I basically plan my vacations around where I'll eat. We're coming to your fair city on the first Wednesday in December and leaving Saturday. Let me state outright, I'm from Austin, Texas and expect your weather to knock me on my ass. This being said, the warmest thing we have is long johns and dark jeans (dress clothes wouldn't work there well). So, keeping in mind we'll be wearing jeans, boots and nice sweaters, please advise on below schedule, staying at Omni downtown by the pier and will be cabbing it:
Wednesday: Arrive and have lunch at both Al's Beef and Portillo's and comparing the two. Stroll the Mag Mile (goal is to find a nice, fitted leather jacket - suggestions?) and have dinner at Shaw's Crab House (in the bar around 6:30).
Thursday: Shedd Aquarium. Lunch at Lou Malnati's (I've been told I should go to the Gold Coast location, which is close to the hotel, but there's one on 8th and State we could take a lunch break - is this a good idea?). Museum of Natural History. Dinner at Sable 6:30 pm (we don't want to stand out as "hicks" wearing jeans).
Friday: No lunch pick yet. Art Institute. Dinner at Ba Ba Reeba, again 6:30.
Please let us know if we'd be more comfortable packing an extra bag with nicer clothes or if we'd be okay with the above, and IF we're packing nicer clothes, should we sub out some of the above places. Many thanks, y'all!