Great Lakes - Weekend trip Chicago to Milwaukee- looking for advice

A couple of friends and I are taking a trip up to Milwaukee in a couple weeks.
Since none of us have done any all day rides before, any advice is appreciated.
Specifically,

- is it feasible to get from Chicago to Milwaukee in one day?
- is the Green Bay bike path the fastest/ easiest way to go?
- most importantly, what's the essential thing to do in Milwaukee? We figure we'll get there by 6 or 7 pm at the earliest, so maybe good (cheap) dinner and a bar. Any must-try places?

Thanks for reading, any help is appreciated.

I've only been there a handful of times, but I always try to visit The Office. It's a little bar and everyone is super nice. I haven't biked there yet, but 90 miles is definitely feasible in a day. How much have you ridden? I would try to fit in a couple 30-40 mile days before you do a 90 mile one

- is it feasible to get from Chicago to Milwaukee in one day?
- is the Green Bay bike path the fastest/ easiest way to go?
.

- If you done centuries before - yes , you can get there in one day , may be even faster. North Shore Century ride is from Evanston to Kenosha and back - most people do it in 6 hours. Start early to avoid all the traffic.

Green Bay bike path is not paved all the way - so taking the streets may be a better option from speed prospective. I rode it once from Lake Cook Road to Navy Pier - took me almost 3 hours on cyclocross bike and it was slow even for me . The trail is confusing when it merges with streets and there are no clear signs.

Good luck with the trip!

Yeah, I don't think there is an easy route from Chicago to Milwaukee. If you can get yourself across the state line, it's pretty easy sailing up to Milwaukee, just about whatever route you take. South of the border, I can't really help you.

Where in Milwaukee will you be staying? Lots to do up here.

Thanks for the replies!

None of us have done full centuries, but we're getting some practice in.
Right now it's looking like we'll take the Green Bay path up until it gets too rough (we're all riding road bikes) then...something else.

As far as when we get there, that's still totally unknown at this point. We'll probably grab a room at a cheap hotel somewhere, and check out some bars or food.
I've been looking at this list for ideas,
http://onmilwaukee.com/ent/articles/100things.html
but I don't how touristy any of those options are. (Or available after 8, 9pm)

So, the Office is a good place? Any other recommendations? Preferably decently priced, or a good beer selection. More into microbrews than going clubbing.

Try the cheese. I hear it's great.

Here is a safe route from the Chicago Lakefront bike path to Kenosha: http://www.mapmyride.com/route/us/il/chicago%20to%20kenosha/528127111128830235

I've done this route several times; it’s a direct route that avoids some un-friendly riding near downtown Waukegan. However, I have only gone as far as the Wisconsin state line. I would try to get local guidance to help you find the best route in Wisconsin.

From Kenosha just take 31 to 32 right into the city. No problem. Go right up the lakeshore to downtown or where ever.

If you are there Friday night Lakefront Brewery has a fun fish fry - just north of downtown. Fish, beer, music!

Good food and coffee at the Fuel Cafe, it's a big part of the vintage motorcycle scene there too.

East side - the ultimate cycling bar/restaurant - Cafe Hollander (http://www.cafehollander.com/)!

They sponsor a cycling team and are right on the Downer Avenue course!

http://www.cafehollander.com/photos/8.jpg

Cafe Hollander is good as is Wolskis

http://www.wolskis.com/