83 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Homes
Townhomes
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Cottages
Estates
Farmhouses
Hotels
Lodges
Studios
Villas
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

83 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chicago Downtown Vacation Rentals with Online Payment(83)

83 Results
$625 - $1,253
per night
3 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night min stay
(116)
$260 - $450
per night
3 - 5 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(201)
$299 - $875
per night
2 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night min stay
(105)
$625 - $1,235
per night
3 - 4 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 4 night min stay
(54)
$500 - $1,235
per night
2 - 4 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night min stay
(15)
$195 - $250
per night
2 - 4 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night min stay
(8)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night min stay
(32)
$550 - $1,110
per night
3 - 5 night min stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night min stay
(51)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night min stay
(20)
$550 - $1,110
per night
3 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night min stay
(35)
$189 - $199
per night
2 - 4 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night min stay
(23)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night min stay
(12)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(33)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(28)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night min stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(64)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night min stay
(15)
$439
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(65)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 - 4 night min stay
1 Review
$799
per night
2 - 4 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night min stay
(4)
  • 3 BR,
  • 1 HF BA,
  • Sleeps 8
3 - 4 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
28 - 30 night min stay
1 Review
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
2 Reviews
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 16
3 night min stay
(11)
$399
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(12)
$245 - $285
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night min stay
(8)
 View map Map
Advertisement
 

Recent Chicago Reviews

A wonderful place to stay

5 of 5
We really enjoyed our stay. We had 7 adults and one toddler and we were very comfortable. The town home was beautiful and clean.The location was great. A charming, safe neighborhood with great access to public transit, great restaurants, shopping, theaters, parks, etc. Bridget took very good care of us. I would definitely stay here again.
  • Submitted: Apr 22, 2015
  • Stayed: Apr 2015

Wow........ticks all the boxes

5 of 5
We had a fabulous time in Chicago made all the more special by staying Penthouse 8 at Grand Plaza. 'It is what it says on the label' Having searched many options the owners of this one delivered excellent customer service from enquiry to end of stay. It is clear they care and go the extra mile to make your stay a memorable one. Its not often you get to ooze about something so here is my opportunity The location is perfect. For a family with teenagers and young adults it ticked every box. It gave us quick and easy access to everything - magnificent mile, restaurants, navy pier, the lake, museums and much more. Being there during Easter our children wanted to enjoy a special family roast dinner. This was possible with the fully equipped kitchen (including blenders/full crockery/glass and cutlery/roasting & serving dishes), dining table overlooking the fabulous skyline and access to groceries. With a market store right below the building, ‘The Eately’, a modern outpost featuring a range of Italian food markets just a block away and ‘Whole foods’ a couple of blocks down we were able to get all we needed including special treats. If you want to eat out there are so many options for every taste and pocket. We were surrounded by great restaurants, which were all within walking distance. Our favourites were the famous “Pizzeria Uno’, Bub City, Beatrix and West Town Bakery which served a great donut treat. There were so many restaurants to choose from. There is a cinema just a couple of blocks away so the whole families needs can be met. The penthouse itself....well were do I start....the view is spectacular……especially the incredible sunsets….wow!!! 24 hours of changing lights, colours and activity will be sure to awaken all your senses. The decor and furnishings are perfect for all tastes and couldn’t get any closer to feeling ‘at home’ inviting a cosy night in by the fire. It is clean and so well stocked with all you need including plenty of those essentials that make a real difference - shampoo, conditioner, shower gel, cleaning materials…… even spices in the kitchen. Just another indication of the attention to detail the owners consider for their guests. To add even more value the staff on reception are friendly and very helpful, especially David, with great knowledge of sightseeing If you want to be confident of a great place to stay I thoroughly recommend this Penthouse. The only negative was that our daughter is now asking how often we can return!!
  • Submitted: Apr 10, 2015
  • Stayed: Apr 2015

What a truly delightful find!!

5 of 5
It is my pleasure to recommend this property to most anyone who needs "a home away from home." My husband had serious surgery at Northwestern Hospital and our daughters traveled some distance to support us. This apartment was perfect for us girls while my husband was in the hospital. After his discharge from the hospital, my husband and I were greeted with warm hugs and delicious pastries made by our generous host - Nadiya. At that point it was just the two of us in this darling unit. Nadiya treated us like family and just looking at the picture above again - makes me homesick for it. The unit and owner are both a true delight! Thanks again for making us feel so at “home” in your home. We shall return!!!
  • Submitted: Mar 17, 2015
  • Stayed: Feb 2015