Arrival/Check-In: The Drake stands out in Chicago for its deep history more than for cutting‑edge modernity. Opened in 1920 and a member of the Historic Hotels of America since 2014, the hotel was a Roaring Twenties favorite and remains a storied destination today. Small historical touches—like the famed initials Marilyn Monroe and Joe DiMaggio left in the Cape Cod Room’s bar—underscore its legacy.
I spent a long Mother’s Day weekend here with my mom. The Drake isn’t the newest property in the city, but it delivers warmth, comfort and an unbeatable location. Our arrival set the tone: check‑in was quick and friendly, and the impressive floral arrangement in the lobby made a strong first impression.
Guest Quarters: Some rooms could benefit from a refresh, but our double‑bedded corner room offered generous space and an excellent view of Lake Michigan. The layout began with a short entry hall, the bathroom to the right and a large walk‑in closet to the left. The sleeping area featured two beds with a nightstand between them, plus a flat‑screen TV, mini refrigerator, couch, coffee table, armchair and a sizable desk with chair. There was plenty of room for two people to unpack and spread out comfortably.
The hotel’s thoughtful touches continued in the room: a fresh bouquet and a Mother’s Day card for my mom, along with a small tea and mug gift that felt personal and welcoming.
Services/Amenities: Afternoon tea at Palm Court is a signature experience here. For our celebration we enjoyed peach Bellinis while a harpist played, creating a distinctly elegant atmosphere. Dining options on property include Palm Court, Coq d’Or, the Cape Cod Room, Lavazza Café and Drake Bros’. In‑room dining is offered on a scheduled basis rather than 24/7.
As part of the Hilton family, The Drake participates in HHonors and supports digital conveniences like mobile check‑in and express check‑out. The hotel also offers a 3,000‑square‑foot fitness center, paid access to a nearby Equinox facility, a business center, retail shops and more than 33,000 square feet of meeting and event space.
The Experience: The Drake’s charm is its greatest asset. Even if some areas feel slightly dated, the property’s character and historic elegance come through strongly. Staff convey the hotel’s personality with warmth and professionalism, and the location is nearly perfect—steps from the lake and along Michigan Avenue, convenient for walking to shopping and attractions. My mom and I found it a wonderful base for exploring Chicago on foot.
GT CHECKLIST
Doorman/valet: yes
Check‑in under 10 minutes: yes
Separate tub and shower: no
Large vanity: yes
High‑quality towels: yes
Powerful, unattached hair dryer: yes
High‑quality bed linens: yes
Large, flat‑screen television: yes
Large desk with convenient outlets: yes
Large, complimentary laptop safe: yes
Complimentary in‑room Wi‑Fi: not listed
Complimentary bottled water: yes
Stocked minibar: yes
Ample lighting: yes
In‑room coffeemaker: yes
Iron and ironing board: yes
On‑site restaurant: yes
24‑hour room service: no
24‑hour state‑of‑the‑art fitness center: no (fitness center on site; 24‑hour access not specified)
Turn‑down service: no
The Drake
140 E. Walton Place
Chicago, IL 60611
tel 312 787 2200
thedrakehotel.com