Central Chicago Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Central Chicago holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,048 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is HK$855
HK$1,233 total
includes taxes & fees
19 Jan - 20 Jan
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (411 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Desk, iron/ironing board, travel cot, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$538
HK$1,290 total
includes taxes & fees
25 Jan - 26 Jan
Chic Studio in the Heart of the Gold Coast
Dining

Downtown 2bd #5 +Gym near Park, Lake, Museums

Downtown 2bd #5 +Gym near Park, Lake, Museums
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
The price is HK$734
HK$2,270 total
includes taxes & fees
22 Jan - 23 Jan
Downtown 2bd #5 +Gym near Park, Lake, Museums
Interior

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
Downtown Chicago
The price is HK$538
HK$1,485 total
includes taxes & fees
19 Jan - 20 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown
Beach nearby

Downtown Mag Mile Sleep 20 | 6bd/6ba

Downtown Mag Mile Sleep 20 | 6bd/6ba
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great units, fabulous location, very attentive property managers. Loved the place. Only downside was a grumpy downstairs neighbor who complained about the noise of the children and noise of adults even before quiet hours and no music playing."
United States
Cathy E.
The price is HK$2,703
HK$8,842 total
includes taxes & fees
21 Jan - 22 Jan
Downtown Mag Mile Sleep 20 | 6bd/6ba
TV, offices

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$491
HK$1,314 total
includes taxes & fees
18 Jan - 19 Jan
Complete 1BR Home Sum
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$780
HK$2,439 total
includes taxes & fees
3 Feb - 4 Feb
River North Rooftop With In and Out Parking 3
TV, offices

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$756
HK$1,624 total
includes taxes & fees
16 Feb - 17 Feb
The One: A 1BR Stay That Feels Like Home
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
Downtown Chicago
The price is HK$491
HK$1,314 total
includes taxes & fees
18 Jan - 19 Jan
Chicago-Themed 1BR in a Central Spot near Downtown
Interior

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$538
HK$1,485 total
includes taxes & fees
18 Jan - 19 Jan
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$491
HK$1,314 total
includes taxes & fees
22 Jan - 23 Jan
Sleek 1BR Apt w/ Laundry
Desk, iron/ironing board, travel cot, WiFi

Vintage Studio in Chicago’s Gold Coast

Vintage Studio in Chicago’s Gold Coast
Downtown Chicago
The price is HK$538
HK$1,290 total
includes taxes & fees
18 Jan - 19 Jan
Vintage Studio in Chicago’s Gold Coast
TV, offices

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is HK$491
HK$1,314 total
includes taxes & fees
22 Jan - 23 Jan
Stylish Gold Coast 1BR with Vintage Flair
Interior

Trendy Gold Coast Studio Close to Downtown

Trendy Gold Coast Studio Close to Downtown
Downtown Chicago
6.0 out of 10, (1 review)
"Key pad issues with entry, but overall good "
United States
Andrew U.
The price is HK$538
HK$1,290 total
includes taxes & fees
18 Jan - 19 Jan
Trendy Gold Coast Studio Close to Downtown
Fridge, microwave, oven, stovetop

Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
Near South Side
9.2 out of 10, Wonderful, (5 reviews)
"Great communication with Host, was exactly as described."
United States
Doug C.
The price is HK$686
HK$2,729 total
includes taxes & fees
21 Jan - 22 Jan
Smart Simple and Spacious 4BR Apt
Interior

Stylish 4BR Stay-Prime Location

Stylish 4BR Stay-Prime Location
Near South Side
6.8 out of 10, (6 reviews)
"Incredibly clean and spacious apartment. The beds were comfortable, and we really appreciated having multiple bathrooms. The kitchen was well stocked and the location was a short Lyft/uber from everywhere we wanted to be. Would definitely stay here again."
United States
Jessica F.
The price is HK$686
HK$2,729 total
includes taxes & fees
22 Jan - 23 Jan
Stylish 4BR Stay-Prime Location
Fridge, microwave, oven, stovetop

Less is more! Pet friendly Tiny Home near Chicago!

Less is more! Pet friendly Tiny Home near Chicago!
Burr Ridge
9.8 out of 10, Exceptional, (37 reviews)
"We loved it! We were in for a short time and it was perfect!!"
United States
nicole l.
The price is HK$789
HK$1,612 total
includes taxes & fees
31 Jan - 1 Feb
Less is more! Pet friendly Tiny Home near Chicago!
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$491
HK$1,314 total
includes taxes & fees
22 Jan - 23 Jan
West Loop Living – Bright 1BR
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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Top Central Chicago Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"hotel was nice and conveniently located. Really enjoyed the big hotel bar. Would stay again"
Mayra 3-night trip
Posted 3 days ago
Hyatt Regency Chicago

Find out more about Central Chicago

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