Check rooms and rates
Check rooms and rates
exclusive online offers!
Destination
Sorry, we don't recognise this name.Enter a destination to start the search
We can’t find that destination
Try to change your search
The Internet connection seems to be slow. It may take a few more seconds to load the page. Thank you for your patience.
×
Check-in
Select date
Check-out
Select date
Rooms and Guests
2Guests1room

Holiday Homes in Chicago, IL

Search among 15 available holiday homes in Chicago from 50+ providers.

Check rooms and rates
exclusive online offers!
Destination
Sorry, we don't recognise this name.Enter a destination to start the search
We can’t find that destination
Try to change your search
The Internet connection seems to be slow. It may take a few more seconds to load the page. Thank you for your patience.
×
Check-in
Select date
Check-out
Select date
Rooms and Guests
2Guests1room
Check rooms and rates
exclusive online offers!
Destination
Sorry, we don't recognise this name.Enter a destination to start the search
We can’t find that destination
Try to change your search
The Internet connection seems to be slow. It may take a few more seconds to load the page. Thank you for your patience.
×
Check-in
Select date
Check-out
Select date
Rooms and Guests
2Guests1room
Check rooms and rates
exclusive online offers!
Destination
Sorry, we don't recognise this name.Enter a destination to start the search
We can’t find that destination
Try to change your search
The Internet connection seems to be slow. It may take a few more seconds to load the page. Thank you for your patience.
×
Check-in
Select date
Check-out
Select date
Rooms and Guests
2Guests1room
18May2022Wednesday
19May2022Thursday
Get Prices
1Filter by
View map
Sort by
View map
1-15 out of 15
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Applied filters
Villas ×
View on map6.1 km from City Centre700 m from
From   C$ 497 /nightSelect
Not available
10 adults
3 bedrooms
3 beds
View on map3.4 km from City Centre1.6 km from Lincoln Park Zoo
Located in Old Town district, this villa features a terrace along with a mini-kitchen.
From   C$ 512 /nightSelect
Not available
8 adults
3 bedrooms
5 beds
7.9 km from City Centre500 m from Viaduct Center
Featuring a terrace along with 3 bedrooms, this villa is set 2.6 km from Sheil Park.
From   C$ 187 /nightSelect
Not available
21 adults
4 bedrooms
8 beds
3.4 km from City Centre1.6 km from Lincoln Park Zoo
Located 3 km from Millennium Park, the self-catering villa consists of 4 bedrooms, a mini-kitchen and 4 bathrooms equipped with a bath, a rain shower and a bidet.
From   C$ 897 /nightSelect
Not available
3.0 km from City Centre1000 m from Water Tower Place
Situated 150 metres from Clark/Division tube station, the property is composed of a kitchen and 1 bathrooms.
Select
Not available
3.0 km from City Centre1.9 km from Michigan Avenue
Situated 950 metres from North/Clybourn tube station, the property is composed of a kitchen and 4 bathrooms.
Select
Not available
3.0 km from City Centre1000 m from Water Tower Place
Select
Not available
5.5 km from City Centre400 m from Treasure Island Market Square Shopping Center
Select
Not available
21.0 km from City Centre400 m from Historic Pullman Foundation
Select
Not available
9.8 km from City Centre800 m from Kindred Hospital-Chicago North
Wrigley Field is 2.5 km from this villa that offers 5 bedrooms along with a fully equipped kitchen.
Select
Not available
6.1 km from City Centre1.9 km from Lincoln Park Zoo
Select
Not available
3.0 km from City Centre1000 m from Water Tower Place
Select
Not available
16 adults
6 bedrooms
6 beds
8.3 km from City Centre800 m from
Composed of 6 bedrooms and 4 bathrooms, this holiday home is set only 1.3 km from California & Milwaukee.
Select
Not available
10 adults
5 bedrooms
5 beds
3.0 km from City Centre500 m from Water Tower Place
Composed of 5 bedrooms and 3 bathrooms, this holiday home is set only 0.9 km from The Magnificent Mile.
Select
Not available
24 adults
5 bedrooms
11 beds
3.6 km from City Centre1.4 km from Lincoln Park Zoo
Situated next to Lincoln Park Zoo, this 5-bedroom property features a play area and board games for families with kids.
From   C$ 1 075 /nightSelect
Not available

Filtering results

Please wait...

15 hotels found

FAQs about holiday houses in Chicago

Discover these 8 answers and find your perfect holiday home to stay in Chicago.

What are the most popular pet-friendly holiday houses in Chicago?

If you want to stay with pets, iBooked.ca offers 15 options to choose from. We recommend Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok (rating: 8.0/10), a perfect villa with board games, ironing and live performances. It's set a 5-minute walk from UP Comedy Club. Another great option is Webster House at the cost of 235C$ per one night. Other suitable properties are Charming Apartments Near Downtown Howard Johnson Inn -.

What are the top holiday houses in Chicago with hot tubs?

If you want to relax during your trip, there are 8 deals featuring jacuzzi on iBooked.ca. You may like The Boom Boom Room offering shopping service, a Jacuzzi and 24-hour front desk assistance at the price of 557C$ per one night.

What are the top lakefront holiday houses in Chicago?

Find out Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok at the price of 506C$ per night.

What are the top holiday houses in Chicago that are good for couples?

According to iBooked.ca travel data, there are 5 deals for couples. To make your stay fantastic, book Howard Johnson Inn - with massage treatments and restaurant. This high-rated holiday house is set 700 metres from Oak Street and costs 156C$ per night.

What are the top holiday houses in Chicago offering a kitchenette?

To stay at the top holiday house with a kitchen, iBooked.ca offers 3 properties to choose from. Customers who enjoy cooking may like Oakwood 200 Squared with an outdoor swimming pool, an indoor swimming pool and a gym, situated 700 metres from Ford Center Theater.

Which holiday houses in Chicago provide free parking?

If you want to stay at the place with free parking, iBooked.ca has 10 deals to offer. For instance, Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok, a good choice located 3 km from Willis Tower. It features board games, ironing and live performances. Alternatively, you may book The Avondale Guesthouse for about 185C$ per night. This villa provides cots, laundry and cars on site.

What are the most popular holiday houses in Chicago not far from Millennium Park?

If you wish to stay not far from this tourist destination, on iBooked.ca you can easily book one of 6 accommodations. For instance, find out Stay Alfred At Park Michigan rated 8.0/10, located a 20-minute walk from the attraction for 904C$ per night. Another good option is Modern 2Br/2Bath Apt In Streeterville providing fitness classes and ironing for 471C$ per night.

What are the most popular luxury holiday houses in Chicago?

According to iBooked.ca travel data, one of the top accommodations is Printers Penthouse 450 metres from Wabash Arts Corridor. It costs 778C$ per night.

Guest reviews of hotels in Chicago