Minimap with link to location map
Filters
Price
Rating
Distance from Center
Rating (according to Stars)
Facilities

Check availability






Holiday homes in Chicago You’ll Love (Page 2)

Top-Rated Chicago Holiday homes for Every Budget and Style!

Looking for a holiday home in Chicago (Illinois)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $53.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chicago.

We found 48 Holiday-homes in Chicago and the surrounding area (within 20 miles)

Steel and Sky in Chicago, USA

Steel and Sky

Holiday home in Chicago, Illinois , 1358 North Campbell Avenue
Steel and Sky offers accommodations in Chicago, 2.5 miles from United Center and 3.6 miles from Lincoln Park Zoo.
  • Parking
  • Pets allowed

no reviews

from $1.440.48 Show details »

Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome in Chicago, USA

Couture Themed 3 Bedroom in Prime Spot w...

Holiday home in Chicago, Illinois , 329 West Schiller Street Back
Just 1.1 miles from North Avenue Beach and a 16-minute walk from Lincoln Park Zoo, Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Firepla...
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 24 Reviews 9.8

from $469.29 Show details »

Luxury Retreat with Home Theater in Chicago, USA

Luxury Retreat with Home Theater

Holiday home in Chicago, Illinois , West Beach Avenue 1621
Luxury Retreat with Home Theater offers accommodations in Chicago, 2.2 miles from United Center and 2.5 miles from Lincoln Park Zoo.
  • Parking

Exceptional 2 Reviews 10.0

from $456.73 Show details »

Designer Smart Home in Chicago, USA

Designer Smart Home

Holiday home in Chicago, Illinois , 59 West Schiller Street
Offering a fitness center and a garden, Designer Smart Home in Chicago is close to North Avenue Beach and Lincoln Park Zoo.
  • Parking
  • Pets allowed
  • Fitness centre

no reviews

from $1.251.87 Show details »

5 Bedroom House in Best Location Parking Fireplace Back Yard Home office in Chicago, USA

5 Bedroom House in Best Location Parking...

Holiday home in Chicago, Illinois , 1426 North North Park Avenue
5 Bedroom House in Best Location Parking Fireplace Back Yard Home office offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.3 mile...
  • Parking
  • Pets allowed
  • Family rooms
  • Kids' outdoor play equipment

Very good 3 Reviews 8.3

from $1.029.16 Show details »

Old Town Pied-a-Terre with Private Terrace and Parking! in Chicago, USA

Old Town Pied-a-Terre with Private Terra...

Holiday home in Chicago, Illinois , 1515 North Wells
A 14-minute walk from North Avenue Beach in Chicago, Old Town Pied-a-Terre with Private Terrace and Parking! offers accommodations with access to a ho...
  • Parking

Exceptional 1 Reviews 10.0

from $58.00 Show details »

2 MTM Fully Furnished Rental in Old Town 2f&2r in Chicago, USA

2 MTM Fully Furnished Rental in Old Town...

Holiday home in Chicago, Illinois , 1556 North La Salle Drive
2 MTM Fully Furnished Rental in Old Town 2f&2r is located in Chicago, just 1.4 miles from 360 Chicago and 1.4 miles from Water Tower Chicago.

no reviews

from $81.00 Show details »

Beautiful Remodeled Penthouse Unit in Old Town in Chicago, USA

Beautiful Remodeled Penthouse Unit in Ol...

Holiday home in Chicago, Illinois , 1556 North La Salle Street
Beautiful Remodeled Penthouse Unit in Old Town offers accommodations in Chicago, 1.4 miles from 360 Chicago and 1.4 miles from Water Tower Chicago.

Exceptional 14 Reviews 9.6

from $288.34 Show details »

Luxe SFH Bucktown Retreat with Garage Parking in Chicago, USA

Luxe SFH Bucktown Retreat with Garage Pa...

Holiday home in Chicago, Illinois , 1629 N Rockwell S
Providing a garden, Luxe SFH Bucktown Retreat with Garage Parking offers accommodations in Chicago.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $1.168.39 Show details »

No. 1 Rated Lincoln Park House - Golf Simulator in Chicago, USA

No. 1 Rated Lincoln Park House - Golf Si...

Holiday home in Chicago, Illinois , 210 W St Paul Ave, Chicago, IL 60614, USA
No. 1 Rated Lincoln Park House - Golf Simulator offers accommodations in Chicago, a 7-minute walk from Lincoln Park Zoo and 1.6 miles from 360 Chicago...

Good 3 Reviews 7.3

from $382.00 Show details »

5BR 5BA Architectural Estate-Theatre Gym Rooftop in Chicago, USA

5BR 5BA Architectural Estate-Theatre Gym...

Holiday home in Chicago, Illinois , 1856 North Fairfield Avenue
5BR 5BA Architectural Estate-Theatre Gym Rooftop is located in Chicago, just 3.3 miles from Lincoln Park Zoo and 3.4 miles from United Center.
  • Parking
  • Fitness centre

Fabulous 3 Reviews 8.7

from $53.00 Show details »

MAGNIFICENT NEW Home w/8 Beds & Free Parking in Chicago, USA

MAGNIFICENT NEW Home w/8 Beds & Free Par...

Holiday home in Chicago, Illinois , 2019 North Bingham Street
MAGNIFICENT NEW Home w/8 Beds & Free Parking offers accommodations in Chicago, 3.9 miles from Wrigley Field and 4 miles from Water Tower Chicago.
  • Parking

Exceptional 16 Reviews 9.5

from $74.00 Show details »

The Village Inn by Dakota Gal Digs in Chicago, USA

The Village Inn by Dakota Gal Digs

Holiday home in Chicago, Illinois , 2111 North Kenmore Avenue Unit 1
The Village Inn by Dakota Gal Digs is located in Chicago, just 1.8 miles from Fullerton Beach and 1.8 miles from North Avenue Beach.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 3 Reviews 10.0

from $384.32 Show details »

Lincoln Park 2 Bedroom Condo Wmid Century Flair in Chicago, USA

Lincoln Park 2 Bedroom Condo Wmid Centur...

Holiday home in Chicago, Illinois , 2204 North Clybourn Avenue #2
Lincoln Park 2 Bedroom Condo Wmid Century Flair offers accommodations in Chicago, 1.6 miles from Lincoln Park Zoo and 2.5 miles from Wrigley Field.
  • Parking
  • Pets allowed

no reviews

from $63.00 Show details »

Logan Square Oasis in Chicago, USA

Logan Square Oasis

Holiday home in Chicago, Illinois , 2508 N Spaulding Ave
Logan Square Oasis offers accommodations in Chicago, 4.2 miles from Wrigley Field and 4.6 miles from United Center.
  • Pets allowed

Exceptional 2 Reviews 10.0

from $79.00 Show details »

Suite 2 on Southport 4 Queen Beds in Chicago, USA

Suite 2 on Southport 4 Queen Beds

Holiday home in Chicago, Illinois , 2501 North Southport Avenue
Suite 2 on Southport 4 Queen Beds is located in Chicago, just 1.8 miles from Wrigley Field and 3.4 miles from 360 Chicago.
  • Parking

Fabulous 21 Reviews 8.8

from $226.23 Show details »

Lincoln Park Living - 3 Queen Beds - Sleeps 6 in Chicago, USA

Lincoln Park Living - 3 Queen Beds - Sle...

Holiday home in Chicago, Illinois , 1147 West Diversey Parkway
Lincoln Park Living - 3 Queen Beds - Sleeps 6 is located in Chicago, just 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.
  • Parking

Fabulous 48 Reviews 9.0

from $125.87 Show details »

Lincoln Park Living - Suite 1 in Chicago, USA

Lincoln Park Living - Suite 1

Holiday home in Chicago, Illinois , West Diversey Parkway
Lincoln Park Living - Suite 1 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.
  • Parking

Very good 38 Reviews 8.1

from $182.22 Show details »

Lincoln Park Living - Suite 2 in Chicago, USA

Lincoln Park Living - Suite 2

Holiday home in Chicago, Illinois , 1147 West Diversey Parkway
Lincoln Park Living - Suite 2 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.
  • Parking

Very good 21 Reviews 8.4

from $192.09 Show details »

Modern Lincoln Park Hideaway 1 Bd and 1Bath in Chicago, USA

Modern Lincoln Park Hideaway 1 Bd and 1B...

Holiday home in Chicago, Illinois , 1410 W Diversey Pkwy
Modern Lincoln Park Hideaway 1 Bd and 1Bath is located in Chicago, just 1.5 miles from Wrigley Field and 1.8 miles from Lincoln Park Zoo.
  • Parking
  • Pets allowed
  • Fitness centre
  • Spa and wellness centre

Good 1 Reviews 7.0

from $67.00 Show details »

The Logandale: HUGE Mid-Century Home, sleeps 15 in Chicago, USA

The Logandale: HUGE Mid-Century Home, sl...

Holiday home in Chicago, Illinois , 2920 North Gresham Avenue
The Logandale: HUGE Mid-Century Home, sleeps 15 offers accommodations in Chicago, 4.6 miles from Lincoln Park Zoo and 5.1 miles from United Center.
  • Parking
  • Family rooms
  • Kids' outdoor play equipment

Fabulous 6 Reviews 9.0

from $243.33 Show details »

The Avondale Guesthouse in Chicago, USA

The Avondale Guesthouse

Holiday home in Chicago, Illinois , 2973 North Elston Avenue
The Avondale Guesthouse is a recently renovated vacation home in Chicago where guests can make the most of the garden and barbecue facilities.
  • Parking
  • Family rooms

Exceptional 125 Reviews 9.6

from $115.86 Show details »

Roscoe Village Family Hideaway in Chicago, USA

Roscoe Village Family Hideaway

Holiday home in Chicago, Illinois , 1811 West Eddy Street
Roscoe Village Family Hideaway is located in Chicago, just a 19-minute walk from Wrigley Field and 3.2 miles from Lincoln Park Zoo.
  • Parking
  • Family rooms

Fabulous 1 Reviews 9.0

from $53.00 Show details »

You are currently on page 2 of Holiday homes in Chicago You’ll Love
Accommodation data and pictures provided by Booking.com