Chicago Filter : Where should we stay? What should we do?

You can stay at the http://www.hichicago.org/index.shtml in the South Loop. A private room w/shared bath is $90 a night. You'd be very close to downtown attractions and the hub of the CTA trains, and http://www.cafecitochicago.com/ is next door. Not much nightlife beyond http://www.buddyguy.com/ (full of tourists) or many bars to recommend, though. http://www.margaritainn.com/ in Evanston is another budget place with shared baths. Evanston is Chicago's most cosmopolitan suburb (it has an el line) but it's a bit of a haul if you're coming back from, say, Logan Square late at night. http://hopleaf.com/ is the place to go if you're into beer. You could follow up a meal there with the long-running theater/performance show, http://en.wikipedia.org/wiki/Too_Much_Light_Makes_the_Baby_Go_Blind http://neofuturists.org/, just around the corner. Other notable bars for beer include http://fountainheadchicago.com/ (good whiskey too, but the food is nothing special, unless their new chef really turned things around) and the http://maproom.com/ (no food). For cocktails, try http://theviolethour.com/, http://whistlerchicago.com/, or http://www.tinylounge.com/. The Chicago Reader http://www.chicagoreader.com/chicago/BarGuide has good suggestions by neighborhood and will steer you clear of http://www.complex.com/city-guide/2012/04/the-25-douchiest-bars-in-chicago# and tourist traps. You can rely on their restaurant and cultural/nightlife recommendations too.

http://ask.metafilter.com/212670/Help-two-New-Yorkers-navigate-3-days-in-Chicago. Most of the time tourists stay in River North or the Loop, since that is where most of the hotels are, in order to be close to Michigan Avenue, Cloud Gate/Millenium Park, the Art Institute, Shedd Aquarium, etc. Having a hotel there is quite convenient if you want to see the tourist sights. And it's not like it's a foodie desert. In the River North area, for example, you can find Rick Bayless' Topolobampo/Frontera Grill/Xoco there as well as the Purple Pig, the original Pizzeria Uno (unrelated to the chain Uno), Doughnut Vault, Lou Malnati's, GT Fish & Oyster, Naha, and the newly opened Brindille. For Frontera/Topolobampo, call and book 8-12 weeks ahead for dinner. They are quite popular. We love staying at the Hotel Palomar due to their customer service & excellent cocktail bar, Sable. However, if food and a cool neighborhood to hang out in at night is a big concern, I'd try to stay in the West Loop (perhaps through AirBnB). You can take the Green line into the touristy areas downtown quite easily from there. The neighborhood has changed quite a bit in the last few years and you can see meatpacking businesses next to high end condos. It's not as "neighborhood-y" as other places, but the dining scene has really exploded. You'll find Publican/Publican Quality Meats, Girl and the Goat/Little Goat, Au Cheval, Maude's Liquor Bar, Next, the Aviary, iNG, Belly Q, Blackbird, Avec, Sepia, and more in the West Loop. Pro-tip: Girl and the Goat books up 3 months on OpenTable but 6 over the phone. As soon as you lock down your dates, call and make a reservation. It's surprisingly affordable for what you get. Stephanie Izard (from Top Chef) also just won Best Chef: Great Lakes at the James Beard Awards. A must go. Or look for a room at Longman & Eagle in Logan Square. They only have 6 rooms, though and book up quickly, and I'm guessing you'd need two. A quick glance at the L&E schedule indicates that weekends in September/October are almost full already while November looks pretty open. If you score a room at L&E or an AirBnB in Logan Square, you would be within distance of Lula Cafe, Billy Sunday, the Whistler, Fat Rice, Parson's Chicken and Fish, and Yusho, etc. Plus, Longman & Eagle is also a great restaurant, too. Logan Square is on the Blue line as well, so you're a short train ride away from Wicker Park, near Big Star, The Violet Hour, Trencherman, Bongo Room, and Mindy's Hot Chocolate, and others. Since Chicagoland is so big, I find the maps on Chicago Eater to be very helpful, such as the http://chicago.eater.com/archives/2013/06/06/the-eater-chicago-heatmap-where-to-eat-right-now-6.php and http://chicago.eater.com/archives/2013/04/09/updated-the-38-essential-chicago-restaurants-april-13.php.

For food, definitely check out http://www.lthforum.com/bb/index.php. I'm usually using points or other discounts and wind up staying at one of the two Embassy Suites in the tourist area. They are very convenient. It is nice to be able to step out the door and walk to Millennium Park and the Art Institute.

Park your car at the hotel and take the el and the bus.

The best tacos can be foundhttp://www.metafilter.com/127410/This-is-basically-a-love-letter-from-my-stomach. THE BEST TACOS. The http://www.danahotelandspa.com/ is really cool. We send our corporate guest people there. (If you like it, memail me and I can hook you up with a reduced rate.) Definitely see some improv while you're here unless you hate funny. I like http://ioimprov.com/chicago/.

We just came back from a trip to CHI. Try to make time to take one of the Architecture Foundation tours. We did the http://www.architecture.org/tours/boat-tours and the http://Modern%20Skyscrapers. Both were really cool. The three standout food things we did were http://blackbirdrestaurant.com/ (fancy),http://www.hotdougs.com/ (not fancy but a little pricy, but get there before they open or you'll be waiting in line for 30-60 minutes, I'd guess), and http://www.katherine-anne.com/

Food wise, these stuck out for me on my trips: http://www.trekronorrestaurant.com/ http://slurpingturtle.com/home.php http://www.yelp.com/biz/the-noodle-chicago-3 You may want to check out AirBNB in the Logan Square/Wicker Park area if you are looking for hip. Cheaper than most hotels per night and your hosts can give you suggestions!

Yes to Longman & Eagle.

Seconding the Architecture Boat Tours...especially if you can book one that goes out on the lake during sunset. You could grab some tacos from http://www.rickbayless.com/restaurants/xoco.html and hit the Jay Pritzker Pavilion for a free concert depending on the weather. Also, check out the upside-down pizza at http://www.chicagopizzaandovengrinder.com. (We always get the flat-bread and salad there, too.) SO GOOD.