I'm moving to Chicago this summer and plan on buying a bike after I move. I'm interested in something for rides along the shore, vacation biking, or running errands.

Any suggestions? Also, I want something with a vintage look and feel.

Thanks!

Jay

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sounds like your looking for an upright position bike. Look for a beach cruiser or comfort bike at any used bike shop, you will most likely find many vintage/ vintage looking bikes that way.

Dutch Bike Co. is a great place to start.

im becoming a fan of Linus bikes - http://www.linusbike.com/models/

 

nice straighforward models, good pricing.

 

also a fan of the giant via - http://www.giant-bicycles.com/en-us/bikes/model/via.1.2011/7243/43943/

 

my appreciation of bike types has greatly changed over the years as a city rider with commuting and hauling shit taking more and more focus.  the amount of time and money to build up my pista nearly 5 years ago seems like an utter waste at this point.

 

maybe its time to start selling off those parts.

Boulevard Bikes in Logan Square, right off the Logan Square blue line sometimes carry used bikes that fit your description, and if not there is always new there as well. In that case, is there a price point you have in mind already?
Thank you for the tips and help! I'll want a tour once I finally move. I'll also need someone to come with me to make sure I'm making the right bike choice.
If you are looking for a used bike. Working Bikes 2434 S. Western ave (Workingbikes.org) has a good selection of used beach cruisers and older 3 speed/single speed cruisers.

Chicago is a nice flat place so a 3-speed bike can work quite well.  There are many people riding around on single-speeds so 3 speeds is almost extravagant. 

 

There are many companies today building 3-speed bikes and the 3-speed comfort bike is making a comeback.  That said, the modern low-end bikes just can't compete with the high-quality vintage bikes made in the 50's-70's because people are just not willing to pay for that kind of craftsmanship.  

 

From what I read of your tastes in your OP your best bet might just be a used 3-speed vintage bike -the English 3-speeds are awesome city bikes and hold up well over the decades, because they were built to do just that.  Boulevard Bikes usually has an assortment of Vintage 3-speeds they have tuned up and made ready to ride.  There are also a couple of people on craigslist who are fixing these bikes up for sale.  I do this myself but focus on the Step-through frames and not the Diamond-framed "men's" bikes.  There are also a few nicer Schwinn 3-speeds that were not too bad although they tend to be a little bit heavier than their English counterparts and not quite as well built IMHO. 

a folding bike would be another great option with less hassles boarding on buses, trains, or planes. not to mention the peace of mind knowing that your vehicle is secure (stashed under your desk) as most buildings will allow you to take them in with you.

Not a tip on bikes, but be sure to get good locks.  Cables and cheap chain won't cut it here.  Be sure to lock your frame and both wheels somehow.  If the bike has a quick release saddle, get rid of the quick release or lock it as well.  If it isn't locked down, someone will steal it.

Another non bike tip:  its a lot colder here then in Indianapolis.  Invest in a wool coat with a hood and stock up on wool socks.

 

You will be amazed how much colder and longer the winter is just a few hundred miles away.

Duly noted. I've tromped around in Chicago enough to know you speak the truth.

So, to recap, I need a vintage Batcycle with a wool suit for winters. ;)

 

In all seriousness, you're going to make this transition way too easy.

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