Chicago Vacation Rentals, Apartments, & More

1-38 of 38 Chicago Rentals

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Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$315

/ night

Email Owner
1 / 17

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”2 Reviews

from

$149

/ 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 / 11

Chicago Apartment
3 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”25 Reviews

from

$140

/ night

Email Owner
1 / 15

Chicago Apartment
Studio / 1 Bathroom / Sleeps 2

from

$99

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 37

Chicago Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”23 Reviews

from

$200

/ 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 - Home
1 / 16

Chicago Home
2 Bedrooms / 1 Bathroom / Sleeps 10

from

$65

/ night

Email Owner
1 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”6 Reviews

from

$105

/ night

Email Owner
1 / 6

Chicago Condo
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$300

/ night

Email Owner
1 / 6

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3

“ Excellent ”5 Reviews

from

$89

/ 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 - Apartment
1 / 14

Chicago Apartment
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

from

$275

/ night

Email Owner
Front Door To Biddle House
1 / 18

Chicago Guesthouse
4 Bedrooms / 2 Bathrooms / Sleeps 10

“ Excellent ”3 Reviews

from

$225

/ 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 - Condo
1 / 14

Chicago Condo
4 Bedrooms / 4 Bathrooms / Sleeps 14

from

$295

/ 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 - Apartment
1 / 23

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$195

/ night

Email Owner
Chicago Illinois Vacation Rentals - Condo
1 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

from

$270

/ night

Email Owner
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 - Apartment
1 / 5

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 5

from

$200

/ 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 / 10

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3

“ Excellent ”8 Reviews

from

$100

/ night

Email Owner
Living Area with Queen Pull-Out Sofa
1 / 9

Chicago Apartment
Studio / 1 Bathroom / Sleeps 2

from

$89

/ 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 - Condo
1 / 15

Chicago Condo
1 Bedroom / 1.5 Bathrooms / Sleeps 4

“ Excellent ”11 Reviews

from

$145

/ 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
Bella's livingroom
1 / 8

Chicago Apartment
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”11 Reviews

from

$150

/ night

Email Owner
1 / 10

Chicago Condo
10 Bedrooms / 8 Bathrooms / Sleeps 20

from

$50

/ 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
1 / 8

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 3

“ Excellent ”1 Review

from

$92

/ 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 Travel Tips

Chicago, the biggest metropolitan city in the Midwest, teems with rich culture, an eclectic art scene, exciting nightlife, die-hard sports fans, and of course, deep-dish pizza. This city isn't just a great travel destination for adults; it also has much to offer families and kids of all ages. If you have started to look for Chicago condo rentals for your upcoming family vacation, be sure to check out the following travel tips that will help you and your family enjoy your time in the "Windy City".
Admire the Awesome Animal Life
Chicago is a fun destination for are animal-lovers of any size. With all of its entertainment options and aquatic life, a visit to The John G. Shedd Aquarium can fill up an entire day. From dolphin shows to a 400,000-gallon underground shark tank, the Shedd Aquarium is a fun outing for the whole family. Try to buy your tickets for the aquarium online, as this can save you both time and money the day of your trip. For families looking to save some money on attractions, a trip to the Lincoln Park Zoo is a must, as kids will enjoy watching the animals and parents will appreciate the free admission.
Enjoy a Day at the Museum
Chicago is home to several world-class museums, including many that will excite the kids. For dinosaur enthusiasts, don't miss the Field Museum, which is home to the largest tyrannosaurus rex skeleton ever uncovered. Other great museums for children include the LEGO Discovery Center, the Museum of Science and Industry, and the Children's Museum. If you wish to be in walking distance of certain museums, make sure to keep that in mind while searching through the Chicago condo rentals for your trip - it's all about location, location, location - especially for busy families.
Ride the attractions at Navy Pier
As one of the most popular attractions in Chicago, Navy Pier is a great place for both children and adults. There are many Chicago condos for rent that are perfectly located for easy access to the Navy Pier, which offers carnival-like rides, boat rides, a Ferris wheel, fun restaurants, and many more family-oriented attractions. If you plan on spending a significant amount of time at Navy Pier, check to see if there are any Chicago vacation rentals by owner that are within walking distance of this hot spot.
Easy and Unique Public Transportation
Chicago has one of the best public transportation systems in the country, which can be extremely beneficial for visitors, especially those traveling with children. Not only is public transportation inexpensive, but kids can also experience riding the L-train - the elevated train that provides great views of downtown Chicago. If you plan on taking public transportation during your trip, choose from our selection of Chicago condos for rent close to a train station or bus stop.
If you are trying to find the perfect family vacation destination that offers a wide variety of options for condo rentals, Chicago is a great choice! Searching for condo rentals doesn't need to be challenging; we're here to help you find a place that fits all of your family's needs and aim to help you plan a memorable and comfortable family vacation. We provide a variety of vacation rentals by owner, Chicago and surrounding areas. With these affordable and fitting accommodations, Chicago might just be your new favorite family vacation spot.
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