Book Holiday Homes in Chicago

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Featured Holiday Homes in Chicago

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

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

Chicago
Stay at this vacation home in Chicago. Enjoy an in-room coffeemaker. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stunning / Spacious 6BD Home + garage - Bucktown!

Stunning / Spacious 6BD Home + garage - Bucktown!

Chicago
Stay at this vacation home in Chicago. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Wrigley Field and Michigan Avenue are ...
Stunning / Spacious 6BD Home + garage - Bucktown!
Great 3 bedroom rental unit near Logan Square

Great 3 bedroom rental unit near Logan Square

Chicago
Stay at this vacation home in Chicago. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Wrigley Field and United Center are located ...
Great 3 bedroom rental unit near Logan Square
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New Your Home Away From Home! - Near Great Lakes Naval Base!!

New Your Home Away From Home! - Near Great Lakes Naval Base!!

North Chicago
Stay at this vacation home in North Chicago. Enjoy free WiFi, a garden, and air conditioning. Popular attractions Six Flags Great America and Asylum Skate Park ...
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Belmont House, Classy & Chic/walk to Wrigley Field

Belmont House, Classy & Chic/walk to Wrigley Field

Chicago
Stay at this vacation home in Chicago. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Wrigley Field and Michigan Avenue are located ...
Belmont House, Classy & Chic/walk to Wrigley Field
Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis

Chicago
Stay at this vacation home in Chicago. Enjoy a fitness center, a garden, and balconies. Popular attractions Wrigley Field and Copernicus Center are located ...
Chicago Riverhouse with private fenced in oasis
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Chicago
Stay at this vacation home in Chicago. Enjoy free WiFi, a garden, and patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Spacious 5-bedroom house with movie room, game room and more!

Spacious 5-bedroom house with movie room, game room and more!

Berwyn
Book a stay at this family-friendly vacation home in Berwyn. Enjoy a fitness center, a garden, and an in-room coffeemaker. Popular attractions Frank Lloyd Wright ...
Spacious 5-bedroom house with movie room, game room and more!
Elegant 4 br Old Town Home;  Private Yard; Parking; Amazing Location

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Chicago
Stay at this vacation home in Chicago. Enjoy free WiFi, a fitness center, and daily housekeeping. Popular attractions Michigan Avenue and Chicago Riverwalk are ...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
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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.

Chicago Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chicago vacation homes are the perfect way for you to wing it.

Holiday houses in Chicago let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chicago in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chicago adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chicago with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chicago vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chicago Holiday Homes essential information

Accommodation
675 Holiday Homes
Lowest Price
NZ$193
Highest Price
NZ$341
Popular accommodation
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Stunning / Spacious 6BD Home + garage - Bucktown!, Great 3 bedroom rental unit near Logan Square, New Your Home Away From Home! - Near Great Lakes Naval Base!!, Belmont House, Classy & Chic/walk to Wrigley Field, Chicago Riverhouse with private fenced in oasis, Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow, Spacious 5-bedroom house with movie room, game room and more!, Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Top trending hotels in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 24 Dec to 25 Dec
NZ$217
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$193 per night from 22 Jan to 23 Jan
NZ$193
includes taxes & fees
22 Jan - 23 Jan 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$341 per night from 10 Jan to 11 Jan
NZ$341
includes taxes & fees
10 Jan - 11 Jan 2025
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
Hyatt Regency Chicago
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Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is NZ$235 per night from 7 Jan to 8 Jan
NZ$235
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Don't see what you're looking for?
See all available properties 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.