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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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, (1,200 reviews)
"Great location"
United States
JAVIER
The price is HK$1,193
HK$1,631 total
includes taxes & fees
5 Jul - 6 Jul
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, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is HK$2,181
HK$2,753 total
includes taxes & fees
6 Jul - 7 Jul
Level Chicago – Old Town
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is HK$2,243
HK$5,099 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$1,309
HK$1,731 total
includes taxes & fees
1 Jul - 2 Jul
LIVN Millennium Park Downtown Chicago Studio
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is HK$1,263
HK$2,127 total
includes taxes & fees
1 Jul - 2 Jul
Kasa River North Chicago
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, (5 reviews)
The price is HK$1,223
HK$1,630 total
includes taxes & fees
1 Jul - 2 Jul
LIVN West Loop Chicago Classic Queen Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is HK$3,717
HK$7,897 total
includes taxes & fees
2 Jul - 3 Jul
Modern West Loop Gem-City Views & Prime Location 4
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)
"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$2,078
HK$4,713 total
includes taxes & fees
1 Jul - 2 Jul
River North Rooftop With In and Out Parking 3
2 bedrooms, desk, iron/ironing board, travel cot

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$2,486
HK$5,274 total
includes taxes & fees
2 Jul - 3 Jul
South Loop Rooftop With In & Out Parking 1
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is HK$1,662
HK$4,123 total
includes taxes & fees
7 Jul - 8 Jul
Downtown Chicago Stay with Free In & Out Parking 5
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 check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is HK$1,309
HK$1,741 total
includes taxes & fees
6 Jul - 7 Jul
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,568
HK$2,093 total
includes taxes & fees
1 Jul - 2 Jul
LIVN Millennium Park Downtown Chicago 2BR
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, (9 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is HK$1,153
HK$1,547 total
includes taxes & fees
1 Jul - 2 Jul
LIVN West Loop Chicago Queen Superior Studio
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$1,443
HK$1,916 total
includes taxes & fees
6 Jul - 7 Jul
LIVN Millennium Park Downtown Chicago Superior 1BR
TV, offices

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
River North Private Balcony With In and Out Parking
TV, books

Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
West Town
The price is HK$711
HK$1,555 total
includes taxes & fees
5 Jul - 6 Jul
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (24 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
The price is HK$10,452
HK$16,710 total
includes taxes & fees
31 Jul - 1 Aug
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location."
United States
Nicoll M.
The price is HK$1,639
HK$2,185 total
includes taxes & fees
1 Jul - 2 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
The price is HK$2,470
HK$3,287 total
includes taxes & fees
4 Jul - 5 Jul
LIVN West Loop Chicago King 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$1,239
HK$1,648 total
includes taxes & fees
1 Jul - 2 Jul
LIVN Millennium Park Downtown Chicago 1 BR
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
"Good breakfast with a thoughtful selection of food. The quality of the ingredients is high, the dining area is well-maintained, and the overall choice is better than average."
Andreas 7-night trip
Posted 1 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 King Comfort apartment, Quiet, Clean, AC & WiFi.

How many holiday rentals are there in Chicago?

With 889 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 Lake Michigan 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.