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, (1,368 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥24,696
￥28,990 total
includes taxes & fees
Nov 10 - Nov 11
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, (63 reviews)
"Location is perfect"
United States
Mary
The price is ￥28,337
￥43,102 total
includes taxes & fees
Nov 1 - Nov 2
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, (540 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is ￥43,874
￥55,409 total
includes taxes & fees
Nov 2 - Nov 3
Level Chicago – Old Town
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

4. 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 ￥33,720
￥84,211 total
includes taxes & fees
Oct 13 - Oct 14
River North Rooftop With In and Out Parking 6
A hotel room with a wooden headboard, white bedding, a small bedside table with a vase of flowers, and a brown leather bag on the bed.

5. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"This spot is great and very close to The Bean. Lots of restaurants and bars in walking distance and there’s a great coffee shop right next door too. Would definitely stay here again!!"
United States
Karlise J.
The price is ￥45,277
￥60,576 total
includes taxes & fees
Oct 14 - Oct 15
LIVN Millennium Park Downtown Chicago Studio
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 ￥34,195
￥84,995 total
includes taxes & fees
Oct 14 - Oct 15
South Loop Rooftop With In and Out Parking 3
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

7. 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 ￥22,163
￥46,266 total
includes taxes & fees
Nov 2 - Nov 3
2BR Apt with 2 Baths & Laundry
A spacious lobby with leather sofas, a coffee table, and a TV screen.

8. Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (6 reviews)
"Spacious, free parking, family friendly"
United States
Majid
The price is ￥30,237
￥84,262 total
includes taxes & fees
Oct 29 - Oct 30
Downtown Chicago Stay with Free In & Out Parking 1
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

9. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (63 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ￥24,791
￥29,102 total
includes taxes & fees
Nov 3 - Nov 4
Wrigleyville Suites
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

10. 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 ￥19,765
￥37,692 total
includes taxes & fees
Oct 13 - Oct 14
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

11. 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, (10 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 ￥25,330
￥72,492 total
includes taxes & fees
Nov 3 - Nov 4
River North Rooftop With In and Out Parking 3
A rooftop terrace with a brick wall, large windows, and a metal railing.

12. 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, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is ￥18,997
￥53,186 total
includes taxes & fees
Oct 13 - Oct 14
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a fire pit, seating area, and a city skyline view.

13. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
The price is ￥18,111
￥37,507 total
includes taxes & fees
Nov 4 - Nov 5
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
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 ￥20,897
￥50,314 total
includes taxes & fees
Oct 13 - Oct 14
Stylish Gold Coast 1BR with Vintage Flair
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

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

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (26 reviews)
"Great location! "
United States
Andrea B.
Flexhome East Village • Modern 2BR • Quiet Street
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
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is ￥10,623
￥26,783 total
includes taxes & fees
Nov 2 - Nov 3
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

17. 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 ￥15,989
￥40,030 total
includes taxes & fees
Oct 20 - Oct 21
3BR Complete and Spacious Apartment in Ideal Spot
A hotel room with a bed, two bedside tables, and three wall-mounted paintings.

18. Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is ￥25,013
￥49,206 total
includes taxes & fees
Nov 2 - Nov 3
Stylish Japanese-Themed 2BR Apt Close to Downtown
A modern bedroom with a bed, a sofa, and a hanging plant.

19. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 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 ￥9,974
￥22,075 total
includes taxes & fees
Nov 2 - Nov 3
Cozy studio in Andersonville Chicago
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
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is ￥11,968
￥37,226 total
includes taxes & fees
Oct 13 - Oct 14
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

The Wade

The Wade

8/10 Good
"Large hotel about a 10-15 min walk from Michigan Ave. and therefore many restaurants & bars. Busy lobby. Okay bar. Lake views."
Laura 3-night trip
Posted 1 hour ago
The Wade

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 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.