Central Chicago Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Central Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 417 reviews
"I just wish that the valet parking wasn’t $75 a night! What a nightmare! Asides from that, it’s super clean and super easy to check in, and there’s an infinity pool!"
The price is CA $257
CA $342 total
includes taxes & fees
Jun 16 - Jun 17
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 303 reviews
"Everything was great!"
The price is CA $246
CA $289 total
includes taxes & fees
Jun 6 - Jun 7
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, 244 reviews
"Host was easily accessible. We had a relaxing stay and the apartment is very comfortable as well as clean. Definitely will stay here again."
The price is CA $260
CA $444 total
includes taxes & fees
Jun 5 - Jun 6
Kasa Magnificent Mile Chicago
Save an average of 15% on thousands of hotels when you're signed in
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 210 reviews
"Nice"
The price is CA $457
CA $559 total
includes taxes & fees
Jun 9 - Jun 10
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, 130 reviews
"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 CA $258
CA $302 total
includes taxes & fees
Jun 27 - Jun 28
Found Chicago powered by Sonder
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, 67 reviews
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
The price is CA $362
CA $426 total
includes taxes & fees
Jun 13 - Jun 14
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, 104 reviews
"Loved it "
The price is CA $325
CA $382 total
includes taxes & fees
Jun 6 - Jun 7
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, 161 reviews
"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, 68 reviews
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is CA $269
CA $316 total
includes taxes & fees
Jun 23 - Jun 24
Sonder The Plymouth
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, 200 reviews
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, 14 reviews
"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 CA $415
CA $487 total
includes taxes & fees
Jun 12 - Jun 13
Sonder The Opal
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, 2 reviews
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is CA $250
CA $327 total
includes taxes & fees
Jun 16 - Jun 17
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, 7 reviews
"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!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, 70 reviews
"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
Stay in the Heart of the City! Complimentary Bicycles for exploring!
10.0 out of 10, Exceptional, 2 reviews
"Enjoyed the walkability of this location to all downtown Chicago has to offer. The onsite amenities were also wonderful"
The price is CA $260
CA $338 total
includes taxes & fees
Jun 16 - Jun 17
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Million Dollar Views! Luxury Downtown Skyhouse!
10.0 out of 10, Exceptional, 92 reviews
"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 CA $948
CA $1,863 total
includes taxes & fees
Jun 18 - Jun 19
Million Dollar Views! Luxury Downtown Skyhouse!
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
9.4 out of 10, Exceptional, 3 reviews
"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 CA $311
CA $408 total
includes taxes & fees
Jul 1 - Jul 2
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
10.0 out of 10, Exceptional, 267 reviews
"Great stay. The owners are very communicative. We checked in easily with the door staff. We arrived early and the door staff was helpful and allowed us to store our bags and explore the area. The inside matches the pictures. The outside has to been seen day or night to appreciate the pictures. Beds are very comfortable. Kitchen is well appointed. (A grocery store is ten steps away from downstairs entry.) the bathrooms were clean. The washer and drier are very useful. It is a two story unit....
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.0 out of 10, Wonderful, 44 reviews
"Communication was fantastic. Location is excellent. I stayed there with my wife and kids and there was plenty of room. Would be great for a big group of friends or a bachelor party weekend."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Prime location Historic Chicago Townhouse
9.4 out of 10, Exceptional, 59 reviews
"Gorgeous, large townhouse. We loved the location and the townhouse itself. The lock box was a little confusing because there are 2. In the age of door codes, I wasn’t expecting this. Another word of note: the staircase is old and the wood is worn on some places. If you have small children or someone who is unstable on their feet you might want to consider this."
Prime location Historic Chicago Townhouse
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 Vacation 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, 6,818 reviews
"Be aware there is only Analog TV in the room"
The price is CA $255
CA $300 total
includes taxes & fees
Jun 5 - Jun 6
Congress Plaza Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, 2,928 reviews
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal. "
The price is CA $216
CA $254 total
includes taxes & fees
Jul 1 - Jul 2
River Hotel
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very good, 1,992 reviews
"Thank you everything was great "
The price is CA $233
CA $273 total
includes taxes & fees
Jun 30 - Jul 1
Eurostars Magnificent Mile
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Central Chicago vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Central Chicago vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Central Chicago vacation rentals we have selected for you start as low as CA $246 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 vacation 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 vacation.

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