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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (1,354 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
The price is ￥27,655
￥37,098 total
includes taxes & fees
Oct 25 - Oct 26
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (55 reviews)
"Location is perfect"
United States
Mary
The price is ￥28,266
￥42,991 total
includes taxes & fees
Nov 5 - Nov 6
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, (535 reviews)
"Location and facility was very nice"
United States
Brian
The price is ￥35,827
￥45,952 total
includes taxes & fees
Nov 2 - Nov 3
Level Chicago – Old Town
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

4. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is ￥11,113
￥47,982 total
includes taxes & fees
Oct 26 - Oct 27
Sleeps 7 • Huge Projector • Designated Workspace
A modern bedroom with a bed, a sofa, and a hanging plant.

5. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (101 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is ￥9,945
￥22,011 total
includes taxes & fees
Oct 26 - Oct 27
Cozy studio in Andersonville Chicago
A spacious lobby with a sectional sofa, a dining area, and large windows.

6. 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 ￥23,520
￥69,944 total
includes taxes & fees
Oct 14 - Oct 15
South Loop Rooftop With In and Out Parking 3
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.

7. 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 ￥10,244
￥26,277 total
includes taxes & fees
Nov 2 - Nov 3
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern living room with a blue sofa, a patterned rug, and a television.

8. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is ￥11,054
￥34,385 total
includes taxes & fees
Oct 13 - Oct 14
Great Area Logan Square Apt Games Pets - Sleeps 5
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

9. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
The price is ￥8,612
￥45,819 total
includes taxes & fees
Oct 14 - Oct 15
Private Workspace • Sleeps4 • Modern Stylish Stay
A modern bathroom with a glass shower enclosure, a toilet, and a sink with a mirror above it.

10. 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 ￥18,784
￥42,463 total
includes taxes & fees
Oct 15 - Oct 16
3BR Complete and Spacious Apartment in Ideal Spot
A modern kitchen with stainless steel appliances, wooden cabinets, and a brick wall.

11. River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Everything was amazing"
United States
Kimberly R.
The price is ￥17,844
￥51,940 total
includes taxes & fees
Nov 2 - Nov 3
River North Rooftop With In and Out Parking 5
A bedroom with a bed, two bedside tables, a window with a brick pattern, and a painting on the wall.

12. Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants

Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
Downtown Chicago
The price is ￥23,741
￥74,253 total
includes taxes & fees
Nov 4 - Nov 5
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

13. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is ￥22,581
￥46,508 total
includes taxes & fees
Nov 2 - Nov 3
2BR Apt with 2 Baths & Laundry
A bedroom with a bed, bedside tables, a ceiling fan, framed pictures, and a window.

14. Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is ￥22,423
￥52,619 total
includes taxes & fees
Oct 7 - Oct 8
Stylish Gold Coast 1BR with Vintage Flair
Private kitchen

15. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is ￥12,628
￥35,054 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

16. 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 ￥16,028
￥32,754 total
includes taxes & fees
Oct 26 - Oct 27
Chic Urban Retreat Near Wrigley Field w/Parking
Game room

17. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is ￥11,365
￥43,751 total
includes taxes & fees
Oct 13 - Oct 14
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A hotel room with a bed, a view of a cityscape, and a window with curtains.

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

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is ￥22,541
￥49,091 total
includes taxes & fees
Oct 8 - Oct 9
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A bedroom with a large bed, a bedside table, a nightstand, a window with blinds, and a wall-mounted artwork.

19. Comfortable 3BR/2BA Haven | Ideal for Families

Comfortable 3BR/2BA Haven | Ideal for Families
Avondale
9.4 out of 10, Exceptional, (15 reviews)
"Great neighborhood - excellent communication - large space for family."
United States
Marc
The price is ￥23,362
￥48,994 total
includes taxes & fees
Nov 3 - Nov 4
Comfortable 3BR/2BA Haven | Ideal for Families
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

20. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is ￥12,780
￥64,279 total
includes taxes & fees
Oct 7 - Oct 8
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
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

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"I loved this hotel! It was very clean, chic, updated, and modern. I stayed here for a solo trip, and the room was extremely spacious, definitely more than enough room for just me. The location was one of my favorite things about the hotel. It was very central, and so much was within walking distance, including Millennium Park, restaurants, and many of the attractions I wanted to visit. It made exploring the city really convenient because I could simply walk to most places. The staff was also very nice and helpful throughout my stay. I had a late flight on my last day, and they allowed me to store my luggage at the hotel after checkout, which made things so much easier. My only small complaint was that the only full-length mirror was in the bathroom. Other than that, I had a great experience and would absolutely stay here again!"
Brandi 2-night trip
Posted less than an hour ago
L7 Chicago by LOTTE

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 Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub.

How many vacation rentals are there in Chicago?

With 933 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.