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Chicago Recs?

jellyfish10

HB Legend
Aug 10, 2009
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My 30th class reunion is this spring and a high school friend is organizing a trip to Chicago. I’m not in touch with the majority of the people going and quite honestly have no desire to go. However my buddy that is organizing it has had some health problems and we are still close so I feel compelled to go. Truth be told I would rather sit in the woods around a fire and eat mushrooms and smoke bud.

I don’t know where we are staying yet but it will be at the end of April. I haven’t been to Chicago in years (not a big city person) but any suggestions outside of the standard? Live music, outdoor activities, etc or should I just make an excuse and go sit in the woods by myself? TIA.
 
Second City for a night of comedy? Ravinia Festival for chill wine and music? With no idea when this is, anything more is hard to get your head around. Maybe the Architectural Boat Tour or a lake cruise?
 
Might be a little early still for a lot of outdoor activities in Chicago. The lakefront will still be pretty chilly from the water temp still being cold. Doesn’t mean you can’t do things on the lakefront. Lots of parks and trails that will be open but the actual organized outdoor activities will probably be limited
 
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30th high school class reunion road trip to Chicago?,.. no thank you.
Oh I totally agree. Some of the dudes are the total jock type which is fine, but I couldn’t be more opposite than that and factor in that I have had little contact with most of them in 30 years…yeah a little weird for sure.
 
Second City for a night of comedy? Ravinia Festival for chill wine and music? With no idea when this is, anything more is hard to get your head around. Maybe the Architectural Boat Tour or a lake cruise?
Second city is always a good time. I haven’t been in 10+ years tho but when we lived in chicago we attended quite often
 
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Second City for a night of comedy? Ravinia Festival for chill wine and music? With no idea when this is, anything more is hard to get your head around. Maybe the Architectural Boat Tour or a lake cruise?
Ravinia is a cool vibe. We make an annual trip to see friends in Highland Park and do a night at Ravinia. Think college football tailgate + an outdoor concert.
 
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Ravinia is a cool vibe. We make an annual trip to see friends in Highland Park and do a night at Ravinia. Think college football tailgate + an outdoor concert.
Honestly Ravinia is great and everything but it really has no business in a Chicago recommendations thread. It's like recommending Milwaukee.
 
Oh I totally agree. Some of the dudes are the total jock type which is fine, but I couldn’t be more opposite than that and factor in that I have had little contact with most of them in 30 years…yeah a little weird for sure.

Find out what the itinerary is, travel for a single event, bolt on your schedule...
 
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Buddy Guys on South Wabash for Blues....
City Winery on Randolph in the West Loop for assorted concerts..
Chicago Pizza and Oven Grinder in Lincoln Park for best and unusual pizza...
Rush and Division Bars...
Wriglyville Bar scene....
Northerly Island concert venue...
The Salt Shed...venue for music
 
Oh I totally agree. Some of the dudes are the total jock type which is fine, but I couldn’t be more opposite than that and factor in that I have had little contact with most of them in 30 years…yeah a little weird for sure.

Sounds like you’ll be at Wrigley pounding beers (which is always awesome)
 
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