Heart of Chicago Vacation Rentals & Ski-in/Ski-out Homes

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

New Spacious Pilsen 4 Bed 4 Bath Family Retreat
Apartment
Spacious Pilsen 4 Bed 4 Bath Family Retreat
From US $479 per night
New
4 Bedrooms 8 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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Villa Dubois Guest House Room 5
Bed & Breakfast
Villa Dubois Guest House Room 5
From US $241 per night
New
1 Bedroom 2 Guests
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MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Condo
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
From US $354 per night
10.0 (23 Reviews)
2 Bedrooms 6 Guests
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Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Apartment
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
From US $309 per night
New
3 Bedrooms 10 Guests
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Family Friendly 2-Bedroom w/Kitchen & Laundry
Apartment
Family Friendly 2-Bedroom w/Kitchen & Laundry
From US $263 per night
10.0 (20 Reviews)
2 Bedrooms 5 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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Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
Condo
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
From US $380 per night
10.0 (8 Reviews)
2 Bedrooms 6 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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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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Charming 2-bedroom apartment in hip Chicago
Apartment
Charming 2-bedroom apartment in hip Chicago
From US $243 per night
10.0 (5 Reviews)
2 Bedrooms 4 Guests
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Hamaline Luxury Guest House
Villa
Hamaline Luxury Guest House
From US $289 per night
|
10.0 (2 Reviews)
3 Bedrooms 6 Guests
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Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
Apartment
Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
From US $823 per night
10.0 (4 Reviews)
1 Bedroom 4 Guests
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Luxéry Stay South Loop - McCormick/Wintrust Area
Apartment
Luxéry Stay South Loop - McCormick/Wintrust Area
From US $759 per night
10.0 (4 Reviews)
1 Bedroom 4 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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The Landmark; a comfy suite near McCormick Place
Apartment
The Landmark; a comfy suite near McCormick Place
From US $228 per night
10.0 (3 Reviews)
1 Bedroom 2 Guests
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Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Apartment
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
From US $168 per night
10.0 (3 Reviews)
1 Bedroom 5 Guests
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Designer 2BR in Walkable Fulton Market
Apartment
Designer 2BR in Walkable Fulton Market
From US $590 per night
10.0 (2 Reviews)
2 Bedrooms 5 Guests
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Downtown 2bd #6 +Gym near Park, Lake, Museums
Condo
Downtown 2bd #6 +Gym near Park, Lake, Museums
From US $365 per night
10.0 (2 Reviews)
2 Bedrooms 5 Guests
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2 Bedroom Home near West Loop with Parking
Apartment
2 Bedroom Home near West Loop with Parking
From US $352 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Downtown 2bd #4 - Near Grant Park, Museums, Lake
Condo
Downtown 2bd #4 - Near Grant Park, Museums, Lake
From US $343 per night
10.0 (2 Reviews)
2 Bedrooms 5 Guests
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1F Cozy Home in Little Italy near Downtown West Loop United Center
Apartment
1F Cozy Home in Little Italy near Downtown West Loop United Center
From US $172 per night
|
9.9 (74 Reviews)
3 Bedrooms 6 Guests
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Luxéry Stay "Game of Thrones" Downtown/McCormick/WinTrust Area
Apartment
Luxéry Stay "Game of Thrones" Downtown/McCormick/WinTrust Area
From US $778 per night
10.0 (2 Reviews)
1 Bedroom 4 Guests
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Downtown Penthouse Lake Views #1|Gym, Parking+Pool
Condo
Downtown Penthouse Lake Views #1|Gym, Parking+Pool
From US $530 per night
10.0 (2 Reviews)
2 Bedrooms 7 Guests
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Relaxing Studio with Private Patio Downtown Chicago
Apartment
Relaxing Studio with Private Patio Downtown Chicago
From US $526 per night
10.0 (2 Reviews)
1 Bedroom 4 Guests
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Charming Pilsen Studio - Quick Access to Downtown Chicago!
Apartment
Charming Pilsen Studio - Quick Access to Downtown Chicago!
From US $186 per night
10.0 (2 Reviews)
1 Bedroom 3 Guests
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Cozy Charming Art 🎨 Food🌮 Close to Train 🚉 Parking!
Apartment
Cozy Charming Art 🎨 Food🌮 Close to Train 🚉 Parking!
From US $211 per night
9.8 (93 Reviews)
2 Bedrooms 4 Guests
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First Floor Condo In Chicago
Apartment
First Floor Condo In Chicago
From US $178 per night
9.7 (15 Reviews)
2 Bedrooms 12 Guests
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Mccormick Place Guest House
House
Mccormick Place Guest House
From US $109 per night
|
8.2 (31 Reviews)
1 Bedroom 2 Guests
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The Upscale Getaway Near Downtown
Condo
The Upscale Getaway Near Downtown
From US $305 per night
9.8 (89 Reviews)
2 Bedrooms 6 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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Art Villa
Apartment
Art Villa
From US $1,240 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
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Safe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
Condo
Safe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
From US $400 per night
9.8 (41 Reviews)
2 Bedrooms 6 Guests
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The Wheeler Mansion
Hotel
The Wheeler Mansion
From US $724 per night
|
10.0 (1 Review)
1 Bedroom 2 Guests
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MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba
Condo
MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba
From US $391 per night
9.8 (26 Reviews)
2 Bedrooms 6 Guests
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Spacious 5-BR House near Transit w Parking
House
Spacious 5-BR House near Transit w Parking
From US $941 per night
|
9.6 (13 Reviews)
5 Bedrooms 16 Guests
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MICH AVE #23 2bd/2ba Downtown, Museums w/Views
Condo
MICH AVE #23 2bd/2ba Downtown, Museums w/Views
From US $361 per night
9.8 (24 Reviews)
2 Bedrooms 6 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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DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
Condo
DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
From US $490 per night
9.8 (16 Reviews)
2 Bedrooms 6 Guests
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Cozy Chicago Apartment next to the River
Apartment
Cozy Chicago Apartment next to the River
From US $153 per night
|
9.5 (12 Reviews)
2 Bedrooms 6 Guests
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Downtown Penthouse #5 | Vintage +gym & balcony
Condo
Downtown Penthouse #5 | Vintage +gym & balcony
From US $376 per night
9.8 (13 Reviews)
1 Bedroom 7 Guests
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Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
Condo
Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
From US $520 per night
9.8 (10 Reviews)
2 Bedrooms 7 Guests
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Downtown Mich Ave #7| Park View Penthouse +gym
Condo
Downtown Mich Ave #7| Park View Penthouse +gym
From US $363 per night
9.8 (6 Reviews)
2 Bedrooms 6 Guests
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Welcome to Lux! 2BR in Chicago!
Apartment
Welcome to Lux! 2BR in Chicago!
From US $208 per night
9.8 (6 Reviews)
2 Bedrooms 5 Guests
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Bridgeport Place - free parking, McCormick Place-Sox Park
Apartment
Bridgeport Place - free parking, McCormick Place-Sox Park
From US $227 per night
|
9.4 (9 Reviews)
1 Bedroom 4 Guests
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Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
Condo
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
From US $363 per night
9.6 (30 Reviews)
2 Bedrooms 6 Guests
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Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From US $294 per night
9.3 (3 Reviews)
2 Bedrooms 4 Guests
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Fun Downtown Penthouse #3 | Vintage +balcony&gym
Condo
Fun Downtown Penthouse #3 | Vintage +balcony&gym
From US $399 per night
9.6 (14 Reviews)
1 Bedroom 7 Guests
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About Heart of Chicago Vacation Rentals

Explore over 1497 vacation rentals in Heart of 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 Heart of 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 Heart of Chicago. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Heart of Chicago tailored to your preferences. On average, these rentals offer 781.94 ft² of space, and are priced at an average of US $376 per night.

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

Other Places to Stay in Heart of Chicago, IL


St Adalbert Church 2,708 Properties
Cooper Dual Language Academy 2,523 Properties
Mexican Fine Arts Center Museum 2,220 Properties
National Museum of Mexican Art 2,217 Properties
Canalport Riverwalk Park 1,643 Properties
Lower West Side 909 Properties

Frequently Asked Questions About Heart of Chicago?

What are the top vacation rentals in Heart of Chicago?

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

Discover the ideal vacation rental in Heart of Chicago with SunSki Resorts™. We provide an extensive selection of over 1497 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Heart of Chicago.

Nearby Neighborhood (5)

Neighborhood Property Count
Near West Side Vacation Rentals in Chicago, Illinois 63
University Village / Little Italy Vacation Rentals in Chicago, Illinois 743
Lower West Side Vacation Rentals in Chicago, Illinois 909
Pilsen Vacation Rentals in Chicago, Illinois 3300
McKinley Park Vacation Rentals in Chicago, Illinois 739

There are 1497 Heart of Chicago, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Heart of Chicago