How to Deal With The Drake Hotel In Chicago
Staying at The Drake Hotel In Chicago is straightforward if you know what you are doing. The hotel sits right on North Michigan Avenue near Ohio Street. It has been around since 1917. There is not much mystery to it, but there are a few details that trip people up. The main thing to understand is that this is a full-service hotel in a very busy part of town. You are walking distance from Water Tower Place, the Magnificent Mile shopping, and the Chicago River. The rooms are smaller than you might expect for a historic downtown hotel. Standard rooms run about 250 square feet. If you have a lot of luggage, that matters. I learned this the hard way on a spring trip. I booked a standard room assuming I could unload two large checked bags and still move around. The layout puts the closet directly across from the bathroom door. Once both suitcases were open, nobody could get to the bed. My workaround was simple. I put one bag in the overhead luggage rack, which the hotel provides, and used a hook for the other. The hotel staff had extra hangers and a coat rack available at the front desk if you ask before you go up.
Check-in can take 20 to 45 minutes during peak season. They do not offer mobile check-in unless you are a member of their loyalty program, which most casual visitors are not. If you arrive between 2 PM and 8 PM on a Friday or Saturday, expect to wait. I usually just drop my bag at the bell stand and go find a drink at the bar downstairs. The lounge gets crowded but moves faster than the lobby. Parking is another issue worth mentioning. The hotel has a valet operation, but it costs around $75 per night during the summer and $60 during the rest of the year. That price does not include tips. If you are driving your own car, you can save money by parking at a nearby garage like the Millennium Hotel structure on Ohio Street, which runs about $35 per night. Walk back through the pedestrian passage to the hotel. The Wi-Fi is free for guests but it is not fast. Expect download speeds between 10 and 20 megabits per second. It works fine for email and browsing. Video calls during peak hours from 7 to 9 PM tend to buffer. I switched to using a local coffee shop for important calls on my last visit, which is more reliable.
The breakfast situation is worth noting. The hotel used to include a complimentary breakfast for many rates, but that changed a while back. Now it is available for purchase at the cafe on the ground floor. The eggs and coffee are decent, but you are paying market rate for it. If you do not need hotel food, there are better options two blocks south on Illinois Street. A couple of solid spots there will save you $30 to $50 a day. One thing beginners miss is the noise factor. The hotel faces Michigan Avenue, which is a major road. Even rooms on upper floors get truck and bus noise from early morning. If you are a light sleeper, ask for a room facing the courtyard. Those rooms exist but there are fewer of them, so request it at booking time, not at check-in. The courtyard-facing rooms are quieter but they also tend to book up first. The location works well for most visitors. The Red, Brown, and Purple line stations are within a half mile walk. The Magnificent Mile is essentially at your doorstep. The hotel is not ideal if you are trying to see the lakefront because you have to cross a busy intersection and walk a bit. But for shopping, dining, and business meetings downtown, it is convenient enough.
Get the Full Details

Book directly through the hotel website rather than a third party. The rate is usually the same, but room requests and late checkout are easier to get when you go direct. I have tried it both ways and the difference shows up within the first five minutes at the desk. Third-party bookings often require verification that slows things down.