Vacation Homes in Chicago
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Featured Vacation Homes in Chicago

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Wrigley Field/Lakeview -Entire Home- Large Groups!

Clarendon Hills Top Floor

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Belmont House, Classy & Chic/walk to Wrigley Field

Spacious House ~3min walk WrigleyField~Free Prkg

Home in DT Libertyville near Corp HQs & Naval Base

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Entire 3 Bedroom Cozy Unit

Roxan Corner

Family frndly TwnHm by navy base

3-bedroom hillside property in woods with fireplace and lake view
Top trending hotels in Chicago

citizenM Chicago Downtown
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 | 842 Vacation Homes |
|---|---|
Lowest Price | CA $145 |
Highest Price | CA $434 |
Popular accommodation | Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed, Wrigley Field/Lakeview -Entire Home- Large Groups!, Clarendon Hills Top Floor, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Belmont House, Classy & Chic/walk to Wrigley Field, Spacious House ~3min walk WrigleyField~Free Prkg, Home in DT Libertyville near Corp HQs & Naval Base, Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families , Entire 3 Bedroom Cozy Unit, Roxan Corner, Family frndly TwnHm by navy base , 3-bedroom hillside property in woods with fireplace and lake view |





