Here's my "go-to" email I send to folks when they say, "do you have any restaurant recommendations in Chicago."
But before I post, let me second the suggestion to visit the Signature Room at the Hancock so you don't have to pay to ride an elevator; instead, you pay for a drink and the view.
J.Parker is my favorite rooftop right now.
Arami (Japanese Food (homemade ramen)/sushi; excellent food/comfortable space/taxi-ride/casual but a great meal!)
1829 West Chicago Ave
www.aramichicago.com
Antico (“Neighborhoody” Italian restaurant; homemade pastas; great meats; great wines)
1946 North Leavitt
www.anticochicago.com
Kuma’s Corner (best hamburger in Chicago; usually has a long wait)
2900 West Belmont Ave
http://www.kumascorner.com
La Scarola (Classic Italian, near River North, nothing fancy just the best Italian in the city!)
721 West Grand
www.lascarola.com
Belly Shack (Quick dine-in; lots of unique things; BYOB; directly at Western blue line stop)
1912 North Western
www.bellyshack.com
Mexique (Upscale “Mexican Fusion”)
1529 West Chicago Ave
www.mexiquechicago.com
The Bristol (Contemporary American, good meats (sometimes exotic), great craft beer list)
2152 North Damen Ave.
www.thebristolchicago.com
Laschet’s Inn (old world German place; schnitzel and potato pancakes)
2119 West Irving Park
www.laschetsinn.com
Parson’s Chicken & Fish (best fried chicken, great cocktail list, cool outdoor patio area)
2952 West Armitage Ave
www.parsonschickenandfish.com
Sola (Fusion, American, Californian, great Sunday brunch)
3868 North Lincoln
www.sola-restaurant.com
Ming Hin (Chinatown, has good dim sum and good Chinese food)
2168 S. Archer (in the Chinatown mall)
www.minghincuisine.com
Enoteca Roma (Italian Food/Wine Bar; great “Mangia Mangia” deal for groups of 6 or more; good outdoor seating, right in Division St. Scene)
2146 West Division
www.enotecaroma.com
Mercat a la Planxa
638 South Michigan
www.mercatchicago.com
Longman & Eagle (upscale gastropub, awesome brunch, great drink list, no reservations)
2657 North Kedzie Ave.
www.longmanandeagle.com
Katsu (very authentic Japanese, excellent fish quality/freshness, not cheap but worth it)
2651 West Peterson
Wasabi (BYO; good ramen, skewers, and sushi; cool, casual place)
2115 North Milwaukee Ave
www.wasabichicago.com
Tango Sur (Argentine, BYOB – great food & prices)
3763 North Southport
www.tangosur.qpg.com
Macello (Cozy Italian place, wood fired pizzas)
1235 West Lake Street
www.macellopizza.com
Toast (Breakfast/lunch; Stuffed French Toast)
746 West Webster
2046 North Damen
www.toast-chicago.com
Fat Rice (Macanese cuisine, long wait so arrive early, excellent food)
2957 West Diversey
www.eatfatrice.com
Julius Meinl (same place in Austria! Great breakfast and Viennese coffee)
3601 North Southport
www.meinl.com
Girl & the Goat (Stephanie Izzard’s place; book in advance; get the stuffed calamari and pig’s face!)
809 West Randolph
www.girlandthegoat.com
Southport Grocery (great breakfast/brunch place)
3552 North Southport
www.southportgrocery.com
Lula Café (Great food, no reservations, excellent weekend brunch)
2537 North Kedzie Blvd.
www.lulacafe.com
Yusho (Izakaya grill and other Asian dishes; fun and good!)
2853 North Kedzie
www.yusho-chicago.com
Big Star (Mexican, cash only, awesome whiskey bar, very cool place)
1531 North Damen
www.bigstarchicago.com
Shanghai Terrace (Chinese; dim sum; nicer place; great outdoor patio)
Inside the Peninsula Hotel
http://chicago.peninsula.com/pch/dining_01.html
Sapori Trattoria
2701 N. Halsted
www.saporitrattoria.net
Lillie’s Q (barbecue; great bar)
1856 West North Ave
www.lilliesq.com
Signature Room (BAR ONLY – DO NOT EAT HERE, it’s overpriced and not good food; top of Hancock Building; amazing view)
John Hancock Building, 875 North Michigan Ave
www.signatureroom.com