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Chicago Vacation Rentals

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Contact Owner
Nightly rate from
$149
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 1
Hi Laurie & Arlyn We had a wonderful time in Chicago. Alyn and I did a lot of walking around your city. Your city blocks seem much smaller than ours so the ...
  • Nightly
    $149 - $249
  • Weekly
    $995 - $1,495
  • Monthly
    $4,500 - $6,500
Contact Owner
Nightly rate from
$299
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 3
Arlyn, We all LOVED the condo!!! And I was the hero for finding it & making all the arrangements. The location & view couldn't have been any better. The ...
  • Nightly
    $299 - $399
  • Weekly
    $1,995 - $2,495
  • Monthly
    $6,500 - $9,500
Contact Owner
Nightly rate from
$107
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 2
This is an amazing rental with many luxurious amenities at a great price. The view in the picture is the Chicago Skyline View from our Deck. We are located ...
  • Nightly
    $107 - $185
  • Weekly
    $750 - $1,150
  • Monthly
    --
Contact Owner
Nightly rate from
$119
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 1
Writers' Retreat is your chance to get away. With plenty of room for relaxing and so many little touches to get in touch with your creative side, you're stay ...
  • Nightly
    $119 - $150
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
$119
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 5
Bathrooms: 1
Old Irving Loft is a two bedroom upper available for vacation and executive rentals.Decorated in the style of 1940's old Chicago and situated in a convenient ...
  • Nightly
    $119 - $150
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
$180
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
This lovely 2 Bedroom, 2 Bathroom condo located in the South Loop Chicago is the perfect temporary home for you while visiting Chicago for pleasure or ...
  • Nightly
    $180
  • Weekly
    $1,080
  • Monthly
    $3,750
Contact Owner
Nightly rate from
$179
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 1
Luxury Inn -- Beautiful, fully restored graystone building. This 1,200 square foot unit is located in the heart of Wrigleyville/Southport Corridor in the ...
  • Nightly
    $179
  • Weekly
    $1,100
  • Monthly
    $3,500
Contact Owner
Nightly rate from
$109
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 6
Bathrooms: 2
Min stay:2
...prepare your senses for the ultimate "escape from it all" luxury living... -Fully furnished Ultra-Luxury rental--all linens, bedding, cooking apparatus, ...
  • Nightly
    $109 - $129
  • Weekly
    $999 - $1,199
  • Monthly
    --
Contact Owner
Nightly rate from
$99
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 6
Bathrooms: 3
Situated on a quiet, tree-lined street in Chicago�s Edgewater/ Andersonville neighborhood, Magnolia Studios offers a choice of three unique chicago ...
  • Nightly
    $99 - $149
  • Weekly
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  • Monthly
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Contact Owner
Nightly rate from
$200
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 7
Bathrooms: 1
Min stay:1
Two beautifully rehabbed penthouses located on the 55th and 54th floors. These condos have a Magnificent location and the most spectacular views in Chicago! ...
  • Nightly
    $200 - $300
  • Weekly
    --
  • Monthly
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Contact Owner
Nightly rate from
$350
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Located just steps from the world's best shopping, dining, culture, and entertainment. 30 East Huron reflects the comfort and style of the best hotels the ...
  • Nightly
    $350
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
$170
Management: Verified owner
Property: Rental Home
Bedrooms: 1, sleeps 3
Bathrooms: 1
Min stay:3
Just a few blocks from five-star hotels and Chicago's most upscale shopping and dining, this cutting edge high-rise stands as proof that the Magnificent Mile ...
  • Nightly
    $170
  • Weekly
    $1,350
  • Monthly
    $3,200
Contact Owner
Nightly rate from
$88
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 2
Bathrooms: 1
Min stay:3
Beaches, parks, vintage apartments -- these features and more make Rogers Park a desirable Chicago neighborhood. Bordered by Devon Avenue on the south, ...
  • Nightly
    $88
  • Weekly
    $550
  • Monthly
    $1,550
Contact Owner
Nightly rate from
$220
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 1
Luxury 2 BR (1 BR/den) Gold Coast condo available for daily, weekly or possibly monthly rental. Better than a hotel. 1 1/2 blocks from Michigan Ave., ...
  • Nightly
    $220
  • Weekly
    --
  • Monthly
    --
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 1
Nestled in a lively corner of Lakeview you will find my 2 bedroom 1 bath condo. Superbe dining, shops, cafes and theatres all a short stroll away. This 125 ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    $2,900
Chicago Vacation Rental Advice
Posted by Dave148, Oct 28, 2009
http://www.vrbo.com/vacation-rentals/usa/illinois/chicago ... more
Posted by AZdesertma, Sep 28, 2009
Hello, We are visiting Chicago and considering a vacation rental at 480 McClurg Ct. Is this a safe, decent area? We are a family of 5. Anyone familiar with Steps to Everything rental company? Many thanks! ... more
Posted by berechr, Sep 24, 2009
There is no ample parking anywhere you would want to be in the city. There are ads for vacation apartment rentals on craigslist under the temporary/sublet section. ... more
Posted by baalbebb, Sep 24, 2009
... night would be nice - suburbs are fine. I need a car though, so actually suburbs are perfect. I want something that is private where I don't have to deal with the owners (I'm thinking some sort of studio temporary rental or bed and breakfast would do nicely). thanks ... more
Posted by shallow_shoals, Sep 25, 2009
... corporate apartment for six days rental. Take a look at: http://www.habitatcsn.com You're best bet it a "Suites" Hotel. Expect to pay around $200.00 per night - plus tax - plus $50.00 extra parking per day for a downtown location. The suburban hotels usually have parking lots ... more
Posted by Dave148, Sep 5, 2009
http://www.vrbo.com/vacation-rentals/usa/indiana ... more
Posted by deex9, Aug 11, 2009
... t want to drive my rental car from downtown. The Museums aren't cheap and they charge extra for almost every different exhibit. We wanted to see the play Aladdin,but learned most of the theatres are closed on Mon. & Tues. (our only free nights). It's amazing how much ... more
Posted by Anabelly, Aug 11, 2009
Thanks for sharing! We are going to Chicago in less than 2 weeks and are so excited!!! I love reading the trip reports from others. I can't wait to write mine. Although, that will mean vacation is over so I am not trying to rush things too much. LOL. ... more
Posted by luv2fishpinkColumbus, Jul 14, 2009
... When I check out apartment rentals, they are all listed by area or district. Please help. Also, is it legal to rent an apartment? I tried to do it in NYC and they said it is illegal and all of the listings on VRBO.com where illegal and in fact ... more
Posted by luv2fishpinkColumbus, Jul 14, 2009
I'm assuming this applies to other vacation home rental sites also? Thanks for your help. Maybe I'll just stick with a hotel. ... more
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns