Next to Sydney, Chicago is one of my most favourite cities to live. I lived there for a short stint in 2003 and it taught me so much. when I was there I had zero money, but still managed to have a wonderful time.
I lived in the gold coast area about half a block from the lake in the summer and with so much at my doorstep I must say I hardly left that area. so unfortunately my version of chicago is fairly limited to downtown but on the upside because I was so poor, most of my tips are free or cheap :) like the Ashkenaz Deli for the best tuna salad I have ever tasted! the pizza place on north and division which makes the biggest pizzas I have ever seen (mmm thin crust pepperoni pizza) and the Oak Street Beach for great people watching, and the Zebra Lounge - a piano bar where everyone sang at the top of their voices to frank sinatra, tom jones and neil diamond songs (so much fun!)
mostly I liked to ride my bike around the neighbourhoods and look at the gorgeous architecture, walk along the lake and ponder how it was actually a lake and not an ocean... and walk through the streets on sunny days when everyone was out on a patio really soaking up the sun. coming from Sydney you don't really appreciate the sunshine until you live through a chicago (or toronto in my case) winter... they really use every bit of sunshine they get!
the john hancock building is worth a visit for the amazing view, and the sears tower so you can be dorky and relive that scene from ferris bueller's day off. i loved seeing this painting at the art institute (which you have to see close up to see why), definitely take a boat tour on the river, and take a walk to the end of grant park for a great view of the city. millennium park was being built while I lived there, but when I went back to visit a couple of years back, I could have spent days taking photos of the cloud gate sculpture (or the bean - as seen in this photo) and this one here too - in fact I went back there at night time to take some shots and nearly got arrested by a big burly black woman who wasn't going to fall for any 'australian accent' saying, I travelled all round the world to see this thing...
lots of the museums have free days in chicago so make sure you check their websites to see when they're free.
and since my knowledge is limited to only a small part of this amazing city I am so glad that melina played along and shared some great info for the rest of chicago:
Seeing all things Frank Lloyd Wright is a tourist must, but it's actually very cool for locals, too. The Architectural Tour in a boat down the Chicago river is super touristy, but actually, I love it SO much, I think it's the best *tourist trap* in Chicago; we ARE known for our architecture of course! Museums of note are the Art Institute and the Field Museum and the Contemporary Art Museum. Do NOT go to Navy Pier, it is a bore and filled with fast food restaurants and one can admire it from afar, better. Magnificent Mile, aka Michigan Ave., is alright - lots of shopping (but no specialty shops, just stuff you can find everywhere: Gap, JCrew, Burberry, etc) and crowds, but you don't want to be there late at night, there aren't many good bars or restaurants downtown. For said bars and restaurants, I'd go toTimeOutChicago.com - everyone's tastes are different, but the city has almost TOO much to choose from, which is why that website is a godsend. Deep dish pizza is famous here, but personally I dislike it, so I can't recommend anything. However, if meat is going to be consumed, you'll be in paradise - it is honest to god the best thing about this city, in my opinion. Notable neighborhoods to hang out in/shop in/eat it/drink in include Wicker Park (super gentrified nowadays, but still reigning champ), Logan Square (a bit less developed as it's up and coming, but brilliant restaurants and bars), Lincoln Park (older and more bougie, but very historical/pretty and has a good selection of restaurants), Pilsen (mexican neighborhood, but also up and coming in an artsy sort of way, go for both the amazing mexican dishes and the little shops and bars and galleries). Stay away from Wrigleyville unless you are a diehard sports fan. Lakeview, Roscoe Village, Edgewater, Bucktown, Andersonville, Ukranian Village and West Town are also pretty good to visit for an overall great assortment of restaurants, bars, shops, etc. Bars are open til both 2am and 4am; on Saturday, that turns into 3am and 5am. However, be aware that 4/5am bars are madhouses come 2am and charge very expensive drinks and are very crowded. The local *paper* with current events and restaurants reviews and concert listings, etc, is called the Chicago Reader, they're free and a new one appears all over the place on Thursdays. And lastly, if I can recommend my favorite bar, it would be the Whistler in Logan Square on Milwaukee avenue - it's a *speakeasy* sort of bar that plays great music (usually rock or soul) and has the most delicious drinks; and for a true meat lover's feast (of which I am, but there's also veggie options), I recommend Kuma's Corner on Belmont for hamburgers. It's a metal bar - they play metal music and have named all their hamburgers after metal bands such as Black Sabbath and High on Fire and they've been featured on TV shows for years; but I'm not kidding, they're the best hamburgers I've ever had. Be prepared to wait a LONG time - last time I went it was over a 2 hour wait, though you can always eat at the bar counter - but trust me, trust me, it's SO worth it. Oddly enough, they make the best mussels I've ever had, too!
thank you melina!
our next stop on this virtual vacation is Orlando, and since I am limited to a trade show in the middle of summer and running round disney land with my work colleagues to try and get a whole day into 3 hours... I need some help on fun stuff to do in Orlando! I thought maybe she should go to miami, is that reasonable? anyone?