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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Central Chicago vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,273 reviews)
"Nice stay"
United States
Heather
The price is ￥23,924
￥32,729 total
includes taxes & fees
Sep 9 - Sep 10
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is ￥37,648
￥48,100 total
includes taxes & fees
Aug 31 - Sep 1
Level Chicago – Old Town

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (17 reviews)
"Great location and super clean!"
United States
Erica
The price is ￥26,672
￥41,117 total
includes taxes & fees
Sep 10 - Sep 11
Kasa Lake Shore Chicago
A modern kitchen with a central island, bar stools, and a dining table.

4. River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is ￥175,002
￥288,454 total
includes taxes & fees
Sep 6 - Sep 7
River North Private Deck With In and Out Parking
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

5. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ￥30,202
￥40,755 total
includes taxes & fees
Aug 23 - Aug 24
LIVN Millennium Park Downtown Chicago 2BR
A kitchen with white cabinets, a microwave, a kettle, and a toaster.

6. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
The price is ￥131,460
￥220,241 total
includes taxes & fees
Aug 22 - Aug 23
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

7. River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.0 out of 10, Wonderful, (9 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
The price is ￥29,726
￥79,263 total
includes taxes & fees
Sep 8 - Sep 9
River North Rooftop With In and Out Parking 3
A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

8. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
The price is ￥85,919
￥161,086 total
includes taxes & fees
Aug 27 - Aug 28
Envitae Hotel, 4BR Modern Sleek Apartment
A modern kitchen with a dining area, large windows, and a city view.

9. Modern 2BR Retreat Near Old Town & Lincoln Park

Modern 2BR Retreat Near Old Town & Lincoln Park
Near North Side
9.2 out of 10, Wonderful, (22 reviews)
"Such a great apartment! Perfect size for 2 couples and the location was excellent. I’d highly recommend staying here- we’ll definitely stay again when we return to Chicago!"
United States
Josephine P.
The price is ￥38,133
￥111,297 total
includes taxes & fees
Aug 26 - Aug 27
Modern 2BR Retreat Near Old Town & Lincoln Park
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

10. Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"My overall experience was great! This 4 bedroom apartment.2 bath with included parking is a great place to stay when you are visiting Chicago and doing activities in the city.The management staff was great to work with. The front desk staff was also great.My family felt safe and we would return.Thigpen Family"
United States
Kimberly T.
The price is ￥42,442
￥101,871 total
includes taxes & fees
Sep 21 - Sep 22
Downtown Chicago Stay with Free In & Out Parking 1
A modern building with a glass facade, surrounded by a parking area and greenery.

11. Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (30 reviews)
"An incredible experience and wonderful place to stay. A perfect location, quiet, and my twin boys loved having their own spaces. Thank you so much!"
United States
Miriam B.
The price is ￥23,208
￥72,972 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 4BR Central Apartment w/ Skyline Views

12. 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 ￥43,873
￥98,484 total
includes taxes & fees
Sep 3 - Sep 4
South Loop Rooftop With In and Out Parking 2
A room with a large window, a round table with chairs, a television, and a lamp.

13. 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 ￥24,798
￥33,428 total
includes taxes & fees
Aug 23 - Aug 24
LIVN Millennium Park Downtown Chicago Superior 1BR
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

14. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is ￥25,116
￥33,802 total
includes taxes & fees
Aug 23 - Aug 24
LIVN Millennium Park Downtown Chicago Studio
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

15. 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 ￥26,546
￥35,678 total
includes taxes & fees
Aug 23 - Aug 24
LIVN Millennium Park Downtown Chicago Prem Studio
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

16. 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 ￥25,116
￥33,802 total
includes taxes & fees
Aug 23 - Aug 24
LIVN Millennium Park Downtown Chicago 1 BR
A modern living room with a blue sofa, a leather armchair, and a geometric coffee table.

17. LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (8 reviews)
"We loved the location."
United States
Nicoll M.
The price is ￥69,466
￥93,912 total
includes taxes & fees
Aug 26 - Aug 27
LIVN Millennium Park Downtown Chicago Superior 2 BR

18. 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, (4 reviews)
"Clean, comfortable, and stylish!"
United States
Maurya K.
The price is ￥37,026
￥92,163 total
includes taxes & fees
Sep 2 - Sep 3
Premium Urban 4BR - Perfect Mix of Comfort & Location
A modern bar area with high stools, a counter, and a flat-screen TV.

19. Downtown Chicago Stay with Free In & Out Parking-2

Downtown Chicago Stay with Free In & Out Parking-2
Downtown Chicago
The price is ￥43,355
￥102,967 total
includes taxes & fees
Aug 30 - Aug 31
Downtown Chicago Stay with Free In & Out Parking-2
A spacious lobby with leather sofas, a coffee table, and a TV screen.

20. Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6
Downtown Chicago
The price is ￥30,855
￥80,853 total
includes taxes & fees
Aug 30 - Aug 31
Downtown Chicago Stay with Free In & Out Parking 6
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"This hotel is well located for experiencing any of the sites Chicago has to offer. You can easily walk to downtown, the Magnificent Mile, Navy Pier and Millenium Park. The rooms are spacious (we had a Standard King) and well appointed. There are several stairs that lead from the entry and bathroom to the main part of the room. Makes the room feel bigger, but could be dangerous in the dark. They offer an amenity package that is worth the small added charge especially because the breakfast buffet is excellent."
jolynn 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile

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