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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
9.0 out of 10, Wonderful, (1,336 reviews)
"Great venue"
United States
Arthur Noel
The price is ￥23,956
￥32,742 total
includes taxes & fees
Sep 27 - Sep 28
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (38 reviews)
"The property was in a very nice location."
United Kingdom
Nehal Manish
The price is ￥27,260
￥40,281 total
includes taxes & fees
Sep 27 - Sep 28
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (527 reviews)
"Location and facility was very nice"
United States
Brian
The price is ￥47,693
￥59,871 total
includes taxes & fees
Sep 27 - Sep 28
Level Chicago – Old Town
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

4. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (13 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ￥43,299
￥57,636 total
includes taxes & fees
Sep 27 - Sep 28
LIVN Millennium Park Downtown Chicago 2BR
A modern room with a sofa, a dining table, and a window with a view of buildings.

5. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great property"
United States
duane
The price is ￥45,188
￥60,240 total
includes taxes & fees
Sep 27 - Sep 28
LIVN West Loop Chicago 2 BR City View
A modern lounge area with a black leather sofa, a small table, and chairs. There is a television mounted on the wall and an exit sign above the door.

6. 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, (13 reviews)
"Best location"
United States
Eric Dallas
The price is ￥39,992
￥92,110 total
includes taxes & fees
Sep 27 - Sep 28
Downtown Chicago Stay with Free In & Out Parking 3
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a gray sofa and patterned cushions.

7. 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 ￥41,844
￥90,923 total
includes taxes & fees
Sep 29 - Sep 30
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern kitchen with a central island, bar stools, and a dining table.

8. 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, (15 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is ￥54,950
￥115,477 total
includes taxes & fees
Oct 18 - Oct 19
River North Private Deck With In and Out Parking
A modern living room with a sectional sofa, a coffee table, and a dining area with chairs and a table.

9. Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.6 out of 10, Exceptional, (11 reviews)
"Great location, lots of food options, park near by for children. Great communication with hosts."
United States
Jackie S.
The price is ￥43,456
￥111,156 total
includes taxes & fees
Oct 21 - Oct 22
Modern West Loop Gem-City Views & Prime Location 2
A spacious lobby with a sectional sofa, a dining area, and large windows.

10. 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 ￥26,294
￥73,071 total
includes taxes & fees
Oct 14 - Oct 15
South Loop Rooftop With In and Out Parking 3
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

11. Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Lakeview
9.8 out of 10, Exceptional, (28 reviews)
"Location cannot be beat! So close to Wrigley and so fun! "
United States
Celia A
The price is ￥75,351
￥170,631 total
includes taxes & fees
Sep 28 - Sep 29
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
A hotel room with a large bed, two pillows, a teal throw blanket, and a view of buildings through a window.

12. Bronzeville Gem: Balcony, Gym & Rooftop Deck

Bronzeville Gem: Balcony, Gym & Rooftop Deck
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
The price is ￥51,864
￥111,601 total
includes taxes & fees
Sep 26 - Sep 27
Bronzeville Gem: Balcony, Gym & Rooftop Deck

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

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
9.6 out of 10, Exceptional, (9 reviews)
"Great location with large beds which made it amazing for our group. Easy access to public transport and a cute neighborhood"
United States
Kortnee
The price is ￥54,793
￥115,802 total
includes taxes & fees
Sep 27 - Sep 28
Premium Urban 4BR - Perfect Mix of Comfort & Location
A spacious room with exposed brick walls, a large window with a city view, a gray sofa, a dining table with chairs, and a small side table.

14. River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.6 out of 10, Exceptional, (13 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is ￥44,401
￥88,123 total
includes taxes & fees
Oct 7 - Oct 8
River North Rooftop With In and Out Parking 1
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

15. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is ￥62,980
￥148,044 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

16. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
8.8 out of 10, Excellent, (15 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is ￥19,917
￥39,151 total
includes taxes & fees
Oct 1 - Oct 2
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

17. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (23 reviews)
"Great location! "
United States
Andrea B.
The price is ￥27,192
￥47,155 total
includes taxes & fees
Oct 18 - Oct 19
Flexhome East Village • Modern 2BR • Quiet Street
A living room with a sofa, coffee table, TV, and a ceiling fan.

18. Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.6 out of 10, Exceptional, (7 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
The price is ￥105,454
￥190,214 total
includes taxes & fees
Oct 11 - Oct 12
Newly Remodeled Gem | Heart of Chicago
A living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

19. 5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly

5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly
Lakeview
9.6 out of 10, Exceptional, (11 reviews)
"Great location. Nice big unit. Very good place for a group. Beds were comfortable Kitchen was big Parking in garage was good. Lots of stuff to walk too… Great transit location."
United States
Jason D.
The price is ￥31,962
￥70,257 total
includes taxes & fees
Sep 24 - Sep 25
5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly
A balcony with a wooden table and chairs, a potted plant, and a lattice screen.

20. 2R- ❤️ Stylish and Cozy 2BR in Logan Square!

2R- ❤️ Stylish and Cozy 2BR in Logan Square!
Logan Square
10.0 out of 10, Exceptional, (58 reviews)
"Excellent stay. Nice location"
United States
Daniel R.
The price is ￥28,316
￥54,810 total
includes taxes & fees
Sep 28 - Sep 29
2R- ❤️ Stylish and Cozy 2BR in Logan Square!
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

River Hotel

River Hotel

8/10 Good
"Staff were nice and welcoming."
Angelica 3-night trip
Posted less than an hour ago
River Hotel

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
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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 LUXE 3 BR, 2 BA + Hot Tub and Cozy 3-bedroom house in family-oriented Melrose Park..

How many vacation rentals are there in Chicago?

With 934 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.