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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Browse Select Winnetka Apartments

Twice as Nice: Chic 2BR Stay with Style & Space
Interior

Twice as Nice: Chic 2BR Stay with Style & Space

9.0 out of 10, Wonderful, (2)
"Had a very nice time in Chicago!"
The price is CA $158
CA $341 total
includes taxes & fees
Aug 26 - Aug 27
Twice as Nice: Chic 2BR Stay with Style & Space
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is CA $144
CA $303 total
includes taxes & fees
Sep 2 - Sep 3
The One: A 1BR Stay That Feels Like Home
Your Chicago get Away
Interior

Your Chicago get Away

10.0 out of 10, Exceptional, (2)
"Clean, fun space and responsive host! Loved the views from our room!"
Your Chicago get Away
Stylish 1BR in West Loop
TV

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 1BR in West Loop
River North | Rooftop With In & Out Parking | 5
TV, offices

River North | Rooftop With In & Out Parking | 5

10.0 out of 10, Exceptional, (1)
"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "
The price is CA $223
CA $534 total
includes taxes & fees
Sep 22 - Sep 23
River North | Rooftop With In & Out Parking | 5
South Loop | Rooftop With In & Out Parking
Outdoor dining

South Loop | Rooftop With In & Out Parking

9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
The price is CA $230
CA $550 total
includes taxes & fees
Sep 22 - Sep 23
South Loop | Rooftop With In & Out Parking
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop

West Loop Living – Bright 1BR

The price is CA $148
CA $313 total
includes taxes & fees
Sep 2 - Sep 3
West Loop Living – Bright 1BR
1BR Modern Luxe Apt with In-Unit Laundry
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

The price is CA $144
CA $306 total
includes taxes & fees
Sep 2 - Sep 3
1BR Modern Luxe Apt with In-Unit Laundry
River North | Rooftop With In & Out Parking | 1
Fridge, microwave, oven, stovetop

River North | Rooftop With In & Out Parking | 1

River North | Rooftop With In & Out Parking | 1
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3
Sun-Drenched 1BR Apartment
Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

8.4 out of 10, Very good, (15)
"Good experience. Would stay there again "
The price is CA $127
CA $280 total
includes taxes & fees
Sep 1 - Sep 2
Clean & Equipped 1BR Apt
Chic Studio - In Downtown Highland Park, by Metra
1 bedroom, iron/ironing board, free WiFi, bed sheets

Chic Studio - In Downtown Highland Park, by Metra

8.8 out of 10, Excellent, (13)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
The price is CA $111
CA $227 total
includes taxes & fees
Sep 1 - Sep 2
Chic Studio - In Downtown Highland Park, by Metra
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
Dining

Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

2.0 star property
The price is CA $100
CA $582 total
includes taxes & fees
Aug 26 - Aug 27
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (39)
"Great place to stay when you’re in town for the Cubbies! "
The price is CA $148
CA $403 total
includes taxes & fees
Aug 26 - Aug 27
2-bedroom apartment just 2 minutes drive to Wrigley Field
3BR Luxury Modern Apartment
Property grounds

3BR Luxury Modern Apartment

2.0 star property
9.2 out of 10, Wonderful, (13)
"Our family of 5 really enjoyed our stay! The apartment was awesome with a great view of downtown Chicago, and the location was safe and close to the city."
The price is CA $635
CA $1,228 total
includes taxes & fees
Sep 10 - Sep 11
3BR Luxury Modern Apartment
Sleeps 10 - Heart of Logan Square 3BR + Garage & Patio
Fridge, microwave, oven, stovetop

Sleeps 10 - Heart of Logan Square 3BR + Garage & Patio

2.5 star property
8.0 out of 10, Very good, (10)
"Property check in was seamless, there were no problems with the house, and the host messaged me make sure we had everything we needed."
The price is CA $127
CA $455 total
includes taxes & fees
Aug 26 - Aug 27
Sleeps 10 - Heart of Logan Square 3BR + Garage & Patio
Uptown Studio Gem Sum
TV

Uptown Studio Gem Sum

7.0 out of 10, Good, (4)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
The price is CA $127
CA $266 total
includes taxes & fees
Sep 1 - Sep 2
Uptown Studio Gem Sum
Flexhome East Village 2BR H1
Fridge, microwave, oven, stovetop

Flexhome East Village 2BR H1

9.4 out of 10, Exceptional, (3)
"great place! clean, comfortable, safe and in a great area! highly recommend. "
The price is CA $148
CA $302 total
includes taxes & fees
Aug 26 - Aug 27
Flexhome East Village 2BR H1
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Fridge, microwave, oven, stovetop

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

9.0 out of 10, Wonderful, (18)
"It was great for our needs! Definitely hear EVERYTHING though as usual for most older places in the city."
The price is CA $97
CA $294 total
includes taxes & fees
Aug 26 - Aug 27
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Terrace/patio

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (38)
"This was convenient and check-in process was easy. We would stay here again."
The price is CA $80
CA $313 total
includes taxes & fees
Aug 27 - Aug 28
Artistic Loft Rooftop | 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 Winnetka Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"As a solo traveler, I felt safe the entire time I was here and in the areas surrounding the hotel. The staff were friendly and the interior of the hotel lobby is beautiful. The hotel was clean and centrally located to all the things you “have to see/do” when in Chicago! "
Michelle 2-night trip
Posted 9 hours ago
Hilton Chicago