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Chicago Vacation Rentals

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Our top choices for Chicago vacation rentals

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,237 reviews)
"Great property and location."
United States
Michael
The price is ¥25,112
¥34,108 total
includes taxes & fees
Aug 23 - Aug 24
Sentral Michigan Avenue

2. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is ¥29,024
¥39,135 total
includes taxes & fees
Aug 9 - Aug 10
LIVN West Loop Chicago Queen Superior Studio

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (512 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is ¥37,399
¥47,794 total
includes taxes & fees
Sep 1 - Sep 2
Level Chicago – Old Town

4. South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is ¥32,652
¥83,130 total
includes taxes & fees
Aug 19 - Aug 20
South Loop Rooftop With In and Out Parking 3

5. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.6 out of 10, Exceptional, (8 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is ¥32,652
¥43,394 total
includes taxes & fees
Aug 12 - Aug 13
LIVN Millennium Park Downtown Chicago Studio

6. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (10 reviews)
"Great location and super clean!"
United States
Erica
The price is ¥47,892
¥66,314 total
includes taxes & fees
Sep 2 - Sep 3
Kasa Lake Shore Chicago

7. 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, (8 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 ¥41,801
¥96,171 total
includes taxes & fees
Aug 19 - Aug 20
River North Rooftop With In and Out Parking 3

8. Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (10 reviews)
"Perfect Stay!"
United States
Miyauna G.
The price is ¥59,153
¥118,946 total
includes taxes & fees
Sep 2 - Sep 3
Downtown Chicago Stay with Free In & Out Parking 3

9. Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
The price is ¥43,063
¥116,032 total
includes taxes & fees
Sep 1 - Sep 2
Modern West Loop Gem-City Views & Prime Location 1

10. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
The price is ¥45,308
¥95,823 total
includes taxes & fees
Aug 11 - Aug 12
Plymouth Collection: 3BD 2BA High Floor with Gym

11. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
Envitae Hotel, 4BR Modern Sleek Apartment

12. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is ¥29,340
¥38,337 total
includes taxes & fees
Aug 12 - Aug 13
LIVN West Loop Chicago Classic Queen Studio

13. 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 ¥29,576
¥38,605 total
includes taxes & fees
Aug 11 - Aug 12
LIVN Millennium Park Downtown Chicago Prem Studio

14. 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 ¥30,759
¥40,006 total
includes taxes & fees
Aug 12 - Aug 13
LIVN Millennium Park Downtown Chicago Superior 1BR

15. 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 ¥42,748
¥57,389 total
includes taxes & fees
Aug 9 - Aug 10
LIVN Millennium Park Downtown Chicago 1 BR

16. 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 ¥42,274
¥56,832 total
includes taxes & fees
Aug 9 - Aug 10
LIVN Millennium Park Downtown Chicago 2BR

17. 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)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is ¥36,438
¥49,007 total
includes taxes & fees
Aug 9 - Aug 10
LIVN West Loop Chicago 2 BR City View

18. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is ¥36,596
¥49,192 total
includes taxes & fees
Aug 9 - Aug 10
LIVN West Loop Chicago King Studio

19. LIVN West Loop Chicago 1 BR

LIVN West Loop Chicago 1 BR
Downtown Chicago
2.0 out of 10, (1 review)
"Unfortunately, this property was in disrepair and the surroundings were so loud that it was impossible to sleep."
United States
Brittany C.
The price is ¥37,858
¥50,872 total
includes taxes & fees
Aug 9 - Aug 10
LIVN West Loop Chicago 1 BR

20. LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (6 reviews)
"We loved the location."
United States
Nicoll M.
The price is ¥45,114
¥59,970 total
includes taxes & fees
Aug 12 - Aug 13
LIVN Millennium Park Downtown Chicago Superior 2 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

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 928 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.