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Featured Vacation Homes in Chicago

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Essence Suite W/spa Bath

Essence Suite W/spa Bath

South Holland, IL
 
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Prime Location Suburban Townhome

Prime Location Suburban Townhome

Schaumburg, IL
Situated in Schaumburg, this vacation home is 1.9 mi (3 km) from Schaumburg Medieval Times and 2.8 mi (4.5 km) from Woodfield Mall. The Water Works Indoor Water Park and Harper College are also within 3 mi (5 km).
 
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Cambridge Estates

Cambridge Estates

4.0 out of 5.0 Cambridge Court, Darien, IL
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.
 
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Quaint Bungalow, Near Great Lakes Naval Base

Quaint Bungalow, Near Great Lakes Naval Base

Mundelein, IL
A garden is available at this vacation home.
 
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Million Dollar View on Chain O'lake "

Million Dollar View on Chain O'lake "

Fox Lake, IL
This vacation home features ski-in/ski-out access, a garden, and barbecue grills.
 
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4 Bedroom House Close to Many Corp Hq's

4 Bedroom House Close to Many Corp Hq's

Libertyville, IL
Situated in Libertyville, this vacation home is 0.2 mi (0.3 km) from MainStreet Libertyville and within 3 mi (5 km) of Advocate Condell Child Day Center and Independence Grove Beach. Lambs Farm is 2.6 mi (4.1 km) away. Libertyville Station is 12 minutes by foot.
 
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Stunning Lake Views, Relaxing Getaway on the Chain O'lakes

Stunning Lake Views, Relaxing Getaway on the Chain O'lakes

Fox Lake, IL
This vacation home features barbecue grills.
 
$160
Fox Lake Semi Secluded Waterfront! 3 Properties!

Fox Lake Semi Secluded Waterfront! 3 Properties!

McHenry, IL
A garden is available at this vacation home.
 
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1821

1821

3.5 out of 5.0 1821 North Hampton Drive, Highlands Rese, Berwyn, IL
An outdoor pool is available at this vacation home. Take advantage of the free self parking.
 
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Luxury Lakefront Estate On 80 Acres ~ Private Golf Course ~ Tennis Court ~ Pool

Luxury Lakefront Estate On 80 Acres ~ Private Golf Course ~ Tennis Court ~ Pool

Lake Villa, IL
This resort features an outdoor tennis court and a fitness center. A spa tub and a garden are also provided.
 
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The Country Life - House

The Country Life - House

Markham, IL
Limo/town car service and a garden are available at this vacation home.
 
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4 Bedroom House Walk to Downtown Libertyville

4 Bedroom House Walk to Downtown Libertyville

Libertyville, IL
Situated in Libertyville, this vacation home is within 1 mi (2 km) of MainStreet Libertyville and Advocate Condell Child Day Center. Lambs Farm and Independence Grove Beach are also within 3 mi (5 km). Libertyville Station is 13 minutes by foot.
 
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Chicago Vacation Home Rentals

What kind of vacation do you want in Chicago? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation home is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Chicago that will speak to you.

Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Chicago, including luxury vacation home rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.

Take a look at what we have on offer. You’ll find rental houses close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation homes a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.


Top trending hotels in Chicago

See all 2,318 Properties in Chicago
$115
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5.0 85 East Wacker Drive, Chicago, IL
Located in The Loop, this luxury hotel is steps from Chicago Riverwalk and Michigan Avenue. Grant Park and Chicago Theatre are also within 10 minutes. Clark-Lake Station is 7 minutes by foot and State Station is 8 minutes.
 
$143
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5.0 20 E Chestnut St, Chicago, IL
Located in Near North Side, this luxury hotel is within a 5-minute walk of State Street, Water Tower Place, and John Hancock Center. Chicago Water Tower and Michigan Avenue are also within 10 minutes. Chicago Station (Red Line) is only a 3-minute walk and Grand Station (Red Line) is 10 minutes.
 
$72
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5.0 1100 S Michigan Ave, Chicago, IL
Located in The Loop, this hotel is within a 10-minute walk of Grant Park and Columbia College Chicago. Field Museum of Natural History and John G. Shedd Aquarium are also within 15 minutes. Roosevelt Station and Chicago Museum Campus-11th Street Station are within a 5-minute walk.
 
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.