A city skyline at dusk with illuminated buildings reflecting on the water.

Central Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Central Chicago vacation rentals

Lake

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
The price is ￥39,253
￥56,259 total
includes taxes & fees
Jul 8 - Jul 9
Kasa Lake Shore Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,206 reviews)
"Great location"
United States
JAVIER
The price is ￥28,662
￥38,383 total
includes taxes & fees
Jul 9 - Jul 10
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (499 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is ￥51,046
￥63,920 total
includes taxes & fees
Jul 8 - Jul 9
Level Chicago – Old Town
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (15 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is ￥31,065
￥83,929 total
includes taxes & fees
Jul 8 - Jul 9
ENVITAE Hotel, 4BR Luxury Modern Apartments
TV, offices

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 ￥49,911
￥67,194 total
includes taxes & fees
Jul 12 - Jul 13
LIVN Millennium Park Downtown Chicago 2BR
Interior

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 ￥42,755
￥97,769 total
includes taxes & fees
Jul 26 - Jul 27
River North Rooftop With In and Out Parking 3
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is ￥76,488
￥144,792 total
includes taxes & fees
Aug 6 - Aug 7
River North Rooftop With In and Out Parking 6
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (25 reviews)
"Great location, close to public transport and Whole Foods. The property was clean, quiet, and easy to access. The host was great with communication. We would stay again! "
United States
Susan R.
The price is ￥189,252
￥305,407 total
includes taxes & fees
Jul 31 - Aug 1
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6
Downtown Chicago
The price is ￥96,582
￥172,588 total
includes taxes & fees
Jul 10 - Jul 11
Downtown Chicago Stay with Free In & Out Parking 6
Pool

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.
South Loop Rooftop With In and Out Parking 2
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (814 reviews)
"Great place to stay."
United States
Benedictine
The price is ￥31,452
￥46,393 total
includes taxes & fees
Jul 8 - Jul 9
Kasa Magnificent Mile Chicago
TV, offices

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is ￥39,044
￥82,336 total
includes taxes & fees
Jul 9 - Jul 10
River North Private Balcony With In and Out Parking
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
Downtown Chicago Stay with Free In & Out Parking 5
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.2 out of 10, Wonderful, (5 reviews)
The price is ￥46,466
￥61,918 total
includes taxes & fees
Jul 9 - Jul 10
LIVN Millennium Park Downtown Chicago Superior 2 BR
TV, offices

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.4 out of 10, Exceptional, (6 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is ￥52,758
￥111,508 total
includes taxes & fees
Jul 12 - Jul 13
Downtown Chicago Stay with Free In & Out Parking 4
2 bedrooms, desk, iron/ironing board, travel crib

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 ￥53,242
￥112,902 total
includes taxes & fees
Jul 29 - Jul 30
South Loop Rooftop With In & Out Parking 1
Dining

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.
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

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 ￥23,821
￥31,966 total
includes taxes & fees
Jul 8 - Jul 9
LIVN Millennium Park Downtown Chicago Superior 1BR
Dining

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 ￥39,044
￥52,009 total
includes taxes & fees
Jul 9 - Jul 10
LIVN Millennium Park Downtown Chicago Studio
TV, offices

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Perfect Stay!"
United States
Miyauna G.
Downtown Chicago Stay with Free In & Out Parking 3
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Loved everything about this stay. The view was amazing! Would stay here again."
Gabrielle 3-night trip
Posted 3 hours ago
Hyatt Regency Chicago

Find out more about Central Chicago

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