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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Chicago holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,219 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is HK$1,248
HK$1,695 total
includes taxes & fees
20 Aug - 21 Aug
Sentral Michigan Avenue
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (13 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is HK$1,811
HK$2,417 total
includes taxes & fees
26 Jul - 27 Jul
LIVN West Loop Chicago Queen Superior Studio
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$1,309
HK$1,760 total
includes taxes & fees
27 Jul - 28 Jul
LIVN Millennium Park Downtown Chicago 1 BR
TV, offices

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is HK$1,670
HK$3,740 total
includes taxes & fees
10 Aug - 11 Aug
River North Rooftop With In and Out Parking 1
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, (504 reviews)
"Perfect location"
United States
Diana
The price is HK$2,223
HK$2,803 total
includes taxes & fees
17 Aug - 18 Aug
Level Chicago – Old Town
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is HK$1,372
HK$3,755 total
includes taxes & fees
19 Aug - 20 Aug
River North Rooftop With In and Out Parking 6
Interior

Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
The price is HK$2,603
HK$5,750 total
includes taxes & fees
28 Jul - 29 Jul
Downtown Chicago Stay with Free In & Out Parking 1
Fitness facility

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is HK$2,101
HK$4,771 total
includes taxes & fees
29 Jul - 30 Jul
South Loop Rooftop With In & Out Parking 1
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.6 out of 10, Exceptional, (12 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is HK$3,575
HK$7,732 total
includes taxes & fees
9 Aug - 10 Aug
Modern West Loop Gem-City Views & Prime Location 4
TV, offices

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
The price is HK$2,956
HK$3,935 total
includes taxes & fees
24 Jul - 25 Jul
LIVN Millennium Park Downtown Chicago Superior 1BR
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.0 out of 10, Wonderful, (4 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$2,423
HK$3,270 total
includes taxes & fees
28 Jul - 29 Jul
LIVN Millennium Park Downtown Chicago Studio
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
The price is HK$1,866
HK$2,491 total
includes taxes & fees
26 Jul - 27 Jul
LIVN Millennium Park Downtown Chicago Prem Studio
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
The price is HK$1,537
HK$2,065 total
includes taxes & fees
27 Jul - 28 Jul
LIVN West Loop Chicago Classic Queen Studio
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
The price is HK$2,078
HK$4,741 total
includes taxes & fees
19 Aug - 20 Aug
River North Rooftop With In and Out Parking 3
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,803
HK$2,427 total
includes taxes & fees
27 Jul - 28 Jul
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.2 out of 10, Wonderful, (5 reviews)
The price is HK$3,034
HK$4,075 total
includes taxes & fees
27 Jul - 28 Jul
LIVN Millennium Park Downtown Chicago Superior 2 BR
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
LIVN West Loop Chicago King Studio
Coffee/tea maker, fridge, microwave, oven

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is HK$3,615
HK$7,095 total
includes taxes & fees
23 Jul - 24 Jul
River North Private Deck With In and Out Parking
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (26 reviews)
"Great location. "
United States
Tom S.
The price is HK$3,379
HK$7,461 total
includes taxes & fees
2 Aug - 3 Aug
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"Everything went well"
United States
Ryan W.
The price is HK$1,709
HK$2,297 total
includes taxes & fees
27 Jul - 28 Jul
LIVN West Loop Chicago 2 BR City View
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 Chicago Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Traveling for work and this hotel was a nice retreat at the end of long work days. Breakfast was a great perk!"
Hannah 3-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Chicago
  • Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chicago while they last

Look no further and take a look at our great range of rental properties in Chicago!

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Six Flags Great America, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed art scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

What are some of the best holiday rentals that Chicago has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated holiday home rental in Chicago is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Chicago are ENVITAE Hotel, 4BR Luxury Modern Apartments and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many holiday rentals are there in Chicago?

With 920 Expedia holiday rentals, you're guaranteed to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Grant Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Wrigley Field and Michigan Avenue.

What are holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.