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Thread: Business Trip/Possible Move to Chicago

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    Business Trip/Possible Move to Chicago

    Hello gentlemen,

    I currently work in Dallas where I have lived pretty much all of my life. My company has a position available in Chicago and are currently working on an offer for me. I would be very excited about the change in location as long as I can really afford to live comfortably there. I'm in my mid twenties, love big cities, and being able to walk places. My manager is taking me up there in February on a business trip and I had a few things to ask the group...

    What should I do/see while I am there on my business trip?
    My manager says I will be able to leave work early while we're there and do some exploring, apartment hunting, whatever. The thing is, I don't have the offer or a start date yet, so I don't know if i will be able to actually look for a place and sign a lease at that time or if I will just be looking around.

    What are some fun, non-touristy things to do in Chicago? I want to get a feel of everyday life.
    Since this is dappered, are there any menswear stores I should check out while there? Dallas has plenty of shopping, but mostly big chains. For example, is there a Suit Supply in Chicago?

    Our office is just west of the loop and I would be depending on public trans for work. Some neighborhoods I've read about that I think would work for a reasonable commute time are Lincoln Park, Lakeview, Bucktown, Streeterville. If anybody has advice or knowledge about these areas feel free to share.

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    If your office is 'west' of the loop you may want to look at Wicker Park and the surrounding areas in that direction. There are a whole bunch of shops in the near north that would be up the Dappered reader'a alley including Independence who stock Oak Street Bootmakers products...and a Suit Supply. Bundle up though, it'll be February in Chicago. Are you ready to deal with the cold?

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    Thanks for the suggestions. I will be sure to check out those areas. As far as the cold - no, I will never be ready for it, lol. But I will adapt.

    Dressing for a real winter will be new to me. Any suggestions on the essentials? Will definitely be getting some wool socks and long johns. I hate the look of puffer jackets, but when there are negative temperatures, I'm sure I would wear anything that keeps me warm.

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    Varsity Member Siepi's Avatar
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    When it's in the negatives, it's definitely function over form (unless you can get both, but sometimes you have to make sacrifices). Get a wool or cashmere hat, some good thick gloves, scarves, and hardy boots. If it's cold enough, a ski mask is extremely helpful and will not look out of place. If you layer appropriately, you probably won't need a Canada Goose or a similar parka, but they definitely don't hurt. And above all, remember the winter adage: "Cotton kills."

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    Yeah, unfortunately what you're able to do while you are here will depend a lot more on the February than the Chicago, if you know what I mean. This winter has not been easy. Hopefully things are more manageable when you're here to check it out.

    As far as tips for bundling, it really depends on your commute. You'll need some warm socks and some wool or cashmere scarves. Get some fashionable gloves for 15-40 and some heavy duty gloves/mittens for when it gets really cold. Ditto on hats. I walk < 12 minutes to and from the train and I usually don't get too cold during that time(don't need to wear long johns even when it's in the negatives).

    As far as things to do and where to shop, the north Michigan up to Oak Street area (close to where Suit Supply will be) will have just about every kind of national or international brand you want. There will be some smaller more boutique-y type places in Wicker Park/Bucktown or in Lincoln Park.

    As far as things to do (assuming you're staying close to work), the Art Institute is world class and is a definite must as it is weather-independent. Sure, there can be tourists, but they are there for a reason. It's fantastic.

    An often underappreciated gem is the Chicago Cultural Center which is the site of a former library. They have a Tiffany dome, and multiple rotating exhibits (art and otherwise) and is just a cool building to walk around and explore. It's directly across from Millennium Park and not far from The Art Institute.

    There is lots of good eating both downtown and in the neighborhoods. But to be honest, it will be easier to explore and get a sense of those neighborhoods if it's warm enough to walk around outside without too much trouble.

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    Varsity Member Jano4's Avatar
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    If you are a bar/pub person then there are plenty of great places to get drinks. I've lived in the Chicagoland area my entire life and I am still constantly finding new places. In the summer I sometime just randomly roam from bar to bar with a buddy just to explore. I like the Wicker park, Gold coast, Old town, and Loop area's. Each one has a bit of there own feel to it. Food is pretty amazing out here.

    Living in Chicago is EXPENSIVE. Highest gas prices in the nation. Housing may currently be the most expensive as well. Taxes on everything from housing, utilities, retail goods is in the upper range. I have been really contemplating leaving because everything is quite expensive. But I absolutely love this area when the weather is good and you don't think about the money your spending to be here... oh yeah we have crummy weather for about 9 months.

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    Quote Originally Posted by Jano4 View Post
    If you are a bar/pub person then there are plenty of great places to get drinks. I've lived in the Chicagoland area my entire life and I am still constantly finding new places. In the summer I sometime just randomly roam from bar to bar with a buddy just to explore. I like the Wicker park, Gold coast, Old town, and Loop area's. Each one has a bit of there own feel to it. Food is pretty amazing out here.

    Living in Chicago is EXPENSIVE. Highest gas prices in the nation. Housing may currently be the most expensive as well. Taxes on everything from housing, utilities, retail goods is in the upper range. I have been really contemplating leaving because everything is quite expensive. But I absolutely love this area when the weather is good and you don't think about the money your spending to be here... oh yeah we have crummy weather for about 9 months.
    I found it to be cheaper than Boston, forget SF or NY. Cabs were cheaper, beer / drinks were usually cheaper on average, etc. My friend pays 1350 in one of the highrises that's a few blocks away from the Pier / Michigan Ave. I couldn't even find a tiny studio for less than 1400 this past year in a decent area in Boston.

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    Yes, while not inexpensive, I believe Chicago is less costly than the trio pratyk mentioned. I'd probably throw DC in with Boston, SF, and NY among the priciest in the nation. Gas prices are certainly the highest among major metropolitan areas in recent years, so you can take that into account if you will have a long commute. And I don't discount the fact that the repeated expenses of living in the city can make it feel pricey. I'm just not sure it would be much different in similar-sized cities worldwide.

    I've never spent any time in Dallas, but it may well be a bump up from there. Folks who have lived in both places can probably tell you better than I can.

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    Minneapolis is a whole lot nicer.

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    Anecdotally, Chicago is relatively expensive compared to Dallas; esp. the real estate, tax and gas situation. (FWIW, I've just spent a few days in each city)

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