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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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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
United States, Illinois, Chicago Holiday Rentals
West Loop 3 bd rm Town Home with Roof Top view
Slideshow
4.5 of 5 stars 4 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
344 AUD - 616 AUD
Week:
2,053 AUD
Minimum rental - 3 nights
Check availability
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United States, Illinois, Chicago Holiday Rentals
Vintage Loop Loft
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
307 AUD
Week:
2,001 AUD
Month:
4,054 AUD
Minimum rental - 3 nights
Check availability
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United States, Illinois, Chicago Holiday Rentals
Beautiful and Luxurious 3 Bd/2 Ba Condo
Slideshow
4.5 of 5 stars 6 reviews
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
205 AUD - 246 AUD
Week:
1,232 AUD - 1,478 AUD
Minimum rental - 4 nights
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Also consider
Luxurious...
231 AUD - 257 AUD / night
3 Bedrooms, sleeps 8
2 Bathrooms
Chicago's Best...
164 AUD - 246 AUD / night
3 Bedrooms, sleeps 6
2 Bathrooms
Condo by The...
153 AUD / night
1 Bedroom, sleeps 4
1 Bathroom
55th Floor...
1,332 AUD / night
1 Bedroom, sleeps 4
1 Bathroom
Stunning...
108 AUD / night
1 Bedroom, sleeps 4
1 Bathroom
United States, Illinois, Chicago Holiday Rentals
Pier Gold - B & B Boatel - For Chicago get-a-ways
Slideshow
4 of 5 stars 1 review
  • Guest Room
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Special offer details »
Night:
411 AUD - 821 AUD
Week:
3,079 AUD
Month:
10,263 AUD - 11,289 AUD
Minimum rental - 1 night
Check availability
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United States, Illinois, Chicago Holiday Rentals
Luxurious Lincoln Park! Great for corporate stays!
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 6 Bedrooms, sleeps 12
  • 4 Bathrooms
  • Owner
EMAIL OWNER
Night:
616 AUD - 924 AUD
Week:
4,310 AUD - 5,131 AUD
Month:
12,315 AUD
Minimum rental - 1 week
Check availability
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United States, Illinois, Chicago Holiday Rentals
Longterm Furnished Rental $2000/month WIFI/Cable
Slideshow
4.5 of 5 stars 8 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 5
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
2,053 AUD
Month:
2,053 AUD
Minimum rental - 30 nights
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United States, Illinois, Chicago Holiday Rentals
Fully Furnished Luxury apartment
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
257 AUD
Week:
1,539 AUD
Minimum rental - 1 night
Check availability
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United States, Illinois, Chicago Holiday Rentals
The Penthouse at Grand Plaza #2 - Corporate Rental
Slideshow
4 of 5 stars 2 reviews
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
5,846 AUD
Week:
5,846 AUD
Month:
5,846 AUD
Minimum rental - 30 nights
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United States, Illinois, Chicago Holiday Rentals
Luxury Townhome-Unbeatable Location-Great Reviews!
4.5 of 5 stars 3 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
257 AUD - 282 AUD
Week:
1,539 AUD - 1,745 AUD
Month:
2,668 AUD - 4,618 AUD
Minimum rental - 3 nights
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United States, Illinois, Chicago Holiday Rentals
Ideal Chicago Location: Steps to everything!
Slideshow
4.5 of 5 stars 25 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
308 AUD - 377 AUD
Week:
1,847 AUD - 2,258 AUD
Month:
8,210 AUD
Minimum rental - 3 nights
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United States, Illinois, Chicago Holiday Rentals
A Great Value.  Close to City & McCormick Place
Slideshow
4.5 of 5 stars 5 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
174 AUD - 251 AUD
Week:
1,180 AUD - 1,591 AUD
Minimum rental - 3 nights
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United States, Illinois, Chicago Holiday Rentals
**3bd/2.5ba**W*O**W**Heart of Downtown*Stunning**
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
323 AUD
Minimum rental - 2 nights
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United States, Illinois, Chicago Holiday Rentals
***PENTHOUSE** True Penthouse in Chicago 50th Fl.!
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
323 AUD
Minimum rental - 2 nights
Check availability
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United States, Illinois, Chicago Holiday Rentals
2/1 in Prime Lincoln Park- 1 Block to Fullerton L
Slideshow
4 of 5 stars 7 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
103 AUD - 272 AUD
Week:
924 AUD - 1,538 AUD
Month:
2,412 AUD - 4,054 AUD
Minimum rental - 2 nights
Check availability
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United States, Illinois, Chicago Holiday Rentals
Skyline Views
Slideshow
4.5 of 5 stars 6 reviews
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
307 AUD - 440 AUD
Minimum rental - 3 nights
Check availability
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United States, Illinois, Chicago Holiday Rentals
Wrigley Loft near Wrigley Field and Brown Line
4.5 of 5 stars 9 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 5
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
154 AUD - 180 AUD
Month:
2,514 AUD - 4,618 AUD
Minimum rental - 1 night
Check availability
Show on map

Chicago Apartment Rental Advice

GO Airport Express - BEWARE
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
Family of 7 (5 kids) 1st week of July, lodging & transportat
Posted by momlyn2, 13 Apr 2012
... accomodate all of us. The vacation rental section will let me seach for places that can sleep 7. Kids are ages 13, 10, 10, 8, & 8. Any advice for where a large family can stay would be appreciated. We are considering renting a condo/apartment near Lincoln Park and Raccine ... more
Posted by Dave148, 14 Apr 2012
... on the South Shore - check vacation rentals downtown along S. Michigan Ave. In addition, please type Suite Hotel in the search box above - you'll find previous posts on the subject. It's over 4 miles from the intersection of Lincoln & Racine to Navy Pier. It's about 2 miles ... more
Posted by ChiTownFriend, 27 Apr 2012
... are planning on getting a vacation rental in ... ... individuals each, instead of a vacation rental. (Please note that you'll have to carefully check the maximum capacity - based by fire codes - not many places are big enough to allow 7.) If you are specifically looking for a hotel in Lincoln ... more
Anyone deal with ' Steps to Everything ' vacation condos?
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
Best place to stay near Navy Pier
Posted by pgo, 2 Apr 2012
... of, but any hotel or vacation rental east of Michigan Avenue and north of the river will be within walking distance of Navy Pier. An alternative is to find a hotel along Grand Avenue or Chicago Avenue and use the bus. I'm not sure what "reasonably priced" means to ... more
Vacation Rentals
Posted by BuckeyeGal82, 31 Mar 2012
... have any information on a vacation rental that could accomodate 4 adults? I have a relative in the Wrigleyville area and will be sightseeing in the downtown area I know they do have condo or townhouse rentals ; hopefully somewhere from Streeterville north to Wrigleyville or maybe by the Lake Front ... more
Posted by shallow_shoals, 31 Mar 2012
Check the vacation rentals on TA. You might also ask your relatives to suggest something in their area that the tourists won't know about (yet). ... more
Posted by BuckeyeGal82, 1 Apr 2012
... had numerous problems with "bogus" vacation rentals; where the people pay the money get to the rental and find out it "was a scam". That was why I was asking if there was anyone out there who knew specifically of a vacation rental they may have used or a legitimate ... more
Condo/Apt/Townhome Rental for the First Week of August
Posted by BuckeyeGal82, 1 Apr 2012
... anyone know specifically of a vacation rental they ... ... problem of people doing a "vacation rental" only to get here and find out it was a scam and now their money is gone. I would prefer to got through a place with references or a realtor. If anyone has suggestions that ... more