Here's what I would recommend to any lover of interesting and creative (and DELICIOUS) foods, for three days in Chicago, because these are things that are unique to Chicago and/or that Chicago does particularly well. It's my personal list of "don't miss" recommendations.
1.
Alinea has been widely acclaimed as the best restaurant in the United States and one of the best in the world. I believe they start taking reservations 2-3 months ahead of time. Make yours as soon as they start accepting them for the date you want. I know you said you don't want to spend a lot of money, but if you think you would ever enjoy splurging for a once-in-a-lifetime experience, this is the place to do it. (They currently charge $195 per person for their 17-20 course tasting menu, not including wine/alcohol/tax/tip.)
2. Our creative provincial Mexican restaurants are the best in the country, thanks in great part to Rick Bayless and the local talent he has developed over the years.
Topolobampo is still one of the very best. I believe they start accepting reservations (on Opentable.com) exactly three months to the day ahead, and they fill up quickly. So again, make yours as soon as they start accepting them for the date you want. They are also open for lunch during the week, which doesn't book up as early as dinner and is more reasonable in price.
Topolobampo is not the only such restaurant, although it is probably the best known, the most expensive, and the one that books up first. Other great Mexican restaurants here include
Salpicon in Old Town,
Mundial Cocina Mestiza in Pilsen,
Mexique in West Town, and Mixteco Grill in Lakeview.
3. For an upscale dinner or Sunday brunch, I second Darren's recommendation of
North Pond. The setting in the middle of the park is exquisite, and the contemporary American cuisine from James Beard Award finalist Chef Bruce Sherman is a treat as well. They're also open for lunch on weekdays during the summer.
4. For a not-so-upscale lunch or dinner, have some of our local specialty of deep-dish pizza. It's delicious and you can only get it here in Chicago. The best places IMHO include the original locations of
Uno and Due in River North, as well as the various locations of
Lou Malnati's and
Pizano's (the latter two of which were founded by sons of one of the main characters in the early decades of Uno and Due). Phone ahead with your pizza order to avoid waiting 30-45 minutes while seated for your pizza to bake.
5. Not for meals, but for "grazing" on other delicious food offerings, I recommend checking out (a) one of the
Garrett's Popcorn locations for their delicious caramel popcorn (with or without pecans or cashews) and cheese popcorn; (b)
Fox & Obel in River East, our premier gourmet food store with the very best of everything from basics like fresh meat and fish, to prepared foods of all sorts, sandwiches, and some of the very best baked goods in town (don't miss the cinnamon swirl rolls in the bakery department); and (c) our
French Market which has stalls for some of our best food providers, including Vanille Patisserie, Delightful Pastries, Pastoral (cheeses and sandwiches), and Canady le Chocolatier.
For hotels, I've found the biggest bargains on
Hotwire and
Priceline, although they have a couple of downsides. You can often find hotel rooms for much less than half of what you'd pay when booking through traditional travel websites. One downside is that they are "opaque" websites, meaning that you can't choose a specific hotel; you only choose a neighborhood and a star level indicating how nice the hotel is. They assign the specific hotel. The other downside is that you must pay for the room at the time you make the reservation, and there are no cancellations or refunds. The difference between the two is that Hotwire tells you how much the room will cost for a given star level and neighborhood, whereas you offer whatever price you want on Priceline for a star level and neighborhood, and they either accept it to complete your reservation, or decline it. If they decline it, you can bid for different dates/stars/neighborhood right away, or you can wait 24 hours before rebidding the same dates/stars/neighborhood. When I am reserving well in advance, I start bidding on Priceline with a price that's 20-30 percent less than Hotwire is offering; if it's declined, I wait 24 hours and bid a few dollars higher. I almost always end up with a room for significantly less than Hotwire's rates which are already excellent. You can also find some guidance regarding Hotwire and Priceline bids at the site
betterbidding.com.
I'll add one more link to the sites posted above by leek, and that is for the website of the Chicago Convention and Tourism Bureau, at
choosechicago.com. It's a great guide to what to see and do around the city.
Incidentally, Milwaukee is also a lovely city with its own assortment of excellent offerings for those who love good food. I'm sure your sister will be choosing places that you will enjoy.
Last edited by
nsxtasy on January 17th, 2011, 8:49 am, edited 1 time in total.