Holiday Rentals in Central Chicago

    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

Holiday Rentals in Central Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (442)
"Great stay in a room with a great view!"
The price is €204
includes taxes & fees
17 Jun - 18 Jun
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (314)
"Comfortable to stay"
The price is €175
includes taxes & fees
2 Jul - 3 Jul
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (258)
"Very comfortable accommodations and good amenities and location. "
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (216)
"Great room - fabulous fitness center. Easy access to grocery stores to stock fridge. Room is furnished with all amenities. "
The price is €311
includes taxes & fees
16 Jun - 17 Jun
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (135)
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is €128
includes taxes & fees
14 Jul - 15 Jul
Found Chicago powered by Sonder
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (68)
"Room was great! Spacious, clean and perfect for a night or longer stay. View was also very nice!"
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (111)
"Loved it "
The price is €198
includes taxes & fees
7 Jul - 8 Jul
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (164)
"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 €155
includes taxes & fees
15 Jul - 16 Jul
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
8.2 out of 10, Very good, (15)
"I like that was contactless and easy to access. "
The price is €227
includes taxes & fees
1 Jul - 2 Jul
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 €206
includes taxes & fees
3 Jul - 4 Jul
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
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 €235
includes taxes & fees
30 Jun - 1 Jul
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
Million Dollar Views! Luxury Downtown Skyhouse!
10.0 out of 10, Exceptional, (95)
"Properly was clean and had everything we needed. Our visit went by quickly. Location was close to restaurants and grocery store. We recommend staying here."
The price is €1,012
includes taxes & fees
18 Jun - 19 Jun
Million Dollar Views! Luxury Downtown Skyhouse!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.0 out of 10, Wonderful, (8)
"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 €246
includes taxes & fees
30 Jun - 1 Jul
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (72)
"Stayed with 10 friends for the weekend. Clean unit with plenty of beds. Listing and pictures are accurate. Great location close to bars, restaurants, and train stop. Property manager was very responsive. Very easy check-in/check-out."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
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
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (4)
"The unit was a great size for our 7-person group trip to Chicago. We’ll appointed with pulsated hardware and decor. Super close to transit made getting to Wrigley, Navy Pier, Downtown, and the zoo extremely easy. Rooftop was a amazing and Dan was responsive and made the check in/out process a breeze."
Breathtaking Downtown Penthouse B - Sleeps 11
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
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.

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, (6960)
"Amazing location, gorgeous view from room window over park. No parking valet, but bellmen very helpful. Good bar service and decent sidewalk cafe. I'd happily stay again. "
The price is €180
includes taxes & fees
17 Jun - 18 Jun
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very good, (2382)
"I love the location of this hotel. It’s vey convenient to walk everywhere. Breakfast is awesome. Front desk is lukewarm not the friendliest but not the worse. One is not even paying attention and charged me again even though I prepaid my stayed in Expedia. It’s still showing pending in my CC so I’m hoping it will get dropped off to avoid the hassle of disputing the transaction. I stayed in Embassy in DC before and the front desk were extra nice and they gave us voucher because I was a gold...
The price is €209
includes taxes & fees
1 Jul - 2 Jul
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2952)
"Valet parking was terrible, very rude the guy, it’s the only bad thing the hotel have. "
The price is €178
includes taxes & fees
3 Jul - 4 Jul
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 €128 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