Chicago!
 

My friend and I just booked a trip to Chicago for a month from now. We know it's still going to be pretty cold but were encouraged by a concert going on at the House of Blues that we want to catch. What are some things that can't be missed (weather-friendly or NOT, we can handle some off-lake winds in moderation)? Places to see, eat, we're still looking for a budget-friendly place to stay, etc.!

Hope you have a great time! I'll have the chance to visit in early 2011 at the ACDA National Convention!

I lived in Chicago for five years, and still go back 2-3 times a year for fun. For the famous touristy stuff, I concur with FMLex, who summarized it quite well (the only thing I fervently disagree on is Navy Pier. Don't waste a minute at this tourist trap) What are some interests (food, shopping, sights, etc.) that you and your friend share? Chicago has so much to explore & enjoy off the well-worn tourist paths.

I will say that a great pre/post-show spot to grab a bite and a drink right by House of Blues is the Billy Goat Tavern- http://www.billygoattavern.com/ - the rare place that's loved by locals, tourists, and convention-goers alike. Plus, if you're a fan of baseball (& familiar with the Cubs) or Saturday Night Live (the Cheeseborger Cheeseborger sketch), this place would be no stranger to you.

As for hotels... Priceline is your friend. I routinely stay at one of the Hiltons or the Hyatt downtown for about $50-$55+ tax- and as long as its not a big convention weekend (next month should be fine), you should be able to get the same rate for a 4-star hotel. Check out www.biddingfortravel.com

Thanks!

We're both into music, theater and sports. That Tavern sounds pretty sweet and I think we'd both appreciate it! I haven't even started to look into things to do yet, but am hoping to get to the art museum at the very least to see the original Seurat (I love Sunday in the Park with George!). We're also both from NYC and work in the center of the city, so while we'd probably like to see some of the tourist spots just to say we have, we're not hung up on just seeing those. I get a pretty big dose of tourist working in Times Square!

Chicago is fantastic whatever the time of year you visit. I'm a huge jazz fan so let me know if you are interested in that type of music. There are two strict 'members only' jazz clubs that have good artists every week. Cassandra Wilson, Josh Redman and Donald Fagan (Steely Dan) have all appeared in recent weeks. I live near Oz Park and it is a good area for getting out early evening during the week. Lots of bars and cafes and generally busy with Uni students and staff. Weekends here tends to be focussed around the Italian Delis for brunch. I'm pretty biased on the restaurant front as many of my Italian in-laws own restaurants here. My sister in law manages the cities best vegetarian restaurant (imo) on West Chicago Avenue - drop me a pm if you want to go and other in-laws run restaurants close to the lake. I have lived here 3 years or so and did enjoy the tourist stuff when I first visited. The harbour is great, the boats trips on the lake are good. Just enjoy yourself!

I agree with Luke about Navy Pier, unless you want to catch a show at the Chicago Shakespeare Theater (they do more than Shakespeare plays), otherwise it's a waste of time. The art institute is my favorite. It's free on Thursday nights. If you're not over the let's go into a tall building, you may want to get drinks at the Signature room in the John Hancock building. Beautiful views of the city. I would also try to catch a Second City or Improv Olympic show.

Our PBS station hosts a show called Check, Please, where locals rate all types of restaurants in the Chicago area:
http://www.wttw.com/checkplease

Have fun!

How was your trip? :)

We had a good time! We pretty much lucked out weather wise, it was 65 on Thursday and Friday. Thanks to that, we were able to explore pretty freely on foot and they even opened up the Wendella Boat tours on Friday, so we took the architecture tour which I really enjoyed! We were pretty touristy for the most part. Our hotel was right on Michigan Ave., so we saw a lot of that, walked over to the lake, had drinks in the Hancock building, went to the Art Institute, went to see Wrigley Field, ate deep dish, etc. It snowed on Saturday, which wasn't ideal but we dealt with it since we luckily had saved the more indoor activities for that day. Also got to see a show at the House of Blues, which, I know there's House of Blues in lots of places but was still pretty cool.