A suburban street with a stone house, a tree, and a clear sky.

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November 2026

December 2026

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Our top choices for Winnetka apartments

A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

1. Well-Equipped 2BR Unit with Parking

North Evanston

Ann N.

AED 833 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

2. Chic Studio - In Downtown Highland Park, by Metra

Highland Park

Deborah

AED 562 total

includes taxes & fees

9 Nov - 10 Nov

A patio area with outdoor seating and solar-powered lights.

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

South Evanston

Colleen B.

AED 985 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio area with a wooden fence, outdoor seating with chairs and a table, and multiple ground lamps.

4. Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

South Evanston

Brent S.

AED 985 total

includes taxes & fees

8 Nov - 9 Nov

A living room with a sofa, a leather chair, a coffee table, a TV, and a mirror.

5. Charming 1BR Apt in Evanston

South Evanston

Kim B.

AED 813 total

includes taxes & fees

10 Nov - 11 Nov

A living room with a flat-screen TV, a coffee table, a sofa, and a radiator.

6. Perfectly Located 1-Bedroom Unit

South Evanston

V S.

AED 938 total

includes taxes & fees

6 Dec - 7 Dec

A compact kitchen with white cabinets, a stove, microwave, and a coffee maker.

7. Spacious 2BR Close to it All - Chic Apt in Skokie

West Dempster

Jean W.

AED 912 total

includes taxes & fees

16 Nov - 17 Nov

A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

8. King Bed Non-Smoking

Chicago

Anonymous traveler

AED 279 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with white cabinets, a microwave, and a stove. There is a yellow armchair with a white pillow next to a large gray and white flower painting on the wall.

9. Stunning & Stylish Downtown Studio - Highland Park

Highland Park

Tom B.

AED 564 total

includes taxes & fees

29 Nov - 30 Nov

A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

10. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Downtown Evanston

Brian W.

AED 1,345 total

includes taxes & fees

8 Nov - 9 Nov

A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

11. Chic Studio in Downtown Highland Park near Metra

Highland Park

Jason H.

AED 541 total

includes taxes & fees

29 Nov - 30 Nov

A modern dining area with a round table, black chairs, and a hanging light fixture.

12. Haus Of Hues: MDRN Bright Peaceful Private Apt

South Evanston

Bradie R.

AED 1,401 total

includes taxes & fees

16 Nov - 17 Nov

A modern bedroom with a bed, a sofa, and a hanging plant.

13. Cozy studio in Andersonville Chicago

Edgewater

Sherry M.

AED 496 total

includes taxes & fees

30 Nov - 1 Dec

A rooftop terrace with a brick wall, large windows, and a metal railing.

14. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Uptown

Michael S.

AED 913 total

includes taxes & fees

9 Nov - 10 Nov

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

Uptown

Paul J.

AED 913 total

includes taxes & fees

9 Nov - 10 Nov

A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

16. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Irving Park

Meagan C.

AED 976 total

includes taxes & fees

18 Nov - 19 Nov

A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

17. Cozy apartment with AC and WiFi in awesome Chicago

Rogers Park

Andrew O.

AED 1,206 total

includes taxes & fees

19 Nov - 20 Nov

A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

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

Chicago

Anonymous traveler

AED 280 total

includes taxes & fees

23 Nov - 24 Nov

A modern bedroom with a bed, a window, and a view of an outdoor area.

19. The Lincoln Square Hideaway

Lincoln Square

Ian

AED 1,482 total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a blue sofa, a patterned rug, and a television.

20. Great Area Logan Square Apt Games Pets - Sleeps 5

Avondale

Deborah J.

AED 678 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Learn more about Winnetka

Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theater.

See all hotels in Winnetka

Top reviews in Winnetka

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

Holiday Inn Chicago O'Hare – Rosemont by IHG

Rosemont

10/10 Excellent

Eero

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 Chicago by LOTTE

Downtown Chicago

10/10 Excellent

Erin

A three-tiered fruit basket on a wooden table against a wall with framed pictures.

Heart O' Chicago

Edgewater

10/10 Excellent

Anonymous traveler

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

Hotel Riu Plaza Chicago

Downtown Chicago

10/10 Excellent

We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...

Donna

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

Hampton Inn & Suites Chicago Downtown

Downtown Chicago

10/10 Excellent

Shatani

A dining table set for six with a cityscape view through large windows.

Swissotel - Chicago

Downtown Chicago

10/10 Excellent

Brian

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

10/10 Excellent

Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.

Michael

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

10/10 Excellent

I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable. The property is very nice, although we didn't get the two...

Joanna

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

10/10 Excellent

Forever one of my favorite hotels and one of my two favorite Courtyard properties I've ever stayed at! This is the 3rd year in a row we've stayed here when coming to Chicago and it never disappoints. It feels like a high-end hotel for an affordable price (considering where it is)! The staff is great super helpful, rooms are so clean and overall just is one of the nicest places! Highly recommend if you're looking for a spot in Chicago!

adriana

A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

10/10 Excellent

Claribeth

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

10/10 Excellent

We will definitely be staying here again! Great location, clean room, and great service. They even have a great complimentary breakfast which is a must have in a city like Chicago. The staff was great also. We had to switch trains for an earlier one due to weather and got into Chicago in the AM. Check in is 4pm and with two small children we were worried about what to do for hours but the staff helped us out and luckily had a room available.

Alexander

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Griffin

A hotel lobby with a bar area, a chandelier, and a reception desk.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Excellent

Sergio

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

10/10 Excellent

Anne

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 5431 lodging choices including 1775 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 top apartments in the area: King Bed Non-Smoking: It's situated in Des Plaines, 8.9 mi/14.3 km away. Includes Smart TVs. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley: Located 11 mi/17.7 km away in Chicago. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. 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 get outside and enjoy nature. Wrigley Field and Navy Pier 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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Economy Car Rentals in North Evanston
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Search Apartments in Winnetka

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Winnetka apartments

1. Well-Equipped 2BR Unit with Parking

2. Chic Studio - In Downtown Highland Park, by Metra

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

4. Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

5. Charming 1BR Apt in Evanston

6. Perfectly Located 1-Bedroom Unit

7. Spacious 2BR Close to it All - Chic Apt in Skokie

8. King Bed Non-Smoking

9. Stunning & Stylish Downtown Studio - Highland Park

10. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

11. Chic Studio in Downtown Highland Park near Metra

12. Haus Of Hues: MDRN Bright Peaceful Private Apt

13. Cozy studio in Andersonville Chicago

14. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

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

16. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

17. Cozy apartment with AC and WiFi in awesome Chicago

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

19. The Lincoln Square Hideaway

20. Great Area Logan Square Apt Games Pets - Sleeps 5

Learn more about Winnetka

Top reviews in Winnetka

Holiday Inn Chicago O'Hare – Rosemont by IHG

10/10 Excellent

Frequently Asked Questions

What's it like to stay at an apartment in Winnetka?

How do you know if an apartment is the best choice for your stay?

What's a favorite apartment for a stay in Winnetka?

What can I expect from the weather in Winnetka?

What should I see in Winnetka?

What's the best way to get to and around Winnetka?

Explore a world of travel with Expedia