Central Chicago Holiday Rentals

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Check prices for these dates

Tonight
18 Apr - 19 Apr
Tomorrow
19 Apr - 20 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

Holiday Rentals in Central Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (729)
"I've stayed here before so I was glad to see the experience was just as great the second time around. The staff is very friendly and helpful. I was able to check in a bit earlier than expected, and was able to get a later check out time with a fee. The apartment and building is clean and easily accessible, with so many surrounding restaurants and cafes. I had a test of multiple food all within a ten minute walking distance. I will definitely stay here again in a future visit."
The price is HK$851
HK$1,227 total
includes taxes & fees
20 Apr - 21 Apr
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (473)
"It was clean and neat place! We love the location and easy to park on the street!! However!!!! You can hear the train all night long… I can barely sleep.."
The price is HK$890
HK$1,045 total
includes taxes & fees
20 Apr - 21 Apr
Sonder South Wabash
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (303)
"Only thing was no communication on the pool location and the arcade games so I just didn't go and how to work the stove other that it was a beautiful experience. I think you should let people smoke on the balcony. I mean it is a expensive location and marijuana is legal a recreational use think about it. "
The price is HK$1,360
HK$1,769 total
includes taxes & fees
22 Apr - 23 Apr
Level Chicago – Old Town
Sonder Onterie
Miscellaneous

Sonder Onterie

3.5 star property
8.4 out of 10, Very good, (13)
"The stove, washer/drier, plates, silverwear, beds, everything was obviously cleaned throughly. Was very impressed with how spotless everything was"
The price is HK$1,308
HK$1,536 total
includes taxes & fees
23 Apr - 24 Apr
Sonder Onterie
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (390)
"it was as it advertising. clean, tourist friendly "
Kasa Magnificent Mile Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.4 out of 10, Very good, (146)
"This was the perfect stay for us this past weekend "
The price is HK$1,201
HK$1,410 total
includes taxes & fees
20 Apr - 21 Apr
Sonder Jewelers Row
Kasa South Loop Chicago
City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (275)
"We had a great time"
Kasa South Loop Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (97)
"The location for this property was ideal for the main areas in Chicago. We had a 4 bedroom apartment. They were spacious enough for what we needed. We did have an issue with no remote control but the live chat sorted that within minutes. "
The price is HK$1,094
HK$1,284 total
includes taxes & fees
12 May - 13 May
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (33)
"Very very cozy and clean! All messages and questions were answered promptly, and checking in and out was smooth! getting into the building was easy, everything was perfect. "
The price is HK$749
HK$880 total
includes taxes & fees
11 May - 12 May
Sonder The Opal
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (136)
"Wow was the word we all exclaimed when we walked in the door. Beautiful corner rooms, light and airy, wonderful experience. "
The price is HK$925
HK$1,086 total
includes taxes & fees
21 Apr - 22 Apr
Kasa River North Chicago
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (90)
"The space was perfect for multiple families who want to stay in a great neighborhood, close to the train, shopping, restaurants bars and more. Worked out perfectly for a few friends and their kids with plenty of space for sleeping and hanging out. Even had 2 spaces for cars in a garage!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (33)
"What an exceptional property! Perfect for a two-person getaway. It's right around the corner from shops and restaurants in the terrific Gold Coast neighborhood. Beautiful, modern decor with vintage building charm. It is very safe, quiet and comfortable - we got great sleep here. The host was communicative and everything was very easy. Definitely plan to come back to this gem!"
Chic & Historic Apartment Steps from Mag Mile
McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests
Interior

McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests

McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Smart TV, fireplace, books

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (288)
"Jim does a great job of communicating with us. The property is truly a gem!"
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Fridge, microwave, oven, stovetop

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (53)
"Super convenient for Old Town and train station, will stay there again."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
3BR/2BA Luxury Glass Apartment | Amazing Views
Fridge, microwave, oven, stovetop

3BR/2BA Luxury Glass Apartment | Amazing Views

9.8 out of 10, Exceptional, (34)
"Apartment was great!"
The price is HK$4,891
HK$8,642 total
includes taxes & fees
23 Apr - 24 Apr
3BR/2BA Luxury Glass Apartment | Amazing Views
Beautiful, Remodeled Penthouse Unit in Old Town!
Fridge, microwave, oven, stovetop

Beautiful, Remodeled Penthouse Unit in Old Town!

9.4 out of 10, Exceptional, (21)
"Super nice property, and the host was so helpful and kind. Super happy with the house overall, would recommend! "
Beautiful, Remodeled Penthouse Unit in Old Town!
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Fridge, microwave, oven, stovetop

Perfect 4 Bedroom/3 Bath in the HEART of Old Town

10.0 out of 10, Exceptional, (57)
"This was the second time we have stayed at this property. We like everything about it. Clean property, plenty of room, cool outlooks from the windows, all the amenities. And the neighborhood has plenty of restaurants, coffee shops, well located to other parts of town. And even a very convenient parking space. Highly recommend it. Lastly, the property manager is very responsive and friendly and helpful. "
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Full-sized fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (86)
"I liked the location, Communication with the host was good, listing accuracy and cleanliness of the property. "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
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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includes taxes & fees
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Swissotel - Chicago
Front of property – evening/night

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4.5 star property
8.8 out of 10, Excellent, (2068)
"The staff were exceptionally helpful and polite. "
The price is HK$1,397
HK$1,868 total
includes taxes & fees
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Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2149)
"Great location to almost everything "
The price is HK$1,079
HK$1,266 total
includes taxes & fees
21 Apr - 22 Apr
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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.