A Luxury City Escape at the Waldorf Astoria Chicago: Here’s What You Need To Know

My wife and I live in the suburbs of Chicago, and we tend to take 2 or 3 staycations every year. We try to stay at different hotels each time to see how the city’s hotels compare.

A Chicago staycation in September 2025 was the perfect opportunity to redeem an expiring free night reward with my Hilton Honors American Express Aspire Card, with numerous Hilton properties to choose from. We chose the Waldorf Astoria Chicago, widely regarded as one of the city’s best and most luxurious hotels. Here’s a look at some things to know about the property.

1. It’s an Excellent Use of a Hilton Free Night Reward

The Hilton Aspire card is arguably the most valuable in my wallet and definitely one of my favorites. It offers a plethora of perks and benefits, including top-tier Hilton Diamond status, up to $400 in annual Hilton Resort credits, and up to $200 in annual flight credits.

However, my favorite perk of the card is the anniversary free night reward, which can be redeemed at almost any Hilton Honors property worldwide when a standard room is available, including luxury properties such as the Waldorf Astoria Chicago.

You can also book the property using Hilton Honors points. A standard room can be booked with 110,000 Hilton Honors points, while cash rates often exceed $700 per night.

We value Hilton Honors points at 0.5 cents a piece, making 110,000 points worth $550. With cash rates higher than $550 throughout the year, booking the Waldorf Astoria Chicago can provide above-average value.

2. It Has a Prime Location in the Heart of the Gold Coast

The Waldorf Astoria Chicago is on East Walton Street in the historic Gold Coast neighborhood. It is one of Chicago’s most affluent neighborhoods, with numerous high-end restaurants, luxury shopping venues, historic churches, mansions, and local bars.

The property is less than a 10-minute walk from many of Chicago’s tourist attractions, including Oak Street Beach, the Museum of Contemporary Art, the Holy Name Cathedral, 360 Chicago, and Washington Square Park. The Magnificent Mile, Chicago’s premier commercial district, is just a block away from the hotel.

It is less than a 10-minute walk from many of Chicago’s best hotels, including the Four Seasons Hotel Chicago, The Ritz-Carlton, Chicago, The Peninsula Chicago, and Park Hyatt Chicago.

3. Rooms Are Modern and Luxurious

As expected of a luxury hotel, the Waldorf Astoria Chicago featured a modern and luxurious room. Although we had originally booked a Superior King room (the only standard room available at the time of booking), we were upgraded to a Deluxe King with Fireplace room upon check-in.

The room was refined and elegant, with high-end furnishings, including side tables and lamps. The king-size bed was extremely comfortable and featured a plush, padded headboard. Of course, the linens were also top-notch.

The room featured a spacious living area with plush armchairs and rounded glass tables. Tucked into one corner was a compact workstation. Of course, the highlight was the fireplace, which added warmth and a sense of cozy intimacy.

The room also included a generously sized bathroom adorned with elegant marble finishes. It offered a deep soaking tub and a separate walk-in shower, combining luxury and practicality. My wife found the tub incredibly relaxing.

4. The Amenities Are High-End

The Waldorf Astoria Chicago offers guests numerous luxurious amenities, including an award-winning full-service spa, a business center, a fully equipped fitness center, and an indoor swimming pool.

The spa features separate Jacuzzis, steam rooms, and saunas for men and women and offers a long list of spa treatments and services, such as manicures and pedicures.

However, the indoor lap swimming pool was the highlight of the stay. Although a bit tight, the pool was well-maintained and private.

5. On-Site Dining Options Are Limited

The Waldorf Astoria Chicago features 2 on-site food and beverage options: Brass Tack and Bernard’s. Brass Tack is the hotel’s upscale restaurant, boasting a diverse menu emphasizing American cuisine. Bernard’s is the hotel’s speakeasy cocktail lounge.

We had breakfast at Brass Tack. As a Hilton Honors Diamond member, I received a daily food and beverage credit ($25 per person daily), which we used for breakfast.

My wife ordered the mini golden waffles served with fresh strawberries, strawberry compote, and powdered sugar. I chose the blueberry buttermilk pancakes covered with lemon blueberry confiture.

Unfortunately, the food was not all that delicious. I found the lemon blueberry confiture a bit too sour, taking away from the taste of the sweet pancakes. Not only was the food lackluster, but it was also quite expensive, and the food and beverage credit barely covered the cost of the simple breakfast.

6. The Property Is an Amex Fine Hotels + Resorts Hotel

The Waldorf Astoria Chicago is also an American Express Fine Hotels + Resorts (FHR) property.

Cardholders who book hotels through the FHR program can expect to receive additional perks, including:

• Early check-in at noon (when available)
• Room upgrade upon arrival (when available)
• Daily breakfast for 2 guests per room
• Guaranteed 4 p.m. late checkout
• Complimentary unique property benefit

To use the Amex FHR program, you must have one of the following cards: the Platinum Card^® from American Express, The Business Platinum Card^® from American Express, or the Centurion^® Card from American Express.

Final Thoughts

The Waldorf Astoria Chicago is a fantastic luxury property in one of the best locations in Chicago. The property has much to offer, including spacious rooms, fantastic on-site amenities, and a fine-dining restaurant.

Best of all, I could book the Waldorf Astoria Chicago for 1 night using a free night reward I earned from having the Hilton Aspire card in my wallet. I plan to stay at the property again, as I had an amazing time.