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Holiday Rentals in Central Chicago

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Our top choices for Central Chicago holiday rentals

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (94 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is €218
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,416 reviews)
"Great for extended stays."
United States
Jeff
The price is €204
includes taxes & fees
13 Dec - 14 Dec
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 €212
includes taxes & fees
7 Dec - 8 Dec
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, (564 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is €204
includes taxes & fees
23 Nov - 24 Nov
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, (13 reviews)
"Great location"
United States
Jason P.
The price is €217
includes taxes & fees
16 Nov - 17 Nov
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 €250
includes taxes & fees
17 Nov - 18 Nov
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.
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.
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 €592
includes taxes & fees
2 Dec - 3 Dec
Wabash 4BR - Pool, Free In & Out Parking 4

10. Stylish 4BR South Loop Home

Stylish 4BR South Loop Home
South Loop
The price is €292
includes taxes & fees
16 Nov - 17 Nov
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 €336
includes taxes & fees
23 Nov - 24 Nov
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.
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.
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 €503
includes taxes & fees
16 Nov - 17 Nov
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 €280
includes taxes & fees
20 Nov - 21 Nov
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 €229
includes taxes & fees
20 Nov - 21 Nov
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 €325
includes taxes & fees
20 Nov - 21 Nov
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 €261
includes taxes & fees
20 Nov - 21 Nov
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 €325
includes taxes & fees
20 Nov - 21 Nov
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

Everything you need to know about Central Chicago holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Central Chicago holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Central Chicago holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Central Chicago holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Central Chicago. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Central Chicago holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Central Chicago holiday rentals we have selected for you start as low as €204 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Central Chicago rentals

At Expedia, we put the best Central Chicago holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Central Chicago rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Central Chicago holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Central Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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