Vacation Homes in Chicago

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Featured Vacation Homes in Chicago

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Vacation Rentals in Chicago

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 rental 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 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 rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals 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.

Chicago Vacation Homes essential information

Accommodation
678 Vacation Homes
Lowest Price
CA $120
Highest Price
CA $201
Popular accommodation
Cozy Midway Home , Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!, Lincoln Park Living - Suite 2!, Great 3 bedroom rental unit near Logan Square, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!, New Humble Home! - Near Six Flags & Naval Base!!, Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills, Chicago Bootlegger House Sleeps 11-22 with 3 parking spots, New Your Home Away From Home! - Near Great Lakes Naval Base!!, ⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, Entire Beautiful Grove Home