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

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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

Teresa

NT$23,218 total

includes taxes & fees

Oct 4 - Oct 5

A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Jorge

NT$19,679 total

includes taxes & fees

Oct 4 - Oct 5

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

3. The Langham, Chicago

Downtown Chicago

Saramae

NT$22,690 total

includes taxes & fees

Oct 29 - Oct 30

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

4. The Peninsula Chicago

Downtown Chicago

Levi

NT$25,484 total

includes taxes & fees

Sep 29 - Sep 30

A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Downtown Chicago

Luis

NT$24,870 total

includes taxes & fees

Oct 25 - Oct 26

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

6. Nobu Hotel Chicago

Downtown Chicago

Abhay

NT$18,093 total

includes taxes & fees

Oct 4 - Oct 5

A couple dining at a table with a view of a cityscape and a sunset.

7. Park Hyatt Chicago

Downtown Chicago

Tom

NT$24,294 total

includes taxes & fees

Oct 27 - Oct 28

A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

8. The Ritz-Carlton, Chicago

Downtown Chicago

Fred

NT$18,877 total

includes taxes & fees

Oct 25 - Oct 26

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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.

River Hotel

75 East Wacker Drive Chicago IL

NT$5,906

per night

Oct 25 - Oct 26

8.8/10 Excellent! (5,455 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.

Top Old Town Chicago Hotel Reviews

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$6,757

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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