Central Chicago Vacation Rentals

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Vacation Rentals in Central Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (424)
"Property was beautiful and well kept. Room was comfortable and felt like home. The pool was disappointing and much smaller than it appears. Communication during check in and valets could be better. "
The price is $199
$263 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (309)
"Sonder rocks!"
The price is $190
$223 total
includes taxes & fees
Jun 9 - Jun 10
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (248)
"Parking should be available at a discounted rate. Not free, but in and out privileges at the least would stay agin, if I did not need to travel all over Chicago"
Kasa Magnificent Mile Chicago
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Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"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 $189
$222 total
includes taxes & fees
Jul 1 - Jul 2
Found Chicago powered by Sonder
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (211)
"Loved all the neighborhood dogs & farmers market"
The price is $297
$366 total
includes taxes & fees
Jun 16 - Jun 17
Level Chicago – Old Town
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"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!"
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (105)
"Loved it "
The price is $223
$262 total
includes taxes & fees
Jun 18 - Jun 19
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (162)
"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)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is $218
$256 total
includes taxes & fees
Jul 2 - Jul 3
Sonder The Plymouth
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (200)
"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)
"Great location and great apartment. Next nine we are in Chicago we’ll be staying here."
The price is $232
$273 total
includes taxes & fees
Jul 1 - Jul 2
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 $164
$216 total
includes taxes & fees
Jun 30 - Jul 1
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
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 $678
$1,340 total
includes taxes & fees
Jun 18 - Jun 19
Million Dollar Views! Luxury Downtown Skyhouse!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (71)
"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!
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 $208
$273 total
includes taxes & fees
Jun 30 - Jul 1
Stay in the Heart of the City! Complimentary Bicycles for exploring!
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 $190
$249 total
includes taxes & fees
Jun 30 - Jul 1
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, (44)
"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
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
10.0 out of 10, Exceptional, (267)
"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
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (3)
"This property was very clean and spacious and close to everything we needed to be walking distance from. Parking was easy and extra parking was cheap and affordable."
Breathtaking Downtown Penthouse B - Sleeps 11
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, (6840)
"Perfect location to museum and restaurants. Good for family and friends "
The price is $167
$196 total
includes taxes & fees
Jun 16 - Jun 17
Congress Plaza Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2950)
"Perfect area for walking around chicago even at night. Felt 100 percent safe and the weather mafe for an emalculat trip. "
The price is $179
$210 total
includes taxes & fees
Jun 30 - Jul 1
River Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very Good, (2353)
"Loved the location"
The price is $201
$237 total
includes taxes & fees
Jul 2 - Jul 3
Embassy Suites by Hilton Chicago Downtown River North
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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Central Chicago in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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