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

Winnetka 4 Stars Hotels

Dates

November 2026

December 2026

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Our top choices for Winnetka 4-star hotels

A modern reception area with a check-in counter, seating, and a decorative wall.

1. Hilton Chicago O'Hare Airport

O'Hare

Cassandra L

NT$8,752 total

includes taxes & fees

Dec 10 - Dec 11

A grand lobby with a central bar, high ceilings, and classical architecture.

2. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Ebony

NT$4,648 total

includes taxes & fees

Dec 3 - Dec 4

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

3. River Hotel

Downtown Chicago

Shelby

NT$4,140 total

includes taxes & fees

Dec 10 - Dec 11

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

4. The Wade

Downtown Chicago

Sara

NT$4,648 total

includes taxes & fees

Nov 23 - Nov 24

A rooftop lounge with outdoor seating, a fire feature, and transparent dome structures.

5. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Silvia

NT$4,077 total

includes taxes & fees

Nov 23 - Nov 24

A rooftop terrace with outdoor seating, a view of the city skyline, and a building with a brick facade.

6. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Alicia

NT$4,530 total

includes taxes & fees

Nov 11 - Nov 12

A modern kitchen with a marble island, fruit bowls, and a city view.

7. Fairmont Chicago at Millennium Park

Downtown Chicago

Joel

NT$8,945 total

includes taxes & fees

Nov 24 - Nov 25

A multi-story building with a prominent entrance featuring a large archway and a sign.

8. Hilton Chicago

Downtown Chicago

Jordan

NT$6,243 total

includes taxes & fees

Nov 22 - Nov 23

A historic building with a prominent entrance, multiple flags, and a classic architectural style.

9. Warwick Allerton - Chicago

Downtown Chicago

Muhammad

NT$3,613 total

includes taxes & fees

Dec 9 - Dec 10

The Intercontinental hotel facade with a large American flag and a floral display.

10. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Faye

NT$8,415 total

includes taxes & fees

Dec 10 - Dec 11

A dining area with a table set for four, large windows offering a cityscape view at dusk.

11. The Royal Sonesta Chicago Downtown

Downtown Chicago

Frédéric

NT$6,090 total

includes taxes & fees

Dec 9 - Dec 10

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.

12. L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

Matthew

NT$5,663 total

includes taxes & fees

Nov 24 - Nov 25

13. Arlo Chicago

Downtown Chicago

Daniel

NT$6,269 total

includes taxes & fees

Nov 23 - Nov 24

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

14. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Grace

NT$3,341 total

includes taxes & fees

Dec 9 - Dec 10

A modern rooftop lounge with white seating, a glass ceiling, and city views.

15. The Godfrey Hotel Chicago

Downtown Chicago

Tamiya

NT$5,394 total

includes taxes & fees

Dec 7 - Dec 8

A modern interior with a central spiral sculpture, multiple levels, and seating areas.

16. Hyatt Regency O'Hare Chicago

Rosemont

Garth

NT$5,061 total

includes taxes & fees

Nov 26 - Nov 27

A hotel with a prominent 'HOTEL FELIX' sign, surrounded by tall buildings and a tree-lined street.

17. Hotel Felix River North/Magnificent Mile

Downtown Chicago

Amy

NT$4,265 total

includes taxes & fees

Dec 8 - Dec 9

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

18. Swissotel - Chicago

Downtown Chicago

Oleg

NT$6,215 total

includes taxes & fees

Nov 26 - Nov 27

A restaurant interior with a stone accent wall, a bar area, and a seating section.

19. Loews Chicago O'Hare Hotel

Rosemont

Arnulfo

NT$5,429 total

includes taxes & fees

Nov 27 - Nov 28

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

20. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Lorena

NT$6,586 total

includes taxes & fees

Nov 23 - Nov 24

Top Winnetka Hotel Reviews

An outdoor seating area with wicker chairs and a sofa, surrounded by trees and a building facade.

Renaissance Chicago North Shore Hotel

Northbrook

10/10 Excellent

Jose

A bar area with wooden flooring, bar stools, and a counter with various bottles. There are framed pictures on the walls and a menu board.

DoubleTree by Hilton Chicago - North Shore Conference Center

Skokie

10/10 Excellent

Pran

A living room with a sofa, armchairs, a coffee table, and a rug. There is a window with curtains and a view of a building outside.

Graduate by Hilton Evanston

Downtown Evanston

10/10 Excellent

I wish I had been notified that the elevator was out of service. The young lady who checked me in gave me a room on the second floor but when I returned that evening I was out on the 4th floor. I unfortunately have a knee which was in extreme pain after walking all over Downtown. Two elderly women were MORTIFIED that they had to climb stairs to the FIFTH FLOOR, of course the stairwell was thick with humidity and NO air conditioning… This situation for SUCH A LANDMARK is disappointing to say the...

Diana

A spacious lobby with a fireplace, comfortable seating, and a high ceiling with multiple balconies.

Embassy Suites by Hilton Chicago North Shore Deerfield

Deerfield

10/10 Excellent

This facility is so well managed. It isn’t a new building, but you can tell they take pride in maintaining the property and taking good care of their customers. Breakfast was amazing with made to order omelets in addition to so many other options. They even switch it up from day to day so you have different choices. An in-house restaurant offers an excellent option for other meals and they offer free drinks and appetizers every evening. The pool is clean and well maintained. Staff are friendly,...

Dan

A spacious lobby with a central seating area, a piano, and a large window overlooking a garden.

Hyatt Regency Deerfield

Deerfield

10/10 Excellent

Mohammaderfan

Loews Chicago O'Hare Hotel

Rosemont

10/10 Excellent

The hotel is right next to 3 restaurants and a fashion mall so it’s a quick walk from there. Also super convenient for events like conventions at the Donald Convention Center. Good service and free WiFi is a plus. Great parking garage location with easy access, plus 18 check in so that’s a bonus for me. Overall, excellent experience worth the money spent on for the nights my buddy and I stayed.

Chi

A modern hotel lobby with a sofa, coffee table, and a reception desk.

Renaissance Chicago O'Hare Suites Hotel

O'Hare

10/10 Excellent

Joseph

Hyatt Regency O'Hare Chicago

Rosemont

10/10 Excellent

Caleb

An outdoor seating area with tables and chairs, a sofa, and a lamp post.

The Rose Chicago, Tapestry Collection by Hilton

Rosemont

10/10 Excellent

Brian

A hotel with a modern design, featuring a prominent DoubleTree by Hilton sign, a well-lit entrance, and a parking garage in the background.

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

Rosemont

10/10 Excellent

Jane

A bar area with a wine rack, seating, and a counter.

Embassy Suites by Hilton Chicago O'Hare Rosemont

Rosemont

10/10 Excellent

SHAUN

A spacious lobby with a marble floor, a central seating area, and a wall of bookshelves.

Chez Hotel Arlington Heights

Arlington Heights

10/10 Excellent

Michal

A modern lobby with a wooden floor, a staircase with glass railings, and a seating area with leather sofas.

The Hotel at Midtown

Bucktown

10/10 Excellent

Becky

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

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

Swissotel - Chicago

Downtown Chicago

10/10 Excellent

Brian

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

An outdoor patio area with multiple tables and chairs, umbrellas, and potted plants.

Loews Chicago Hotel

Downtown Chicago

10/10 Excellent

This is a great place to stay with kids! We have a 7 yrs, 5 yrs and 18 month old and the hotel was very welcoming. The indoor pool was nice for the kids and one of the reasons we stayed here (the pool was a bit chilly, so hopefully they can get it a bit warmer for winter stays). The lobby is fun and feels cozy with the fire. It's a fun place to hang out at night time and the room was clean and spacious enough for our family while not breaking the bank.

Tabitha

Frequently Asked Questions

What are the best 4-star hotels in Winnetka?

Renaissance Chicago North Shore Hotel is a 4-star hotel in Winnetka that's popular among Expedia customers. Concierge services and designer toiletries are just a couple of its amenities. Travelers also recommend DoubleTree by Hilton Chicago - North Shore Conference Center. From concierge services to a swimming pool, it features conveniences that cater to every aspect of your relaxation and enjoyment.

How much does it cost to stay in a 4-star hotel in Winnetka?

Expedia can help you easily find the ideal 4-star hotel for your trip to Winnetka. Use our filter tool to tailor your search by things like price, conveniences and star rating and get access to terrific deals in a few clicks.

Search for the lowest price from NT$2,904

What's the difference between 5-star and 4-star hotels in Winnetka?

Treat yourself to luxury during your Winnetka vacation by staying at a 4-star hotel. As well as featuring upscale accommodations, these properties are typically packed with amenities like large beds, bathrobes and more. A 5-star hotel will go the extra mile to make your stay an even more indulgent and unforgettable one. Concierge assistance, elegant décor and gourmet dining are just the start of the exclusive conveniences and services you'll likely have access to.

Does Winnetka have any 4-star all-inclusive resorts?

Search for a 4-star all-inclusive hotel in Winnetka with Expedia's handy filters. If nothing is available, we have some other choices here that make a superb base for your break. DoubleTree by Hilton Chicago - North Shore Conference Center and Renaissance Chicago North Shore Hotel are both rated 4 stars and strike an excellent balance between comfort, amenities and price.

Are there any 4-star casino hotels in Winnetka?

To find your perfect getaway in Winnetka, use our filter tool to narrow down your search. Offering resort-style amenities and a superior level of service, our 4-star casino hotels are a safe bet for a good time.

Winnetka 4 Stars Hotels

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winnetka 4-star hotels

1. Hilton Chicago O'Hare Airport

2. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

3. River Hotel

4. The Wade

5. The Chicago Hotel Collection - Magnificent Mile

6. The Chicago Hotel Collection Ambassador Gold Coast

7. Fairmont Chicago at Millennium Park

8. Hilton Chicago

9. Warwick Allerton - Chicago

10. InterContinental Chicago Magnificent Mile by IHG

11. The Royal Sonesta Chicago Downtown

12. L7 CHICAGO by LOTTE HOTELS

13. Arlo Chicago

14. Hotel Saint Clair- Magnificent Mile

15. The Godfrey Hotel Chicago

16. Hyatt Regency O'Hare Chicago

17. Hotel Felix River North/Magnificent Mile

18. Swissotel - Chicago

19. Loews Chicago O'Hare Hotel

20. LondonHouse Chicago, Curio Collection by Hilton

Top Winnetka Hotel Reviews

Renaissance Chicago North Shore Hotel

10/10 Excellent

Frequently Asked Questions

What are the best 4-star hotels in Winnetka?

How much does it cost to stay in a 4-star hotel in Winnetka?

What's the difference between 5-star and 4-star hotels in Winnetka?

Does Winnetka have any 4-star all-inclusive resorts?

Are there any 4-star casino hotels in Winnetka?

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