Five Star Hotels in Chicago

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top 5 Stars Hotels in Chicago

Trump International Hotel & Tower Chicago
Terrace/patio
Trump International Hotel & Tower Chicago
5.0 star property
9.4 out of 10, Exceptional, (1433)
" The room was gorgeous with an excellent view of the city. The window actually appears bigger in person due to the high ceiling of the room. The room was fully stocked with a small kitchen. The bathroom was large and spacious and included a TV in the mirror. The only thing I didn’t like in the bathroom was that it didn’t fully close. It’s a sliding door with a gap and you can hear whoever is in the restroom which can make it awkward with a partner. A member of the staff made my girlfriend and I...
The price is S$621
includes taxes & fees
27 Nov - 28 Nov
Trump International Hotel & Tower Chicago
The Peninsula Chicago
Front of property – evening/night
The Peninsula Chicago
5.0 star property
9.8 out of 10, Exceptional, (1001)
"Nice property, excellent housekeeping staff. Nice amenities and a nice pool. "
The price is S$827
includes taxes & fees
24 Nov - 25 Nov
The Peninsula Chicago
The Langham, Chicago
Lobby lounge
The Langham, Chicago
5.0 star property
9.8 out of 10, Exceptional, (1000)
"Love my stays here. The staff have an eye for detail. I know you’re somewhere special when you stay at the Langham."
The price is S$720
includes taxes & fees
22 Dec - 23 Dec
The Langham, Chicago
Waldorf Astoria Chicago
Exterior
Waldorf Astoria Chicago
5.0 star property
9.4 out of 10, Exceptional, (1001)
"Felt like royalty during my stay thank you "
The price is S$591
includes taxes & fees
16 Dec - 17 Dec
Waldorf Astoria Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
Nobu Hotel Chicago
5.0 star property
9.4 out of 10, Exceptional, (573)
"Nice "
The price is S$493
includes taxes & fees
15 Dec - 16 Dec
Nobu Hotel Chicago
Four Seasons Hotel Chicago
Reception
Four Seasons Hotel Chicago
5.0 star property
9.4 out of 10, Exceptional, (999)
"Needs an update "
The price is S$654
includes taxes & fees
15 Dec - 16 Dec
Four Seasons Hotel Chicago
Park Hyatt Chicago
Premium bedding, down duvets, pillow-top beds, minibar
Park Hyatt Chicago
5.0 star property
9.6 out of 10, Exceptional, (1001)
"Great Breakfast and amazing room with a view of the lake."
The price is S$647
includes taxes & fees
8 Dec - 9 Dec
Park Hyatt Chicago
The Ritz-Carlton, Chicago
Exterior
The Ritz-Carlton, Chicago
5.0 star property
9.2 out of 10, Wonderful, (1001)
"A beautiful hotel with lovely amenities!! 10/10 "
The price is S$609
includes taxes & fees
15 Dec - 16 Dec
The Ritz-Carlton, Chicago
The St. Regis Chicago
Indoor pool
The St. Regis Chicago
5.0 star property
8.6 out of 10, Excellent, (46)
"The cleaning services were lacking. We had to ask to have our room cleaned when it still wasn’t cleaned at 5pm. They forgot to refill the coffee pods and water 1 day. And left used towels after one of the cleaning. Sub-par performance for a hotel at these prices."
The price is S$745
includes taxes & fees
16 Dec - 17 Dec
The St. Regis Chicago
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 Chicago.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL
The price is S$181 per night from 10 Dec to 11 Dec
S$181
includes taxes & fees
10 Dec - 11 Dec
8.2/10 Very Good! (3,221 reviews)
Still don't see what you're looking for?
See all properties in Chicago.
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.

Frequently asked questions

What are the best 5-star hotels in Chicago?
Based on Expedia guest reviews, The Langham, Chicago, Trump International Hotel & Tower Chicago and The Peninsula Chicago are among the best 5-star hotels in Chicago. Providing top-quality amenities and unmatchable service, you’ll enjoy an indulgent and memorable stay.
How much does it cost to stay in a 5-star hotel in Chicago?
You’ll find many different pricing options for a 5-star hotel in Chicago on Expedia. The amount you pay will depend on your holiday dates, length of stay and other factors. Compare all of the available accommodation for your chosen dates and use our pricing and other filters to discover the perfect luxury stay.

  • Search for the lowest price per night from S$143

What makes a hotel 5 stars in Chicago?
Flawless guest service chatacterises every 5-star hotel in Chicago. From the minute you arrive, staff are at your beck and call, whether arranging customised tours or providing in-room massage treatments. What’s more, hotels must offer upscale conveniences to qualify for a 5-star rating. These can include luxury bathrobes, a wellness centre, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chicago?
Expedia’s filter tool is the easiest way to narrow down what you want. Select “5-star” and “All inclusive” to see the most upscale resorts in Chicago where your room, meals, activities and entertainment are included in the price. At these retreats, your trip is pure extravagance from the moment you enter the lobby.
What are the top 5-star spa hotels in Chicago?
Spoil yourself with decadent massages and other restorative treatments at The Peninsula Chicago. It’s among Chicago’s most impressive 5-star spa properties. Trump International Hotel & Tower Chicago and The Langham, Chicago also combine high-end accommodation with wellness activities.
Are there any 5-star holiday rentals in Chicago?
Our site doesn’t offer any 5-star holiday rentals in Chicago. However, you will still find some top-rated stays where the only item on your itinerary will be to kick back and enjoy yourself. See what’s available by searching through our holiday rentals in Chicago.
Are there any 5-star hotels in downtown Chicago?
Book a room at The Langham, Chicago. This 5-star hotel is perfect if you want to immerse yourself in Chicago’s lively downtown scene.