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Chicago

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Vacation Rentals in Chicago, IL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified 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
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Chicago Holiday Rentals

Located on the shores of Lake Michigan, Chicago is a stunning city bursting with attractions. Accommodation can be pricey, but choosing a rental property rather than a hotel is the ideal way to save money. Whether you prefer a spacious apartment in the city centre or a family house in a quieter area, you will feel relaxed and be able to organise your schedule as it suits you. You will of course find a host of restaurants catering to all tastes, but when you are tired of eating out, you can prepare your own food in a fully equipped kitchen.

Chicago attractions

You might not know where to begin seeing the sights of Chicago, so take a trolley tour to give you and your family an overview. A Wellenda Boat tour along the Chicago River and Lake Michigan is another wonderful way to see the city's architecture. Don't miss the Magnificent Mile, where the John Hancock Observatory offers spectacular views of the skyscrapers and Lake Michigan beyond. Art lovers should make a beeline for the Art Institute of Chicago, with its world-class collections of French and American Impressionists and Dutch Masters. The whole family will enjoy a visit to Millennium Park, where the star attractions are the Crown Fountain and the Chicago Bean, an enormous silver sculpture. You can try out the restaurant there, and you might be lucky enough to catch a music festival as well.

Chicago holiday rentals for families

Animal lovers must find time to visit Lincoln Park Zoo, where the Regenstein African Ape Centre, the Kovler Lion House and the Primate House will impress. The youngest members of the family will find the sea lions and penguins especially entertaining to watch. Before you leave Lincoln Park, children will love a visit to Adams Playground. If the weather calls for an indoor activity, head for Chicago Children's Museum at Navy Pier with its interactive exhibits. When you feel like a break from the city, spend some time on one of Lake Michigan's beaches, where you can swim, sunbathe, or go kayaking or canoeing.

Budget holiday rentals in Chicago

For a holiday in a vibrant city, Chicago is hard to beat. Hotels can be expensive, but renting your accommodation is the ideal low-cost alternative. Decide whether you would rather be in the city centre within walking distance of the attractions or in the quieter suburbs. Then have a look at our range of apartments and houses and choose the one that suits you best. It's worth reading through our unbiased customer reviews to help you. After that, you can look forward to what promises to be a holiday to remember in Chicago.

 
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Also consider
€2,863 / month
1 Bedroom, sleeps 3
1 Bathroom
€102 / night
1 Bedroom, sleeps 4
1 Bathroom
€75 - €147 / night
1 Bedroom, sleeps 4
1 Bathroom
€1,959 - €2,411 / night
5 Bedrooms, sleeps 18
7 Bathrooms
€143 - €181 / night
4 Bedrooms, sleeps 9
1 Bathroom

Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
€147 - €192
Week:
€750 - €1,051
Month:
€2,109 - €3,917
Minimum rental - 2 nights
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€97 - €135
Week:
€451 - €715
Month:
€1,356 - €2,260
Minimum rental - 2 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€117 - €147
Month:
€1,846 - €3,616
Minimum rental - 1 night
Check availability
Also consider
€2,863 / month
1 Bedroom, sleeps 3
1 Bathroom
€102 / night
1 Bedroom, sleeps 4
1 Bathroom
€75 - €147 / night
1 Bedroom, sleeps 4
1 Bathroom
€1,959 - €2,411 / night
5 Bedrooms, sleeps 18
7 Bathrooms
€143 - €181 / night
4 Bedrooms, sleeps 9
1 Bathroom
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
€237
Minimum rental - 2 nights
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 5
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€113 - €132
Month:
€1,846 - €3,390
Minimum rental - 1 night
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
€237
Minimum rental - 2 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Special offer details »
Night:
€298 - €316
Minimum rental - 3 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€117 - €147
Month:
€1,846 - €3,616
Minimum rental - 1 night
Check availability
  • Holiday Rental House
  • 3 Bedrooms, sleeps 5
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Check availability
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
€207 - €245
Week:
€1,356 - €1,582
Month:
€3,767 - €5,273
Minimum rental - 3 nights
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
€170 - €188
Week:
€1,055 - €1,205
Month:
€3,013 - €4,520
Minimum rental - 2 nights
Check availability
  • Holiday Rental House
  • 3 Bedrooms, sleeps 9
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
€1,506 - €2,636
Minimum rental - 4 nights
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Special offer details »
Night:
€151 - €181
Week:
€904 - €1,085
Minimum rental - 3 nights
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Month:
€4,520
Minimum rental - 4 weeks, 2 nights
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
€211 - €264
Minimum rental - 3 nights
Check availability

Chicago Apartment Rental Advice

Posted by Alison78, 27 Dec 2011
... if the owner has a vacation rental license from the City of Chicago. By asking, you'll let the owner know you've done your homework! The license applies to the owner, not the renter, so there's no requirement for you. Information on the license, if you're interested ... more
Posted by globetrekker010, 27 Nov 2011
Consider one of the vacation rentals in chicago. Click on the "vacation rental" section of this tripadvisor. You will find great vacation rentals which are comparable if not better than most 5 star hotels. ... more
Posted by Canthespam, 8 Jun 2011
... the street after vacating several vacation rental apartments. From now on cabs or town cars for us - we don't need the aggravation. We have taken public transportation, usually trains from various airports into town, but if you are traveling for any length of time and there is more than ... more
Posted by JeffnCincinnati, 25 Oct 2011
... a 4 year old. What is the best for a family, staying inside the city in a vacation rental or maybe staying in a suite in the suburbs? Is it best to take the subway or to drive an park in a garage? Any thoughts would be appreciated. Thank you ... more
Posted by suzanneparisvacation, 3 Nov 2011
... small children. Stay in a vacation rental where you'll have space and the rates are cheaper than a hotel. When you contact the rentals, ask for their address then look at a chicago map and see how close they are to navy pier and the museum of science and ... more
Posted by Scotiascott, 7 Mar 2011
... we were researching various Chicago vacation rentals, I was able to locate and contacted one of their previous clients. Everything was as it should be and this person was satisfied with their transaction. We did not rent with them for our upcoming trip due to the somewhat negative reviews on ... more
Posted by mackiecat, 17 Oct 2011
What about a vacation rental in the Lincoln Park area- you may find one large home that all could use ... more
Posted by Alison78, 19 Sep 2011
Whatever vacation rental you choose, you'd be wise to ask if they have the required City of Chicago vacation rental license. If nothing else, it will let the owner know you're doing your homework. See http://www.cityofchicago.org/city/en/depts/bacp/provdrs/bus/alerts/2010/dec ... more
Posted by ChiTownFriend, 20 Apr 2011
... that if you use a vacation rental (through ... ... on the books that these "vacation rentals" need ... ... change to come about, I suggest that you take a look at the June 30, 2010 article in the Clout Street portion of the Chicago Tribune entitled "Chicago Condo 'Vacation Rentals' to Face Regulations ... more
Posted by shallow_shoals, 21 Apr 2011
I know that this is a silly question because you are already using TA - but - have you looked at the left menu under "vacation rentals"? The rentals on this site have reviews, pictures and MAPS. ... more
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