Solo Weekend Trips from Chicago
 

My boyfriend is interested in taking a weekend trip by himself sometime in the next few months. We live in Chicago, and he wants to fly somewhere 1-2 hours away. He likes culture (vague, I know), history, architecture, the arts, museums, nature and music- with the power of our two heads combined, we've come up with Philadelphia, New York, and Toronto as possibilities. He wants to go somewhere where a 20-something guy alone will be able to keep himself entertained (no, not by going to strip bars!) and feel comfortable. Does anyone have any other ideas or suggestions? We really appreciate your input!

Washington DC (the smithsonian is heaven for a museum lover)

Smokey Mountains National Park ( for the nature lover), fly to Louisville and drive down. Couls possibly include Elvis Town for the music lover part??

Mammoth Caves is another good option.

River rafting in W.Virginia.

Boston, plenty of history there.

Have fun deciding!

Thanks for the good replies so far! We're planning a trip to Boston together in the spring, so Boston is out for the solo trip. Indianapolis is an interesting idea- we'll start doing some more research. The reason he needs to fly is because he doesn't have a car and can't rent one right now, so flying makes more sense. He's leaning towards Philadelphia right now...any other advice or ideas?

Save New York for the two of you.

He'd be fine in Toronto my wife is in a meeting at the moment with a man who flew his girlfriend in to Toronto just for dinner with him last night. He's in meetings all day, and she's apparently having a good time on her own during the day.

Toronto's got several good museums, the Hockey Hall of Fame, SkyDome tours, some very interesting restaurants where individual diners are more than welcome, reasonable hotel rates, direct flights from Chicago...

BAK

Hello chicgal. You helped me out with some info the other day - I have a new question for you. Still contemplating a trip to Chicago but this time only to fly through on the way to visit friends in Indy. (Using Alaska voucher so have to fly into ORD again). My question-how long is the drive to Indy? Or since we will already be inside ORD, is a $117 RT from ORD-IND a better plan? (I think it is, but didn't know if there is anything worth seeing on the drive from Chicago to Indianapolis - this would be in February so not likely, right? Not to mention we could have bad weather issues. Sounds as if I've answered my question already but would love your input)
Thanks.

Not who you asked, but I'll toss in my two cents....the drive between Chicago and Indy is about 3-3 1/2 hours. And it is flatter than flat. And in February?? Yech! Just my 2 cents....

Thanks arjay. I think a cheap airfare from ORD-IND makes it much more appealing, so if we go, think we'll do that. Thanks for your input!