A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chicago vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,283 reviews)
"Nice stay"
United States
Heather
The price is SAR 568
SAR 777 total
includes taxes & fees
9 Sep - 10 Sep
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (20 reviews)
"Great location and super clean!"
United States
Erica
The price is SAR 637
SAR 980 total
includes taxes & fees
7 Sep - 8 Sep
Kasa Lake Shore Chicago
1 bedroom, iron/ironing board, travel crib, WiFi

3. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is SAR 620
SAR 820 total
includes taxes & fees
31 Aug - 1 Sep
LIVN West Loop Chicago Queen Superior Studio
TV, offices

4. 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 SAR 635
SAR 842 total
includes taxes & fees
31 Aug - 1 Sep
LIVN Millennium Park Downtown Chicago 1 BR
Full-size fridge, microwave, oven, stovetop

5. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 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 SAR 903
SAR 1,153 total
includes taxes & fees
1 Sep - 2 Sep
Level Chicago – Old Town
Interior

6. River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.0 out of 10, Wonderful, (9 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 SAR 980
SAR 2,266 total
includes taxes & fees
3 Sep - 4 Sep
River North Rooftop With In and Out Parking 3
Interior

7. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, and stylish!"
United States
Maurya K.
The price is SAR 770
SAR 2,034 total
includes taxes & fees
2 Sep - 3 Sep
Premium Urban 4BR - Perfect Mix of Comfort & Location
Exterior

8. Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (30 reviews)
"An incredible experience and wonderful place to stay. A perfect location, quiet, and my twin boys loved having their own spaces. Thank you so much!"
United States
Miriam B.
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

9. 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 SAR 1,126
SAR 2,451 total
includes taxes & fees
16 Sep - 17 Sep
Downtown Chicago Stay with Free In & Out Parking 3
Property grounds

10. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
The price is SAR 2,294
SAR 4,184 total
includes taxes & fees
16 Sep - 17 Sep
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

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

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 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 SAR 909
SAR 2,072 total
includes taxes & fees
30 Aug - 31 Aug
Plymouth Collection: 3BD 2BA High Floor with Gym
TV, offices

12. 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
Dining

13. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is SAR 593
SAR 798 total
includes taxes & fees
30 Aug - 31 Aug
LIVN Millennium Park Downtown Chicago Studio
TV, offices

14. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is SAR 751
SAR 1,016 total
includes taxes & fees
31 Aug - 1 Sep
LIVN Millennium Park Downtown Chicago 2BR
1 bedroom, iron/ironing board, travel crib, WiFi

15. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is SAR 586
SAR 780 total
includes taxes & fees
31 Aug - 1 Sep
LIVN West Loop Chicago Classic Queen Studio
TV, offices

16. LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
8.6 out of 10, Excellent, (10 reviews)
"We loved the location."
United States
Nicoll M.
The price is SAR 856
SAR 1,158 total
includes taxes & fees
31 Aug - 1 Sep
LIVN Millennium Park Downtown Chicago Superior 2 BR
1 bedroom, iron/ironing board, travel crib, WiFi

17. 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.
LIVN West Loop Chicago 1 BR
1 bedroom, iron/ironing board, travel crib, WiFi

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
LIVN West Loop Chicago King Studio
Dining

19. 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.
LIVN Millennium Park Downtown Chicago Prem Studio
Studio | Living area

20. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is SAR 376
SAR 678 total
includes taxes & fees
9 Sep - 10 Sep
Ground Floor Studios in Chicago by 747 Lofts
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"The room was nice we had the river view. Location was amazing, close to a lot of things we wanted to do. The only thing was our room was right next to the elevator and we heard it constantly. At first I thought it was a train, just to give reference to the noise level. We asked on the first night about switching rooms, we were told they were fully booked and the elevators close to the rooms stop in the night. I have a video of the one beside our room still operating at 2 am. I would stay here again but if you are a light sleeper that room might be a deal breaker."
Chyeann 3-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown

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 theater 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 Vintage Escape 1BR Two Blocks Away From Beach.

How many vacation rentals are there in Chicago?

With 929 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 Soldier Field and Navy Pier.

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.