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Central Chicago Vacation Rentals

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Our top choices for Central Chicago vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,200 reviews)
"Great location"
United States
JAVIER
The price is CA $228
CA $309 total
includes taxes & fees
Jul 5 - Jul 6
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is CA $395
CA $499 total
includes taxes & fees
Jul 6 - Jul 7
Level Chicago – Old Town

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is CA $399
CA $921 total
includes taxes & fees
Jul 8 - Jul 9
ENVITAE Hotel, 4BR Luxury Modern Apartments

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is CA $334
CA $450 total
includes taxes & fees
Jul 5 - Jul 6
LIVN Millennium Park Downtown Chicago 2BR

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is CA $244
CA $403 total
includes taxes & fees
Jul 5 - Jul 6
Kasa River North Chicago

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is CA $376
CA $866 total
includes taxes & fees
Jul 8 - Jul 9
River North Rooftop With In and Out Parking 3

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is CA $606
CA $1,214 total
includes taxes & fees
Jul 9 - Jul 10
Premium Urban 4BR - Perfect Mix of Comfort & Location

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is CA $398
CA $896 total
includes taxes & fees
Jul 21 - Jul 22
South Loop Rooftop With In and Out Parking 2

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is CA $234
CA $312 total
includes taxes & fees
Jul 2 - Jul 3
LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
The price is CA $248
CA $332 total
includes taxes & fees
Jul 5 - Jul 6
LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is CA $237
CA $319 total
includes taxes & fees
Jul 7 - Jul 8
LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is CA $237
CA $319 total
includes taxes & fees
Jul 7 - Jul 8
LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location."
United States
Nicoll M.
The price is CA $284
CA $382 total
includes taxes & fees
Jul 5 - Jul 6
LIVN Millennium Park Downtown Chicago Superior 2 BR

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is CA $396
CA $894 total
includes taxes & fees
Jul 19 - Jul 20
South Loop Rooftop With In and Out Parking 3

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (24 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
The price is CA $1,893
CA $3,027 total
includes taxes & fees
Jul 31 - Aug 1
Spacious 4BR Central Apartment w/ Skyline Views

Stylish friendly 3BR Suite near McCormick

Stylish friendly 3BR Suite near McCormick
Near South Side
The price is CA $162
CA $668 total
includes taxes & fees
Jul 5 - Jul 6
Stylish friendly 3BR Suite near McCormick

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is CA $443
CA $959 total
includes taxes & fees
Jul 2 - Jul 3
South Loop Rooftop With In & Out Parking 1

McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11

McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11
Near South Side
The price is CA $287
CA $695 total
includes taxes & fees
Jul 6 - Jul 7
McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11

3BR · Steps from McCormick · Balcony & Gym

3BR · Steps from McCormick · Balcony & Gym
Near South Side
9.6 out of 10, Exceptional, (4 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
The price is CA $246
CA $702 total
includes taxes & fees
Jul 5 - Jul 6
3BR · Steps from McCormick · Balcony & Gym

Chicago Spacious 3Br Smoke Ok Near McCormick Place

Chicago Spacious 3Br Smoke Ok Near McCormick Place
Near South Side
The price is CA $271
CA $673 total
includes taxes & fees
Jul 6 - Jul 7
Chicago Spacious 3Br Smoke Ok Near McCormick Place
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Central Chicago Hotel Reviews

Find out more about Central Chicago

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Central Chicago. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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