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Illinois Medical District vacation rentals

We found 1,421 vacation rentals — enter your dates for availability

Discover a selection of 1,500 vacation rentals in Illinois Medical District, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $80 per night, and condos and houses are popular options for a stay in Illinois Medical District. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Condos/Apartments

View 1,114 Condos/Apartments

Houses

View 213 Houses

Townhouses

View 15 Townhouses

Studios

View 1,028 Studios

Find the best place to stay — Illinois Medical District

Finest Flat in UIC/Medical District w Parking

Sleeps 5 · 2 Bedrooms · 2 Bathrooms
$137 avg/night
(66)

Entire Apt. Private entrance near United Center, RUSH, UIC & Downtown

Sleeps 5 · 2 Bedrooms · 1 Bathroom
$80 avg/night
(11)

55/56th Floor Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$686 avg/night
(212)

52nd Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Pool, WiFi

Sleeps 4 · 1 Bedroom · 1 Bathroom
$252 avg/night
(329)

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 Bedroom · 1 Bathroom
$251 avg/night
(124)

Bella Villa onTaylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$167 avg/night
(52)

Search 1,421 vacation rentals

Top rated rentals — Illinois Medical District
Stayed Feb 2021

Cant beat these views!

Nothing but good things to say about this location and the apartment. It’s exactly as pictured, the apartment is supplied with everything needed, and the views are stunning. Renters are communicative and detailed. Check in and out is easy and fast. W...

Sarah S.
Sarah S.
Stayed Feb 2021

"A MILLION DOLLAR SKYLINE VIEW OF SOME OF THE MOST ICONIC ARCHITECTURAL BUILDINGS IN THE WORLD"

This 52nd Story Condo had all of the little traveling amenities that a guest would need without having to bring while on a traveling vacation. Perfect size condo unit for overnight stays. Ideal location for fine dining and miracle mile shopping visi...

Michael H.
Michael H.
Stayed Feb 2021

Superb Condo - Clean, Great Hosts & Location

My wife and I was able to stay in one of James & Jeri’s penthouses and we had a great experience. Unfortunately, we needed to extend our rental due to a winter storm there and the hosts were very accommodating to us. They extended our rental for a co...

Armour S.
Armour S.
Stayed Feb 2021

Only way to stay in Downtown Chicago

We decided to take a chance and make the trip to Chicago in order to celebrate our son's 26th birthday. We found the Penthouse at Grand Plaza and thought it would be the perfect place for the extended weekend trip. When we arrived, we were greeted by...

Stacey L.
Stacey L.
Stayed Jan 2021

Great Downtown Stay!

We really enjoyed our week in the sky in downtown Chicago. While we are from this area, we have never had a chance to enjoy the city from this height or location. We explored the neighborhood, and the building! The building amenities were excellent, ...

Suzanne M.
Suzanne M.
Stayed Dec 2020

I felt at home

I wasn’t sure what to expect cause I’ve never stayed in that area, but the neighborhood was nice, supermarket 2 blocks away, plenty of restaurants, a bar next door. Cause of COVID we needed a place where we could cook and enjoy together as a family. ...

Francis R.
Francis R.

Dominican republic

Stayed Dec 2020

Great Stay!!

Myself & A Couple of my family & friends stayed at Ms Linnie property & the stay was great. The house is beautiful & everything we needed was at the house. Ms Linnie was very Professional & the house looks exactly like the photos. I would definitely ...

Tiffany W.
Tiffany W.
Stayed Dec 2020

Graduation Celebration

Nice lofted space with plenty of room for our family to celebrate an online COVID style graduation. Ami was a great host with great communication. Other than an issue with parking (if you need spaces, be sure to let Ami know, and avoid direct SpotHer...

Travis A.
Travis A.
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How many vacation rentals are available around Illinois Medical District, US?

Our 2021 property listings offer a large selection of 1,421 vacation rentals around Illinois Medical District. From 1,114 condo and apartment rentals to 213 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.