Our other sites
Get A Free World Heritage Guide »
SeatGuru
Family Vacation Critic
Cruise Critic
BookingBuddy
We recommend:
We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Chicago Vacation Rentals

Search Chicago Vacation Rentals

Clear dates

Advanced Search

Recommended by Travelers

[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Contact Owner
Nightly rate from
€160
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 1
Min stay:2
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
    €160 - €180
  • Weekly
    €1,115
  • Monthly
    €2,787
Contact Owner
Nightly rate from
€208
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 3
Min stay:1
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
    €208 - €278
  • Weekly
    €1,390 - €1,739
  • Monthly
    €4,530 - €6,620
Contact Owner
Nightly rate from
€83
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
    €83 - €105
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
€75
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 2
Min stay:2
This is an amazing rental with many luxurious amenities at a great price. The view in the picture is our luxurious hot tub. It's a great way to relax after ...
  • Nightly
    €75 - €129
  • Weekly
    €523 - €801
  • Monthly
    --
Contact Owner
Nightly rate from
€125
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
    €125
  • Weekly
    €753
  • Monthly
    €2,613
Contact Owner
Nightly rate from
€104
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 1
Min stay: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
    €104 - €174
  • Weekly
    €693 - €1,042
  • Monthly
    €3,136 - €4,530
Contact Owner
Nightly rate from
€83
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
    €83 - €105
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
€69
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
    €69 - €104
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
€345
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Chicago Guest House offers six private fully furnished vacation rental suites in Chicago's wonderful Lakeview neighborhood; just 4 miles north of downtown. ...
  • Nightly
    €345
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
€61
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 2
Bathrooms: 1
Beaches, parks, vintage apartments -- these features and more make Rogers Park a desirable Chicago neighborhood. Bordered by Devon Avenue on the south, ...
  • Nightly
    €61
  • Weekly
    €383
  • Monthly
    €1,080
Contact Owner
Nightly rate from
€174
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
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 ...
  • Nightly
    €174
  • Weekly
    €1,045
  • Monthly
    €3,484
Contact Owner
Nightly rate from
€157
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. Our Guesthouse is located above Cinnamon Boutique, a new women's clothing and ...
  • Nightly
    €157
  • Weekly
    €941
  • Monthly
    €3,484
Contact Owner
Nightly rate from
€244
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
    €244
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
€105
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 4, sleeps 9
Bathrooms: 1
Min stay:1
Beautiful Victorian in the heart of Lincoln Park, one of Chicago's most desirable neighborhoods. Safe neighborhood, on a quiet street. "Free" visitor parking ...
  • Nightly
    €105 - €118
  • Weekly
    €627 - €801
  • Monthly
    €1,533 - €1,951
Contact Owner
Nightly rate from
€366
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
The Penthouse at Grand Plaza is a magnificent unique rental in Chicago. Towering 56 floor above the city, with dramatic two story living areas and exquisite ...
  • Nightly
    €366
  • Weekly
    --
  • Monthly
    --
Chicago Vacation Rental Advice
Posted by Markhan, Dec 29, 2009
... we are collecting a car at the airport due to moving on to Niagara and Boston later in the vacation. Found a Fairfield Inn at Lombard that looks fine for us and only $99 a night for a King room. Planning on using the Metra to go into the city ... more
Posted by Markhan, Dec 30, 2009
... decided not to collect the rental car till we leave Chicago and after a recommendation from a friend who stayed in Chicago last year I have made a reservation at the Doubletree Hotel on E.Ohio Street, $209 a night. So with the saving on 4 days car rental and 4 ... more
Posted by Chicago Flyer, Jan 1, 2010
Not sure why one would need to go out to O'Hare to pick up a rental car with most major car rental companies having locations downtown. Otherwise, if you have to go to an airport to pick up the car, consider Midway - shorter L ride than O'Hare. ... more
Posted by GreginIllinois, Jan 4, 2010
... under 12 and would like to stay downtown, but don't want the expense of (2) rooms. Most of the "discount" sites don't allow that many people in one room. Any suggestions? Are there condo rentals available that are comparable in cost ot a hotel room? Any help appreciated ... more
Posted by KKKKKerry, Jan 4, 2010
Try vrbo.com (Vacation Rental By Owner) ... more
Posted by ChiTownFriend, Nov 30, 2009
... please do *NOT* get a rental vehicle when you are visiting Chicago. It is unnecessary to spend your vacation dollars in that manner. Besides, I'll wager you wouldn't want to be driving in icy/snowy conditions (if that is what we have in store for us). But *DO ... more
Posted by Dave148, Dec 1, 2009
http://www.vrbo.com/vacation-rentals/usa/illinois ... more
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
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