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$999

3 BR / 5 BA / Sleeps 6

Modern Luxury in Wicker Park, 14 night minimum - Chicago vacation rentals
1 / 55

$999

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Modern Luxury in Wicker Park, 14 night minimum

Chicago house
3 BR / 5 BA / Sleeps 6 | Quick view

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Architecturally significant single family home in Chicago's best neighborhood, Wicker Park. This home has been featured in design magazines and is ideal for entertaining. Filled with mid-mod furnishings throughout. Forbes rated Wicker Park #4 in the country for hippest neighborhoods, and this home is in the heart of …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children

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$199

3 BR / 2 BA / Sleeps 5

4 Reviews

$199

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Amazing Luxury Townhouse located in Chicago loop , stunning , 100% verified photos

Chicago house
3 BR / 2 BA / Sleeps 5 | Quick view
Very Good4 Reviews

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Reviews

(4)

An Urban Oasis! This sophisticated end unit, 3-story townhome features exquisite mosaic, stone and marble thruout, island kitchen w/dark-stained cherry cabinets, imported granite and wallpaper, custom flooring/tiles. State-of-the-art Master BA w/Grohe fixtures, rain and steam w/multiple shower heads. 1-car garage, …
  • Hot Tub/Jacuzzi
  • Sauna
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(4)

A beautiful townhouse with somewhat misleading advertising

Left on Jun 23, 2014 for a stay in June 2014

This was, as advertised, a beautiful townhouse. The reason for the average rating is that it was advertised as a 3 bedroom which would sleep 5 and in fact there is only 1 bedroom, 1 bed.

My husband and I were travelling with 3 adult children so the sleeping arrangements were challenging.There is a very large sofa in the main room and a sofa on the bottom level and a massage table in another …

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$399

2 BR / 2 BA / Sleeps 5

1 Reviews

$399

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Luxury City Living!

Chicago condo
2 BR / 2 BA / Sleeps 5 | Quick view
Poor1 Reviews

Details

Reviews

(1)

Location. Situated in the heart of Chicago, this lovely building is within walking distance of American Medical Association Headquarters, Wrigley Building, and Tribune Tower. Also nearby are Hancock Tower and Millennium Park. Property Features. The front desk is open 24 hours a day. Guest parking is available for …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(1)

Not So Great

Left on May 11, 2015 for a stay in May 2015

The location is great but the condo needs a lot of touching up & work done to it.

All the furniture was " yard sale grade " - very uncomfortable and cheap ! No tables - nothing on the walls - air mattress had a hole in it - no hair dryer ( which was promised & requested a 2nd time to no avail ).

A few dollars spent on this place could make it nice - as it is I would not recommend to anyone.

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$205

1 BR / 1 BA / Sleeps 4

1 Reviews

$205

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Magnificent Mile Gold Coast Luxury Brownstone [2]

Chicago condo
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

First Class Chicago vacation rentals by owner gives you the loveliest choice in Chicago Brownstone vacation rentals. Located in the Gold Coast neighborhood, these brownstones will surpass your expectations for quality and comfort. You will never want for a Magnificent Mile hotel as First Class Chicago will forever …
  • Waterfront
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Excellent Stay!

Left on Nov 19, 2013 for a stay in November 2013

Excellent apartments in an excellent location! Amenities are just as described. Comfortable beds. Our group was a total of 8 women staying in these 2 condos. The space was perfect for our reunion weekend! Would absolutely stay here again.

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$300

2 BR / 1 BA / Sleeps 6

Luxury 2 Bedroom Condo In The Heart Of The City - Chicago vacation rentals
1 / 23

$300

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Luxury 2 Bedroom Condo In The Heart Of The City

Chicago condo
2 BR / 1 BA / Sleeps 6 | Quick view

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The South Loop is classic Chicago. In the South Loop, streets with decades of history come alive as music and life pulse magnetically. Chicago's South Loop is a neighborhood that's buzzing with bars, restaurants and entertainment; it's the perfect place to stay during your time in Chicago. The location itself is …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating

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$159

2 BR / 2 BA / Sleeps 6

6 Reviews

$159

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Chicago North Shore Luxurious 2 bedroom condo

Chicago condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent6 Reviews

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Reviews

(6)

Residnence on the Avenue. A Spacious Vintage condo in a stunning 1928 Art Deco building on a tree lined avenue. A very quiet and secure 4 unit building with front lobby entrance. Property manager on site to answer any questions and to make sure that your stay at Residence on the Avenue is a wonderful experience. The …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(6)

Great time!

Left on Oct 10, 2012 for a stay in September 2012

My 2 sisters, 2 nieces, and I decided to spend the weekend in Chicago. I found this condo on Vrbo & Homeaway. William was very helpful and patient with all my questions and concerns. The condo was perfect for our needs and centrally located for easy access into downtown. Ross, the building manager, was also very helpful and nice. The condo was clean and very comfortable. All in all we had a great…

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$195

3 BR / 2 BA / Sleeps 8

5 Reviews

$195

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Luxurious Vintage Condo on Chicago's North Shore

Chicago condo
3 BR / 2 BA / Sleeps 8 | Quick view
Very Good5 Reviews

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Reviews

(5)

Residence on the Avenue. A Spacious 2000sq.ft. condo in a stunning blonde brick/limestone 1928 building on a tree lined avenue. A very quiet and secure 4 unit building with front lobby entrance. The entrance boxwood garden which is enclosed by beautiful wrought iron fencing is a hint of what awaits you inside the …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(5)

home away from home

Left on Dec 19, 2011 for a stay in October 2011

We had the pleasure of staying here for two nights in October. The unit is beautifully decorated, cosy and very clean. The property manager is extremely friendly and is happy to assist with any questions you may have. There is a train line within a few short block and the neighborhood is just darling.

If you want to get away from a busy hotel and enjoy "home away from home" amenities, I …

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$439

2 BR / 2 BA / Sleeps 6

27 Reviews

$439

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Luxury Resort in the Heart of Downtown Chicago

Chicago condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent27 Reviews

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Reviews

(27)

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 of 35,000 square feet…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(27)

Fantastic!

Left on Sep 23, 2011 for a stay in September 2011

My fiancé and I came to Chicago on September 13th for a four-day stay to celebrate our engagement. Upon arrival at our suite, we were very pleasantly surprised to find pastries and a bottle of champagne waiting for us! This was such a nice touch, and very unexpected - it definitely set off our romantic adventure on the right foot. We enjoyed our stay immensely. As they say, location is key...and…

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$135

3 BR / 2 BA / Sleeps 6

30 Reviews

$135

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Great Value and Luxury. City & McCormick Place.

Chicago condo
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent30 Reviews

Details

Reviews

(30)

We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow and ice). They are …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(30)

Best value for money for staying in Chicago

Left on Oct 14, 2009 for a stay in October 2009

Bob C is a fine man, he provided everything we needded in our stay in his apartment, the apartment is very confortable and if you have a car the parking is not a problem at all. The train to the city center in only 8 blocks away which makes visiting downtown very easy and cheap.

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$305

2 BR / 2 BA / Sleeps 8

6 Reviews

$305

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Magnificent Mile Gold Coast Luxury Brownstone [1]

Chicago condo
2 BR / 2 BA / Sleeps 8 | Quick view
Very Good6 Reviews

Details

Reviews

(6)

Apartment - 2 Bedrooms + Convertible bed(s) - 2 Baths - (Sleeps 4-8) Another First Class Chicago property! City of Chicago Vacation Rental License #2125365. Rent Legally! You've found it! Location, Location, Location! An historic 1890's brownstone in the heart of the exclusive Gold Coast where Chicago's elite reside…
  • Waterfront
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(6)

Perfect location and ambiance!

Left on Jan 09, 2013 for a stay in December 2012

My wife and I stayed in the second floor condo the first part of December. The weather was great which made everything seem perfect. The condo is in a very good location, and really felt like home. The furnishings were very comfortable, and the updated kitchen is fabulous. The flat screen has HD and tivo. Very well maintained. We both agreed that we would stay here again. Communications with the …

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$218

2 BR / 2 BA / Sleeps 6

2 Reviews

$218

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Save on Luxurious 2 Bd/2 Ba Condo

Chicago condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Want to live like a local while staying in Chicago and save? Reserve now and take advantage of fall savings! Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our city! A family-owned, Chicago boutique property near Wrigley Field, The Guesthouse features …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(2)

Awesome home base for visiting Chicago

Left on Mar 12, 2013 for a stay in March 2013

This property is everything the ad promises and more. From the luxurious appointments like the surround shower in the master suite to the fireplace and chef-quality kitchen, you will feel right at home in the Andersonville Guest House. We saved money by grilling steaks on the balcony and preparing healthy and yummy brunches, allowing us to splurge on the restaurants and attractions the city has…

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$300

2 BR / 2 BA / Sleeps 6

1 Reviews

$300

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Luxury OldTown Penthouse

Chicago condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Top floor unit in historic Old Town Neighborhood. Close to shopping, Brown Line El stop. Downtown . And North Avenue Beach! We do allow 1-2 nights stays Monday-Thursday with a cleaning fee. Over any weekend we have minimum nights stay of 3,4,5 or 6 nights. Please ask how many nights your weekend requires. …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Linens Provided
  • Towels Provided
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(1)

Greay apartment, great location

Left on Oct 04, 2012 for a stay in September 2012

The apartment is 2 bed, 2 bath, apartment was spotless upon arrival. Bathrooms were spotless, fresh bed linen and fresh towels. Great location, well worth staying here as only 5 mins from downtown and very close to several good places to eat and drink. Overall, i could not fault it

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$115

2 BR / 2 BA / Sleeps 6

14 Reviews

$115

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Luxury and Value.. Skyline View & McCormick Place.

Chicago condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent14 Reviews

Details

Reviews

(14)

We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow and ice). They are …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(14)

Great home away from home!

Left on May 26, 2011 for a stay in May 2011

The first thing that I noticed was how very clean the apartment was! This is usually the first thing that I look for and I was truly impressed with this. It is a beautiful apartment that is very open and spacious. The rooftop deck is perfect for hanging out and enjoying the city views, gorgeous! The shower is absolutely amazing, love the body sprays!

Another thing that I found very …

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$350

2 BR / 2 BA / Sleeps 5

1 / 7

$350

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Luxury City Living!

Chicago condo
2 BR / 2 BA / Sleeps 5 | Quick view

Details

Location. Situated in the heart of Chicago, is within walking distance of American Medical Association Headquarters, Wrigley Building, and Tribune Tower. Also nearby are Hancock Tower and Millennium Park. Property Features. The front desk is open 24 hours a day. Guest parking is available for a surcharge. This …
  • Hot Tub/Jacuzzi
  • Sauna
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$300

3 BR / 2 BA / Sleeps 8

9 Reviews

$300

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Luxurious Condo in Perfect Location...Sleep 8

Chicago condo
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent9 Reviews

Details

Reviews

(9)

Come enjoy Chicago at its finest where the real heart of the city beats. Located on a quiet street, but surrounded by countless activities for guests to enjoy. Relax in the large park around the corner, walk to Wrigley Field for a game, enjoy the exciting nightlife, or hop on the nearby El and be anywhere in the …
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (9)

    Super clean

    Left on Apr 23, 2010 for a stay in March 2010

    Like owning your own pad in Chicago. I lived in Chicago for 10 years. Every time I came back to visit I stayed in a hotel....it's not the same. This is located so close to the "L" and all the hot spots in Lincoln Park. I will stay here again and recommend to all friends and family.

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    $250

    2 BR / 2 BA / Sleeps 6

    3 Reviews

    $250

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    Luxury Guesthouse in Roscoe Village

    Chicago condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent3 Reviews

    Details

    Reviews

    (3)

    Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. Our Guesthouse is located above Cinnamon Boutique, a new women's clothing and accessory store and one of many fantastic places to shop in the village. We are approximately 4.5 blocks from the Paulina brown stop, which will take you downtown in…
    • Internet Access
    • Outdoor Dining Area
    • A/C or climate control
    • Linens Provided
    • Towels Provided
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (3)

    LADIES LOVED IT!

    Left on Feb 15, 2012 for a stay in February 2012

    Got all my gals together to enjoy a snowy weekend in Chicago, and loved our cozy place above Cinnamon boutique (WHERE WE ALL GOT AMAZING FUN STUFF TO WEAR). The hardwood floors, modern feel, gorgeous countertops, and space made a girls weekend really amazing. There is everything you need and a little more!

    It's great to have the extra bathroom space especially when getting many women sassed …

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    $300

    3 BR / 2 BA / Sleeps 8

    3 Reviews

    $300

    Inquire

    Luxury condo Close to Downtwn!

    Chicago condo
    3 BR / 2 BA / Sleeps 8 | Quick view
    Very Good3 Reviews

    Details

    Reviews

    (3)

    Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. Our Guesthouse is located a block from Cinnamon Boutique, a new women's clothing and accessory store and one of many fantastic places to shop in the village. We are approximately 4.5 blocks from the Paulina brown stop, which will take you …
    • Internet Access
    • Housekeeping Optional
    • A/C or climate control
    • Linens Provided
    • Towels Provided
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (3)

    Wonderful and relaxing neighborhood stay

    Left on Aug 04, 2012 for a stay in July 2012

    We absolutely loved this option, provided a contrast to hectic downtown and mag mile by allowing us a quaint and comfortable stay. Plenty of room and kitchen amenities. Lovely neighborhood with lots of nearby services. Free parking on the street,easy access to El. I did not want to leave. If you can ask for upstairs unit as we were downstairs, and just normal walking of guests above us was …

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    $125

    1 BR / 1 BA / Sleeps 4

    1 / 11

    $125

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    Luxury Downtown Studio

    Chicago condo
    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    ENTIRE SPACE This is an ideal location for visitors. This is modest but nice and completely private studio condo in the Gold Coast located near Water Tower Place, the Hancock Tower, and the Museum of Contemporary Art. It’s 1/2 block from the public transportation stop ( trains and buses), 4 blocks from both …
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

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      $1,250

      3 BR / 4 BA / Sleeps 8

      1 / 13

      $1,250

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      Luxury Home in West Lakeview

      Chicago house
      3 BR / 4 BA / Sleeps 8 | Quick view

      Details

      Stunning Roscoe Village high end beautifully decorated single family home. Media room, gym, 3 bedrooms, on quiet lovely street.
      • Wireless Internet
      • Fireplace
      • Housekeeping Optional
      • Washing Machine
      • Clothes Dryer
      • Suitable for the elderly - ask

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      $380

      0 BR / 3 BA / Sleeps 10

      1 / 19

      $380

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      Luxury Chicago Vacation Aprtment, Fully furnished

      Chicago condo
      0 BR / 3 BA / Sleeps 10 | Quick view

      Details

      Spacious 4 bedroom 3 ½ bathroom penthouse duplex feels like a single family. Set upon a quiet gas-lit street, this 2,640 square foot home boasts soaring ceilings, elegant & original detail, renovated eat-in kitchen and gorgeous hardwood floors throughout. With a walking score of 89 this home is only steps to Whole …
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $550

      2 BR / 2 BA / Sleeps 4

      1 / 18

      $550

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      "Experience Luxury At It's Best"

      Chicago condo
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      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 charge. There is …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Wireless Internet
      • Housekeeping Optional
      • Suitable for children
      • Suitable for the elderly - elevator access
      • Wheelchair accessible

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      $160

      1 BR / 1 BA / Sleeps 2

      1 Reviews

      $160

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      Studio in luxury building in heart of Chicago

      Chicago condo
      1 BR / 1 BA / Sleeps 2 | Quick view
      Very Good1 Reviews

      Details

      Reviews

      (1)

      This Cozy Studio is in the heart of the prestigious River North neighborhood in downtown Chicago. The new 50 story high rise is surrounded with great shopping, numerous restaurants and exciting night life. Getting anywhere is easy because building located few blocks away from the CTA-Grand Red Line and Blue-Clark Lake…
      • Shared outdoor pool (unheated)
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Suitable for children
      • Suitable for the elderly - elevator access
      • Wheelchair accessible

      Details

      Reviews

      (1)

      Beau studio bien situé

      Left on May 12, 2015 for a stay in May 2015

      Séjour de 9 jours, passé au cœur de Chicago. l'appartement est au 16 étage, bien équipé et calme. Tout est à proximité (commerces, restaurants, transports). Nous avons fait toutes les visites à pied, même pour aller au lac , il suffit de descendre Illinois street. Accès à la salle de sport, wifi, terrasse et piscine qui sont situés au 12éme étage.

      9 day stay, spent in the …


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