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Chicago Vacation Rentals

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Our top choices for Chicago vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,218 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 ¥25,854
¥35,116 total
includes taxes & fees
Aug 19 - Aug 20
Sentral Michigan Avenue

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (13 reviews)
"Beautiful place exciting city everything was wonderful"
United States
Kyna C.
The price is ¥31,506
¥42,600 total
includes taxes & fees
Jul 27 - Jul 28
LIVN West Loop Chicago Queen Superior Studio

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 ¥30,369
¥40,063 total
includes taxes & fees
Jul 20 - Jul 21
LIVN Millennium Park Downtown Chicago 1 BR

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 ¥33,942
¥73,858 total
includes taxes & fees
Aug 10 - Aug 11
River North Rooftop With In and Out Parking 1

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (502 reviews)
"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."
United States
Serigne abdou
The price is ¥51,010
¥63,885 total
includes taxes & fees
Aug 16 - Aug 17
Level Chicago – Old Town

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 ¥32,642
¥83,782 total
includes taxes & fees
Aug 19 - Aug 20
River North Rooftop With In and Out Parking 6

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 ¥57,002
¥122,311 total
includes taxes & fees
Aug 19 - Aug 20
Downtown Chicago Stay with Free In & Out Parking 1

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 ¥39,626
¥93,203 total
includes taxes & fees
Jul 21 - Jul 22
South Loop Rooftop With In & Out Parking 1

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 ¥53,592
¥130,284 total
includes taxes & fees
Aug 9 - Aug 10
Modern West Loop Gem-City Views & Prime Location 4

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 ¥53,917
¥71,916 total
includes taxes & fees
Aug 3 - Aug 4
LIVN Millennium Park Downtown Chicago Superior 1BR

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 ¥28,095
¥37,997 total
includes taxes & fees
Jul 27 - Jul 28
LIVN Millennium Park Downtown Chicago Studio

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 ¥33,779
¥45,667 total
includes taxes & fees
Jul 27 - Jul 28
LIVN Millennium Park Downtown Chicago Prem Studio

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 ¥31,343
¥42,409 total
includes taxes & fees
Jul 27 - Jul 28
LIVN West Loop Chicago Classic Queen Studio

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 ¥43,036
¥98,811 total
includes taxes & fees
Jul 26 - Jul 27
River North Rooftop With In and Out Parking 3

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 ¥48,070
¥64,849 total
includes taxes & fees
Jul 26 - Jul 27
LIVN Millennium Park Downtown Chicago 2BR

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 ¥48,558
¥65,625 total
includes taxes & fees
Jul 26 - Jul 27
LIVN Millennium Park Downtown Chicago Superior 2 BR

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 ¥57,327
¥76,724 total
includes taxes & fees
Jul 23 - Jul 24
LIVN West Loop Chicago King Studio

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 ¥75,354
¥147,963 total
includes taxes & fees
Jul 23 - Jul 24
River North Private Deck With In and Out Parking

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 ¥70,969
¥155,935 total
includes taxes & fees
Aug 2 - Aug 3
Modern West Loop Gem-City Views & Prime Location 6

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 ¥44,660
¥60,449 total
includes taxes & fees
Jul 27 - Jul 28
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

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:

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Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want 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 vacation rentals in Chicago?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, 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 you can cook with friends or family. Other favorite 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 vacation rentals are there in Chicago?

With 920 Expedia vacation rentals, you're sure 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 vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.