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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Chicago holiday rentals

Lake

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
Kasa Lake Shore Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,208 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$1,436
HK$1,916 total
includes taxes & fees
9 Aug - 10 Aug
Sentral Michigan Avenue
Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
The price is HK$1,943
HK$4,690 total
includes taxes & fees
12 Jul - 13 Jul
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
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, (500 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$2,737
HK$3,407 total
includes taxes & fees
9 Aug - 10 Aug
Level Chicago – Old Town
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$2,109
HK$2,853 total
includes taxes & fees
16 Jul - 17 Jul
LIVN Millennium Park Downtown Chicago 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$2,077
HK$4,710 total
includes taxes & fees
19 Jul - 20 Jul
River North Rooftop With In and Out Parking 3
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)
The price is HK$1,935
HK$2,601 total
includes taxes & fees
12 Jul - 13 Jul
LIVN West Loop Chicago King Studio
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, (25 reviews)
"Great location. "
United States
Tom S.
The price is HK$3,463
HK$7,524 total
includes taxes & fees
2 Aug - 3 Aug
Modern West Loop Gem-City Views & Prime Location 6
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (16 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is HK$8,016
HK$13,276 total
includes taxes & fees
30 Jul - 31 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Exterior detail

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)
"My overall experience was great! This 4 bedroom apartment.2 bath with included parking is a great place to stay when you are visiting Chicago and doing activities in the city.The management staff was great to work with. The front desk staff was also great.My family felt safe and we would return.Thigpen Family"
United States
Kimberly T.
The price is HK$1,881
HK$4,695 total
includes taxes & fees
13 Jul - 14 Jul
Downtown Chicago Stay with Free In & Out Parking 1
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (816 reviews)
"Great place to stay."
United States
Benedictine
Kasa Magnificent Mile Chicago
Miscellaneous

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$2,766
HK$5,744 total
includes taxes & fees
29 Jul - 30 Jul
South Loop Rooftop With In & Out Parking 1
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (26 reviews)
"Great location, close to public transport and Whole Foods. The property was clean, quiet, and easy to access. The host was great with communication. We would stay again! "
United States
Susan R.
The price is HK$8,858
HK$14,384 total
includes taxes & fees
31 Jul - 1 Aug
Spacious 4BR Central Apartment w/ Skyline Views
TV

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Great host any concerns that I had were addressed and handled!"
United States
Keana
The price is HK$917
HK$4,518 total
includes taxes & fees
12 Jul - 13 Jul
4BR Retreat w/ Theater, Arcade, Gym and Firepit
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$1,787
HK$2,407 total
includes taxes & fees
12 Jul - 13 Jul
LIVN Millennium Park Downtown Chicago Superior 2 BR
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$1,653
HK$2,222 total
includes taxes & fees
12 Jul - 13 Jul
LIVN West Loop Chicago Classic Queen 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.
LIVN Millennium Park Downtown Chicago Superior 1BR
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$1,912
HK$2,573 total
includes taxes & fees
12 Jul - 13 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
8.8 out of 10, Excellent, (10 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$1,920
HK$2,583 total
includes taxes & fees
12 Jul - 13 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$1,968
HK$2,658 total
includes taxes & fees
16 Jul - 17 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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great location. Nice room layout. Helpful,friendly staff"
kai 1-night trip
Posted 1 hour ago
Hilton Chicago/Magnificent Mile Suites

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.