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Compare 1701 Apartments in Winnetka with updated reviews, rates, and availability.

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Exterior detail

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

9.8 out of 10, Exceptional, (125)
"My husband and I were visiting our daughter nearby for a few days. We loved our stay here. The home was clean, spacious and warm....comfortable beds and wonderful sectional for relaxing. Easy walk to wonderful restaurants. Would definitely stay again when back in Chicago. Highly recommend."
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Wrigley/Southport Corridor Garden Oasis +parking!
Living area

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (68)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!
1F Chicago's Little italy Graystone nearDowntown
Enjoy the Linden trees from the sunny bay window.

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (119)
"John had the apartment well stocked with coffee, teas, candy, towels, toiletries, and warm robes. Bed were comfy with nice bedding. We would stay here again!! "
1F Chicago's Little italy Graystone nearDowntown
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Living area

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

3.0 star property
8.4 out of 10, Very Good, (14)
"The property was excellent, for my stay "
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Open Concept Living Room

Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (216)
"What a beautiful apartment...and the Christmas decorations were so lovely."
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Chic, Cozy home, by Blue Line Train Stop + Free parking
Private kitchen

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (38)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Living Room

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

10.0 out of 10, Exceptional, (267)
"Clean, comfortable and communication was great. Would recommend. "
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Beautiful Unit CHI in Prime River North - 3
Living Room / Dining Room with Fully stocked kitchen

Beautiful Unit CHI in Prime River North - 3

9.8 out of 10, Exceptional, (16)
"Nice place, everything as advertised. Host was very accommodating, we will definitely book again when in area. "
Beautiful Unit CHI in Prime River North - 3
Chic & Historic Apartment Steps from Mag Mile
Living area

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (29)
"We very much enjoyed our stay at this property! We were visiting Chicago for a fun weekend trip to celebrate our anniversary. The location was on a quiet street but within close walking distance to plenty of restaurants and shopping. The apartment was clean and very quiet in a beautiful, historic building. We highly recommend Tempo Cafe for breakfast. On our last morning in town, we actually saw Larry David, Jeff Garlin and Susie Essman at brunch there! "
Chic & Historic Apartment Steps from Mag Mile
Charming Wrigleyville Home Close to the Cubs!
Bedroom 1

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (14)
"This place was perfect for us, and right where we needed it to be. "
Charming Wrigleyville Home Close to the Cubs!
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover
Our converted storefront condo has high ceilings and large windows, lending the living area an airy and open feel

PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

9.4 out of 10, Exceptional, (26)
"Nice open space with large bedrooms. Quiet and clean! Perfect location to walk to local restaurants and shops "
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover
Walk to Wrigley Field/Monthly Discounts Available
Panoramic view of Living room with 50 inch flatscreen TV!

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (128)
"Clean and great location "
Walk to Wrigley Field/Monthly Discounts Available
Luxury Loft Collection 02 - Terrace - River North

Luxury Loft Collection 02 - Terrace - River North

10.0 out of 10, Exceptional, (11)
"We loved our stay. Close to everything. New unit. Plenty of space. Balcony was a bonus! Definitely recommend."
Luxury Loft Collection 02 - Terrace - River North
Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago
Living area

Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago

8.8 out of 10, Excellent, (15)
"Enjoyed our stay, great location, we will stay there again on our next trip to Chicago"
Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large sunny living room great for get togethers with friends and family.

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

10.0 out of 10, Exceptional, (102)
"We came to town for a hockey weekend and will absolutely book with them again when we come back. Everything was exactly as pictured or described. Cozy beds, plenty of blankets, pillows, towels, etc. Quiet neighborhood on a beautiful street, and a great location to call home while commuting to and from the rinks. "
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Lovely 4 Bedroom Spot located in Charming Old Town
A beautiful place to catch up with friends!

Lovely 4 Bedroom Spot located in Charming Old Town

10.0 out of 10, Exceptional, (23)
"The apartment was AMAZING! Even better than the photos. All the furnishings were of the finest quality, including the bed linens and towels. The mattresses were exceptionally comfortable. The kitchen was also well stocked with every type of culinary tool, plenty of glasses of every variety. We were a family of 13 and we had plenty of room. The bean bag chairs were a big hit for all ages. We loved the neighborhood. We have some members with food allergies and there were several places they...
Lovely 4 Bedroom Spot located in Charming Old Town
Regal Stylish Uptown Loft Beachfront RooftopWFHGym

Regal Stylish Uptown Loft Beachfront RooftopWFHGym

8.6 out of 10, Excellent, (10)
"Although it's posted as small, it had plenty of room for us. VERY clean and comfortable, and walking distance to all that we needed. Will definitely stay here again"
The price is SAR 180
SAR 719 total
includes taxes & fees
30 Dec - 31 Dec
Regal Stylish Uptown Loft Beachfront RooftopWFHGym
Spirit of Evanston
Living area

Spirit of Evanston

9.6 out of 10, Exceptional, (5)
"Great stay. Beds were comfortable. Apartment was very clean and well appointed. "
Spirit of Evanston
Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym

Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym

9.4 out of 10, Exceptional, (14)
"we really enjoyed our stay here!! it was super nice and the bed was comfortable. there were a lot of useful amenities which we really liked. the location was convenient because it had a lot of food/bar options and was right by the music venue we went to. will definitely stay here again if we come back to chicago. thank you to the host for this little find!! "
Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym
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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Other property types in Winnetka

Sentral Michigan Avenue
Garden

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (629)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is SAR 412
SAR 593 total
includes taxes & fees
29 Dec - 30 Dec
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
Front of property

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (343)
"Great stay "
Kasa Magnificent Mile Chicago
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"Outstanding accommodations! Will choose this property again for my travels."
The price is SAR 466
SAR 547 total
includes taxes & fees
15 Jan - 16 January 2025
Sonder South Wabash
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.

Frequently asked questions

What's it like to stay at an apartment in Winnetka?
There are plenty of places to stay with in the Chicago area, with 4912 lodging choices including 2434 apartments. Visit some favorite sights in the larger region like Naval Base Great Lakes and Michigan Avenue.
How do you know if an apartment is the best choice for your stay?
An apartment is often more spacious than a traditional hotel room and comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples looking for something with a more local feel.
What's a favorite apartment for a stay in Winnetka?
Here’s a popular apartment in the area: Wrigley/Southport Corridor Garden Oasis +parking!: Situated in Chicago, 12 mi/19.3 km from the heart of Winnetka. Includes Smart TVs.
What can I expect from the weather in Winnetka?
Though weather is just one factor, it can really affect your travel plans, especially if you’re planning an extended stay in Winnetka. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Winnetka is 48 inches.
What should I see in Winnetka?
Lake Michigan and Elder Lane Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. Naval Base Great Lakes and Michigan Avenue are other popular places to visit in the area.
What's the best way to get to and around Winnetka?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Chicago, IL (PWK-Chicago Executive), which is located 8.4 mi (13.5 km) from the city center. Otherwise, look for flights into Chicago O’Hare Intl. Airport (ORD), which is 12.5 mi (20.2 km) away. To explore the surrounding area, ride one of the trains from Winnetka Station or Winnetka Indian Hill Station.