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, (1,343 reviews)
"Great venue"
United States
Arthur Noel
The price is ￥27,555
￥36,963 total
includes taxes & fees
Oct 26 - Oct 27
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, (42 reviews)
"Location is perfect"
United States
Mary
The price is ￥27,406
￥41,935 total
includes taxes & fees
Sep 30 - Oct 1
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, (530 reviews)
"Location and facility was very nice"
United States
Brian
The price is ￥47,509
￥59,652 total
includes taxes & fees
Oct 26 - Oct 27
Level Chicago – Old Town
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

4. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is ￥15,964
￥32,040 total
includes taxes & fees
Sep 28 - Sep 29
Chic Urban Retreat Near Wrigley Field w/Parking
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.

5. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (25 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is ￥55,363
￥69,462 total
includes taxes & fees
Oct 2 - Oct 3
LIVN West Loop Chicago Queen Superior Studio
A modern living room with a sofa, a coffee table, a floor lamp, a television, and a black cabinet.

6. Modern 1BR in Prime West Loop Location

Modern 1BR in Prime West Loop Location
Downtown Chicago
The price is ￥22,648
￥49,285 total
includes taxes & fees
Sep 29 - Sep 30
Modern 1BR in Prime West Loop Location
A compact laundry room with a front-loading washer and dryer, a framed picture on the wall, and a towel rack.

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 ￥20,289
￥57,074 total
includes taxes & fees
Sep 28 - Sep 29
Plymouth Collection: 3BD 2BA High Floor with Gym
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

8. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
The price is ￥24,064
￥46,225 total
includes taxes & fees
Oct 26 - Oct 27
2BR Apt with 2 Baths & Laundry
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

9. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is ￥34,602
￥44,504 total
includes taxes & fees
Oct 1 - Oct 2
LIVN Millennium Park Downtown Chicago Studio
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

10. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is ￥26,108
￥59,887 total
includes taxes & fees
Oct 12 - Oct 13
River North Private Balcony With In and Out Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

11. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is ￥10,003
￥39,477 total
includes taxes & fees
Sep 28 - Sep 29
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

12. 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 ￥84,459
￥144,994 total
includes taxes & fees
Oct 2 - Oct 3
River North Rooftop With In and Out Parking 6

13. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
Cozy Studio Suite, Steps from River North & Shops
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

14. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.8 out of 10, Good, (58 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ￥23,356
￥27,418 total
includes taxes & fees
Sep 29 - Sep 30
Wrigleyville Suites
A modern bedroom with a bed, a sofa, and a hanging plant.

15. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (99 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
The price is ￥9,909
￥21,931 total
includes taxes & fees
Oct 26 - Oct 27
Cozy studio in Andersonville Chicago
A bedroom with a bed, a wardrobe, a bench, and a floor lamp.

16. Wabash 4BR - Pool, Free In & Out Parking 4

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
The price is ￥41,207
￥105,797 total
includes taxes & fees
Sep 29 - Sep 30
Wabash 4BR - Pool, Free In & Out Parking 4
A modern kitchen with wooden cabinets, a stainless steel dishwasher, a microwave, a coffee maker, and a toaster.

17. Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
Near South Side
8.2 out of 10, Very good, (12 reviews)
"Everything was exactly as described."
United States
Sydney D.
The price is ￥22,019
￥61,520 total
includes taxes & fees
Sep 29 - Sep 30
Smart Simple and Spacious 4BR Apt
A modern apartment with a living area, kitchen, and large windows offering city views.

18. 3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.6 out of 10, Exceptional, (36 reviews)
"The property was great. Perfect location, beautiful, good decor. Definitely recommend it and stay again there. Host was very good too, very responsive when I needed it."
United States
Adrian
3BR Luxury Suite w/Gym and Balcony
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

19. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is ￥15,099
￥37,296 total
includes taxes & fees
Sep 28 - Sep 29
3BR Complete and Spacious Apartment in Ideal Spot
A hotel room with a bed, a view of a cityscape, and a window with curtains.

20. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.4 out of 10, Very good, (10 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is ￥10,003
￥33,545 total
includes taxes & fees
Sep 28 - Sep 29
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Great stay! Everyone was so nice from check in with Joao until we walked out the doors."
Mathew 1-night trip
Posted 1 hour ago
Hilton 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
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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.