The first thing that popped into my mind when I read “cute” hotel is just south of River North: Hotel Allegro. It was very trendy when it opened, but it’s been a while since I lived there, so.
I’ve stayed in the Hotel Monaco, which, like the Allegro, is just south of River North (I think I got that right…), and it’s definitely cute. You can even get a goldfish in your room if you want. There’s not much cuter than THAT!
Nice location, good service, very nice rooms. I really liked it.
Second this recommendation. The goldfish is a nice touch. They have a wine get together late in the afternoon.
I will note that I stayed there about 8 years ago, and only paid about $125 a night. I recommended it to a coworker some months later, and the cheapest room was around $250. I think that the late May time frame worked to my advantage.
We were there about 2.5 years ago, and paid $152/night (I just looked it up). That was in November, Thanksgiving. week So I’m guessing if you go at the right time you can find a decent deal.
Ah! The Monaco’s the one I was thinking of, actually. I couldn’t remember the name, but I knew it was a Kimpton hotel. I’d checked it out when I was living there, and I’ve stayed in Kimpton hotels in other cities and they’re always lovely. So I Googled it, and the first hit was the Allegro (which is also a Kimpton). It was not where I remembered it, but close, so I figured I was just being dumb, as is my way. It seems the Allegro is supposed to be a little more “modern luxury”, while the Monaco is more “quirky-funky cute”.
But lo and behold, there are actually fourKimptons in Chicago, and one, the Palomar, is smack dab in the middle of River North. I think they all do the wine reception in the evenings, but it looks like only the Monaco has the goldfish (see Guppy Love).
zoid, isn’t the Drake where guests on “Oprah” always stayed? That might be kind of cool, if jools’ boss was into that whole thing.
Hotel Allegro seems to “cool” enough for her and not too far from the Convention Center there’s also the Marriott Downtown Magnificent Mile, which is way to expensive for me but that’s an indication that it’s good enough for her.
I’ll go check out the Monaco and the Drake and give her different choices.
You / she might also consider the James Hotel; it’s just off of the Mag Mile (a block north of that Marriott), and is more of a “boutique” hotel, like the Allegro or Monaco: