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Holiday rentals in Chicago, IL

Search among 375 available holiday rentals in Chicago from 50+ providers

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17May2022Tuesday
18May2022Wednesday
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The largest option:
4 adults
View on map1.2 km from City Centre500 m from House of Blues Chicago
Only a 20-minute walk from LaSalle "L" (Blue Line) metro station, the apartment with a swimming pool can be a good choice for your stay in the downtown part of Chicago.
7.8
Very good29 reviews
From   C$ 264 /nightSelect
Not available
The largest option:
4 adults
2 bedrooms
3 beds
View on map2.5 km from City Centre100 m from Scales and Tales
Situated a 10-minute drive to McCormick Place, this villa features the balcony and a terrace.
8.2
Great23 reviews
From   C$ 157 /nightSelect
Not available
The largest option:
5 adults
2.2 km from City Centre1.3 km from House of Blues Chicago
Situated in Chicago, within a 15-minute walk from Water Tower Chicago, this apartment features a terrace with a shower and a seating area.
7.8
Very good26 reviews
From   C$ 469 /nightSelect
Not available
Homestay
The largest option:
12 adults
1 bedroom
1 bed
6.2 km from City Centre600 m from
Located 1.8 km from The Young Church, this villa offers 9 rooms.
8.2
Great2 reviews
From   C$ 198 /nightSelect
Not available
4.9 km from City Centre900 m from
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Not available
9.8 km from City Centre400 m from Coastal Capital Corp
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Not available
4 adults
1 bedroom
2 beds
3.9 km from City Centre400 m from
The apartment is located 1.4 km from Flat Iron Building and comes with a kitchen and a private bathroom.
8.0
Great1 review
From   C$ 179 /nightSelect
Not available
The largest option:
10 adults
3 bedrooms
4 beds
8.0 km from City Centre800 m from
Nestled in Roscoe Village district of the city, the venue is about 20 km from Midway airport.
8.2
Great7 reviews
From   C$ 441 /nightSelect
Not available
The largest option:
4 adults
2 bedrooms
2 beds
1.7 km from City Centre600 m from House of Blues Chicago
Located a few steps from Skydeck Chicago, the hotel features 188 rooms with views over the city.
8.0
Great3 reviews
From   C$ 218 /nightSelect
Not available
8 adults
2 bedrooms
2 beds
7.4 km from City Centre700 m from
Nestled in Bronzeville district within 30 minutes' walk of Guaranteed Rate Field, the apartment offers 130 m² of space for up to 4 guests.
8.0
Great6 reviews
From   C$ 142 /nightSelect
Not available
7.6 km from City Centre500 m from
Select
Not available
6 adults
3 bedrooms
3 beds
2.2 km from City Centre900 m from Chicago Theater
This 3-bedroom apartment can accommodate up to 6 people, within a 15-minute walk from CIBC Theatre.
From   C$ 1 007 /nightSelect
Not available
6.1 km from City Centre700 m from
From   C$ 499 /nightSelect
Not available
The largest option:
2 adults
2.9 km from City Centre500 m from Michigan Avenue
Since 1924 the apartment welcomes guests in a shopping area, just steps from Lake Michigan.
8.6
Great139 reviews
From   C$ 162 /nightSelect
Not available
400 m from City Centre300 m from Union Station
There is a specialty restaurant available in the budget hotel set in Near North Side district.
9.0
Perfect6 reviews
From   C$ 192 /nightSelect
Not available
The largest option:
4 adults
2.2 km from City Centre800 m from Michigan Avenue
Located near Navy Pier, this pet-friendly hotel features an American breakfast.
6.8
Nice44 reviews
From   C$ 159 /nightSelect
Not available
2.4 km from City Centre900 m from Michigan Avenue
Offering convenient proximity to Tribune Tower, the hotel is also close to Millennium Park.
From   C$ 892 /nightSelect
Not available
2.4 km from City Centre800 m from Michigan Avenue
Located within a 20-minute walk of LaSalle "L" (Blue Line) underground station, this apartment features an own balcony.
From   C$ 789 /nightSelect
Not available
4.2 km from City Centre700 m from
Located less than 3.8 km from University of Illinois, this venue features an individual balcony and a kitchen.
From   C$ 570 /nightSelect
Not available
The largest option:
6 adults
2 bedrooms
3 beds
2.5 km from City Centre1.4 km from United Center
Featuring a terrace with garden views, the apartment is placed next to Michigan Avenue.
8.2
Great4 reviews
From   C$ 438 /nightSelect
Not available

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375 hotels found

FAQs about holiday lettings in Chicago

Discover 10 answers from our FAQ and find your perfect holiday cottages in Chicago.

What are the best holiday rentals in Chicago Loop district?

If you want to discover Chicago Loop district, book Printers Paradise, which offers windsurfing, bowling and cycling.

What are the most popular luxury holiday rentals in Chicago?

These luxury accommodations will make your journey memorable: Dch 215 Lake and Printers Penthouse. Go here to see more holiday rentals.

What are the finest Chicago holiday rentals to stay with pets?

Lowest Rates! Spacious Duplex With Free Parking! is an excellent choice among 15 pet-friendly holiday rentals in Chicago.

What are the best cheap holiday rentals to stay in Chicago?

You might choose Near South Side Apartment at the cost of 218C$ per night. See more budget accommodations here.

How much does a 3-bedroom holiday house cost for a week?

A 3-bedroom home in Chicago costs about 369C$. You can check the top-rated option Swank Victorian Near United Center W/ Backdeck.

What are the top apartments close to a beach?

If you are searching for a beach villa, Family Retreat Chicago is a great option to consider.

What are the top-ranked holiday rentals with swimming pools in Chicago?

To enjoy an onsite pool, rent Envitae 2Br 1 Block To Mag Mile or Envitae 2Br Corner Glass Penthouse W Balcony. Check more popular holiday accommodations here.

What are the best holiday rentals with free wifi in Chicago?

According to iBooked.ca travel statistics, the most popular holiday rental with free wifi is Mccormick Place Guest House rating: 3.5/5.

What holiday rentals near Navy Pier would you recommend?

3Br Premium Executive Penthouse W/ Pool & Parking is the most popular holiday accommodation not far from Navy Pier, one of the top Chicago attractions.

What are the top Chicago holiday rentals featuring free parking?

If you want to park your car on site, check Field Museum Experience At Ellis Place, in which prices start from 103C$.

Guest reviews of hotels in Chicago