Vacation Homes in Chicago
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Featured Vacation Homes in Chicago

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

ENVITAE Hotel, 4BR Luxury Modern Apartments

Chic Chicago Retreat (2-Bedroom Home) by RedAwning

McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus

Charming Home in Portage Park

Cozy Home by O'Hare + EV Plug

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Vintage Escape 1BR Two Blocks Away From Beach

Pleasant 3-bedroom house with occupied basement separate entrance.

Wrigley Field/Lakeview -Entire Home- Large Groups!
Top trending hotels in Chicago

Hyatt Regency O'Hare Chicago
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 | 821 Vacation Homes |
|---|---|
Lowest Price | CA $215 |
Highest Price | CA $1,367 |
Popular accommodation | Historic Coach House in Evanston One Block to Beach and Close to Town and NU!, ENVITAE Hotel, 4BR Luxury Modern Apartments, Chic Chicago Retreat (2-Bedroom Home) by RedAwning, McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus, Charming Home in Portage Park, Cozy Home by O'Hare + EV Plug, 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line, Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24, Vintage Escape 1BR Two Blocks Away From Beach, Pleasant 3-bedroom house with occupied basement separate entrance., Wrigley Field/Lakeview -Entire Home- Large Groups!, Breathtaking home close to Schaumburg, Chicago |






