Central Chicago Holiday Rentals

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Holiday Rentals in Central Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (679)
"I loved this place will be staying again! Love love loved it!"
The price is AU$249
includes taxes & fees
18 Feb - 19 Feb
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (432)
"Even though this is a busy area, it was quiet. a lot of restaurants within walking distance."
The price is AU$164
includes taxes & fees
10 Mar - 11 Mar
Sonder South Wabash

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (288)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is AU$353
includes taxes & fees
19 Feb - 20 Feb
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (362)
"Great extended stay with full kitchen and area. "
Kasa Magnificent Mile Chicago

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is AU$223
includes taxes & fees
10 Mar - 11 Mar
Found Chicago powered by Sonder

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (257)
"Best place to stay in Chicago. "
Kasa South Loop Chicago

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (124)
"The property is very nice, we will definitely coming back soon "
The price is AU$172
includes taxes & fees
18 Feb - 19 Feb
Kasa River North Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (137)
"Loved it Had to leave early but loved "
The price is AU$189
includes taxes & fees
24 Feb - 25 Feb
Sonder Jewelers Row

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is AU$179
includes taxes & fees
12 Mar - 13 Mar
Sonder The Opal

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (90)
"Great apartment, we were given an extra bedroom which we used as a wardrobe. Well equipped, modern and well decorated. Full cooker, fridge freezer, microwave. We were provided with tablets for laundry and dishwasher. Washing up.liquids, towels and toilet roll. Great shower. Loved the location. We enjoy cities and walking. Trains a very short walks (several L stations). Target was a 15 minute walk, great independent coffee shop 2 mins from entrance. We will use Sonder again. "
The price is AU$212
includes taxes & fees
23 Feb - 24 Feb
Sonder The Plymouth

Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago

10.0 out of 10, Exceptional, (285)
"This place is incredible. I wish we could stay forever. The view never gets old, and it looks even better at night. "
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (86)
"Location of house is great, communication with owner is great. The house "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (31)
"Great amenities, great location, spacious and comfortable. Check in a few days prior was difficult as the owner/manager didn’t message me or email me back… I had to call VRBO to have them investigate. Once they were made aware, smooth sailing from then on. Also, they listed a jacuzzi on site which was an error,and that was disappointing as I planned on that. Overall, despite these two things, great place ti stay! "
Chic & Historic Apartment Steps from Mag Mile

Art Park #12 - Mich Ave 2bd Penthouse gym+rooftop

10.0 out of 10, Exceptional, (18)
"Our stay was great. When we walked in the room it was nice and warm. It looked clean and well decorated. A little compact but the perfect amount of space for a family of 5. We had extra towels and a washer/dryer to use with laundry soap. I was super happy about the laundry accessibility. "
Art Park #12 - Mich Ave 2bd Penthouse gym+rooftop

Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

10.0 out of 10, Exceptional, (5)
"This apartment has almost everything you could hope for! From the shoe covers and socks by the front door, to a heated towel rack in the bathroom. The only thing missing is a soaking tub! If you’re looking for a fantastic view of the city with spacious accommodations, look no further! The host was more than accommodating and very quick to reply when I had questions "
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

Beautiful, Remodeled Penthouse Unit in Old Town!

9.4 out of 10, Exceptional, (18)
"I am an FCA advisor at a small rural school in Mid-Mo. We volunteer every year at the Operation Christmas Child facilities. I brought 6 high school students with me. The OCC facility is about 40 minutes from Chicago but we all wanted to experience the big city since we come from such a small rural area. The apartment was just as shown. We struggled with finding a parking spot as we drove a 10 passenger van but Dan does state that on the rental info there is no designated parking. We found...
Beautiful, Remodeled Penthouse Unit in Old Town!

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

9.8 out of 10, Exceptional, (83)
"We had a wonderful visit in Chicago and this VRBO was a great place to stay for our group. There are plenty of bedrooms and bathrooms and it is close to all the restaurants, bars, and an El stop. "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

10.0 out of 10, Exceptional, (182)
"Great location! very comfortable!"
51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

Prime location Historic Chicago Townhouse

9.4 out of 10, Exceptional, (66)
"Beautiful old Gold Coast Townhouse within walking distance of everything we needed. Spacious accommodations with a lovely large dining area and comfortable TV lounging area at back of house. Close to plenty of dining options and Lake Michigan. Fully stocked kitchen, comfortable beds and bedding. Plenty of towels, coffee and tea. Comfy robes in every bedroom. Overall a wonderful experience."
Prime location Historic Chicago Townhouse

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (52)
"Apartment was spacious. The 2 1/2 bathrooms were great to have for our group. Location was great for quick Uber to downtown area. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
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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Other types of properties in Central Chicago you may be interested in

Congress Plaza Hotel

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7.8 out of 10, Good, (8510)
"It was lovely "
The price is AU$158
includes taxes & fees
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Congress Plaza Hotel

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1646)
"all good"
The price is AU$238
includes taxes & fees
23 Feb - 24 Feb
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Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (1653)
"I look forward to staying again!"
The price is AU$359
includes taxes & fees
22 Feb - 23 Feb
Hilton 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.