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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chicago vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,281 reviews)
"Nice stay"
United States
Heather
The price is ￥24,034
￥32,877 total
includes taxes & fees
Sep 7 - Sep 8
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (17 reviews)
"Great location and super clean!"
United States
Erica
The price is ￥29,441
￥44,452 total
includes taxes & fees
Sep 10 - Sep 11
Kasa Lake Shore Chicago
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

3. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (20 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is ￥26,227
￥35,305 total
includes taxes & fees
Aug 30 - Aug 31
LIVN West Loop Chicago Queen Superior Studio
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

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 ￥26,545
￥35,286 total
includes taxes & fees
Aug 24 - Aug 25
LIVN Millennium Park Downtown Chicago 1 BR
A modern kitchen with a large island, bar stools, and a city view.

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 ￥37,820
￥48,317 total
includes taxes & fees
Aug 31 - Sep 1
Level Chicago – Old Town
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

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 ￥27,498
￥76,118 total
includes taxes & fees
Sep 8 - Sep 9
River North Rooftop With In and Out Parking 3

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.
Premium Urban 4BR - Perfect Mix of Comfort & Location
A modern building with a glass facade, surrounded by a parking area and greenery.

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.
The price is ￥22,253
￥71,593 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 4BR Central Apartment w/ Skyline Views

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 ￥47,685
￥104,363 total
includes taxes & fees
Sep 16 - Sep 17
Downtown Chicago Stay with Free In & Out Parking 3
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

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 ￥89,171
￥165,349 total
includes taxes & fees
Sep 16 - Sep 17
ENVITAE Hotel, 4BR Luxury Modern Apartments
A kitchen with white cabinets, a microwave, a kettle, and a toaster.

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 ￥25,591
￥69,313 total
includes taxes & fees
Sep 2 - Sep 3
Plymouth Collection: 3BD 2BA High Floor with Gym
A room with a large window, a round table with chairs, a television, and a lamp.

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.
The price is ￥29,247
￥39,436 total
includes taxes & fees
Aug 30 - Aug 31
LIVN Millennium Park Downtown Chicago Superior 1BR
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

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 ￥28,770
￥38,682 total
includes taxes & fees
Aug 30 - Aug 31
LIVN Millennium Park Downtown Chicago Studio
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

14. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ￥30,201
￥39,968 total
includes taxes & fees
Aug 24 - Aug 25
LIVN Millennium Park Downtown Chicago 2BR
A modern hotel room with a large bed, a small dining table, a bench, and a view of the city through a large window.

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 ￥29,247
￥39,436 total
includes taxes & fees
Aug 30 - Aug 31
LIVN West Loop Chicago Classic Queen Studio
A modern living room with a blue sofa, a leather armchair, and a geometric coffee table.

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 ￥33,538
￥45,257 total
includes taxes & fees
Aug 24 - Aug 25
LIVN Millennium Park Downtown Chicago Superior 2 BR
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

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.
The price is ￥33,221
￥44,885 total
includes taxes & fees
Aug 30 - Aug 31
LIVN West Loop Chicago 1 BR
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

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
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

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.
The price is ￥30,995
￥41,096 total
includes taxes & fees
Aug 25 - Aug 26
LIVN Millennium Park Downtown Chicago Prem Studio
A compact living space with a kitchenette, a sofa, a bed, and a television mounted on the wall.

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 ￥14,313
￥26,756 total
includes taxes & fees
Sep 9 - Sep 10
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Beautiful property and is also in a GREAT area, everything is in that vicinity"
Jabree 3-night trip
Posted less than an hour ago
Hyatt Regency 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!

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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 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.