Search Holiday Rentals in Central Chicago

Save an average of 15% on thousands of properties with Expedia Rewards

Become a member for free and get more than just a booking discount. Members also earn points towards their next trip.

Search over 2.9 million properties and 550 airlines worldwide.

Top Holiday Rentals in Central Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (399)
"It was amazing to have a whole apartment for the price of a hotel room... less actually. Their system is simple and painless. I will book here again!"
The price is £140
includes taxes & fees
27 May - 28 May
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (222)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is £181
includes taxes & fees
28 May - 29 May
Sonder South Wabash
Save an average of 15% on thousands of hotels when you're signed in
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (127)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is £203
includes taxes & fees
6 Jun - 7 Jun
Found Chicago powered by Sonder
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is £301
includes taxes & fees
27 May - 28 May
Level Chicago – Old Town
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (101)
"The entire experience was fantastic. Clear instructions in how to get into the building and the apartment, fully stocked kitchen and extremely comfortable bed"
The price is £197
includes taxes & fees
28 May - 29 May
Sonder Jewelers Row
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (66)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is £246
includes taxes & fees
27 May - 28 May
Sonder The Plymouth
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is £227
includes taxes & fees
28 May - 29 May
Sonder The Opal
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, (2)
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is £173
includes taxes & fees
27 May - 28 May
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
9.4 out of 10, Exceptional, (3)
"Easy check in, staff on property were so nice. Property has a lap pool and a gym. Location was great and price was very comfortable."
The price is £189
includes taxes & fees
27 May - 28 May
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.0 out of 10, Wonderful, (43)
"We stayed at this property for a weekend family gathering in Chicago. This property had exactly the attributes we needed: separate spaces in which to sleep, a common space to gather, and a central location. It was a bit noisy, but nothing unexpected considering we were in Chicago on a weekend. Would recommend!"
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Luxury Gold Coast Apartment 18
Luxury Gold Coast Apartment 18
Million Dollar Views! Luxury Downtown Skyhouse!
10.0 out of 10, Exceptional, (92)
"WOW! That's what we say about this place. My family and I loved it! The location and the views-WOW! It is floor to ceiling windows in the living room and the bedrooms. Absolutely so cool. We were met when we arrived, shown the parking space for our car-a great space and totally worth having one. Then taken up to our floor-the elevators are quick and smooth. It was easy to get in and out--we used uber and it was super easy for them-close to everything, a fantastic location. The A/C worked well...
The price is £830
includes taxes & fees
23 May - 24 May
Million Dollar Views! Luxury Downtown Skyhouse!
Stay in the Heart of the City! Complimentary Bicycles for exploring!
10.0 out of 10, Exceptional, (2)
"Enjoyed the walkability of this location to all downtown Chicago has to offer. The onsite amenities were also wonderful"
The price is £209
includes taxes & fees
27 May - 28 May
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
10.0 out of 10, Exceptional, (266)
"My husband, teenager and I stayed here for a long weekend trip. The views and location were excellent! We were pleased with how clean it was as well. Would highly recommend!"
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Don't see what you're looking for?
See all available properties in Central Chicago
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.

Central Chicago Holiday Rental Travel Info

Popular accommodation
Central Chicago apartments
International airport
Chicago, IL (ORD-O'Hare Intl.)

Other types of properties in Central Chicago you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6733)
"Great location for walking to both museums and Magnificent Mile. Restaurants on site if you don't get out to eat. Late check out (noon). "
The price is £139
includes taxes & fees
27 May - 28 May
Congress Plaza Hotel
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2584)
"Very clean"
The price is £110
includes taxes & fees
27 May - 28 May
Warwick Allerton - Chicago
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2873)
"I enjoyed staying in this hotel. Very convenient and nearby to tourist attractions. The staff are very accommodating. I will definitely book this hotel if I’m in Chicago. "
The price is £159
includes taxes & fees
28 May - 29 May
River Hotel
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.

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 £140 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. 

Recent reviews of Central Chicago properties
Expedia verified reviews