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Check prices for these dates

Compare 1813 Apartments in Winnetka with updated reviews, rates, and availability.

Sonder Onterie

3.5 star property
9.4 out of 10, Exceptional, (9)
"The stove, washer/drier, plates, silverwear, beds, everything was obviously cleaned throughly. Was very impressed with how spotless everything was"
The price is SAR 391
SAR 459 total
includes taxes & fees
23 Apr - 24 Apr
Sonder Onterie

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

9.2 out of 10, Wonderful, (74)
"Loved this location near Wrigley Stadium. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

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

9.4 out of 10, Exceptional, (46)
"This property is very clean and very cozy. The location is great, except at night, I was able to hear the train and highway traffic. My husband wasn't bothered at all. We still liked it and suited our needs. The amenities were excellent. There's plenty of parking. "
Chic, Cozy home, by Blue Line Train Stop + Free parking

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (8)
"The property is very quiet, clean, well appointed, and is in a great location. It’s only a 3 minute walk to the Brown Line which easily gets you downtown in half an hour and not worry about parking. I did notice the absence of a microwave which would have been an added convenience. Overall, it suited my needs perfectly and will consider it again if I get back to Chicago."
The price is SAR 319
SAR 906 total
includes taxes & fees
1 Apr - 2 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field

Charming Wrigleyville Home Close to the Cubs!

9.6 out of 10, Exceptional, (17)
"Great neighborhood. Free and easy parking. "
Charming Wrigleyville Home Close to the Cubs!

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (135)
"The location was amazing! Right on Clark Street a quick walk to Wrigley field and all of the nearby nightlife. Came for Saint Patrick's Day weekend and couldn't have picked a better location, ease of access to the city through the red and brown lines was great. The unit was spacious and clean. When I return to Chicago I will definitely stay here again if the unit is available. "
Walk to Wrigley Field/Monthly Discounts Available

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (33)
"What an exceptional property! Perfect for a two-person getaway. It's right around the corner from shops and restaurants in the terrific Gold Coast neighborhood. Beautiful, modern decor with vintage building charm. It is very safe, quiet and comfortable - we got great sleep here. The host was communicative and everything was very easy. Definitely plan to come back to this gem!"
Chic & Historic Apartment Steps from Mag Mile

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (34)
"Everything was nice and neat. They were super easy to communicate with. We had a little issue with the main building door keyless entry. Other than that everything was great."
Remodeled West Loop Apartment Near United Center

Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

8.8 out of 10, Excellent, (27)
"We are visiting from the United Kingdom and was very happy with this property. Perfect size for our needs, the property was clean and catered with all our needs, the host was very prompt on our requests.Thank you "
Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

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

10.0 out of 10, Exceptional, (46)
"Property was easy to access. Great place to relax and enjoy some peace. Loved the decor! Hosts were super friendly and it was easy to communicate with them. Fenced yard for our dogs was great! "
Stylish, Inviting 2-BR near Logan Square and Wrigley Field

Cozy, Comfortable and Convenient apartment. Close to everything!

9.8 out of 10, Exceptional, (55)
"My stay was amazing, the place fit the description and was very clean and felt like a home away from home. The host was very accommodating and easy to communicate with. I had an amazing time, we weren’t too far from downtown which was great, and everything in the home was neat and clean. "
The price is SAR 450
SAR 1,034 total
includes taxes & fees
1 Apr - 2 Apr
Cozy, Comfortable and Convenient apartment. Close to everything!

Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94

10.0 out of 10, Exceptional, (3)
"This is the perfect place for a couple to stay for a weekend in the Windy City! It has everything you need, and youre close to the big attractions! Parking can be a little tricky, but the fact that its free helps a lot! Toby is a wonderful host. You'll feel taken care of, and enjoy your time at this property!"
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94

The Logan Square Guest House - Classic Vintage Comfort With Free Parking!

10.0 out of 10, Exceptional, (23)
"This was the perfect place to stay for a four day visit to Chicago. The host was super responsive and the apartment is stunning with beautiful original artwork and every convenience you could possibly need. As a frequent Chicago visitor I will definitely rent this space again!"
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!

Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!

9.8 out of 10, Exceptional, (16)
"We stayed here for just over a week for our daughter's wedding. The VRBO was clean, comfortable and very convenient to the things we were doing. Judy, the host, was easy to communicate with. Highly recommend."
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!

Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover

8.6 out of 10, Excellent, (7)
"This lovely apartment was a great location for our family. Close to shops and restaurants. Easy walk to the Red Line train. The place was well stocked with bedding and the mattresses were quite comfy. We enjoyed cooking and hanging out in the living area. "
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover

Bright Garden Studio

9.0 out of 10, Wonderful, (20)
"clean & nice. "
The price is SAR 308
SAR 900 total
includes taxes & fees
1 Apr - 2 Apr
Bright Garden Studio

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (95)
"We had an amazing stay at Jamie’s place. Quiet location, great host, and lovely accommodations. If you’re visiting Chicago, highly recommend staying at Jamie’s. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!

10.0 out of 10, Exceptional, (87)
"Property and location were great! Very responsive to questions and check in and out were easy."
Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

9.6 out of 10, Exceptional, (80)
"Walked into the unit to find several items were needed/missing: namely a crib and various necessary kitchen items. Host was quick to answer my texts and to connect w/ his staff to purchase and deliver the missing items. The disappointing part was that i could not come into the unit and immediately begin prepping dinner for my family who were due to arrive an hour later. Had to deal with texts/calls to host to get the items we needed, which all took time. Ali was very attentive to my...
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Perfect 4 Bedroom/3 Bath in the HEART of Old Town

10.0 out of 10, Exceptional, (55)
"This unit served our family of five well for a few days get away in the city. The hot water went out while we were there but the owner communicated and responded timely. It was a bit dusty, as if it hadn't been occupied in some time, but otherwise it was fine. Can't beat the location and Old Town is awesome."
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
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

4.0 star property
9.2 out of 10, Wonderful, (706)
"Our family celebrated Christmas at this hotel. It was beautiful and clean. I will definitely stay here again."
The price is SAR 443
SAR 630 total
includes taxes & fees
1 Apr - 2 Apr
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (453)
"Great stay "
The price is SAR 412
SAR 483 total
includes taxes & fees
6 Apr - 7 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (267)
"Appartement spacieux, super fonctionnel, lit et divan lit très confortables. Très bien situé, à 2 min du metro dans un quartier hyper sécuritaire."
The price is SAR 400
SAR 470 total
includes taxes & fees
22 Apr - 23 Apr
Sonder Market Hall
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 4975 lodging choices including 2460 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?
Here’s a popular apartment in the area: Sonder Onterie: Situated in Chicago, 16 mi/25.8 km from the heart of Winnetka.
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.