Central Chicago Holiday Rentals

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Check prices for these dates

Tonight
13 Jul - 14 Jul
Tomorrow
14 Jul - 15 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Central Chicago

Sentral Michigan Avenue
Relax in a spacious area with comfortable seating and lush greenery.

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (818)
"Great stay!"
The price is HK$1,528
HK$2,024 total
includes taxes & fees
16 Jul - 17 Jul
Sentral Michigan Avenue
Level Chicago – Old Town
Located in a bustling urban area, this high-rise building offers stunning city views.

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (325)
"Hotel was nice"
The price is HK$3,515
HK$4,301 total
includes taxes & fees
30 Jul - 31 Jul
Level Chicago – Old Town
Kasa Magnificent Mile Chicago
Relax on the spacious balcony with a city view, featuring a sofa, armchair, and outdoor seating area.

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (441)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Enjoy a city view from the large window, with a comfortable sofa and potted plant adding to the inviting atmosphere.

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (565)
"Great place and location. "
The price is HK$1,719
HK$2,018 total
includes taxes & fees
24 Jul - 25 Jul
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Kasa South Loop Chicago
Enjoy the city view from this balcony with a comfortable Adirondack chair and a small table.

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (318)
"Great stay"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Enjoy the city view from this stylish balcony with a sofa, chair, and table.

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.2 out of 10, Very good, (114)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is HK$827
HK$971 total
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of the city outside.

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is HK$1,321
HK$1,551 total
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Kasa River North Chicago
Meetings take place around a large, rectangular table surrounded by six chairs with chrome legs.

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (155)
"Great stay, clean room!"
Kasa River North Chicago
Sonder by Marriott Bonvoy The Opal Apartments River North
Enjoy a panoramic city view from this rooftop terrace, featuring a round table, wicker chairs, and a sofa with a throw blanket.

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is HK$1,782
HK$2,092 total
includes taxes & fees
27 Jul - 28 Jul
Sonder by Marriott Bonvoy The Opal Apartments River North
Michigan Ave 2BR: Balcony, Exclusive Access
Relax by the pool surrounded by lush flower beds and a glass wall offering a city view.

Michigan Ave 2BR: Balcony, Exclusive Access

10.0 out of 10, Exceptional, (10)
"Roomy 2 bedroom with great hideaway beds.Excellent location easy to get everywhere. Super responsive hosts Nice building with gym and parking option for visitors "
Michigan Ave 2BR: Balcony, Exclusive Access
2 Connecting Suites at a 5⭐️ Hotel
Classic Chicago hotel with a symmetrical facade, large windows, and a central entrance.

2 Connecting Suites at a 5⭐️ Hotel

The price is HK$21,328
HK$28,417 total
includes taxes & fees
10 Aug - 11 Aug
2 Connecting Suites at a 5⭐️ Hotel
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi
Relax in this stylish living room with a panoramic city view, featuring a comfortable sofa, coffee table, and chair.

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

9.8 out of 10, Exceptional, (10)
"stunning views of lake Michigan, The south loop and the skyline of Chicago"
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi
Downtown Chicago Studio in Prime Location
Enjoy cooking in this fully equipped kitchen with a refrigerator, dishwasher, stove, and oven.

Downtown Chicago Studio in Prime Location

9.6 out of 10, Exceptional, (10)
"The property is in downtown and very close to everything "
Downtown Chicago Studio in Prime Location
McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6
Relax on the rooftop terrace with comfortable lounge chairs and a central seating area, taking in the city views.

McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6

9.0 out of 10, Wonderful, (2)
"Overall stay, I would rate a 4.2 out of 5. The host was very responsive. The only problems I did encounter was parking, the inconsistency of the thermostat, and beds. Overall I would book again. So that should say a lot. "
McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6
BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)
Relax in this open-plan living area with a comfortable sofa and dining table for four, featuring a well-equipped kitchen and a cozy side table.

BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)

9.4 out of 10, Exceptional, (16)
"Large and spacious shared space and living room, lots of amenities like blankets, pillows, and towels. Comfortable beds and many beds and couches. AC in every room. Fantastic place to stay"
BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
Enjoy the city view from this rooftop deck with a seating area and potted plants.

Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

10.0 out of 10, Exceptional, (1)
"This property is the perfect luxe option for a stay in Chicago! Our family came into town for our daughter’s graduation and the property was absolutely perfect for our family to stay and celebrate. It is nestled optimally in the Gold Coast neighborhood on the top of Magnificent Mile and a very short walk to the water. The home is perfectly appointed with all that you need and want for your stay. It is designed to allow plenty of gorgeous natural light in, with top quality linens and many...
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
Walk Everywhere! 5 mins to Magnificent Mile, River
Stunning hallway with polished floors, dark paneling, and an elegant chandelier.

Walk Everywhere! 5 mins to Magnificent Mile, River

10.0 out of 10, Exceptional, (1)
"Loved the location. Clean and any concerns were addressed timely. "
Walk Everywhere! 5 mins to Magnificent Mile, River
Luxurious HUGE Penthouse with 4000+ Games, Arcades
Relax in this stylish living room with a comfortable sofa, coffee table, and large window offering a view.

Luxurious HUGE Penthouse with 4000+ Games, Arcades

8.8 out of 10, Excellent, (3)
"The spot was wonderfuke management was responsive. The space was big and comfortable. Games were available. We did have to deal with missing players ok fusball table and pool may need new accessories but we still enjoyed our time there overall i would recomended. When i advised management of fusball table thry offered to send someone, so props to their respokse time."
Luxurious HUGE Penthouse with 4000+ Games, Arcades
2nd Floor Flat in River North - 2S
Relax in an outdoor seating area with city views, featuring two lounge chairs and a small table.

2nd Floor Flat in River North - 2S

9.6 out of 10, Exceptional, (20)
"Easy to get around the city."
2nd Floor Flat in River North - 2S
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Kitchen features a stainless steel microwave and a window with a decorative grille.

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (56)
"Super convenient for Old Town and train station, will stay there again."
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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