Downtown Chicago Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in Downtown Chicago, Chicago, Illinois, USA

New Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
Apartment
Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
From US $347 per night
New
2 Bedrooms 4 Guests
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Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
Apartment
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
From US $107 per night
|
10.0 (10 Reviews)
3 Bedrooms 10 Guests
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The Publishing House B&B
Bed & Breakfast
The Publishing House B&B
From US $239 per night
|
9.8 (181 Reviews)
1 Bedroom 2 Guests
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Lux Apts with Lake Views and Top Amenities
Apartment
Lux Apts with Lake Views and Top Amenities
From US $1,582 per night
|
10.0 (3 Reviews)
13 Bedrooms 32 Guests
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Chicago Avenue Inn
House
Chicago Avenue Inn
From US $132 per night
7.0 (90 Reviews)
1 Bedroom 2 Guests
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New City Studio Escape Bright, Sleek & Modern
House
City Studio Escape Bright, Sleek & Modern
From US $270 per night
New
1 Bedroom 4 Guests
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Freshly Minted 2BR - Elegance & Comfort in Central Chicago
Apartment
Freshly Minted 2BR - Elegance & Comfort in Central Chicago
From US $349 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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4BR Corporate Suite Central and Modern
Hotel
4BR Corporate Suite Central and Modern
From US $486 per night
10.0 (3 Reviews)
4 Bedrooms 10 Guests
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Gold coast villa with free parking garage sleeps 10
Villa
Gold coast villa with free parking garage sleeps 10
From US $1,676 per night
|
10.0 (1 Review)
4 Bedrooms 10 Guests
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Perfect Location Across from Park & Train Station
House
Perfect Location Across from Park & Train Station
From US $734 per night
|
10.0 (1 Review)
5 Bedrooms 13 Guests
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52nd Floor MagMile Penthouse VIEWS Fireplace Pool
Apartment
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
From US $354 per night
10.0 (398 Reviews)
1 Bedroom 4 Guests
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New Luxury 3 Bdr Apt in Chicago C9
Apartment
New Luxury 3 Bdr Apt in Chicago C9
From US $1,516 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
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53 Floor MagMile Penthouse Views, Balcony, Pool
Apartment
53 Floor MagMile Penthouse Views, Balcony, Pool
From US $420 per night
10.0 (236 Reviews)
2 Bedrooms 6 Guests
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Historic luxury Townhouse in Downtown Chicago
House
Historic luxury Townhouse in Downtown Chicago
From US $1,961 per night
|
9.8 (7 Reviews)
5 Bedrooms 10 Guests
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51st Floor MagMile Penthouse Views Balcony Pool
Apartment
51st Floor MagMile Penthouse Views Balcony Pool
From US $375 per night
10.0 (224 Reviews)
1 Bedroom 4 Guests
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Sage Modern Apartments Near Union Park in West Loop
Apartment
Sage Modern Apartments Near Union Park in West Loop
From US $336 per night
|
9.7 (14 Reviews)
6 Bedrooms 15 Guests
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53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
Apartment
53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
From US $901 per night
10.0 (203 Reviews)
2 Bedrooms 8 Guests
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Fulbrix Bright Designer Apartments with West Loop Views
Apartment
Fulbrix Bright Designer Apartments with West Loop Views
From US $872 per night
|
9.5 (34 Reviews)
13 Bedrooms 32 Guests
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51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
Apartment
51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
From US $837 per night
10.0 (187 Reviews)
2 Bedrooms 7 Guests
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Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
Apartment
Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
From US $350 per night
9.5 (4 Reviews)
2 Bedrooms 4 Guests
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52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
Apartment
52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
From US $375 per night
10.0 (61 Reviews)
1 Bedroom 4 Guests
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Foundry Unmatched Skyline Views at Lincoln Park
Apartment
Foundry Unmatched Skyline Views at Lincoln Park
From US $376 per night
|
9.4 (11 Reviews)
4 Bedrooms 8 Guests
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50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
Apartment
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
From US $296 per night
10.0 (24 Reviews)
1 Bedroom 2 Guests
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The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
Apartment
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
From US $1,103 per night
|
9.2 (28 Reviews)
9 Bedrooms 24 Guests
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K2 Sky High Apartments with Stunning Chicago Views in West Loop
Apartment
K2 Sky High Apartments with Stunning Chicago Views in West Loop
From US $531 per night
|
9.2 (17 Reviews)
17 Bedrooms 43 Guests
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Downtown Guild #3 | Mag Mile Gold Coast The Lake!
Condo
Downtown Guild #3 | Mag Mile Gold Coast The Lake!
From US $312 per night
10.0 (19 Reviews)
1 Bedroom 4 Guests
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ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
Apartment
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
From US $180 per night
|
9.2 (17 Reviews)
3 Bedrooms 6 Guests
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53-54 Floor Penthouse
Apartment
53-54 Floor Penthouse
From US $601 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
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Post Chicago Getaway Ideal 4BR for Groups
Apartment
Post Chicago Getaway Ideal 4BR for Groups
From US $751 per night
|
9.2 (15 Reviews)
24 Bedrooms 48 Guests
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Downtown Charm: 2BR, Comfort, Great Amenities
Apartment
Downtown Charm: 2BR, Comfort, Great Amenities
From US $528 per night
10.0 (7 Reviews)
2 Bedrooms 5 Guests
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Cozy Casa by OHare Airport
Apartment
Cozy Casa by OHare Airport
From US $118 per night
9.2 (6 Reviews)
1 Bedroom 9 Guests
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Unbeatable Top Floor: Views, Central, Modern
Apartment
Unbeatable Top Floor: Views, Central, Modern
From US $619 per night
10.0 (6 Reviews)
2 Bedrooms 6 Guests
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UrbanEden Loft Apartment
Apartment
UrbanEden Loft Apartment
From US $103 per night
9.2 (5 Reviews)
2 Bedrooms 4 Guests
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Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Apartment
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
From US $294 per night
10.0 (6 Reviews)
2 Bedrooms 4 Guests
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ENVITAE 3BR Downtown Luxurious Suite Views & Pool
Apartment
ENVITAE 3BR Downtown Luxurious Suite Views & Pool
From US $1,703 per night
|
9.0 (20 Reviews)
3 Bedrooms 7 Guests
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The Loop 2BR: Historic, Modern Luxury, Amenities
Apartment
The Loop 2BR: Historic, Modern Luxury, Amenities
From US $640 per night
10.0 (5 Reviews)
2 Bedrooms 5 Guests
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Beautiful Chicago 2BD 1BA, minutes from Downtown!
Apartment
Beautiful Chicago 2BD 1BA, minutes from Downtown!
From US $236 per night
10.0 (5 Reviews)
2 Bedrooms 4 Guests
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Chic River North Condo 2BR 2BA with Private Balcony
Apartment
Chic River North Condo 2BR 2BA with Private Balcony
From US $493 per night
10.0 (4 Reviews)
2 Bedrooms 5 Guests
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Stylish 1BR in West Loop
Apartment
Stylish 1BR in West Loop
From US $270 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
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Chic 2BR 2BA Condo with Balcony - River North Chicago
Apartment
Chic 2BR 2BA Condo with Balcony - River North Chicago
From US $460 per night
10.0 (3 Reviews)
2 Bedrooms 4 Guests
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Downtown Retreat: 2BR, Balcony, Resort Comfort
Apartment
Downtown Retreat: 2BR, Balcony, Resort Comfort
From US $575 per night
10.0 (3 Reviews)
2 Bedrooms 7 Guests
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2BR City Escape
Hotel
2BR City Escape
From US $399 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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1BR Adorable Apt with In-unit Laundry - Lake 206 rep
Apartment
1BR Adorable Apt with In-unit Laundry - Lake 206 rep
From US $658 per night
|
9.0 (3 Reviews)
1 Bedroom 2 Guests
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The Langham, Chicago
Hotel
The Langham, Chicago
From US $613 per night
|
9.8 (1007 Reviews)
1 Bedroom 2 Guests
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River North | Rooftop With In & Out Parking | 5
Apartment
River North | Rooftop With In & Out Parking | 5
From US $344 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
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Beautiful 5br home for 14 guests with free parking
Villa
Beautiful 5br home for 14 guests with free parking
From US $1,620 per night
|
9.0 (2 Reviews)
5 Bedrooms 14 Guests
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The Peninsula Chicago
Hotel
The Peninsula Chicago
From US $734 per night
|
9.8 (1005 Reviews)
1 Bedroom 2 Guests
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Spacious 1 bd sleeps 4 quiet and near Michigan Ave
Apartment
Spacious 1 bd sleeps 4 quiet and near Michigan Ave
From US $318 per night
10.0 (1 Review)
1 Bedroom 5 Guests
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*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Apartment
*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
From US $294 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Chic|Comfy|Renovated1Bd1Ba Perfect for Couples
Apartment
Chic|Comfy|Renovated1Bd1Ba Perfect for Couples
From US $293 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
Apartment
New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
From US $464 per night
8.7 (3 Reviews)
5 Bedrooms 10 Guests
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Aurelien Spacious Apartments in the Heart of Gold Coast
Apartment
Aurelien Spacious Apartments in the Heart of Gold Coast
From US $1,810 per night
|
8.6 (42 Reviews)
10 Bedrooms 25 Guests
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Alluring Studio Apartment in Jefferson Park - Leland 1N
Apartment
Alluring Studio Apartment in Jefferson Park - Leland 1N
From US $209 per night
|
8.5 (2 Reviews)
1 Bedroom 2 Guests
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Chic Studio in Heart of Chicago
Apartment
Chic Studio in Heart of Chicago
From US $217 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
Apartment
Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
From US $319 per night
|
8.3 (30 Reviews)
13 Bedrooms 27 Guests
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River North Luxury Condo 2 King Beds 2 Baths
Apartment
River North Luxury Condo 2 King Beds 2 Baths
From US $215 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Studio flat in the heart of Downtown Chicago
Apartment
Studio flat in the heart of Downtown Chicago
From US $346 per night
|
8.0 (16 Reviews)
1 Bedroom 3 Guests
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Luxe Near North 2BR w/Roof & Gym, close to Red Line, by Blueground
Apartment
Luxe Near North 2BR w/Roof & Gym, close to Red Line, by Blueground
From US $203 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Avra Stylish Apartments Prime West Loop Location Near Union Park
Apartment
Avra Stylish Apartments Prime West Loop Location Near Union Park
From US $679 per night
|
7.8 (10 Reviews)
13 Bedrooms 32 Guests
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About Downtown Chicago Vacation Rentals

Explore over 2428 vacation rentals in Downtown Chicago with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Downtown Chicago for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Downtown Chicago. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Downtown Chicago tailored to your preferences. On average, these rentals offer 697.39 ft² of space, and are priced at an average of US $436 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Downtown Chicago at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Other Places to Stay in Downtown Chicago, IL


Chicago 7,285 Properties
Chicago 4,229 Properties
West Loop Gate 2,257 Properties
Central Chicago 1,825 Properties
The Loop 761 Properties
Near North Side 694 Properties
River North 363 Properties
Streeterville 203 Properties
West Loop 199 Properties
Rush and Division 74 Properties
Gold Coast 38 Properties
Killgubbin 33 Properties

Frequently Asked Questions About Downtown Chicago?

What are the top vacation rentals in Downtown Chicago?

How many SunSkiResorts vacation rentals or resorts are available in Downtown Chicago?

Discover the ideal vacation rental in Downtown Chicago with SunSki Resorts™. We provide an extensive selection of over 2428 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Downtown Chicago.

Nearby Neighborhood (16)

Neighborhood Property Count
The Loop Vacation Rentals in Chicago, Illinois 761
Near North Side Vacation Rentals in Chicago, Illinois 694
South Loop Vacation Rentals in Chicago, Illinois 380
Near South Side Vacation Rentals in Chicago, Illinois 368
River North Vacation Rentals in Chicago, Illinois 363
Near West Side Vacation Rentals in Chicago, Illinois 329
West Town Vacation Rentals in Chicago, Illinois 297
Streeterville Vacation Rentals in Chicago, Illinois 203
West Loop Vacation Rentals in Chicago, Illinois 199
Lincoln Park Vacation Rentals in Chicago, Illinois 155
University Village / Little Italy Vacation Rentals in Chicago, Illinois 88
Old Town Vacation Rentals in Chicago, Illinois 54
River West Vacation Rentals in Chicago, Illinois 51
Gold Coast Vacation Rentals in Chicago, Illinois 38
Magnificent Mile Vacation Rentals in Chicago, Illinois 4128
Lakeshore East Vacation Rentals in Chicago, Illinois 735

There are 2428 Downtown Chicago, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Downtown Chicago