Vacation Homes for Rent in Chicago, Illinois, Page 2 of 4

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$89 per Bedroom* 3 BR -Breathtaking Graystone just Minutes from Wrigley Field

— Property 7011802h
Chicago condo rental
3 Bedrooms, Sleeps 8,
Condo, 3 Bathrooms, adventure, air-conditioning
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$89 per Bedroom* 3BR-Brand New Duplex Just Across Wrigley Field!

— Property 7011816h
Chicago condo rental
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, air-conditioning, balcony
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$129 per Bedroom* 4BR - CONTEMPRARY HOME w/ Luxurious Finishes & Great Location

— Property 7006985h
Chicago house rental
4 Bedrooms, Sleeps 12,
House, 4 Bathrooms, air-conditioning, beach
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$129 per Bedroom* 2BR-Gorgeous Condo with Spectacular View Dwntwn/Michigan Ave

— Property 93947h
Chicago condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, air-conditioning, beach
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Beautiful, Spacious & Sunny 3 Bedroom Condo

— Property 212128
Chicago apartment rental - Formal Dining Room
3 Bedrooms, Sleeps 8,
Apartment, 1 Bathroom, 1 Half Bath, downtown, town, balcony
Rates - per property (USD)
$249 - $329/night
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$149* 1BR Modern Condo Downtown, Ride to McCormick & Museums

— Property 93956h
Chicago condo rental - Living Room
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, air-conditioning, beach
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$149* 1BR-Contemporary Design in Chicago's Beautiful Gold Coast

— Property 93955h
Chicago condo rental
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, balcony, beach
SPECIAL OFFER! Stay 4 nights and the 5th night is FREE! (November 12 - November 11)
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Wrigleyville/Southport Corridor Luxury Inn

— Property 203741
Special Offer
Chicago condo rental - Front Doors
2 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, town, garden
Rates - per property (USD)
$179/night
Calendar Updated Nov 19 2009

Property Review

We spent close to a week in Chicago recently and were absolutely smitten with our home base - Chicago Southport Suite. Years ago, before I was married, I lived in Chicago. My husband and I...
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$$79 per Room - Unlimited Skyline Views in this New Contemporary Penthouse

— Property 265846
Chicago condo rental
3 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, downtown, jacuzzi
Rates - per property (USD)
$1,600/week
$4,500/month
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Great Value, Near Downtown & McCormick Place. Hot Tub, Amazing View, & Parking

— Property 225815
Chicago apartment rental - Amazing Skyline View from our Deck.
3 Bedrooms, Sleeps 6,
Apartment, 1 Bathroom, 1 Half Bath, town, sauna
Rates - per property (USD)
$125 - $195/night
$750 - $1,100/week
Calendar Updated Nov 18 2009

Property Review

If you know Chicago, this is a reasonably priced, convenient, clean place with good living space, comfortable beds, and very responsive owners. It was easy to find, easy to get to, in a safe...
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$99 per night!! 2BR HOME BY LINCOLN SQUARE PERFECT LOCATION WALK TO TRAIN

— Property 184803
Chicago house rental - Beautiful Dining Area
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, downtown, pool
Rates - per property (USD)
$99 - $149/night
$693 - $899/week
Calendar Updated Nov 18 2009

Property Review

This property has two levels. These pictures are for the upstairs level. My family stayed in the first level. The pictures are a little different with furnitures but the layout is basically the...
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Truly Stunning Skyline/River Views! All Luxury Perfect Location w/Free Parking!

— Property 184807
Chicago condo rental - Chicago Skyline Sunsets: Your Living Room View!
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, downtown, river, balcony
Rates - per property (USD)
$199 - $299/night
$1,294 - $1,699/week
Calendar Updated Nov 22 2009

Property Review

We had such an amazing time in Chicago while staying at this condo. It was walking distance to EVERYTHING and we had a 20-month-old with us :) The neighborhood was beautiful and safe and the...
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$149* - Gorgeous Modern Condo in Heart of Downtown Mag Mile!

— Property 7011827h
Chicago condo rental
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, air-conditioning, balcony
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SpSuites - Millenium Park

— Property 7017446h
Chicago apartment rental
1 Bedroom, Sleeps 3,
Apartment, 1 Bathroom, air-conditioning, balcony
Rates - per apartment (USD)
$110 - $180/night
$800 - $1,300/week
$2,500 - $3,400/month
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SP SUITES - North Side - Rogers Park -

— Property 7017444h
Chicago apartment rental
2 Bedrooms, Sleeps 4,
Apartment, 1 Bathroom, air-conditioning, clothes dryer
Rates - per apartment (USD)
$120 - $150/night
$700 - $850/week
$2,300 - $2,400/month
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SpSuites - Huron

— Property 7017445h
Chicago apartment rental
1 Bedroom, Sleeps 3,
Apartment, 1 Bathroom, air-conditioning, balcony
Rates - per apartment (USD)
$130 - $180/night
$900 - $1,200/week
$2,500 - $3,000/month
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Sp Suites Budget Rental

— Property 7017443h
Chicago apartment rental - buliding
Studio, Sleeps 2,
Apartment, 1 Half Bath, air-conditioning, clothes dryer
Rates - per apartment (USD)
$75/night
$450 - $480/week
$1,200/month
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SP SUITES - Streeterville

— Property 7020575h
Chicago apartment rental
1 Bedroom, Sleeps 3,
Apartment, 1 Bathroom, accept credit card, air-conditioning
Rates - per apartment (USD)
$250/night
$1,500/week
$6,000/month
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Heart of Chicago Fully Furnished w/Million $$$ views -

— Property 128129
Chicago condo rental - On the 13th floor of 400 W. Ontario
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, downtown, balcony
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Luxury Resort in the Heart of Downtown Chicago

— Property 242128
Chicago condo rental - NorthEast View
2 Bedrooms, Sleeps 5,
Condo, 2 Bathrooms, downtown, lake, tennis court
Rates - per property (USD)
$320 - $360/night
$1,850/week
$5,000/month
Calendar Updated Nov 14 2009

Property Review

Great condo with incredible views (the photos are accurate, you can indeed see Navy Pier on one side, and Grant park on another). Nadiya was fantastic to work with, and the property was very...
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$99 per night!! Gorgeous 2BR Home in Mayfair/Lincoln Square Free Parking!

— Property 224715
Chicago house rental - Spacious Living Room
2 Bedrooms, Sleeps 8,
House, 1 Bathroom, downtown, lake, garden
Rates - per property (USD)
$99 - $149/night
$693 - $899/week
Calendar Updated Nov 20 2009

Property Review

You are right in the city but also in a nice neighborhood with parks and churches...best of both worlds!! Wow!! what a great location and home for the money. In this economy it's nice to find...
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Millennium Park

— Property 7033291h
Chicago apartment rental
2 Bedrooms, Sleeps 1,
Apartment, 2 Bathrooms, air-conditioning, family
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20%til sept 7Luxury Penthouse in A++LincolnPark,Depaul ,'Suites of Old Town #3'

— Property 228768
Chicago condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, downtown, garden
Rates - per property (USD)
$275/night
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Luxury Penthouse Lakeview/Roscoe Village A

— Property 228769
Chicago condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, downtown, village, pool
Rates - per property (USD)
$225/night
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Teri's Chicago Guest House *Clark Suite * Wrigleyville

— Property 146193
Chicago apartment rental - Fully Equipped Dine-In Kitchen (1st floor)
3 Bedrooms, Sleeps 8,
Apartment, 2 Bathrooms, downtown, lake, garden
Rates - per property (USD)
$359 - $449/night
Calendar Updated Nov 10 2009

Property Review

My wife and I spent a long weekend in the Clark Suite with 3 other couples and the accommodations were fantastic. The pictures on the site don't really do this suite justice as it was better than...
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Guesthouse Chicago Lakeview Close to Wrigley Cubs Roscoe Village

— Property 228202
Chicago condo rental
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, downtown, lake, jacuzzi
Rates - per property (USD)
$225/night
Calendar Updated Nov 10 2009

Property Review

We recently had the pleasure of staying at the Roscoe Village Guesthouse in Chicago and had a wonderful experience. The property was beautiful and perfect for all of us - 4 adults and our 5...
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Gold Coast High-rise: 1 Block to Mich Ave Shopping. Best Location

— Property 204526
Chicago condo rental - Views for the unit
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, downtown, terrace
Rates - per property (USD)
$99 - $299/night
$800 - $1,500/week
$2,200 - $4,500/month
Calendar Updated Nov 8 2009

Property Review

Our family of four - including 15yr old and 12 yr old stayed at One Superior for a week at the end of October. Our experience from start to finish was fantastic. JP has been so helpful from our...
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Luxurious Chicago Condo Overlooking Lake Michigan, Soldier Field & Museum Campus

— Property 222634
Chicago condo rental
3 Bedrooms, Sleeps 6,
Condo, 3 Bathrooms, downtown, lake, balcony
Rates - per property (USD)
$400 - $450/night
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Serene Location in Vibrant City - Chicago's Edgewater Vacation

— Property 247576
Chicago condo rental - Stately & Lovely - Chicago Edgewater Vacation Rent
3 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, downtown, balcony
Rates - per property (USD)
$175 - $200/night
Calendar Updated Nov 5 2009

Property Review

From the moment we walked through the front entry, we were struck by how very lovely this home is. The apartment was well laid out, very tastefully decorated and comfortable. We were able to...
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Teri's Chicago Guest House * Wrigley Suite * Wrigleyville

— Property 319203
Chicago apartment rental - Fully Equipped Kitchen (1st floor)
4 Bedrooms, Sleeps 8,
Apartment, 2 Bathrooms, downtown, lake, garden
Rates - per property (USD)
$396 - $495/night
Calendar Updated Nov 4 2009

Property Review

I spent a fabulous four day weekend in the Wrigley apartment with 5 friends. Teri was there to greet us and orient us to all the offerings of the neighborhood. We were in walking distance to all...