Road Warrior Chowhounds have multiple challenges: find good food, keep within the travel budget (except if you have clients along), find new places, replicate that at-home feeling with familiar surroundings wherever you go while sleeping in strange hotel beds.
We go to Chicago quite a bit. As a native New Yorker, I actually prefer eating in Chicago than Manhattan.
Here are our Chicago favorites:
Cutting Edge: Blackbird, outer loop. (see elsewhere on this board). Not fusion, not French, maybe new American--although the skill of preparation and ingredient combinations are far more than any other place that calls itself New American. but skip dessert (pricey, small portion, although tasty). I haven't eaten anything so fresh or well prepared since Paris and Barcelona last year. moderate portion sizes, expensive, good value.
Breakfast--Tempo Cafe, Chestnut and State, 24 hr. The place to eat if your hotel is in the River North area. Not just fresh OJ, but fresh squeezed to order. Beats the hell out of Lou Mitchell, hands down, except no real maple syrup, and cash only. owned by the same people as own...
Santorini's in Greek town. Upscale Greek. moderate price. most everything is good (they do overcook the grilled squid). An absolutely incredible value is the high end cabernet from Greece at about $28--this is an extraordinary steal. portions are huge. share stuff. And they take reservations. Great soups change daily.
French: Savarin. Only one visit, but pretty darn good std French. The staff advised us to avoid weekends
Italian: There's so many, we've focused in on these few:
La Scarola, Grand Ave, outer loop. good to vg homestyle Italian, huge portions, moderate prices, small, make a reservation.
Johnny's Italian Beef--out in Elmwood Park, North Ave west of N. Harlem. there is a line every minute they are open, but it always moves fast. Worth the trip from downtown (or on the way in from O'Hare) for Italian Sausage, Italian Beef, and transcendental Lemon Italian Ice--those 3 things, thats all they sell--suggested by the folks at...
Domino's Bakery, 1700 block of N. Harlem, great Italian cookies and pastries. Owners are elderly, and keep limited jan-feb hours while in FL. We were steered there one night when eating at...
Palermo's, 95th st just west of Cicero, in Oaklawn--10-15 min south of Midway. moderate prices. It was St.Joseph's day, and Palermo's gave us complementary St. Joseph's cakes after dinner. They were so good, we asked who made them, and that's how we discovered Domino's Bakery, above. Back to Palermo's. If you are NY pizza person, forget the pizza. Takeout all day, dining room dinner from 4:00 PM. (hey--its only ten minutes into Indiana and the Eastern Time Zone). vg veal & pasta. Try the Pasta Cristina--fresh mozzarella, tomatoes, basil and cappelini baked briefly together; veal milanese, broccoli rabe, sausage & polenta. About the Palermo's begat story: Several years ago, we were stopped at a traffic light on Garfield near the interstate (a very very rough neighborhood between Midway and I-90 to Gary)... Bob--my partner, peruses the road map. The truck driver stopped next to us shouts down and inquires "Are you lost? D'ya need help?" Bob looks up and fires back "Where's a good Italian restaurant?" Meanwhile the light changes. The truck driver shouts "95th and Cicero" and hauls ass away. We see from his tailgate that he's driving a restaurant supply linen truck!
J.C.'s--Cicero Ave, Alsip, 15-20 minutes south of Midway. Huge, inexpensive homestyle Italian businessman's lunch, good for stoking up before going for often delayed Midway outbound flights
D'Agostino's, Diversey and N. Harlem, Elmwood Park. moderate prices. Small, great, slightly upscale (no pizza) neighborhood Italian in an old house, husband and wife chefs. make a reservation. You will be the only non-heighborhood folks there, as is true of Palermo's, Johnny's and J.C.'s .
Gianotti's, Cumberland and Lawrence (actually two locations, this one is less than $10 taxi from O'Hare). Italian steakhouse, exc prime steaks and veal chops, sausage and broc rabe, decor like a 1970's Vegas hotel, not cheap, reservations wise at lunch or dinner. If you feel oppressed by the decor (as some Zagat readers do), then admit that you don't understand the reality that births the concept of "Camp". Quintessential Chicago experience. forget dessert. Go hungry, or make sure you have a frig' in your hotel room.
The most helpful articles at the Chicago Tribune site http://www.metromix.com are the recurring series about "Where the Chefs Eat". They tell you a lot about a particular Chef, valuable info about evaluating his/her own restaurant, and yield up chef's leads to other good places.