Owner Direct Vacation Rentals in Illinois Medical District

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2123 Illinois Medical District Vacation Homes From $101

Looking for the ideal vacation rental in Illinois Medical District? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Modern Comfort in Tri-Taylor
Modern Comfort in Tri-Taylor
Apartment
Chicago, IL, USA
0.8k from Illinois Medical District center

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

3 Bedrooms8 Guests
New to Booking
$276
Average price / night
Check Availability
Spacious 2BR - 10 mins from Downtown
Spacious 2BR - 10 mins from Downtown
Apartment
Chicago, IL, 60612, United States
0.6k from Illinois Medical District center

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

2 Bedrooms4 Guests
9.0

Fabulous

6 reviews

$276
Average price / night
Check Availability
Newly Updated Vintage 6 Bedroom Single Family Home home
Newly Updated Vintage 6 Bedroom Single Family Home home
House
Chicago, IL, USA
0.8k from Illinois Medical District center

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

6 Bedrooms12 Guests
New to Booking
$535
Average price / night
Check Availability
Landing | Spectacular 1BD, Gym, Rooftop Lounge
Landing | Spectacular 1BD, Gym, Rooftop Lounge
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

AC, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$165
Average price / night
Check Availability
Medical District 1BR w WD Gym nr Hospitals CHI-719
Medical District 1BR w WD Gym nr Hospitals CHI-719
Apartment
Illinois Medical District, Chicago, Illinois, USA
0.8k from Illinois Medical District center

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

1 Bedroom2 Guests
New to Booking
$101
Average price / night
Check Availability
Landing | Modern 1BD, Pool, Yoga Studio
Landing | Modern 1BD, Pool, Yoga Studio
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

AC, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$136
Average price / night
Check Availability
The Upscale Getaway Near Downtown
The Upscale Getaway Near Downtown
Apartment
Chicago, IL, USA
1.0k from Illinois Medical District 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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Quick Drive to Downtown Chicago & Early Check-In
Quick Drive to Downtown Chicago & Early Check-In
Apartment
Chicago, IL, USA
1.0k from Illinois Medical District 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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Landing | Chic 1BD, Pool, Yoga Studio
Landing | Chic 1BD, Pool, Yoga Studio
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

AC, Balcony, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$137
Average price / night
Check Availability
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
1.0k from Illinois Medical District 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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Landing | Incredible 1BD, Rooftop Lounge, Gym
Landing | Incredible 1BD, Rooftop Lounge, Gym
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

AC, Balcony, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$145
Average price / night
Check Availability
2 Bed & 3 Bath Chicago Condo
2 Bed & 3 Bath Chicago Condo
Apartment
Chicago, IL, USA
1.1k from Illinois Medical District center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Condos

2 Bedrooms6 Guests
6.3

Good

7 reviews

$320
Average price / night
Check Availability
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
1.1k from Illinois Medical District center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$120
Average price / night
Check Availability
Landing | Stylish 1BD, Pool, Rooftop Lounge
Landing | Stylish 1BD, Pool, Rooftop Lounge
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

AC, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$138
Average price / night
Check Availability
Landing | Modern 1BD, Yoga Studio, Rooftop Lounge
Landing | Modern 1BD, Yoga Studio, Rooftop Lounge
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

AC, Balcony, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$190
Average price / night
Check Availability
Landing | Beautiful 1BD, Yoga Studio, Pool
Landing | Beautiful 1BD, Yoga Studio, Pool
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

AC, Balcony, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$188
Average price / night
Check Availability
Breathtaking & Bright: Designer 2BD with Garage
Breathtaking & Bright: Designer 2BD with Garage
Apartment
Chicago, IL, 60612, United States
0.7k from Illinois Medical District center

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

1 Bedroom6 Guests
9.0

Fabulous

4 reviews

$235
Average price / night
Check Availability
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
0.8k from Illinois Medical District center

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

1 Bedroom2 Guests
New to Booking
$101
Average price / night
Check Availability
Blueground | Little Italy, pool, nr Union Park
Blueground | Little Italy, pool, nr Union Park
Apartment
Chicago, IL, 60607, United States
0.8k from Illinois Medical District center

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

1 Bedroom2 Guests
New to Booking
$106
Average price / night
Check Availability
Blueground | Little Italy, pool, nr UIC
Blueground | Little Italy, pool, nr UIC
Apartment
Chicago, IL, 60607, United States
0.8k from Illinois Medical District center

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

1 Bedroom2 Guests
New to Booking
$108
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 Illinois Medical District.

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Frequently Asked Questions

There are a lot of options in Illinois Medical District. If you plan on staying in the Illinois Medical District area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Illinois Medical District

You can explore 2123 verified vacation rentals in Illinois Medical District. 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 Illinois Medical District vary depending on the season, property size, and location. Rates typically start from around $101 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 Illinois Medical District 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 Illinois Medical District welcome pets. Currently, 31 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 Illinois Medical District often include amenities such as Fireplace/Heating, Laundry, and Kitchen. 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.