Vacation Rentals in Tri-Taylor, IL: Compare 10+ Sites & Save

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2298 Best Vacation Rentals in Tri-Taylor (Starting from $47)

Newly Updated Vintage 6 Bedroom Single Family Home home
Newly Updated Vintage 6 Bedroom Single Family Home home
House
Chicago, IL, USA
0.1k from Tri-Taylor center

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

6 Bedrooms12 Guests
New to Booking
$535
Average price / night
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Stylish 2-Bedroom Retreat with Parking and Balcony
Stylish 2-Bedroom Retreat with Parking and Balcony
Apartment
Chicago, IL, 60612, United States
0.1k from Tri-Taylor center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$532
Average price / night
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Modern Comfort in Tri-Taylor
Modern Comfort in Tri-Taylor
Apartment
Chicago, IL, USA
0.2k from Tri-Taylor center

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

3 Bedrooms8 Guests
New to Booking
$276
Average price / night
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Enjoy our 2BD 2BD Condo with Parking in Tri Taylor
Enjoy our 2BD 2BD Condo with Parking in Tri Taylor
Apartment
Chicago, IL, 60612, United States
0.1k from Tri-Taylor center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$558
Average price / night
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The Upscale Getaway Near Downtown
The Upscale Getaway Near Downtown
Apartment
Chicago, IL, USA
0.3k from Tri-Taylor center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms6 Guests
8.0

Good

3 reviews

$371
Average price / night
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Spacious Chicago Getaway with Balcony and Parking
Spacious Chicago Getaway with Balcony and Parking
Apartment
Chicago, IL, 60612, United States
0.1k from Tri-Taylor center

AC, Balcony, Breakfast Available, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$570
Average price / night
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Quick Drive to Downtown Chicago & Early Check-In
Quick Drive to Downtown Chicago & Early Check-In
Apartment
Chicago, IL, USA
0.3k from Tri-Taylor center

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

2 Bedrooms4 Guests
9.3

Superb

3 reviews

$293
Average price / night
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Tri-Taylor 2BD 2BA Designer Condo with Parking
Tri-Taylor 2BD 2BA Designer Condo with Parking
Apartment
Chicago, IL, 60612, United States
0.1k from Tri-Taylor center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$624
Average price / night
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The Haven, Great Location near Downtown, Medical District and United Center
The Haven, Great Location near Downtown, Medical District and United Center
Apartment
Chicago, IL, USA
0.5k from Tri-Taylor center

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

3 Bedrooms6 Guests
9.7

Exceptional

8 reviews

$314
Average price / night
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Luxury 2BD Med District Apt w/ Balcony and Parking
Luxury 2BD Med District Apt w/ Balcony and Parking
Apartment
Chicago, IL, 60612, United States
0.1k from Tri-Taylor center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$693
Average price / night
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EMALUX Condo Near Downtown,Bus,Train,Hospitals,United-Center,Fulton Market
EMALUX Condo Near Downtown,Bus,Train,Hospitals,United-Center,Fulton Market
Apartment
Chicago, IL, USA
0.5k from Tri-Taylor center

Parking, Air Conditioner, Internet, Child Friendly

3 Bedrooms6 Guests
6.8

Good

10 reviews

$504
Average price / night
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Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
House
Chicago, IL, 60612, United States
0.1k from Tri-Taylor center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Laundry

6 Bedrooms12 Guests
9.0

Fabulous

21 reviews

$654
Average price / night
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The Banksy-Free Parking -4 bedroom w King bed- Firepit Rooftop near United Center
The Banksy-Free Parking -4 bedroom w King bed- Firepit Rooftop near United Center
Apartment
Chicago, IL, USA
0.7k from Tri-Taylor center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

4 Bedrooms12 Guests
9.2

Superb

11 reviews

$654
Average price / night
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Breathtaking & Bright: Designer 2BD with Garage
Breathtaking & Bright: Designer 2BD with Garage
Apartment
Chicago, IL, 60612, United States
0.1k from Tri-Taylor center

AC, Crib, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

1 Bedroom6 Guests
9.4

Superb

3 reviews

$311
Average price / night
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15mins DT Wicker Park Gem Sleeps 7 FreePark
15mins DT Wicker Park Gem Sleeps 7 FreePark
Apartment
Chicago, IL, USA
0.9k from Tri-Taylor center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms2 Guests
New to Booking
$514
Average price / night
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Spacious 2BR - 10 mins from Downtown
Spacious 2BR - 10 mins from Downtown
Apartment
Chicago, IL, 60612, United States
0.2k from Tri-Taylor center

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

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$320
Average price / night
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Adults Only - Walk to the United Center! Modern Touches Surround You - Check Out the Open Staircase! apts
Adults Only - Walk to the United Center! Modern Touches Surround You - Check Out the Open Staircase! apts
Apartment
Chicago, IL, USA
0.9k from Tri-Taylor center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$120
Average price / night
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Quiet, Furnished Private Room, Utilities & Fast Wi-Fi, Near UIC & Hospitals
Quiet, Furnished Private Room, Utilities & Fast Wi-Fi, Near UIC & Hospitals
House
Chicago, IL, 60612, United States
0.2k from Tri-Taylor center

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

1 Bedroom1 Guest
New to Booking
$47
Average price / night
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Spacious Room by Medical District & UIC
Spacious Room by Medical District & UIC
House
Chicago, IL, USA
1.0k from Tri-Taylor center

Cheap, Accommodations, Parking, Homestays, Lodgings, Places to stay

1 Bedroom1 Guest
9.0

Fabulous

2 reviews

$48
Average price / night
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Modern 2BR, Private Elevator, Near United Center and Secure Parking
Modern 2BR, Private Elevator, Near United Center and Secure Parking
Apartment
Chicago, IL, 60612, United States
0.2k from Tri-Taylor center

AC, Dryer, Heater, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$208
Average price / night
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Charming Shared Condo in Prime Chicago Location, 1 Bedroom and 1 Bathroom
Charming Shared Condo in Prime Chicago Location, 1 Bedroom and 1 Bathroom
House
Chicago, IL, USA
1.1k from Tri-Taylor center

B&bs, Accommodations, Parking, Guest houses, Homestays, Lodgings, Places to stay, Condos

3 Bedrooms6 Guests
1.0

Review score

1 reviews

$160
Average price / night
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Medical District Gem III
Medical District Gem III
Apartment
Chicago, IL, 60608, United States
0.2k from Tri-Taylor center

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

1 Bedroom2 Guests
New to Booking
$101
Average price / night
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Furnished Private Room near Illinois Medical District & UIC
Furnished Private Room near Illinois Medical District & UIC
House
Chicago, IL, 60612, United States
0.3k from Tri-Taylor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV

1 Bedroom1 Guest
New to Booking
$59
Average price / night
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Medical District Gem II
Medical District Gem II
Apartment
Chicago, IL, 60608, United States
0.3k from Tri-Taylor center

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

1 Bedroom2 Guests
New to Booking
$111
Average price / night
Check Availability
Chi-Town Chill - Get Anywhere in the City from This Perfectly Located Duplex by AllSet Turnover
Chi-Town Chill - Get Anywhere in the City from This Perfectly Located Duplex by AllSet Turnover
Apartment
Chicago, IL, 60612, United States
0.3k from Tri-Taylor center

AC, Crib, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.2

Superb

7 reviews

$383
Average price / night
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Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
Apartment
Chicago, IL, 60612, United States
0.3k from Tri-Taylor center

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

2 Bedrooms6 Guests
8.0

Good

15 reviews

$323
Average price / night
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Welcome to our modern Chicago living! Free parking, in the heart of the city.
Welcome to our modern Chicago living! Free parking, in the heart of the city.
Apartment
Chicago, IL, 60612, United States
0.4k from Tri-Taylor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
New to Booking
$198
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 Vacation Rentals in Tri-Taylor.

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Frequently Asked Questions

You can explore 2298 verified vacation rentals in Tri-Taylor. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Tri-Taylor vary depending on the season, property size, and location. Rates typically start from around $47 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Tri-Taylor include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Tri-Taylor welcome pets. Currently, 32 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Tri-Taylor often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.