The Conrad in Chicago is the first hotel in this line that I’ve had the pleasure of staying at, and it was a fantastic experience. The hotel is perfectly situated in the heart of downtown Chicago right off the Magnificent Mile and within walking distance of all the shopping, nightlife, and scenery that defines it.
I booked this hotel back in September 2016 during an amazing Two-For-One sale that Visa was running to promote their Signature Luxury Hotel Collection. The intent was to give a free night for those who stayed AT LEAST two nights, but nothing in the terms of the promotion stated that it had to be MORE than two nights which meant that a two-night stay would qualify for one free. More details about this promo (which was pulled early due to ‘unexpected popularity’) can be found here. Suffice to say, however, that we were very pleased to get two nights at the Conrad Chicago for $297 total. What sweetened the deal even more was the fact that at all Luxury Collection hotels, you receive benefits such as free breakfast, guaranteed room upgrade, late checkout, and a $25 food/beverage credit to be used at their restaurants. Pretty great deal, especially when it’s 50% off!
Needless to say, we were pretty stoked about this stay. It also helped that I am a Hilton Diamond member and, as such, was upgraded to a nice corner suite at check in (which books for $550 per night).
To get to the hotel, I took the L from the airport to State/Lake and walked the rest of the way. It was freakishly warm that day (and the whole time we were there), so the walk was very nice. Upon arrival, we were whisked into the elevator to go to the 21st floor for check-in. Strange, I thought, but I went with it.

The check-in process was a breeze, although we had arrived in the morning and our room wasn’t quite ready. We dropped our bags, walked around the lobby a bit, and went out for lunch


We returned a couple of hours later after getting a text message from the concierge to tell us that the room was ready. When we arrived in the room, our bags were there waiting for us.
As far as the room goes, we were very pleasantly surprised by the size, spaciousness, and view. It was really quite something!








During our stay, we were allowed to take our breakfast at either of the two restaurants on the property (as they did not have a lounge)–which are Baptiste & Bottle and Il Tolivino. After realizing that the latter choice is more of a grab-n-go cafe, we opted for Baptiste and Bottle each morning. The food, service, and view was phenomenal!

Let’s be clear–this is not a place I would choose to have breakfast at in Chicago if it weren’t free. $22 for steak and eggs? Get outta here. Oh, it’s free? I’ll take two! Not really, but I did have it twice–and it was divine.



Our bill for breakfast each morning was about $75 for two of us, which killed me a little bit each time they dropped off the check. But then I was completely revitalized when I had it charged to the room, knowing it would be completely written off at check-out. Win!
After exploring the city for a couple of days and spending some time in the gym (which was fantastic–see my gym review here), it was time to move on. We weren’t going far, just a few blocks down the road, in fact, to spend two nights at the Ritz Carlton Chicago (for free using free night certificates from the Ritz Carlton credit card).
Other than having all our breakfast charges comped and the awesome room for two days, the Conrad had one more Diamond benefit I was looking forward to using: a free ride in the ‘house car’:

It was a real treat to toss our bags in the trunk of this beast and zoom off down the Mag Mile (so much so that I almost wasn’t ashamed to have them drop us off at a competitor’s property).
Summary
This hotel was a great way to being our round-the-world trip. The service, food, location, gym, and room exceeded our expectations and I would definitely consider staying at this property again–even if it wasn’t 50% off!
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Brandon Chase is a writer, endurance athlete, and guide based in Maine. He is a former Foreign Service Officer with the U.S. Department of State and spent nearly a decade overseas serving at embassies in Egypt, Cyprus, and Pakistan.
Along with a 98-day thru-hike of the Appalachian Trail, he has summited Mt. Kilimanjaro, hiked the West Highland Way, fastpacked in the Himalayas, and trekked around New Zealand and South Africa. He also regularly competes in ultramarathons at the 50k, 50-mile, and 100-mile distances. He is a Lead Guide for Andrew Skurka Adventures and the New England Outdoor Center.