Explore top 2026 5 Star Hotels in Winnetka

Name: Art Villa
Rating: 10

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Top Winnetka 5 Star hotels

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$469 nightly

$557 total

Jul 12 - Jul 13

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly ...

9.6/10 Exceptional! (1,910 reviews)

"Great service"

Reviewed on Jun 30, 2026

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$563 nightly

$669 total

Jul 19 - Jul 20

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...

9.8/10 Exceptional! (1,006 reviews)

"Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't ..."

Reviewed on Jul 2, 2026

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$530 nightly

$630 total

Jul 12 - Jul 13

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...

9.4/10 Exceptional! (1,002 reviews)

"This was our first stay at a Four Seasons — if there was 6 stars for the staff, I'd give it. Upon arrival, we were running late and trying to make an event. The Bellman immediately said he'd arrange transportation for us after we quickly went to the restrooms. We come back down to discover that he ..."

Reviewed on Jul 2, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$625 nightly

$743 total

Jul 5 - Jul 6

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. ...

9.8/10 Exceptional! (1,000 reviews)

"Fantastic!"

Reviewed on Jul 1, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$570 nightly

$678 total

Jul 19 - Jul 20

Total with taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi ...

9.4/10 Exceptional! (1,000 reviews)

"Beautiful property with great location in Chicago. Can’t wait to stay again."

Reviewed on Jun 28, 2026

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$575 nightly

$684 total

Jul 26 - Jul 27

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...

9.2/10 Wonderful! (1,001 reviews)

"My wife and I had a reservation for the club level and up graded to a suite at ck in . It was NOT an upgrade . We shared a wall with the lounge kitchen . The smells constantly filled our room AND the cleaning crew started in the lounge at 1 AM making it hard to sleep until they finished cleaning ..."

Reviewed on Jun 30, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$573 nightly

$681 total

Jul 9 - Jul 10

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...

9.6/10 Exceptional! (1,000 reviews)

"Excellent hotel and location. 1 min away from Michigan avenue"

Reviewed on Jun 23, 2026

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$437 nightly

$520 total

Jul 26 - Jul 27

Total with taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour ...

9.4/10 Exceptional! (879 reviews)

"Shower bombs would be a good incentive. Really enjoyed the scenery as well as the customer service."

Reviewed on Jun 27, 2026

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$671 nightly

$798 total

Jul 19 - Jul 20

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...

9.4/10 Exceptional! (124 reviews)

"👌"

Reviewed on Jun 7, 2026

Art Villa

467 N Armour St Chicago IL

A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. ...

10/10 Exceptional! (2 reviews)

Reviewed on Aug 12, 2025

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Winnetka Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Winnetka to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Winnetka 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Winnetka before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Winnetka hotel reviews by fellow wanderers

Travelodge by Wyndham Downtown Chicago

4 out of 5

Posted 3 hours ago

Travelocity Verified Review

"The staff was very helpful in helping us with any questions we had"

A verified traveler stayed at Travelodge by Wyndham Downtown Chicago

Congress Plaza Hotel

5 out of 5

Posted 4 hours ago

Travelocity Verified Review

"Parking was a bit of a walk from the Park 1 And of course we were carrying our items and it was very hot. Your staff at the front desk all were awesome. Friendly helpful. There were no places to have dinner that we would have eaten at in your hotel as the Raphael was closed for some reason. We walked in to the bar restaurant at about 5 minutes till 4:00 because we were confused as to whether we could order food there or not. And there was a very unfriendly man behind the bar whom I asked if we could order a food and he very harshly replied back when I opened you can. Then I asked for a menu and he sighed like I was bothering him and slammed it down on the bar. So we walked about three blocks to get some food because I wouldn't have eaten there with him serving me anyway. He was pretty awful however. Johnny at the concierge was very very nice and gave us directions to a restaurant and a coupon for 10% off. All in all the stay was good but that guy in the bar needed to go . It was a lovely stay. We went to a concert at the bank pavilion a little ways away and the room was quite comfortable."

A verified traveler stayed at Congress Plaza Hotel