Illinois, USA Vacation Rentals

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United States Illinois Chicago vacation rental compare prices direct by owner 26545643

Top Floor Views + Central Comfort

4.8 (150)

2 Bedrooms • 6 Guests

$673 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 32827287

Villa Dubois 3 Bedroom Suite -2

5.0 (1)

3 Bedrooms • 6 Guests

$664 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 36386316

2 Newly Built Luxury Condos with Private Roofdeck!

4.5 (7)

5 Bedrooms • 16 Guests

$590 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 36386317

Brownstone, 2 entire units Gold Coast

4.4 (19)

2 Bedrooms • 14 Guests

$376 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40778135

Villa Dubois Guest House Room 1

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United States Illinois Chicago vacation rental compare prices direct by owner 32816472

Villa Dubois 3 Bedroom Suite - 1

0.0 (0)

3 Bedrooms • 6 Guests

Available on

United States Illinois Chicago vacation rental compare prices direct by owner 40879833

Front Row to the Lake & Skyline: Epic 60th Flr 3BR

5.0 (47)

3 Bedrooms • 7 Guests

$1,824 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40850925

Stylish Kitchenette and Sophisticated Amenities - Elegant Airy Studio

5.0 (80)

1 Bedroom • 2 Guests

$264 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879771

Luxury Downtown 4BR | Exclusive Design PH

5.0 (43)

4 Bedrooms • 9 Guests

$3,205 avg/night

United States Illinois Saint Charles vacation rental compare prices direct by owner 40860189

Grand Estate at the Preserve

5.0 (31)

6 Bedrooms • 16 Guests

$1,724 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879746

Luxury 2BR near Millennium Park + 5-Star Reviews

5.0 (85)

2 Bedrooms • 5 Guests

$846 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879742

5-Star Gold Coast Experience in a Luxe 2BR Retreat

5.0 (134)

2 Bedrooms • 5 Guests

$820 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879764

Elegant 2BR with Resort Amenities & City Views

5.0 (97)

2 Bedrooms • 7 Guests

$1,002 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879773

Prime 4BR Penthouse w/ Skyline Views for Families

5.0 (60)

4 Bedrooms • 8 Guests

$1,233 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879804

Elevated 2BR Retreat + Balcony with Bean Views

4.9 (32)

2 Bedrooms • 6 Guests

$1,323 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879809

43rd-Floor Luxury Escape + Lake Views

4.9 (49)

2 Bedrooms • 5 Guests

$980 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879758

Luxe 1BR: Unmatched Views & Location

4.9 (74)

1 Bedroom • 3 Guests

$567 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879735

Downtown Luxury + Unmatched Comfort

4.9 (74)

2 Bedrooms • 5 Guests

$842 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879790

Exclusive 3BR with Views, Ideal for Tourists

4.9 (86)

3 Bedrooms • 6 Guests

$1,118 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40702476

The Neighborhood Hotel - Lincoln Park 202 - One Bedroom w/ Patio

4.9 (55)

1 Bedroom • 2 Guests

$566 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879749

Panoramic City Views + Prime West Loop Location

4.9 (97)

2 Bedrooms • 5 Guests

$653 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40850926

Modern 1BR in Little Italy, Near West Loop

4.9 (175)

1 Bedroom • 4 Guests

$359 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40879796

Explore Fulton Market + Retreat in Modern Comfort

4.9 (58)

2 Bedrooms • 5 Guests

$634 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40702470

2 Bedroom Apartment in the Heart of Lincoln Park

4.9 (85)

2 Bedrooms • 6 Guests

$660 avg/night

United States Illinois Chicago vacation rental compare prices direct by owner 40702479

Lincoln Park Gem: 1-BR Modern Apartment

4.9 (53)

1 Bedroom • 2 Guests

$441 avg/night

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