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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Winnetka apartments

TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is SAR 330
SAR 751 total
includes taxes & fees
31 Mar - 1 Apr
Modern Comfort: 1BR Unit w/ Laundry
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is SAR 600
SAR 1,732 total
includes taxes & fees
30 Mar - 31 Mar
River North Rooftop With In and Out Parking 3
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is SAR 424
SAR 880 total
includes taxes & fees
1 Apr - 2 Apr
Sun-Drenched 1BR Apartment
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is SAR 330
SAR 756 total
includes taxes & fees
30 Mar - 31 Mar
West Loop Living – Bright 1BR
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Great all around!!!"
United States
Kennedy L.
Modern West Loop Gem-City Views & Prime Location 3
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is SAR 402
SAR 788 total
includes taxes & fees
28 Apr - 29 Apr
Chic Studio in the Heart of the Gold Coast
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is SAR 453
SAR 935 total
includes taxes & fees
30 Mar - 31 Mar
The Oak Park Loft
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (29 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is SAR 308
SAR 716 total
includes taxes & fees
30 Mar - 31 Mar
Nice 1BR Spot, Unwind & Relax
Interior

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is SAR 424
SAR 925 total
includes taxes & fees
30 Mar - 31 Mar
Pine Beam Sloth Apartment next to Blue Line
Lobby

Bright Garden Studio

Bright Garden Studio
South Evanston
8.4 out of 10, Very Good, (32 reviews)
"The place was cute, but not clean. I paid a 150 cleaning fee for a dirty place. The floor was filthy, cloves and crumbs by the bed, hair balls in the bathroom, dirty glasses on dusty shelves, dead spiders, huge dust bunnies under the couch, moldy shower curtain liner, old coffee grounds in the coffeemaker that didn’t even work."
United States
Amy E.
The price is SAR 284
SAR 899 total
includes taxes & fees
6 Apr - 7 Apr
Bright Garden Studio
Interior

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very Good, (33 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is SAR 334
SAR 847 total
includes taxes & fees
30 Mar - 31 Mar
Oak Park Queen
Interior

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

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (98 reviews)
"Cozy place, host was very helpful and responded quickly to all my concerns. I would definitely stay there again. "
United States
Deborah R.
The price is SAR 409
SAR 962 total
includes taxes & fees
31 Mar - 1 Apr
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
TV

Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Ample accommodations for two adults. Clean and in great condition!"
United States
Kathy D.
The price is SAR 368
SAR 856 total
includes taxes & fees
31 Mar - 1 Apr
Chic 2BR Haven Near Irving Park
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.4 out of 10, Exceptional, (66 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is SAR 263
SAR 556 total
includes taxes & fees
31 Mar - 1 Apr
Cozy studio in Andersonville Chicago
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is SAR 510
SAR 692 total
includes taxes & fees
9 Apr - 10 Apr
LIVN West Loop Chicago Queen Superior Studio
Private kitchen

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
9.0 out of 10, Wonderful, (8 reviews)
"Cozy, private, clean. A quick walk to the train and busses. Would stay again."
United States
John D.
The price is SAR 751
SAR 1,667 total
includes taxes & fees
3 Apr - 4 Apr
Cozy apartment with AC and WiFi in awesome Chicago
Property grounds

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Great host, quick communication, and wonderful place to stay in Chicago. Well thought out and made our stay enjoyable. Highly recommend, we will book it again next time we are in Chicago. "
United States
Justin P.
The price is SAR 503
SAR 1,241 total
includes taxes & fees
30 Mar - 31 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
Fridge, microwave, oven, stovetop

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "
United States
Susan G.
The price is SAR 405
SAR 1,113 total
includes taxes & fees
30 Mar - 31 Mar
Cozy, Comfortable and Convenient apartment. Close to everything!
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (12 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is SAR 552
SAR 1,704 total
includes taxes & fees
26 Apr - 27 Apr
Spacious 4BR Central Apartment w/ Skyline Views
Iron/ironing board, WiFi

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is SAR 353
SAR 740 total
includes taxes & fees
30 Mar - 31 Mar
Uptown Studio Gem Sum
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
"The hot tub was plenty warm enough. "
William 2-night trip
Posted 2 hours ago
Hilton Chicago

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 5473 lodging choices including 1639 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 favorite apartments in the area: Charming Wrigleyville Home Close to the Cubs!: Located in Chicago, 11.4 mi/18.4 km from the heart of Winnetka. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Lakeview 2BR Cozy Apartment: Located 12.7 mi/20.4 km away in Chicago. Walk to Wrigley Field/Monthly Discounts Available: Located in Chicago, 11.6 mi/18.7 km from Winnetka. Includes free WiFi, private balconies, and Smart TVs. Access to onsite laundry facilities is available on site.
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.

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