Holiday rentals near Cloud Gate

We found 3,684 holiday rentals — enter your dates for availability

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January 2026

February 2026

Choose the perfect private holiday rental within close proximity to Cloud Gate. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and air conditioning. At the end of the day, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Cloud Gate

Showing deals for:3 Apr - 10 Apr

Exceptional

(5 reviews)

Charming 2-bedroom apartment in hip Chicago

Chicago

14% off

for 7 nights, 1 apartment

AU$332 per night

includes taxes & fees

Very good

(16 reviews)

Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO

Rosemont

12% off

for 7 nights, 1 apartment

AU$297 per night

includes taxes & fees

Exceptional

(19 reviews)

BoHo House - A Chic, 1903 Chicago Workers Cottage

Chicago

11% off

for 7 nights, 1 home

AU$646 per night

includes taxes & fees

Exceptional

(18 reviews)

Luxurious, custom built single family home near Wrigley

Chicago

7% off

for 7 nights, 1 home

AU$2,058 per night

includes taxes & fees

Front 1/2 of first floor (old dining table)

Exceptional

(70 reviews)

1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier

Chicago

7% off

for 7 nights, 1 home

AU$665 per night

includes taxes & fees

Wonderful

(13 reviews)

4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off

for 7 nights, 1 home

AU$751 per night

includes taxes & fees

Exceptional

(183 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

14% off

for 7 nights, 1 home

AU$874 per night

includes taxes & fees

Excellent

(15 reviews)

Brand New 3BR/2BA • Washer/Dryer • 5 Min to Downtown

Chicago

7% off

for 7 nights, 1 apartment

AU$899 per night

includes taxes & fees

Exceptional

(9 reviews)

1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off

for 7 nights, 1 home

AU$745 per night

includes taxes & fees

Exceptional

(15 reviews)

1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off

for 7 nights, 1 apartment

AU$764 per night

includes taxes & fees

Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.

Exceptional

(69 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off

for 7 nights, 1 home

AU$1,234 per night

includes taxes & fees

Excellent

(10 reviews)

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

7% off

for 7 nights, 1 home

AU$1,386 per night

includes taxes & fees

Exceptional

(91 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off

for 7 nights, 1 apartment

AU$2,154 per night

includes taxes & fees

Exceptional

(14 reviews)

Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking

Chicago

14% off

for 7 nights, 1 apartment

AU$401 per night

includes taxes & fees

Wonderful

(14 reviews)

Family fun-house w/POOL & Game Room, 5 min from Airport and Rosement attractions

Des Plaines

9% off

for 7 nights, 1 home

AU$601 per night

includes taxes & fees

Exceptional

(11 reviews)

Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!

Chicago

6% off

for 7 nights, 1 apartment

AU$364 per night

includes taxes & fees

Exceptional

(6 reviews)

Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago

Chicago

7% off

for 7 nights, 1 apartment

AU$678 per night

includes taxes & fees

Open living room features vaulted ceilings and hardwood floors.

Exceptional

(27 reviews)

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Chicago

7% off

for 7 nights, 1 apartment

AU$456 per night

includes taxes & fees

Exceptional

(31 reviews)

Great Evanston Home- great for traveling families! Parking Included

Evanston

15% off

for 7 nights, 1 apartment

AU$600 per night

includes taxes & fees

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Cloud Gate

Find the best place to stay - Cloud Gate

Premier Host

Carriage House

Sleeps 2 · 1 bedroom · 1 bathroom

Cozy 2BR Self-checkin unit in Chicago l Few Steps from DT I Car Rental Available

Sleeps 5 · 2 bedrooms · 1 bathroom

Top rated rentals - Cloud Gate

Premier Host

Fabulous

The property is a fully equipped home, has everything you need and makes life simple while you are there. The owner is also right next door and very responsive, friendly and helpful. Taylor street is a very short walk away, the pink line is a short walk away, great location, very quiet.

Robin N.

Stayed July 2024

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value