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Elder Access Vacation Rentals in Chicago

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
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From
$2,868
Per Month
The Loop
Studio, 1 Bathroom, Sleeps 2
40 photos Details
Reviews (4) Make Enquiry
From
$145
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 4
33 photos Details
Reviews (1) Make Enquiry
From
$322
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (2) Make Enquiry
Also consider
Modern Loft 1BEDROOM POOL GYM LEX Next 2McCormick
1 Bedroom, sleeps 4
$215 - $322 / night
Luxury Downtown Studio
1 Bedroom, sleeps 4
$107 - $537 / night
Luxury Condo Furnished Like a Hotel Best View
1 Bedroom, sleeps 1
$321 - $322 / night
Michigan Avenue 24th floor Condo/Hotel located on the Magnificent Mile!
1 Bedroom, sleeps 1
$268 / night
From
$215
Per Night
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
13 photos Details
Reviews (14) Make Enquiry
From
$376
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details
Reviews (1) Make Enquiry
From
$376
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
26 photos Details
Reviews (14) Make Enquiry
From
$322
Per Night
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details
Reviews (9) Make Enquiry
From
$322
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
19 photos Details
Reviews (1) Make Enquiry
Get the List
From
$86
Per Night
Studio, 1 Bathroom, Sleeps 2
14 photos Details
Reviews (1) Make Enquiry
From
$344
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 4
52 photos Details
Reviews (1) Make Enquiry
From
$322
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
23 photos Details
Reviews (6) Make Enquiry
From
$42
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
20 photos Details
Reviews (2) Make Enquiry
From
$129
Per Night
Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
26 photos Details
Reviews (2) Make Enquiry
From
$268
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
39 photos Details
Reviews (1) Make Enquiry
From
$246
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 10
39 photos Details
Reviews (1) Make Enquiry
From
$268
Per Night
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
15 photos Details
Reviews (2) Make Enquiry
From
$328
Per Night
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
Reviews (5) Make Enquiry
From
$171
Per Night
Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 5
30 photos Details
Reviews (5) Make Enquiry
From
$161
Per Night
DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
14 photos Details
Reviews (1) Make Enquiry
From
$161
Per Night
The Loop
Studio, 1 Bathroom, Sleeps 3
13 photos Details
Reviews (1) Make Enquiry
From
$150
Per Night
Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 3
19 photos Details
Reviews (1) Make Enquiry
From
$215
Per Night
Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
7 photos Details
Reviews (1) Make Enquiry
From
$268
Per Night
Northwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (11) Make Enquiry
From
$91
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (23) Make Enquiry
From
$214
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (1) Make Enquiry
From
$322
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 3
13 photos Details
Reviews (1) Make Enquiry
From
$322
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (2) Make Enquiry
From
$322
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 3
15 photos Details
Reviews (1) Make Enquiry
From
$107
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 3
9 photos Details
Make Enquiry
From
$11,814
Per Month
DePaul
6 Bedrooms, 5 Bathrooms, Sleeps 14
14 photos Details
Make Enquiry
From
$150
Per Night
Lincoln Park
1 Bedroom, 1 Bathroom, Sleeps 3
7 photos Details
Make Enquiry
From
$493
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
13 photos Details
Make Enquiry
From
$255
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
Make Enquiry
From
$215
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
4 photos Details
Make Enquiry
From
$311
Per Night
Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
10 photos Details
Make Enquiry
From
$215
Per Night
Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
4 photos Details
Make Enquiry
From
$215
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
4 photos Details
Make Enquiry
From
$268
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
29 photos Details
Make Enquiry
From
$322
Per Night
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Make Enquiry
From
$268
Per Night
West Town
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Make Enquiry
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Neighbourhood

  • All (107)
  • DePaul (3)
  • East Side (0)
  • Gold Coast (8)
  • Hyde Park (0)
  • Lakeview (12)
  • Lincoln Park (1)
  • Lincoln Square (0)
  • Near North Side (41)
  • Near South Side (0)
  • Northwest Side (6)
  • O'Hare (0)
  • Pilsen (0)
  • Rogers Park (1)
  • Roscoe Village (3)
  • Southwest Side (0)
  • The Loop (23)
  • University Village / Little Italy (0)
  • West Town (1)
  • Wicker Park / Bucktown (1)
Learn about Chicago neighbourhoods

Suitability

  • Wheelchair access (63)
  • Elder access (107)
  • Suitable for children (83)
  • Pet friendly (37)
  • Smoking allowed (0)

Amenities

  • Internet (75)
  • Air Conditioning (73)
  • Other outdoor space (62)
  • Parking (44)
  • Washer/Dryer (44)
  • View all amenities
Chicago Vacation Rentals

Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!

Chicago family vacations

Chicago is a great city for families and a vacation home rental makes it easy to explore all that the second city has to offer. If it’s baseball season, catch a Chicago Cubs game at historic Wrigley Field, one of the oldest ball parks in the country. Or take the kids out to Navy Pier, which features amusement rides, shops and restaurants right on Lake Michigan. If you’re kids are animal lovers, visit the Great Ape House at the Lincoln Park Zoo, where admission is still free. Or see dinosaurs at The Field Museum of Natural History.

Chicago attractions

There's plenty to do in Chicago and a vacation rental in the city will put you within walking distance of most of the city's many attractions. Art lovers will enjoy the Art Institute of Chicago where they can browse the large collection of impressionist and post-impressionist paintings before heading to the newer Modern Wing. After, you’ll want to head over to nearby Millennium Park, which features public art and cultural events year-round. During the warmer months, find a spot on the sand at Oak Street Beach, a great place to people watch with views of downtown skyscrapers and Lake Michigan.

Chicago day trips

For those who want to explore Chicago beyond the city center, there are plenty of short getaways worth exploring, all within an hour or two of your vacation rental. Nearby Oak Park is home to the Frank Lloyd Wright Home and Studio. It’s also the birthplace of Ernest Hemingway. For those looking for outdoor adventure, head south to Starved Rock State Park where you can hike miles of trails through rolling hills or go fishing, boating or horseback riding. Other popular getaways include Lake Geneva in southern Wisconsin or the shores along Lake Michigan outside the city.

Saving money on Chicago vacation rentals

Whether you want to stay in a chic downtown apartment rental in Chicago or a spacious house in the suburbs, we can help you find a deal that fits your budget. There are discounts on every type of property to help you get the most bang for your buck.