Where Should We Stay in Chicago?

I’m going to be in Chicago for a speaking gig in June. We’re adding a couple of days on either side to have a little working holiday.

I’ve never been to the Windy City before. For those who have (and especially those who live there), where would you recommend we stay? I’m not looking for specific hotel recommendations (though I’ll take those). I’m more interested to know what part of town we should stay in.

For an American city like this, we’re your typical cultural tourists–museums, galleries, walking around cool neighbourhoods and the like. Any suggestions?

I promise not to say “da Bears” or “da Bulls” when I’m there.


  1. I was at a convention there in … 2004 or so? Sadly, only had one day to be a tourist, so I didn’t get to do too much. But it’s a fun city. 🙂

    Tourist things to do: You MUST go up at least one of the Very Tall Buildings. I took these pictures from the John Hancock building:


    It’s absolutely fantastic up there. 🙂

    Other things that are worth a look: They’ve got neat architectural boat tours. If you’re into architecture, Chicago’s the place to be. Even if you’re not, fake it, it’s cool. 🙂

  2. My girlfriend used to live in Chicago, and we end up visiting at least once a year. Every time, we stay at the Days Inn at Clark and Diversey, which I think is considered Lincoln Park. I think the area has a rep for white urban go-getters without a speck of authenticity, but it’s close to bars, Wrigley, the museums, Downtown, and everything else in which we’re interested. The one issue right now, though, is that I think the train stop on Diversey is closed until next year.

  3. The Magnificent Mile and the whole downtown area is pretty impressive along the lakeshore. Chicago has a very different feel from other big U.S. cities like New York and L.A., at least from the one day I spent there in 1991. Be aware that the airport is a LONG way from town, so don’t stay out there like I did.

  4. Go with the mag mile or at least in the loop. There are a bunch of hotels out near Ohio Street (marriott) which is the touristy area (with good restuarants, etc). One thing you might want to consider is proximity to the el. It’s more important to be able to get around.

    Contact me directly if you want ideas of things to see (heathham@microsoft.com). I’m from there (though living in Seattle now). happy to share some ideas with you.

    Lincoln Park is where the bars are. I don’t recommend staying ther ebut you may want to spend some time there.

  5. As a current Chicago resident, I’d have to second the Wicker Park recommendation. The broader neighborhood area, which includes Bucktown and Ukrainian Village, has an eclectic mix of old style bars, hidden art galleries, a neat architectural jumble, questionably sustainable boutiques, a few clubs (Double Door included) and at least one old-timey bakery (Alliance–it’s no longer old-timey but still looks the part). Getting out into the neighborhoods gives one a more authentic Chicago experience, although the monolithic Loop architecture is still cool and worth a look. If interested in staying in Wicker Park/Ukrainian Village, I would recommend the Ruby Room, a Spa that has some nice guest rooms attached: http://www.rubyroom.com/suites.htm

    Happy to elaborate on these recs…



  6. Funny enough, I just spent a day there and went on a nighttime walk downtown with a friend who lives there now. Chicago was totally different than I expected! Amazing architecture, and Millennium Park downtown is a pretty neat area with the Cloud Gate, public art, and outdoor ice skating (obviously not in June). I can’t recommend much specifically, but I think you’ll really enjoy that city, even if you just go for a walk downtown!

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