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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Winnetka apartments

Desk, iron/ironing board, travel crib, WiFi
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"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 AED 253
AED 608 total
includes taxes & fees
11 Jan - 12 Jan
Gold Coast Living: Modern Studio Unit
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AED 231
AED 619 total
includes taxes & fees
12 Jan - 13 Jan
1BR Modern Luxe Apt with In-Unit Laundry
1 bedroom, iron/ironing board, travel crib, WiFi
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AED 231
AED 619 total
includes taxes & fees
11 Jan - 12 Jan
West Loop Living – Bright 1BR
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (19)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AED 253
AED 700 total
includes taxes & fees
12 Jan - 13 Jan
Twice as Nice: Chic 2BR Stay with Style & Space
TV, offices
Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.8 out of 10, Exceptional, (11)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is AED 231
AED 619 total
includes taxes & fees
11 Jan - 12 Jan
Modern Comfort: 1BR Unit w/ Laundry
TV, offices
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"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 231
AED 619 total
includes taxes & fees
11 Jan - 12 Jan
Sun-Drenched 1BR Apartment
Interior
River North Rooftop With In and Out Parking 3

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)
"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 367
AED 1,149 total
includes taxes & fees
13 Jan - 14 Jan
River North Rooftop With In and Out Parking 3
TV, offices
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is AED 231
AED 619 total
includes taxes & fees
15 Jan - 16 Jan
The One: A 1BR Stay That Feels Like Home
TV, offices
Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
Downtown Chicago
The price is AED 231
AED 619 total
includes taxes & fees
13 Jan - 14 Jan
Chicago-Themed 1BR in a Central Spot near Downtown
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is AED 231
AED 619 total
includes taxes & fees
21 Jan - 22 Jan
Sleek 1BR Apt w/ Laundry
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is AED 231
AED 619 total
includes taxes & fees
11 Jan - 12 Jan
Complete 1BR Home Sum
Interior
Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
Downtown Chicago
The price is AED 253
AED 709 total
includes taxes & fees
19 Jan - 20 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown
Interior
Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING
Near West Side
9.4 out of 10, Exceptional, (10)
"Great place to stay that was close to downtown"
United States
Michelle B.
The price is AED 213
AED 1,219 total
includes taxes & fees
20 Jan - 21 Jan
Spacious 3-bedroom apartment near downtown, FREE PARKING
Terrace/patio
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (49)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is AED 212
AED 895 total
includes taxes & fees
12 Jan - 13 Jan
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Terrace/patio
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.0 out of 10, Wonderful, (19)
"Had a great stay! Perfect for our needs. Great location. It was an easy walk to the lake and lots of great restaurants nearby!"
United States
Rodney S.
The price is AED 220
AED 915 total
includes taxes & fees
11 Jan - 12 Jan
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
TV, offices
Clean and Equipped 2BR Apartment

Clean and Equipped 2BR Apartment

Clean and Equipped 2BR Apartment
2.0 star property
Lakeview
10.0 out of 10, Exceptional, (1)
"Excellent property and location!"
United States
Chris F.
The price is AED 257
AED 704 total
includes taxes & fees
11 Jan - 12 Jan
Clean and Equipped 2BR Apartment
Interior
Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
Irving Park
10.0 out of 10, Exceptional, (4)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
The price is AED 294
AED 748 total
includes taxes & fees
14 Jan - 15 Jan
Pine Beam Sloth Apartment next to Blue Line
Smart TV, books
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
West Ridge
10.0 out of 10, Exceptional, (5)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
The price is AED 374
AED 1,109 total
includes taxes & fees
12 Jan - 13 Jan
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
Interior
2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
10.0 out of 10, Exceptional, (4)
"Comfortable beds, great location"
United States
Jason
The price is AED 268
AED 717 total
includes taxes & fees
13 Jan - 14 Jan
2BR Chic & Comfortable Furnished Unit
TV, offices
Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
10.0 out of 10, Exceptional, (5)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
The price is AED 253
AED 700 total
includes taxes & fees
11 Jan - 12 Jan
Great Layout – Spacious 2BR Apt
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Beautiful "
Danny 3-night trip
Posted 17 hours ago
Hyatt Regency 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 5612 lodging choices including 1731 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 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 Elder Lane 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.