Chicagoland Vacation Rentals, Apartments, & More

1-38 of 38 Chicagoland Rentals

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Chicago Illinois Vacation Rentals - Apartment
1 / 15

Chicago Apartment
Studio / 1 Bathroom / Sleeps 2

from

$99

/ night

Email Owner
Steps To Navy Pier - Beaches, Shops, Restaurants, Night Life and More!
1 / 37

Chicago Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”23 Reviews

from

$200

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$315

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 24

Chicago Condo
5 Bedrooms / 2 Bathrooms / Sleeps 16

“ Excellent ”3 Reviews

from

$600

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 14

Chicago Condo
4 Bedrooms / 4 Bathrooms / Sleeps 14

from

$295

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 4

from

$110

/ night

Email Owner
Chicago Illinois Vacation Rentals - Guesthouse
1 / 18

Chicago Guesthouse
4 Bedrooms / 2 Bathrooms / Sleeps 10

“ Excellent ”3 Reviews

from

$225

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 14

Chicago Apartment
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

from

$275

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 11

Chicago Apartment
3 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”25 Reviews

from

$140

/ night

Email Owner
1 / 6

Chicago Condo
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$300

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”6 Reviews

from

$105

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 6

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3

“ Excellent ”5 Reviews

from

$89

/ night

Email Owner
Chicago Illinois Vacation Rentals - Home
1 / 16

Chicago Home
2 Bedrooms / 1 Bathroom / Sleeps 10

from

$65

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 11

Chicago Apartment
3 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”39 Reviews

from

$250

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 Bedrooms / 2.5 Bathrooms / Sleeps 10

from

$315

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 17

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”2 Reviews

from

$149

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 7
Chicago Illinois Vacation Rentals - Apartment
1 / 12

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$300

/ night

Email Owner
Chicago Illinois Vacation Rentals - Townhouse
1 / 24

Chicago Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$300

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

from

$270

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 23

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$195

/ night

Email Owner
Chicago Illinois Vacation Rentals - Home
1 / 17

Chicago Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 24

“ Excellent ”6 Reviews

from

$500

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 9

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”3 Reviews

from

$109

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 10

Chicago Condo
10 Bedrooms / 8 Bathrooms / Sleeps 20

from

$50

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 15

Chicago Condo
1 Bedroom / 1.5 Bathrooms / Sleeps 4

“ Excellent ”11 Reviews

from

$145

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”11 Reviews

from

$150

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 3

“ Excellent ”1 Review

from

$92

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 5

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 5

from

$200

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 24

Chicago Condo
3 Bedrooms / 1 Bathroom / Sleeps 7

“ Excellent ”8 Reviews

from

$225

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 10

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3

“ Excellent ”8 Reviews

from

$100

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$350

/ night

Email Owner
Chicago Illinois Vacation Rentals - Home
1 / 13

Chicago Home
5 Bedrooms / 3 Bathrooms / Sleeps 11

“ Excellent ”8 Reviews

from

$459

/ night

Email Owner
Chicago Illinois Vacation Rentals - Guesthouse
1 / 45

Chicago Guesthouse
5 Bedrooms / 2 Bathrooms / Sleeps 9

“ Excellent ”3 Reviews

from

$300

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 9

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”6 Reviews

from

$149

/ night

Email Owner
Chicago Illinois Vacation Rentals - Apartment
1 / 9

Chicago Apartment
Studio / 1 Bathroom / Sleeps 2

from

$89

/ night

Email Owner
Chicago vacation rentals are a great bet for those of you looking to plan something extra special this holiday season. Stunning view of the beaches, easy access to the waterfront, and perfect positioning to reach any shopping destination or restaurant with ease, are some of the benefits you enjoy while staying Chicago.

Most of the condos of Chicago offer great city views, in addition to having facilities like fully equipped kitchens, the latest electronic equipment, high-speed internet, and well-designed interiors.

The windy city, as it is popularly known, is best enjoyed on a cruise boat ride. Chicago boasts of some of the best skyscrapers in the world. Moving along the Chicago River, you come across two of the biggest architectural marvels – the Willis tower and the Tribune Tower.

Most of the Chicago vacation rentals have accessibility to Lake Michigan, which is another feather in Chicago’s cap. Taking a speedboat ride in Lake Michigan and experiencing a view of the Chicago skyline is sure to leave you and your family spellbound. Other spots to be enjoyed while in Chicago include the Chicago harbor, Grant Park, Buckingham fountain, and Museum campus.

The Buckingham fountain is best enjoyed after dusk, ideally around 8 ‘o’ clock in the evening. Commissioned by Kate Buckingham in 1927, this massive fountain has about 134 jets which ensure that the water rises to heights comfortably exceeding 24 feet., and with music and animation it really adds to the appeal.

A trip to Chicago would be incomplete without a visit to Hancock tower. From one of Chicago’s tallest landmarks, one can easily spot 4 states – Michigan, Illinois, Indiana, and Wisconsin. When experiencing the open-air sky deck, at least 1000 feet above the Magnificent Mile, with the wind on your face, you understand what makes people call Chicago as the ‘Windy City’.

Navy pier, parks, world famous restaurants, and museums – the list seems to be endless. Book your Chicago vacation rentals and it will just be a matter of time before your family members say ‘Go-Chicago’.
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