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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Winnetka apartments

TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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 866 total
includes taxes & fees
9 Apr - 10 Apr
Sunlit 1BR Apartment | Warm & Welcoming Space
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 601
SAR 1,715 total
includes taxes & fees
14 Apr - 15 Apr
River North Rooftop With In and Out Parking 3
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is SAR 259
SAR 659 total
includes taxes & fees
12 Apr - 13 Apr
Modern Comfort: 1BR Unit w/ Laundry
Living area

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Plymouth Collection: 2BD with Lobby, Gym, Rooftop
Downtown Chicago
The price is SAR 390
SAR 1,245 total
includes taxes & fees
8 Apr - 9 Apr
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
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 spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is SAR 424
SAR 866 total
includes taxes & fees
8 Apr - 9 Apr
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)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is SAR 522
SAR 2,030 total
includes taxes & fees
22 Apr - 23 Apr
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)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is SAR 402
SAR 789 total
includes taxes & fees
27 Apr - 28 Apr
Chic Studio in the Heart of the Gold Coast
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 383
SAR 542 total
includes taxes & fees
8 Apr - 9 Apr
LIVN West Loop Chicago Queen Superior Studio
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very Good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is SAR 424
SAR 866 total
includes taxes & fees
8 Apr - 9 Apr
1BR Modern Luxe Apt with In-Unit Laundry
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (32 reviews)
"This was a great apartment in the heart of Lincoln Square. The kitchen is fully equipped, the bed was comfortable and there are a lot of amenities and public transportation close by. I will definitely be staying hear again! "
United States
Lisa
The price is SAR 330
SAR 743 total
includes taxes & fees
8 Apr - 9 Apr
Nice 1BR Spot, Unwind & Relax
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 387
SAR 883 total
includes taxes & fees
8 Apr - 9 Apr
Chic 2BR Haven Near Irving Park
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (13 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is SAR 608
SAR 1,784 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 244
SAR 604 total
includes taxes & fees
8 Apr - 9 Apr
Uptown Studio Gem Sum
TV, offices

Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
9.0 out of 10, Wonderful, (9 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
The price is SAR 372
SAR 861 total
includes taxes & fees
8 Apr - 9 Apr
Great Layout – Spacious 2BR Apt
TV, offices

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (18 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
The price is SAR 353
SAR 839 total
includes taxes & fees
9 Apr - 10 Apr
Cozy & Furnished 2BR Unit
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, (66 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is SAR 504
SAR 1,242 total
includes taxes & fees
8 Apr - 9 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field
Lobby

Bright Garden Studio

Bright Garden Studio
South Evanston
8.4 out of 10, Very Good, (32 reviews)
"Easy access. Nice location. Available shrot notice."
United States
Drew H.
The price is SAR 284
SAR 916 total
includes taxes & fees
8 Apr - 9 Apr
Bright Garden Studio
Game room

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10 - Pet Friendly

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10 - Pet Friendly
Lakeview
9.2 out of 10, Wonderful, (5 reviews)
"This was a wonderful stay! The apartment was clean, well furnished, and the communication with the manager was wonderful. My son and I really enjoyed the video games, especially golden tee. The location is fantastic, giving us access to most everything in the Lincoln Park area, as well as Wrigley Field. I can’t recommend this enough. We had a wonderful time!"
United States
Matthew B.
The price is SAR 507
SAR 1,356 total
includes taxes & fees
8 Apr - 9 Apr
5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10 - Pet Friendly
1 bedroom, iron/ironing board, travel crib, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (13 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is SAR 338
SAR 751 total
includes taxes & fees
8 Apr - 9 Apr
Charming Sunlit 1BR Apartment
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 443
SAR 984 total
includes taxes & fees
8 Apr - 9 Apr
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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

River Hotel

River Hotel

10/10 Excellent
"Perfect location. Staff could be nicer. But overall nice stay."
Aiza 3-night trip
Posted 1 hour ago
River Hotel

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 5529 lodging choices including 1660 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. Clean & Equipped 1BR Apt: Located 11.8 mi/19.1 km away in Chicago. Lakeview 2BR Cozy Apartment: It's located in Chicago, 12.7 mi/20.4 km away.
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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