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

Find 4 Star Hotels in Winnetka, IL from AED 324

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

AED 979 total

includes taxes & fees

10 Dec - 11 Dec

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

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

Downtown Chicago

Ebony

AED 520 total

includes taxes & fees

3 Dec - 4 Dec

A river with buildings on both sides, a bridge, and a pedestrian walkway.

3. River Hotel

Downtown Chicago

Shelby

AED 463 total

includes taxes & fees

10 Dec - 11 Dec

A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

4. The Wade

Downtown Chicago

Sara

AED 520 total

includes taxes & fees

23 Nov - 24 Nov

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

5. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Silvia

AED 456 total

includes taxes & fees

23 Nov - 24 Nov

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

AED 506 total

includes taxes & fees

11 Nov - 12 Nov

A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

7. Fairmont Chicago at Millennium Park

Downtown Chicago

Joel

AED 1,000 total

includes taxes & fees

24 Nov - 25 Nov

A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.

8. Hilton Chicago

Downtown Chicago

Jordan

AED 698 total

includes taxes & fees

22 Nov - 23 Nov

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

9. Warwick Allerton - Chicago

Downtown Chicago

Muhammad

AED 384 total

includes taxes & fees

23 Nov - 24 Nov

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

10. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Faye

AED 932 total

includes taxes & fees

9 Dec - 10 Dec

A cityscape with tall buildings, a river, and a bridge.

11. The Royal Sonesta Chicago Downtown

Downtown Chicago

Frédéric

AED 681 total

includes taxes & fees

9 Dec - 10 Dec

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

AED 570 total

includes taxes & fees

25 Nov - 26 Nov

A modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

13. Arlo Chicago

Downtown Chicago

Daniel

AED 701 total

includes taxes & fees

23 Nov - 24 Nov

A modern interior with a dining area, sofas, and artwork on the walls.

14. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Grace

AED 374 total

includes taxes & fees

9 Dec - 10 Dec

A modern hotel lobby with a glass ceiling, white seating areas, and a view of the city.

15. The Godfrey Hotel Chicago

Downtown Chicago

Tamiya

AED 566 total

includes taxes & fees

10 Dec - 11 Dec

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

16. Hyatt Regency O'Hare Chicago

Rosemont

Garth

AED 566 total

includes taxes & fees

26 Nov - 27 Nov

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

AED 477 total

includes taxes & fees

8 Dec - 9 Dec

A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

18. Swissotel - Chicago

Downtown Chicago

Oleg

AED 695 total

includes taxes & fees

26 Nov - 27 Nov

19. Loews Chicago O'Hare Hotel

Rosemont

Arnulfo

AED 607 total

includes taxes & fees

27 Nov - 28 Nov

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

AED 736 total

includes taxes & fees

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

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.

A modern hotel room with a large bed, two armchairs, a small round table, and a view of a cityscape through floor-to-ceiling windows.

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?

If you're looking for high-quality comfort and plenty of amenities on your Winnetka retreat, consider Renaissance Chicago North Shore Hotel. This leading 4-star hotel comes with limousine services and proposal/romance packages. DoubleTree by Hilton Chicago - North Shore Conference Center also gets rave reviews from Expedia travelers. A pillowtop mattress and a swimming pool are among its conveniences.

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 AED 324

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?

Use our convenient filters to search for all-inclusive Winnetka escapes where your accommodations, food, daily activities and most other things are included in the one upfront fee. Can't see anything available? You can also kick back and relax in upscale surroundings at other excellent 4-star stays in the city. DoubleTree by Hilton Chicago - North Shore Conference Center and Renaissance Chicago North Shore Hotel are two popular options.

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Find 4 Star Hotels in Winnetka, IL from AED 324

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?

Explore a world of travel with Expedia