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Apartments in Winnetka

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"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 259
SAR 621 total
includes taxes & fees
26 Nov - 27 Nov
Gold Coast Living: Modern Studio Unit

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is SAR 206
SAR 597 total
includes taxes & fees
30 Nov - 1 Dec
West Loop Living – Bright 1BR

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 SAR 206
SAR 597 total
includes taxes & fees
2 Dec - 3 Dec
Sleek 1BR Apt w/ 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 SAR 206
SAR 597 total
includes taxes & fees
2 Dec - 3 Dec
1BR Modern Luxe Apt with In-Unit Laundry

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.4 out of 10, Exceptional, (3)
"Convenient location and clean place"
United States
David S.
The price is SAR 206
SAR 597 total
includes taxes & fees
3 Dec - 4 Dec
The One: A 1BR Stay That Feels Like Home

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is SAR 206
SAR 597 total
includes taxes & fees
30 Nov - 1 Dec
Stylish 1BR in West Loop

Modern West Loop Gem-City Views & Prime Location 2

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
The price is SAR 566
SAR 759 total
includes taxes & fees
1 Dec - 2 Dec
Modern West Loop Gem-City Views & Prime Location 2

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is SAR 398
SAR 1,177 total
includes taxes & fees
22 Dec - 23 Dec
River North Rooftop With In and Out Parking 1

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

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is SAR 233
SAR 688 total
includes taxes & fees
30 Nov - 1 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is SAR 817
SAR 1,663 total
includes taxes & fees
24 Nov - 25 Nov
Your Chicago get Away

Complete 1BR Home Sum

Downtown Chicago
The price is SAR 206
SAR 597 total
includes taxes & fees
30 Nov - 1 Dec
Complete 1BR Home Sum

River North Private Deck With In and Out Parking

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
The price is SAR 900
SAR 1,866 total
includes taxes & fees
3 Dec - 4 Dec
River North Private Deck With In and Out Parking

Stylish Gold Coast 1BR with Vintage Flair

Downtown Chicago
The price is SAR 206
SAR 597 total
includes taxes & fees
7 Dec - 8 Dec
Stylish Gold Coast 1BR with Vintage Flair

Vintage Studio in Chicago’s Gold Coast

Downtown Chicago
The price is SAR 259
SAR 621 total
includes taxes & fees
27 Nov - 28 Nov
Vintage Studio in Chicago’s Gold Coast

Chic Studio near Downtown Chicago | Gold Coast

Downtown Chicago
6.0 out of 10, (1)
"Key pad issues with entry, but overall good "
United States
Andrew U.
The price is SAR 233
SAR 590 total
includes taxes & fees
23 Nov - 24 Nov
Chic Studio near Downtown Chicago | Gold Coast

Spacious 3-bedroom apartment near downtown, FREE PARKING

Near West Side
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is SAR 218
SAR 1,245 total
includes taxes & fees
23 Nov - 24 Nov
Spacious 3-bedroom apartment near downtown, FREE PARKING

River North Private Balcony With In and Out Parking

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is SAR 529
SAR 1,370 total
includes taxes & fees
4 Dec - 5 Dec
River North Private Balcony With In and Out Parking

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Brighton Park
10.0 out of 10, Exceptional, (1)
"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment [if available]. "
United States
Fabian H.
The price is SAR 266
SAR 969 total
includes taxes & fees
26 Nov - 27 Nov
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

NEW Private West Loop 1br with Backyard near Green Line and CTA

East Garfield Park
9.4 out of 10, Exceptional, (3)
"Clean, and was exactly how described in the booking. Host was quick to respond to any questions we had. "
United States
Cyril M.
The price is SAR 252
SAR 941 total
includes taxes & fees
24 Nov - 25 Nov
NEW Private West Loop 1br with Backyard near Green Line and CTA

Smart Simple and Spacious 4BR Apt

Near South Side
9.2 out of 10, Wonderful, (5)
"Clean, simple check-in."
United States
Shahid
The price is SAR 203
SAR 1,140 total
includes taxes & fees
23 Nov - 24 Nov
Smart Simple and Spacious 4BR 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

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 5533 lodging choices including 2919 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: Clean & Equipped 1BR Apt: Situated in Chicago, 11.8 mi/19.1 km from the heart of Winnetka. Lakeview 2BR Apartment: Located 12.7 mi/20.4 km away in Chicago. Stylish 1BR in West Loop: It's located in Chicago, 16.1 mi/25.8 km away. Remodeled West Loop Apartment Near United Center: Located 16.2 mi/26.1 km away in Chicago. Free WiFi, private balconies, and fireplaces are included. Onsite laundry facilities and a rooftop terrace are on site. 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place: Located in Chicago, 16.7 mi/26.9 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.