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Central Chicago Holiday Rentals

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Our top choices for Central Chicago holiday rentals

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1028)
"My favorite place to stay hands-down"
United States
Michele
The price is NZ$273
includes taxes & fees
5 Jan - 6 Jan 2026
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is NZ$266
includes taxes & fees
4 Jan - 5 Jan 2026
Chicago luxury home suites

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is NZ$285
includes taxes & fees
18 Jan - 19 Jan 2026
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is NZ$290
includes taxes & fees
21 Jan - 22 Jan 2026
Sleek 1BR Apt w/ Laundry

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is NZ$291
includes taxes & fees
15 Jan - 16 Jan 2026
The One: A 1BR Stay That Feels Like Home

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
9.8 out of 10, Exceptional, (9)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is NZ$2,180
includes taxes & fees
5 Jan - 6 Jan 2026
ENVITAE Hotel 4 Bedroom Luxury Apartments
9.6 out of 10, Exceptional, (4)
"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 NZ$540
includes taxes & fees
14 Jan - 15 Jan 2026
River North Rooftop With In and Out Parking 3

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (407)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
2.0 star property
The price is NZ$290
includes taxes & fees
5 Jan - 6 Jan 2026
Chicago-Themed 1BR in a Central Spot near Downtown
9.6 out of 10, Exceptional, (17)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is NZ$328
includes taxes & fees
1 Jan - 2 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is NZ$290
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum

Apartment in Downtown Chicago

Vintage Studio in Chicago’s Gold Coast
The price is NZ$285
includes taxes & fees
4 Jan - 5 Jan 2026
Vintage Studio in Chicago’s Gold Coast

Apartment in Downtown Chicago

Stylish Gold Coast 1BR with Vintage Flair
The price is NZ$290
includes taxes & fees
6 Jan - 7 Jan 2026
Stylish Gold Coast 1BR with Vintage Flair
2.0 star property
The price is NZ$328
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish Japanese-Themed 2BR Apt Close to Downtown

Apartment in Downtown Chicago

Trendy Gold Coast Studio Close to Downtown
6.0 out of 10, (1)
"Key pad issues with entry, but overall good "
United States
Andrew U.
The price is NZ$286
includes taxes & fees
4 Jan - 5 Jan 2026
Trendy Gold Coast Studio Close to Downtown

Apartment in Near South Side

Smart Simple and Spacious 4BR Apt
9.2 out of 10, Wonderful, (5)
"Great communication with Host, was exactly as described."
United States
Doug C.
The price is NZ$601
includes taxes & fees
4 Jan - 5 Jan 2026
Smart Simple and Spacious 4BR Apt

Apartment in Near South Side

Stylish 4BR Stay-Prime Location
7.6 out of 10, Good, (5)
"Incredibly clean and spacious apartment. The beds were comfortable, and we really appreciated having multiple bathrooms. The kitchen was well stocked and the location was a short Lyft/uber from everywhere we wanted to be. Would definitely stay here again."
United States
Jessica F.
The price is NZ$602
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish 4BR Stay-Prime Location
9.8 out of 10, Exceptional, (35)
"The place was very clean, comfortable, and even had a few furry neighbors. Effortless check in while having all the great amenities (Wi-Fi, shower, stove, fridge, TV) was an absolute advantage. No place like it exists and highly recommend staying here."
United States
Ali J.
The price is NZ$361
includes taxes & fees
6 Jan - 7 Jan 2026
Less is more! Pet friendly Tiny Home near Chicago!

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is NZ$290
includes taxes & fees
5 Jan - 6 Jan 2026
West Loop Living – Bright 1BR
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, 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 NZ$266 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.