Top Holiday rentals in Chicago
Find the Top Holiday rentals in Chicago – 10+ Quality Options from Leading Providers
1-19 out of 19 holiday rentals
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4 adults
1 bedroom
2 beds
MapView on map6.1 km from City Centre
From
US$ 81
/night
- Historic building with private entrance
- Fully equipped kitchen with dishwasher
- Streaming services available on TV
Holiday home
8 adults
3 bedrooms
3 beds
MapView on map7.9 km from City Centre
From
US$ 480
/night
- Private entrance for added privacy
- Fully equipped kitchen for cooking
- Outdoor picnic area for relaxation
- Outdoor pool
- Sun terrace
- Private parking
1.5 km from City Centre1.2 km from Chicago Union Station
From
US$ 283
/night
- Stunning city views from apartments
- Seasonal outdoor pool with sun terrace
- Fully equipped kitchens in each unit
Apartment
- Fitness room
- Game area
- Outdoor seating
8.0 km from City Centre
From
US$ 268
/night
- Mini-golf and game facilities available
- Fully equipped kitchens in all units
- Pet-friendly with outdoor dining area
Apartment
6.0 km from City Centre
From
US$ 271
/night
The Neighborhood Hotel Lincoln Park is situated in the Lincoln Park district of Chicago, 23 minutes' drive from Midway International airport.
- Rooftop Pool
- 24-hour Reception
- Sun Terrace
2.5 km from City Centre600 m from Michigan Avenue
From
US$ 266
/night
- Rooftop pool with stunning views
- Fully equipped kitchens in all units
- Private parking on-site available
Apartment
- Flat-screen TV
- Golf course
- Express check-in
14.0 km from City Centre
From
US$ 159
/night
- Private entrance for added privacy
- Fully equipped kitchen for convenience
- On-site golf course available
2.5 km from City Centre300 m from Michigan Avenue
From
US$ 585
/night
- Shared lounge
- Outdoor dining
- Satellite TV
10.0 km from City Centre
From
US$ 106
/night
- Access to picnic area for outdoor relaxation
- Fully equipped kitchen for self-catering
- Free private parking available on site
5.4 km from City Centre
From
US$ 237
/night
Wicker Park and Cards Against Humanity Theater are respectively 1.5 km and 450 metres from the Twin Lions: Bespoke Travel Lodge W/ Speakeasy* Chicago.
Holiday home
19.2 km from City Centre
From
US$ 112
/night
The Home With Spacious Yard 14 Mi To Dtwn is located 25 km from Midway International airport and at 150 metres from Cottage Grove & 107th Street bus stop.
Apartment
- Barbecue area
- Fireplace
- Bike rental
5.1 km from City Centre
From
US$ 232
/night
- Private terrace with garden views
- On-site bicycle rental available
- Children's playground on premises
2.6 km from City Centre900 m from McCormick Place
From
US$ 538
/night
Nestled in the South Loop district of Chicago, the Mccormick Place 3Br-2Ba Unit With Optional Parking - Sleeps 8 is nearly 15 minutes' walk from The Field Museum.
Holiday home
3.0 km from City Centre700 m from Michigan Avenue
From
US$ 1 891
/night
Located 2.4 km from The Art Institute of Chicago, this villa offers a cable flat-screen and a flat screen TV together with 3 bathrooms.
Apartment
1.9 km from City Centre1.0 km from Grant Park
From
US$ 1 002
/night
Featuring a swimming pool, the 3Br Luxury Glass Apartment With Views Pool & Gym lies in the South Loop district of Chicago, around 10 minutes' walk from The Field Museum.
2.7 km from City Centre700 m from McCormick Place
From
US$ 887
/night
Nestled in South Loop district of the city, the venue is about 15 km from Midway International airport.
Holiday home
16.8 km from City Centre
From
US$ 159
/night
3.6 km from City Centre1.8 km from Michigan Avenue
From
US$ 767
/night
Chicago History Museum and Charnley-Persky House Museum are located 0.9 km and 1 km from the 5 Bedroom House In Best Location Parking Fireplace Back Yard Home Office respectively.
- Full Kitchen
- Streaming TV
- Non-Smoking
7.5 km from City Centre1.5 km from Wrigley Field
From
US$ 148
/night
- Fully equipped kitchen with oven
- Flat-screen TV with streaming services
- Non-smoking accommodation available
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