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!
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