Are there any 5-star all-inclusive resorts in Old Town Chicago?

Find a luxurious escape that includes your room, meals, drinks and entertainment in Old Town Chicago with our filter tool. Search for resorts with a 5-star rating and click on the "All inclusive" filter. Make sure you check what's included in the purchase price. That way, you're ready to take advantage of the premium perks on offer when you get there.

What are the top 5-star spa hotels in Old Town Chicago?

Look forward to a respite from the hectic pace of life at one of our 5-star spa stays in or around Old Town Chicago. Popular options are Park Hyatt Chicago , Four Seasons Hotel Chicago and Waldorf Astoria Chicago . Choose from a wide range of restorative treatments and therapeutic programs designed to enhance your overall well-being.

Are there any 5-star vacation rentals in Old Town Chicago?

You won't find any 5-star vacation rentals in Old Town Chicago on our site, but there are a few other top-rated properties worth looking into. Search through our vacation rentals in Old Town Chicago to book the perfect place for your stay.

5 Stars Hotels in Old Town Chicago: Compare Hotel Prices & Find the Cheapest Old Town Chicago, Chicago 5 Stars Hotels

A street with outdoor seating, brick buildings, and signs for a barbershop and a restaurant.

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Our top choices for Old Town Chicago 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Downtown Chicago

ryan

NT$19,378 total

includes taxes & fees

Nov 22 - Nov 23

A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

robert

NT$17,876 total

includes taxes & fees

Nov 8 - Nov 9

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

3. The Peninsula Chicago

Downtown Chicago

Vincent Haley

NT$24,222 total

includes taxes & fees

Nov 22 - Nov 23

A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

4. The Langham, Chicago

Downtown Chicago

Ana

NT$20,928 total

includes taxes & fees

Nov 22 - Nov 23

A hotel entrance with a fountain, a car, and a person standing by the entrance.

5. Waldorf Astoria Chicago

Downtown Chicago

Luis

NT$19,436 total

includes taxes & fees

Nov 22 - Nov 23

A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

6. The Ritz-Carlton, Chicago

Downtown Chicago

Krikour

NT$19,185 total

includes taxes & fees

Nov 22 - Nov 23

A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

7. Nobu Hotel Chicago

Downtown Chicago

Abhay

NT$13,959 total

includes taxes & fees

Nov 22 - Nov 23

A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.

8. Park Hyatt Chicago

Downtown Chicago

Tom

NT$19,959 total

includes taxes & fees

Nov 22 - Nov 23

A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

9. The St. Regis Chicago

Downtown Chicago

Alise

NT$20,773 total

includes taxes & fees

Nov 22 - Nov 23

A rooftop dining area with checkered tablecloths, red and blue plates, and a city skyline in the background.

10. Art Villa

West Town

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Old Town Chicago.

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

NT$6,622

NT$7,774 total

Nov 27 - Nov 28

includes taxes & fees

8.6/10 Excellent! (2,579 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

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Frequently asked questions

What are the best 5-star hotels in Old Town Chicago?

Waldorf Astoria Chicago is one of the leading picks around the North Side neighborhood of Old Town Chicago based on reviews by Expedia customers. Four Seasons Hotel Chicago and Park Hyatt Chicago are other 5-star hotels in this area that rate highly with travelers.

How much does it cost to stay in a 5-star hotel in Old Town Chicago?

How much you pay for a 5-star hotel in Old Town Chicago can vary depending on when you decide to travel and how long you plan to stay, among other factors. Use our price per night filter and other search tools to land the best rate on a luxurious stay.

Search for the lowest price per night from NT$4,612

What makes a hotel 5 stars in Old Town Chicago?

In Old Town Chicago, a hotel needs to provide a specific amount of high-end amenities to earn a 5-star rating. These can include on-site gyms, spas and saunas, gourmet restaurants, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their extraordinary service. You can expect things like nightly turn-down services, concierge services and in-room massages. Some may even offer thoughtful touches like welcome gifts.

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