Short-Term Rentals in Near West Side, IL: Compare 10+ Sites & Save

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2389 Best Short-Term Rentals in Near West Side (Starting from $100)

1F Cozy Home in Little Italy near Downtown West Loop United Center
1F Cozy Home in Little Italy near Downtown West Loop United Center
Apartment
Chicago, IL, USA
0.3k from Near West Side center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

3 Bedrooms6 Guests
9.9

Exceptional

74 reviews

$172
Average price / night
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1F Chicago's Little italy Graystone nearDowntown
1F Chicago's Little italy Graystone nearDowntown
Apartment
Chicago, IL, 60607, United States
0.2k from Near West Side center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

175 reviews

$349
Average price / night
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Medical District 1BR w WD Gym nr Hospitals CHI-719
Medical District 1BR w WD Gym nr Hospitals CHI-719
Apartment
Near West Side, Chicago, Illinois, USA
0.6k from Near West Side center

Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$101
Average price / night
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3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Apartment
Chicago, IL, 60607, United States
0.2k from Near West Side center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

286 reviews

$340
Average price / night
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Chic 2 BR 1 Parking Sleeps 6
Chic 2 BR 1 Parking Sleeps 6
Apartment
Chicago, IL, USA
0.7k from Near West Side center

Security/Safety, Parking, Internet, Fireplace/Heating, Sports/Activities, Air Conditioner, Child Friendly

2 Bedrooms6 Guests
9.7

Exceptional

4 reviews

$368
Average price / night
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Luxurious & Cozy with an Amazing View in an area that offers it all w/transprtn\n
Luxurious & Cozy with an Amazing View in an area that offers it all w/transprtn\n
Condo
Chicago, IL, 60607, United States
0.3k from Near West Side center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$198
Average price / night
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Cozy 1 BR 1 Parking Sleeps 4
Cozy 1 BR 1 Parking Sleeps 4
Apartment
Chicago, IL, USA
0.7k from Near West Side center

Security/Safety, Parking, Internet, Fireplace/Heating, Sports/Activities, Air Conditioner, Child Friendly

1 Bedroom4 Guests
9.7

Exceptional

10 reviews

$265
Average price / night
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Blueground | Little Italy, pool, nr UIC
Blueground | Little Italy, pool, nr UIC
Apartment
Chicago, IL, 60607, United States
0.4k from Near West Side center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom2 Guests
New to Booking
$175
Average price / night
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Avra Stylish Apartments Prime West Loop Location Near Union Park
Avra Stylish Apartments Prime West Loop Location Near Union Park
Apartment
Chicago, IL, USA
0.7k from Near West Side center

Entertainment, Air Conditioner, Wellness Facilities, Business Services, Parking, View, Security/Safety

13 Bedrooms32 Guests
7.8

Good

10 reviews

$679
Average price / night
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Blueground | Little Italy, pool, nr National Museum of Mexican Art
Blueground | Little Italy, pool, nr National Museum of Mexican Art
Apartment
Chicago, IL, 60607, United States
0.5k from Near West Side center

AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$160
Average price / night
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2 Bedroom Home near West Loop with Parking
2 Bedroom Home near West Loop with Parking
Apartment
Chicago, IL, USA
0.8k from Near West Side center

Air Conditioner, Security/Safety, Fireplace/Heating, Pet Friendly, Parking, Internet, Child Friendly

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$351
Average price / night
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Blueground | Little Italy, pool, nr Union Park
Blueground | Little Italy, pool, nr Union Park
Apartment
Chicago, IL, 60607, United States
0.5k from Near West Side center

AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$185
Average price / night
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W Loop Studio w Gym Pool Coworking nr UIC CHI-397
W Loop Studio w Gym Pool Coworking nr UIC CHI-397
Apartment
Near West Side, Chicago, Illinois, USA
0.8k from Near West Side center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$100
Average price / night
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W Loop Studio w Gym Pool Coworking nr UIC CHI-439
W Loop Studio w Gym Pool Coworking nr UIC CHI-439
Apartment
Chicago, IL, USA
0.8k from Near West Side center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$129
Average price / night
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Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Apartment
Chicago, IL, 60607, United States
0.5k from Near West Side center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

338 reviews

$277
Average price / night
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Sage Modern Apartments Near Union Park in West Loop
Sage Modern Apartments Near Union Park in West Loop
Apartment
Chicago, IL, USA
0.9k from Near West Side center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay

6 Bedrooms15 Guests
9.7

Exceptional

14 reviews

$336
Average price / night
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Historic and Vintage Charm + Modern and Renovated Kitchen and Baths = WIN! by AllSet Turnover
Historic and Vintage Charm + Modern and Renovated Kitchen and Baths = WIN! by AllSet Turnover
House
Chicago, IL, 60612, United States
0.5k from Near West Side center

AC, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, Outdoor Space, TV

2 Bedrooms4 Guests
6.8

Good

3 reviews

$261
Average price / night
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2 Br 1 Free Parking Gym
2 Br 1 Free Parking Gym
Apartment
Chicago, IL, USA
0.9k from Near West Side center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$294
Average price / night
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The Neighborhood Hotel - Little Italy One Bedroom w/ Balcony
The Neighborhood Hotel - Little Italy One Bedroom w/ Balcony
Apartment
Chicago, IL, 60607-4625, United States
0.5k from Near West Side center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$380
Average price / night
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Gym Garage Parking Balcony Sleeps 4
Gym Garage Parking Balcony Sleeps 4
Apartment
Chicago, IL, USA
0.9k from Near West Side center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$203
Average price / night
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The Neighborhood Hotel - Little Italy Studio
The Neighborhood Hotel - Little Italy Studio
Apartment
Chicago, IL, 60607-4625, United States
0.5k from Near West Side center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

5 reviews

$308
Average price / night
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Spacious 3-Bed West Loop Townhouse, 1 Car Garage
Spacious 3-Bed West Loop Townhouse, 1 Car Garage
House
Chicago, IL, USA
1.1k from Near West Side center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$513
Average price / night
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Blueground | West Loop, rooftop, nr Union Station
Blueground | West Loop, rooftop, nr Union Station
Apartment
Chicago, IL, 60607, United States
0.6k from Near West Side center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Living Area

1 Bedroom2 Guests
New to Booking
$193
Average price / night
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Spacious 1 BDR Apartment
Spacious 1 BDR Apartment
Apartment
Near West Side, Chicago, Illinois, USA
1.1k from Near West Side center

Internet, Air Conditioner, Wheelchair Accessible, Parking, Child Friendly

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$138
Average price / night
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Blueground | West Loop, rooftop, nr Union Park
Blueground | West Loop, rooftop, nr Union Park
Apartment
Chicago, IL, 60607, United States
0.6k from Near West Side center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Living Area

1 Bedroom2 Guests
New to Booking
$179
Average price / night
Check Availability
Mod Medical District 1BR w/ W/D, Roof & Gym, nr Hospitals, by Blueground
Mod Medical District 1BR w/ W/D, Roof & Gym, nr Hospitals, by Blueground
Apartment
Chicago, IL, 60607, United States
0.6k from Near West Side center

AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom2 Guests
New to Booking
$167
Average price / night
Check Availability
The Neighborhood Hotel - Little Italy Two Bedroom
The Neighborhood Hotel - Little Italy Two Bedroom
Apartment
Chicago, IL, 60607-4625, United States
0.6k from Near West Side center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$426
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Near West Side.

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Near West Side Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 2389 verified short-term rentals in Near West Side, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Near West Side vary depending on location, property size, and travel dates. Rates typically start from around $100 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Near West Side include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Near West Side, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Near West Side often include amenities such as Fireplace/Heating, Wellness Facilities, and Internet, providing a comfortable and convenient stay.

Short-term rentals in Near West Side are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.