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Central Chicago Vacation Rentals

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Our top choices for Central Chicago vacation rentals

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (91 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is CA $199
CA $322 total
includes taxes & fees
Nov 25 - Nov 26
Kasa Lake Shore Chicago

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,415 reviews)
"Great for extended stays."
United States
Jeff
The price is CA $272
CA $320 total
includes taxes & fees
Dec 8 - Dec 9
Sentral Michigan Avenue

3. Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great little spot in a fun area of downtown Chicago. Lots of bars & restaurants within walking distance."
United States
Ryan
The price is CA $127
CA $332 total
includes taxes & fees
Dec 7 - Dec 8
Chic Studio in the Heart of the Gold Coast

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (563 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is CA $242
CA $320 total
includes taxes & fees
Nov 23 - Nov 24
Level Chicago – Old Town

5. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Jason P.
The price is CA $221
CA $281 total
includes taxes & fees
Nov 15 - Nov 16
LIVN Millennium Park Downtown Chicago Studio

6. The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
The price is CA $154
CA $385 total
includes taxes & fees
Nov 16 - Nov 17
The One: A 1BR Stay That Feels Like Home

7. 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, (25 reviews)
"Nice, big apartment with everything you need to travel as a family."
United States
Julia W.
The price is CA $173
CA $725 total
includes taxes & fees
Nov 18 - Nov 19
Modern 2BR Retreat Near Old Town & Lincoln Park

8. Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
9.0 out of 10, Wonderful, (4 reviews)
"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.
The price is CA $262
CA $660 total
includes taxes & fees
Dec 3 - Dec 4
Downtown Chicago Stay with Free In & Out Parking 5

9. Wabash 4BR - Pool, Free In & Out Parking 4

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Nice place to stay."
United States
William H.
The price is CA $345
CA $925 total
includes taxes & fees
Dec 2 - Dec 3
Wabash 4BR - Pool, Free In & Out Parking 4

10. Stylish 4BR South Loop Home

Stylish 4BR South Loop Home
South Loop
The price is CA $128
CA $479 total
includes taxes & fees
Nov 16 - Nov 17
Stylish 4BR South Loop Home

11. Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
South Loop
8.4 out of 10, Very good, (14 reviews)
"Everything was exactly as described."
United States
Sydney D.
The price is CA $163
CA $523 total
includes taxes & fees
Nov 23 - Nov 24
Smart Simple and Spacious 4BR Apt

12. 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, (16 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is CA $377
CA $853 total
includes taxes & fees
Nov 18 - Nov 19
River North Private Deck With In and Out Parking

13. South Loop · 3 Kings · Steps from McCormick Place

South Loop · 3 Kings · Steps from McCormick Place
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Great space!"
United States
Kyle H.
South Loop · 3 Kings · Steps from McCormick Place

14. South Loop Rooftop With In and Out Parking 5

South Loop Rooftop With In and Out Parking 5
Downtown Chicago
8.0 out of 10, Very good, (1 review)
"Good experience!"
United States
Hadeel H.
The price is CA $460
CA $1,082 total
includes taxes & fees
Nov 15 - Nov 16
South Loop Rooftop With In and Out Parking 5

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

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (5 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 CA $392
CA $804 total
includes taxes & fees
Nov 15 - Nov 16
Plymouth Collection: 3BD 2BA High Floor with Gym

16. 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 $221
CA $281 total
includes taxes & fees
Nov 15 - Nov 16
LIVN Millennium Park Downtown Chicago Prem Studio

17. 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 $232
CA $294 total
includes taxes & fees
Nov 16 - Nov 17
LIVN Millennium Park Downtown Chicago 1 BR

18. Trendy Gold Coast Studio Close to Downtown

Trendy Gold Coast Studio Close to Downtown
Downtown Chicago
The price is CA $117
CA $318 total
includes taxes & fees
Nov 16 - Nov 17
Trendy Gold Coast Studio Close to Downtown

19. 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 $244
CA $308 total
includes taxes & fees
Nov 15 - Nov 16
LIVN Millennium Park Downtown Chicago Superior 1BR

20. Gold Coast Hideaway | Vintage & Inviting Studio

Gold Coast Hideaway | Vintage & Inviting Studio
Downtown Chicago
The price is CA $107
CA $310 total
includes taxes & fees
Nov 23 - Nov 24
Gold Coast Hideaway | Vintage & Inviting Studio
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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