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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Winnetka apartments

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
9.8 out of 10, Exceptional, (7 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is AED 577
AED 1,032 total
includes taxes & fees
21 Jul - 22 Jul
Chic Studio in the Heart of the Gold Coast
Fridge, microwave, oven, stovetop

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is AED 1,036
AED 2,088 total
includes taxes & fees
9 Jul - 10 Jul
River North Rooftop With In and Out Parking 5
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very Good, (3 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 AED 683
AED 1,207 total
includes taxes & fees
2 Jul - 3 Jul
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, (5 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 AED 973
AED 2,212 total
includes taxes & fees
6 Jul - 7 Jul
River North Rooftop With In and Out Parking 3
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is AED 779
AED 1,337 total
includes taxes & fees
6 Jul - 7 Jul
Chicago-Themed 1BR in a Central Spot near Downtown
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is AED 613
AED 811 total
includes taxes & fees
28 Jun - 29 Jun
LIVN Millennium Park Downtown Chicago 1 BR
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, (8 reviews)
"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 AED 676
AED 911 total
includes taxes & fees
25 Jun - 26 Jun
LIVN West Loop Chicago Queen Superior Studio
Hair dryer, towels, soap, toilet paper

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is AED 397
AED 716 total
includes taxes & fees
24 Jun - 25 Jun
Cozy studio in Andersonville Chicago
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AED 492
AED 951 total
includes taxes & fees
29 Jun - 30 Jun
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
"Great place to stay for our girls weekend. Very convenient to everything in the city! We had the second unit and just to know this is a walk up with about 40-45 stairs to get to the unit. "
United States
Dawn P.
The price is AED 628
AED 1,641 total
includes taxes & fees
3 Jul - 4 Jul
Beautiful Unit CHI in Prime River North - 2
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (23 reviews)
"Great location. "
United States
Tom S.
The price is AED 1,557
AED 3,472 total
includes taxes & fees
23 Jul - 24 Jul
Modern West Loop Gem-City Views & Prime Location 6
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (21 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
The price is AED 1,601
AED 3,155 total
includes taxes & fees
21 Jul - 22 Jul
Spacious 4BR Central Apartment w/ Skyline Views
3 bedrooms, iron/ironing board, travel crib, WiFi

Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.6 out of 10, Exceptional, (5 reviews)
"Great stay for a family weekend - we were within easy uber distance of our family and downtown - where we went to watch the Chicago marathon."
United States
Surya B.
The price is AED 455
AED 1,028 total
includes taxes & fees
30 Jun - 1 Jul
Relaxing 3BR Getaway Close to Dining & Shopping
TV, offices

1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.0 out of 10, Very Good, (10 reviews)
"Everything was great- great location, very clean and cute, and the hosts were communicative and attentive. "
United States
Elizabeth A.
The price is AED 382
AED 795 total
includes taxes & fees
24 Jun - 25 Jun
1BR/1BA City Comfort
Dining

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (17 reviews)
"We would recommend this location and suite to anyone who has a need to visit in the greater Chicago area as apposed to staying in the city."
United States
David W.
The price is AED 702
AED 1,427 total
includes taxes & fees
24 Jun - 25 Jun
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
1 bedroom

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay"
United States
Anonymous traveler
The price is AED 422
AED 467 total
includes taxes & fees
29 Jun - 30 Jun
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Terrace/patio

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (50 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is AED 496
AED 1,023 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
TV

Portage Park 1BR Retreat

Portage Park 1BR Retreat
Portage Park
9.0 out of 10, Wonderful, (6 reviews)
"Great stay. Very good instructions along with video for entry. Clean and comfortable! Enjoyed our stay. Great Colombian coffee shop right downstairs to the right of the entrance."
United States
Ann F.
The price is AED 283
AED 679 total
includes taxes & fees
24 Jun - 25 Jun
Portage Park 1BR Retreat
Iron/ironing board, travel crib, WiFi, bed sheets

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.4 out of 10, Exceptional, (8 reviews)
"Nice clean space"
United States
Griffin
The price is AED 338
AED 707 total
includes taxes & fees
30 Jun - 1 Jul
Trendy & Comfy Studio Unit
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, (101 reviews)
"Everything was good!"
United States
Brio
The price is AED 598
AED 1,202 total
includes taxes & fees
5 Jul - 6 Jul
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"I was a little concerned about my stay due to some of the other reviews, but we found the hotel and staff to be very helpful and friendly. The valet parking was so HELPFUL, and all of the attendants were excellent. Our room was tidy and clean, the hotel provided shower gel, shampoo and conditioner was a very nice touch. I booked the king room, and we found it had plenty of room for us, air was cold, and the shower was nice and hot, the closet was huge and the built in safe worked well for valuables. We purchased the extra package when we booked as a convenience for our trip so we didn't have to "think" about anything after we checked in. We had the breakfast buffet daily and it was always hot, full and I loved all the fresh fruit options along with more traditional items such as pancakes, french toast, eggs, and a variety of breakfast meats. The bar staff was attentive and our free drink tickets were easy to use in both sections of the bar. One side was a little more upscale with loads of seating and the other was more cozy but both had a relaxing atmosphere. I would recommend staying here and will stay in the future. My only minor thing was I wish there was ice machines on more than two floors and when we went to check out the balcony outside seating area it was closed."
Kimberly 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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 5477 lodging choices including 1663 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?
Below are some of the favorite apartments in the area: LIVN West Loop Chicago 2 BR City View: Located 16.6 mi/26.8 km away in Chicago. Charming Wrigleyville Home Close to the Cubs!: Located in Chicago, 11.4 mi/18.4 km from Winnetka. Includes free WiFi 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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