Perhaps not frozen custard but there are some fantastic ice cream choices here in chicago...
Bobtail - http://www.bobtailicecream.com/menu.html - for instance their Signature Sunset flavor - Merlot wine ice cream with chocolate chips...
Oberweis - http://www.oberweis.com/ - they have the BEST strawberry ice cream I have ever had in my entire life. Normally I can only have a scoop or two of ice cream... but when its this particular strawberry I have found myself eating a pint in minutes.
What makes Chicago special? A huge variety of all cuisines, everything from fine dining to cheap eats to ethnic food of every variety. Top quality is available at all levels, from many of the top chefs in the country to storefront mom-and-pop restaurants. Not that every place is wonderful, but there are wonderful places for every type of food. And restaurants (fine dining restaurants in particular) are not usually astronomically priced, the way they often are in New York or Los Angeles (based on my experience). If you have specific needs, like a particular location or a type of food, then those questions are easier to answer - although they probably already have been discussed in other topics here on Chowhound, so don't forget to try the search feature!
Other topics that may be of interest:
The absolute top restaurants and chefs in town are listed in this topic:
For Greek food:
Again, Chicago has lots more types of food than just these, so if you can narrow down your inquiry by food type, location, etc, we can provide appropriate suggestions.
P.S. Frozen custard is not really a big thing in Chicago. Perhaps you're thinking of Milwaukee, 90 miles to the north. Culver's, a frozen custard chain based in Wisconsin, has locations in Chicago's suburbs.
Thanks for the tips. Yes, I was going to do a search function but came up with soooo many options, meaning I needed a better filter, so I wanted a local's opinion.
My friend was telling me about Lou Malnati. Don't know if I'll be able to bring back him one. They look pretty heavy and traveling on the El Train with luggage and in the rain will be a challenge.
Sorry this is an ignorant Socalian mentality, I assumed that frozen custard might also be big in Chicago but I may be the only weirdo eating that stuff when it's raining, which I heard it'll be like this week. Don't think I'll make it the suburbs. This is a work meeting so I have limited time to explore much and I know the rain isn't going to help.
Basically if I had folks from out of town visiting me in OC. I would say have some good Vietnamese food such as Brodards or if they were in LA I could take them to good Thai or Korean. I want something I can't get in LA or isn't as good but in Chicago. I'm going to justify the unhealthy eating by using my legs for walking instead of the gas pedal and I'm a single gal so I won't get to order as much and share and have variety of options to choose from. *sniff sniff*
Budget friendly, I can go up to midrange. Always quality over quantity but it better be a size where I don't need a microscope.
jen, maybe you could say more specifically where you will be staying and how much time you'll have to explore, weather permitting.
My recommendations below aren't so much focused on food you can't get in Southern California -- rather, they're for good food in neighborhoods that will give you a sense of Chicago.
For example, if you'll need to get lunch in the Loop area you could head to Hannah's Bretzel (for a Euro-sandwich plus chocolate bar) or the new Bombon Cafe (for upscale Mexican tortas and pastries) and at the same time enjoy the densely packed architecture of the Loop, quite a contrast to Orange County. I think you'd also enjoy walking along the Chicago River, and checking out Millenium Park.
For a dinner on your own downtown I'd suggest Avec (small plates) or eating at the bar at Frontera Grill (high-end Mexican).
If you have time to get away from downtown, how about exploring one of Chicago's neighborhoods? Andersonville (take the Red Line el north to the Berwyn stop, walk 6 blocks west, or take the 22 Clark bus north) is a nice mix: originally Swedish (there are still Swedish delis and a bakery), more recently Middle Eastern and Persian, a great bar, Hopleaf, with extensive Belgian beer selections and Belgian style food, a wonderful new Sicilian pastry shop, Pasticceria Natalina, lots of little shops and a good neighborhood feel.
180 W Washington
170 W. Washington
615 W Randolph St
449 N Clark St
5148 N Clark St
5406 N. Clark St
There are lots of different kinds of cheap eats around town. Pizza first. ;) Amata's suggestions are good ones too. Also Greek food in Greek town is inexpensive (see link above). You can eat well by going to many places for lunch rather than dinner, places that might otherwise be more expensive than you'd like to spend.
Most of the Chicago pizza chains allow you to order pizza to be shipped using their website. (Malnati's has a link on theirs to Tastes of Chicago, which ships on behalf of several local restaurant groups.) This would be preferable to taking pizza on an airplane, since it will travel better that way (I think they send it frozen, packed in dry ice). Note that it won't be quite the same as at the restaurant (partly because the restaurants have ovens much hotter than those used at home).
Jen, here's a great place for frozen custard in Wrigleyville. I highly recommend it. It's relatively easy to get to by El train, though the Brown Line is pretty much FUBAR at the moment. Look upon it as an urban adventure. Local color, maybe? :o)
Thanks for the tips. Had Giordano's, which I wasn't really crazy about. Thought the crust was bland and the sauce could have been better. Gino's was just slightly a bit better. Guess I'm not a fan of deep dish pizza, will have to try Lou Malnati another time. But sadly I enjoyed WHITE CASTLE. I know so bad.