiletries. Complimentary wireless Internet access keeps you connected, and the 37-inch plasma TV and iPod docking station are offered for your... View all property information
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From
$344
Per Night
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1 / 4
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand Chicago river front — an intimate haven on the magnificent mile — offering chic accommodations in an exceptional setting. Just outside your door is Chicago's premier shopping avenue with over 450... View all property information
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From
$153
Per Night
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1 / 4
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 1
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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From
$382
Per Night
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1 / 22
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Situated in the South Loop's Prairie District, this stunning corner loft features arched terra cotta tile ceilings & columns, exposed brick, bamboo floors, polished concrete counters, SS appliances, extra large shower with dual heads, side-by-side sinks, soaking tub, balcony with courtyard view,... View all property information
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From
$255
Per Night
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1 / 10
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This is another one of our properties in the South Loop that has amazing amenities and a great feel to it. You will see from the pictures there is a king sized bed along with a sleeper sofa in the loving room which is how this unit can accommodate four people. Please let me know what questions you... View all property information
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From
$637
Per Night
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1 / 10
Payment Protection
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Modern luxury One bedroom with queen size bed Location, Location, Location Hotel type amenities. Queen size bed in your private room 900 square feet space Sleeps 4 Flatscreen TV in the livingroom Wireless Internet is not available Clean freshly-washed white sheets and white Towels waiting for... View all property information
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From
$382
Per Night
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1 / 35
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Stay in luxury at this awesome penthouse unit in the South Loop of Chicago. Beautiful Lake views and a spacious 2 bedroom 2 bathroom apartment in the award winning Lex building. Chinatown and downtown are just a stone's throw away when you stay at this apartment. View all property information
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From
$381
Per Night
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1 / 44
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Experience high rise living in a state of the art building that has just opened up this summer of 2014. This building has everything you could ever want from a brand new high rise off Wacker Drive in Chicago. Location is ideal for anything that you are looking to experience in the city. View all property information
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From
$376
Per Night
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1 / 19
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
This unit is unique because we offer 'Luxury At It's Best'. In addition, we offer luxury & exotic features at a Premium level that you won't get anywhere within the downtown area. All guest have access to all amenities excluding dancing pole and bar area. Both can be purchased at an additional... View all property information
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From
$255
Per Night
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1 / 5
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This lovely 2 Bedroom sits in the Downtown/Gold Coast area. Voted in the top 5 areas that are 'walkable' No need for a car to see this lovely city! Although, there is a parking place provided if needed at no extra cost! Fully upgraded unit, with a fireplace, and balcony for your enjoyment. State of... View all property information
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From
$509
Per Night
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1 / 7
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautifully done high-end furnished 3 bedroom | 2 bath | located downtown Chicago Beds: 1 King Bed, 2 Queen Beds View all property information
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From
$350
Per Night
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1 / 9
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Housekeeping...
  • Internet Access
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
The Tides at Lakeshore East, embrace a new standard of luxury featuring a modern contemporary feel. Situated in the city's newest neighborhood, LakeShore East, you have Millennium Park and the Lakefront right outside your door, with easy access to the Loop as well. Its a little neighborhood perfect... View all property information
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From
$248
Per Night
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1 / 12
The Loop
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Dishwasher
  • Gym
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located on the Magnificent Mile. Industry and creativity converge in Chicago, the birthplace of the skyscraper. Experience the vibrancy of downtown Chicago and delight in the modern, sleek comfort of Wyndham Grand Chicago Riverfront — an intimate haven on The Magnificent Mile — offering chic... View all property information
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From
$153
Per Night
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1 / 10
The Loop
1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Gym
  • Housekeeping...
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Chicago’s newest addition to Lakeshore East, Coast creates a coastal retreat on the shores of Lake Michigan. This beautiful property is situated in Chicago’s most desirable location with magnificent views of the River, the Lake and the world famous Chicago Skyline. View all property information
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From
$190
Per Night
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1 / 17
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Sauna
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Please call/e-mail for more information. Beds: 2 Queen Beds View all property information
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From
$177
Per Night
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1 / 15
The Loop
Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Corporate furnished apartment in the heart of Millennium Park, walking distance to transportation, restaurants and the lake front. The apartment comes fully furnished, has equipped kitchen, flat screen TVs, basic cable, Internet and all utilities are included. Rates vary based on availability... View all property information
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From
$191
Per Night
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1 / 11
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Magnificent mile 1 brm convertible apt off Michigan Avenue in hotel district featuring 24 hr doorman, rooftop gym, sundeck, business ctr and garden patio. Your neighbors are the Hyatt, Fairmont and Radisson Blue. Gym, sundeck on rooftop 48th floor. Insane winter reductions!! North side prices in... View all property information
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From
$102
Per Night
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1 / 6
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Gym
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Hotel Blake is a beautifully appointed hotel right in the heart of Chicago at 500 Dearborn Street. One and two bed units are available. It's close to the train station, Millenium Park, Michigan Avenue, and many of the other well known Chicago sights and downtown shopping areas. Internet access,... View all property information
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