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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chicago vacation homes

A modern kitchen with wooden cabinets, stainless steel appliances, and a white tiled backsplash.

1. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
The price is ￥24,607
￥89,761 total
includes taxes & fees
Oct 26 - Oct 27
Wabash 4BR - Pool, Free In & Out Parking 1
A kitchen with a built-in counter, pendant lights, and decorative wall art.

2. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our group! There was more than enough space. The host let us drop our luggage off early since we arrived in the area before 4. The listing initially had errors, but the host updated the listing and we knew what to expect coming into it. Thank you for a wonderful stay!"
United States
Jamiee B.
The price is ￥29,841
￥119,055 total
includes taxes & fees
Oct 26 - Oct 27
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

3. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
The price is ￥16,444
￥78,681 total
includes taxes & fees
Oct 25 - Oct 26
Game Room • Fire-pit • Playground • Gym • Billiard
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

4. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.2 out of 10, Wonderful, (34 reviews)
"Super clean great location short drive to everything we wanted to see!"
United States
eric p.
The price is ￥29,340
￥79,917 total
includes taxes & fees
Oct 25 - Oct 26
ENVITAE Hotel, 4BR Luxury Modern Apartments
A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

5. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
The price is ￥26,644
￥60,288 total
includes taxes & fees
Oct 27 - Oct 28
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

6. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveler
The price is ￥21,566
￥142,265 total
includes taxes & fees
Oct 25 - Oct 26
Sleeps 18 • 8BR • Game Room • Gym • Theater
♨️ Gas and charcoal grill

7. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is ￥21,027
￥98,709 total
includes taxes & fees
Oct 27 - Oct 28
Theater • Game Room • Gym • Firepit • 4BR Home
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

8. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is ￥28,211
￥58,349 total
includes taxes & fees
Oct 26 - Oct 27
LUXE 3 BR, 2 BA + Hot Tub
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

9. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is ￥33,880
￥92,667 total
includes taxes & fees
Nov 1 - Nov 2
Chicago Riverhouse with private fenced in oasis
A single-story house with a covered porch, a front door, and a small garden area.

10. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ￥28,917
￥52,662 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

11. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
The price is ￥53,758
￥111,015 total
includes taxes & fees
Oct 29 - Oct 30
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

12. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is ￥23,274
￥47,534 total
includes taxes & fees
Oct 26 - Oct 27
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

13. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.6 out of 10, Exceptional, (4 reviews)
"This property fully met our needs for our weekend trip to the Chicagoland area to visit family in Westmont and explore the city. Finding an affordable, conveniently located, and pet friendly location was a major concern on this trip…finding this property relieved all of our concerns."
United States
Chad R.
The price is ￥26,644
￥42,190 total
includes taxes & fees
Nov 11 - Nov 12
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

14. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ￥20,406
￥46,873 total
includes taxes & fees
Nov 17 - Nov 18
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

15. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (89 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is ￥16,786
￥32,573 total
includes taxes & fees
Oct 27 - Oct 28
Master qtr close to nature & easy urban facilities
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

16. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is ￥30,092
￥75,619 total
includes taxes & fees
Oct 29 - Oct 30
Classic Forest Park Foursquare < 1 Mi to Blue Line
A white two-story house with a porch, steps, and a small table with chairs.

17. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is ￥39,147
￥93,888 total
includes taxes & fees
Nov 2 - Nov 3
Oak Park Victorian by FLW Studio
A building with a sign reading 'Hale Street Cantina' and a brick facade.

18. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (74 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is ￥28,211
￥50,329 total
includes taxes & fees
Nov 3 - Nov 4
✽ Charming Cottage ✽ close to College/Town/Station
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

19. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (26 reviews)
"We enjoyed our 2 night stay. The home was exactly what we were expecting. It is on a quiet street and is within walking distance to several restaurants. The beds were comfortable and and the lower level bathroom was especially nice to get ready in."
United States
KIM K.
The price is ￥23,510
￥51,811 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Home by O'Hare + EV Plug
A two-story house with a garage, solar panels, and a red car parked in front.

20. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is ￥19,466
￥60,329 total
includes taxes & fees
Oct 24 - Oct 25
Lombard 1BR & 1BH Suite Close to freeway & Mall
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Lovely hotel in a great location, I stayed on the 23rd floor, the room was brilliant but the windows did not shield the sound of sirens all night!"
Stephen 5-night trip
Posted 5 hours ago
Eurostars Magnificent Mile

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
431
Accommodation
744 Vacation Homes
Lowest Price
￥32,573
Highest Price
￥142,265