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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Winnetka Apartments

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

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

10.0 out of 10, Exceptional, (272)
"Loved this hip 3 bedroom! Lots of art prints and tasteful decor. Well stocked kitchen and comfy beds. Neighborhood had many restaurant offerings."
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
1F Chicago's Little italy Graystone nearDowntown
Exterior

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (123)
"Nice 3 bedroom, 2 bath in a quiet neighborhood The three of us loved this clean and cozy apartment. "
1F Chicago's Little italy Graystone nearDowntown
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Beach

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

9.8 out of 10, Exceptional, (129)
"In town as Chicago is a half-way point to my daughter’s college and we were celebrating her birthday. It was so homey and welcoming. We absolutely LOVED it!"
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Walk to Wrigley Field/Monthly Discounts Available
Fridge, microwave, oven, stovetop

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (132)
"Great host, great location and great stay. Harry is a great host and was easy to work with on the stay. Thank you!"
Walk to Wrigley Field/Monthly Discounts Available
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi
Smart TV, fireplace, printers

Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

10.0 out of 10, Exceptional, (5)
"This apartment has almost everything you could hope for! From the shoe covers and socks by the front door, to a heated towel rack in the bathroom. The only thing missing is a soaking tub! If you’re looking for a fantastic view of the city with spacious accommodations, look no further! The host was more than accommodating and very quick to reply when I had questions "
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (70)
"Great property, perfect for two people. Easy walk to Wrigley. Stayed there on a couple cold winter days, and being a basement unit, the heater couldn’t keep up very well, so it was a little colder than ideal, but nothing a sweatshirt or extra blanket couldn’t fix. Would definitely go back!"
Wrigley/Southport Corridor Garden Oasis +parking!
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (31)
"Great amenities, great location, spacious and comfortable. Check in a few days prior was difficult as the owner/manager didn’t message me or email me back… I had to call VRBO to have them investigate. Once they were made aware, smooth sailing from then on. Also, they listed a jacuzzi on site which was an error,and that was disappointing as I planned on that. Overall, despite these two things, great place ti stay! "
Chic & Historic Apartment Steps from Mag Mile
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Exterior

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (168)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Remodeled West Loop Apartment Near United Center
Interior

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (33)
"Beautiful apartment! We really enjoyed our time in Chicago. We ended up just parking across the street. It was easier, and there was always a spot available. There are many stairs leading up to the third floor apartment, so keep that in mind if you have mobility issues. The host texts you right back if you have concerns or questions."
Remodeled West Loop Apartment Near United Center
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, (5)
"This was a great place and we had a great experience. This is very close to my brother's famly and we hope to stay at this location often, in the future.Thanks for everything!"
The price is CA $245
CA $515 total
includes taxes & fees
Feb 11 - Feb 12
2-bedroom apartment just 2 minutes drive to Wrigley Field
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
Fridge, microwave, oven, stovetop

NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!

10.0 out of 10, Exceptional, (1)
"First of all, the pictures does not do this place justice. It was so bright and sunny and well decorated. It was WELL stocked with anything you could think of. And our hostess was the mostess. Thank you again Tori for everything. I just loved the place! Easy parking as well, that's always a plus in my book!"
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Point of interest

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (219)
"We had a group of couples coming to Chicago from different locations, and this was the perfect spot for us to be all together, but also have our own rooms and spaces. Everything was easy, and when we had a question on parking when we arrived later in the evening, John was very prompt in responding and helping us right away. "
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Entire Below Level Studio w/ Private Sauna
Property grounds

Entire Below Level Studio w/ Private Sauna

10.0 out of 10, Exceptional, (30)
"Great communication with the owners. Very clean and lovely stay in a quiet neighborhood. "
Entire Below Level Studio w/ Private Sauna
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (102)
"Stayed with my husband and our two preteens. I grew up in Oak Park and chose this based off of location and it was perfect. Walkable neighborhood, close to the El and downtown Oak Park. The house was clean and comfortable, on top of having the quintessential Oak Park / Chicago vibe Communication was easy so was check in and out. I would choose to stay here again for sure!"
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Luxurious HUGE Penthouse with 4000+ Games, Arcades
Smart TV, video games, foosball, books

Luxurious HUGE Penthouse with 4000+ Games, Arcades

10.0 out of 10, Exceptional, (1)
"The spot was wonderfuke management was responsive. The space was big and comfortable. Games were available. We did have to deal with missing players ok fusball table and pool may need new accessories but we still enjoyed our time there overall i would recomended. When i advised management of fusball table thry offered to send someone, so props to their respokse time."
Luxurious HUGE Penthouse with 4000+ Games, Arcades
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Smart TV, DVD player, books, stereo

Stylish, Inviting 2-BR near Logan Square and Wrigley Field

10.0 out of 10, Exceptional, (40)
"Great location. Very easy access "
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
5 Bedroom Wrigleyville experience right by stadium
Outdoor dining

5 Bedroom Wrigleyville experience right by stadium

10.0 out of 10, Exceptional, (49)
"The property was spacious, clean and was in an excellent location for walking to restaurants and having food delivered and using ride share. Parking was very easy and the beds were all very comfortable. "
5 Bedroom Wrigleyville experience right by stadium
2 New Construction Suites Same Place
TV

2 New Construction Suites Same Place

9.2 out of 10, Wonderful, (19)
"Great place to stay. Parking was great. Nice to have both places and the whole floor!"
2 New Construction Suites Same Place
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Property grounds

The Holiday Lake House - 2br 2bth - 50 steps from the beach!

10.0 out of 10, Exceptional, (39)
"This was a great place to celebrate the holidays. Kitchen was well stocked with cookware and utensils to make Christmas dinner and we had plenty of room to gather for game night. Beds were comfy and all amenities were in good condition. The apartment looks brand new! Loved the shampoo/conditioner/soap dispensers in the shower! Will definitely be back next Christmas. Thanks for the hospitality!"
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
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
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (669)
"Sandra and Joy are welcoming and helpful. Great front desk."
The price is CA $158
CA $228 total
includes taxes & fees
Feb 2 - Feb 3
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (250)
"Easy to find.Had to drive around a little to find parking, but it worked out fine. Easy access with a code or using the Sonder app.Comfortable bed. Very clean room. We did not have any issues with the night club downstairs, but our room was on the 5th floor. The train goes by right next door, but it was kind of a soothing sound. I would definitely stay here again. "
The price is CA $163
CA $191 total
includes taxes & fees
Feb 20 - Feb 21
Sonder Market Hall
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (426)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is CA $137
CA $161 total
includes taxes & fees
Feb 25 - Feb 26
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 5026 lodging choices including 2530 apartments. Top sights to discover during your visit include Lake Michigan.
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?
Listed below are some of the top apartments in the area: Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC: Situated in Chicago, 16.9 mi/27.2 km from the heart of Winnetka. Includes free WiFi and Smart TVs. Bright Garden Studio: It’s situated in Evanston, 5.7 mi/9.2 km away. Includes private patios, fireplaces, and separate dining areas. Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood: 12.7 mi/20.4 km away in Chicago. Free WiFi, private balconies, and separate dining areas are included. 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place: It’s located in Chicago, 16.7 mi/26.9 km from Winnetka. Includes free WiFi and 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 Maple Street Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. Wrigley Field and Naval Base Great Lakes 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.