Find 5 Star Hotels in Westchester, IL from $196

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Westchester 5 Star Hotels

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14

Compare Westchester 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Trump International Hotel & Tower Chicago
Bar (on property)

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1702)
"Location, staff and accommodations were excellent. "
$461 nightly
The price is $541
Sep 7 - Sep 8
Total with taxes and fees
Trump International Hotel & Tower Chicago
Four Seasons Hotel Chicago
Reception

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (1002)
"Great location "
$590 nightly
The price is $693
Sep 28 - Sep 29
Total with taxes and fees
Four Seasons Hotel Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1005)
"Location can’t be beat. Hotel is excellent! "
$544 nightly
The price is $638
Sep 21 - Sep 22
Total with taxes and fees
The Langham, Chicago
The Peninsula Chicago
Front of property - evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1009)
"Fantastic hotel "
$625 nightly
The price is $734
Sep 1 - Sep 2
Total with taxes and fees
The Peninsula Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1003)
"Great location "
$531 nightly
The price is $624
Sep 21 - Sep 22
Total with taxes and fees
Waldorf Astoria Chicago
Park Hyatt Chicago
Suite, Terrace (Water Tower) | 1 bedroom, premium bedding, down comforters, pillowtop beds

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1002)
"The hotel was amazing. The staff were friendly. There is so much to do in the area. "
$615 nightly
The price is $722
Sep 1 - Sep 2
Total with taxes and fees
Park Hyatt Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (714)
"Great location, amenities and staff. "
$339 nightly
The price is $398
Sep 21 - Sep 22
Total with taxes and fees
Nobu Hotel Chicago
The Ritz-Carlton, Chicago
Bar (on property)

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1003)
"Beautiful place "
$540 nightly
The price is $634
Oct 1 - Oct 2
Total with taxes and fees
The Ritz-Carlton, Chicago
The St. Regis Chicago
2 restaurants, breakfast served

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (73)
"Top tier "
$635 nightly
The price is $745
Sep 28 - Sep 29
Total with taxes and fees
The St. Regis Chicago
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
$980 nightly
The price is $1,240
Sep 1 - Sep 2
Total with taxes and fees
Art Villa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Westchester.
The Wade

The Wade

644 N Lake Shore Dr, Chicago, IL
$167 nightly
The price is $196 total per night from Sep 22 to Sep 23
$196 total
Sep 22 - Sep 23
Total with taxes and fees
8.2/10 Very Good! (1,156 reviews)
Still don't see what you're looking for?
See all properties in Westchester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Top Westchester Hotel Reviews

Find out more about Westchester

Find out more about Westchester

Why not demand the best of accommodations on your excursion to Westchester? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Westchester so popular in the last year. There's no reason to delay a getaway to Westchester any longer. Furthermore, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. Reserve one of our 5-star hotels in Westchester and indulge in the finer things in life for a while. What are you waiting for?

5-Star Hotels in Westchester

Don't be afraid to be pampered during your trip, along with the best conditions. High-end restaurants, top-notch customer care, and fabulous spa offerings are all on offer. You're sure to find exactly the accommodation you need. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. What creature comforts do you want in your lodging? A concierge to help you plan every detail of your day? A rejuvenating facial treatment to help your cares fall away? Beautiful furniture, delectable chocolate desserts, and even a hot tub in the bathroom...these hotels are one-of-a-kind. Want to see for yourself? Plenty of visitors recommend this location.

Can't wait to get outside? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Westchester are the perfect place to rest up after a busy day.

Make Your Escape

The results are in, and Westchester 5-star hotels are the place to be when you book your next vacation. These beautiful hotels are highly rated by the guests who stay in them, and you're about to join their ranks. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Choose one of the 5-star hotels in Westchester today and settle down in complete comfort tomorrow.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Westchester?
The amount you pay for a 5-star hotel in Westchester depends on things like when you plan to go and the length of your escape. Our top tip for scoring an awesome deal? Use our pricing filters to compare all of the available hotels for your preferred dates.

  • Search for the lowest price per night from $196

What makes a hotel 5 stars in Westchester?
Flawless guest service is the defining feature of every 5-star hotel in Westchester. From the instant you arrive, staff attend to your every need, whether recommending activities and tours or providing in-room massage treatments. Plus, hotels must feature upscale conveniences to be considered for a 5-star rating. These can include luxury toiletries, a wellness center, swimming pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Westchester?
Use Expedia's filter tool to find a luxurious escape in Westchester where everything you need is included. After your initial search, narrow down your results for properties that have 5 stars and are deemed "All inclusive." The main thing on the itinerary at these stays? Pure enjoyment and indulgence.