Chicago and Boston: A Timely Olive Branch

(c) Laura Bolesta

[Natalie Hock is a social worker in training. She studied in Italy, went to China for the ultimate funemployment, and is planning a trip to Africa this winter.]

If you Google Boston vs. Chicago right now, what you get is a nice little breakdown of the Stanley Cup situation we have happening. But I’m relatively uninterested in that, and this is a travel blog, people!

I’m more interested in why so many people from Boston have never been to Chicago or really anywhere west of Philadelphia for that matter, despite a seemingly genuine interest in visiting the city. Has traveling west for East Coasters become analogous to traveling too far north or south of one’s neighborhood in Chicago? (Yes, people who don’t know that our fair city extends for miles beyond Wrigleyville and Chinatown, I’m talking to you.)

I was in Boston last weekend for a professional conference, which means the only parts of the city I saw were the innards of the conference facilities and the bars and restaurants that surrounded those conference facilities–in this case, a small liberal arts college campus near Fenway Park–frequented by and employing various kinds of Bostonians.

This wasn’t a trip for pleasure, and it wasn’t a trip for historical meanderings (though every American should really be required to do a Boston walking tour before they die), but despite my lack of time necessary to explore Bean Town, I was actually able to do that very compelling and oft-forgotten about thing that hardly ever happens when you’re traveling with friends/family to sight-see–talk to locals.

Every Bostonian who had never visited Chicago wanted to come to Chicago. They had heard it was like a bigger version of Boston, or a more American Toronto, or a more Yankee Austin. (Why these people were able to find their way to Texas but couldn’t make it to the Great Lakes was beyond most of us.) They were intrigued by the fabled more manageable urban-ness of Chicago as compared with NYC: You go to New York to feel alive… but come to Chicago to live and yadda yadda. They were relieved that Chicago was big and diverse and gritty and not plastic-y like LA or granola-y like the Pacific Northwest.

Aren’t Americans supposed to be constantly, insatiably pushing west?

Maybe it’s easier for Chicagoans to cultivate national wanderlust because we’re at the crossroads of America, have two airports about equidistant from the city center and connected to the city in a fairly non-roundabout public transit way, and pay less in rent than those on the coasts so we have more to spend on travel.

So. Bostonians. This is my olive branch and welcome mat. Come to Chicago. Use Airbnb.  You can stay in my apartment. Or don’t you know someone who graduated from any of the Big Ten schools who lives here and hasn’t yet shoved off for the burbs? (And even if they have, you’ll probably be more comfortable at their three-bedroom house, and there’s always the Metra.) It doesn’t really matter how you get here or where you stay. Just come. We’d love to have you.

Just like we’re going to love skating all over your faces.

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The Important Things

[Apologies for half-assed-ness. It’s been a nutty week.]

So here’s the thing, lovely readers. I just accepted a new job. It’s extremely cool, with a great, small group of people, doing work that I find incredibly meaningful. It’ll be hard and crazy, as start-ups tend to be, but I have a really, really good feeling about it.

What does this have to do with travel? Well, two things.

Number one: When I negotiated my compensation with them, because they’re a start-up, they have relatively little wiggle room on actual base salary. But my tip to you is not to forget the other pieces of the package–and for me, the important piece is vacation time. I was able to get them to bump up my paid time off, which is worth more than a little extra money in a paycheck to me.

Number two: Also during negotiations, I was able to get them to push my start date back a week. Which means I’ve got a week of free time at the beginning of June. I guess I could just sit around Chicago and be lazy and enjoy myself, which might be nice… or, obviously, I could go somewhere. With limited time and funds, it would need to be America-based. It would probably be solo, so city-centric vs. wilderness is probably preferable. I’m thinking a small city. I haven’t been to Seattle or DC, and I haven’t been to Boston since I was a kid or Austin outside of SXSW. Thoughts?

What to Call Cities If You Want to Prove You’re Not From Around Here

Chi-town (acceptable only if you’re a rapper trying to find a rhyme)

Frisco (acceptable only if you’re singing “Sittin on the Dock of the Bay”–which you should, it’s a great song)

The Big Apple (acceptable only if you’re a tour guide on a doubledecker bus)

St. Louie (acceptable only if you’re in the chorus of an old-timey musical)

Beantown (acceptable only if you’re trying to round out a listicle to an even five and you’re like, hmm, what other towns have stupid nicknames no one uses, so you google “city nicknames locals don’t use” and one of the links reminds you, oh, Boston exists, and it has a stupid nickname)

(And yes, I have decided to start my weekend early, why do you ask?)