One Weekend in Chicago -- The Best Picks: Help!

[slough]

We are coming from all over to convene for a weekend of eating and drinking in Chicago. If you care to put together an itinerary of any favorite places, we'd love it. Not interested in the Charlie Trotters type of places so much. We'll be up very late, very hung over in the morning, and quite hungry throughout, willing to travel and big fans of anything local and good. Thanks much in advance for any and all responses! We need recommendations for a few great drinks spots with good viewing, an awesome steak house (along the minetta tavern lines over say, the palm, in New York terms); an awesome burger; some can't miss late night chow; best brunch.

[ChemWork]

slough:

I'm not a native Chicagoan and their recommendations would probably be better than mine. Nevertheless, I can make a stab at some of your requirements. I ate at Minetta Tavern in June and had the best steak of my life. My second best was at Keefer's in Chicago. I've been there twice and had great steak both times. Keefer's is larger than Minetta, but much less cramped and much quieter. You can find plenty of reviews of Keefer's on this board and MANY other steak places. I really love the margaritas at Frontera Grill, but that place gets very crowded these days. The food is great as well. I had an excellent meal at Avec--communal tables and open late. I have seen many positive comments about the Bongo Room for brunch and I'm going to try to make it there next week. Chicago is better known for its hot dogs than its burgers. Hot Dougs gets the most favorable reviews. I hope this helps and I hope that some of the Chicagoans can help--you might refine your questions a little more.

[fooddoggie]

My favorite burger is at Rosebud on Walton. The burger at the Ritz Cafe is also very good, but probably more expensive than at Rosebud. For a Kobe burger Yoshi's in Lakeview is quite good.

I like the steaks at Keefer's and Rosebud/Walton the best.

Tweet for brunch (kid-friendly), but not sure I'd seek it out if you weren't in the Uptown/Andersonville area.

[lbs]

Slough

Where will you be staying? What will you be doing during the day? Do you want to stay in the downtown/Michigan Ave area or are you willing travel? How old is your group? Do you want to drink in the trendy areas with loud music or do you want to hang out in laid back bars?

Hard to suggest itinearies when Chicago has so many options. If you narrowed down what you want, more people can help.

[KateHC]

Okie dokie, Slough... you asked for all over and local... here's the list so far...

Drinks:
Violet Hour - Wicker Park - Great cocktails circa Victorian era and fantastic nibbles
NoMi (Terrace) - River North - Views, views, views... expensive sushi, expensive drinks, beautiful people
Peninsula Hotel Bar (Pen Bar) - sexy, dark, great cocktails
Long Room - River North - cocktail trollies, pretty people, rockin' music on the weekends
Map Room - Bucktown - one of most comprehensive beer lists in the city, hipsters
Goose Island - Lincoln Park - local beer brewed in-house, good burgers/drunk food
Hopleaf - Andersonville - 2nd best beer list in the city; some of the best food around
Publican - Meat Packing District - Best beer list in the city; top 3 best food; top oysters

Mexican:
Rick Bayless is king in these here parts...
XOCO - lunch/breakfast... excellent hangover food, churros, Mexican hot chocolate, amazing pibil; long lines at lunch, but very worth it
Frontera/Topolobampo - evening meal; great margaritas; excellent food

Spanish/Catalan:
Mercat a la Planxa - South Loop - beautiful space across from Millennium Park; fabulous drinks; order the chef's tasting menu

Hot Dog: Hot Doug's (as already mentioned) - Avondale - loooooong lines - not open Sunday - local foodie haven

Hangover Cure: Takashi - Bucktown - authentic Japanese noodles served Sunday lunch only; dinner is also outstanding, but I'd pick elsewhere if you can do Sunday lunch in lieu

Southern Food: Table 52 - Gold Coast - Art Jetter's (Oprah's chef) gem - Fried Chicken!

Burger: The Gage - South Loop - great beer list, too

Dessert/Sweets - Hot Chocolate - Bucktown - also does great brunch
Tru - Gale Gand's old haunts

Where you'll find the locals:
Silver Palm - West Town - this phrase alone: Three Piggies Sandwich -- three types of pork with a fried egg on top... kitchen open late on weekends, best drunk food ever!
Twisted Spoke - West Town - "Biker Bar" - go for the whisky, beer, bloodies, and fried egg sandwich - amazing for a hangover
Bari - West Town - the best sub in town - always a line on weekends
MK - River North - upscale food joint - foie and cake and shake are the best
La Scarola - West Town - Best Italian (hands down) in the City; probably a front, but who gives a damn with food this good
Green City Market - Saturday 7 to 1 - awesome array of local food; great for breakfast
The Publican - brew hall, communal seating, must have reservations, holy trinity of food according to Paul Kahan: oysters, pork, and beer
Avec - also Paul Kahan, no reservations, Basque food, very good people watching
Blackbird - same guy, American fare, very good

I'm no longer getting into a debate over steak -- it's overrated to begin with. All I'll say: Gibson's is a Chicago institution and in the Viagra Triangle.

Also, get the "Chicago mix" at Garrett's popcorn -- two stores located downtown - crazy tourist lines, but so good. Working weekends for toursim, the best hangover crew was always iced coffee from Intelligentsia and a bag of Chicago mix from Garrett's down the street.

Hope this helps!

Happy eating!

[burton]

A second enthusiastic endorsement to the suggestions from KateHC.

Hope Slough is still awake and alert. Quite a few 'local and good' spots have been identified. Oh, and awesome too. Slough - you there?

[chicgail]

Great post, KateHC, with a really good cross-section of recommendations.

As good as it is, I'm struck with how it barely scratches the surface of the riches we have regarding food in this city

[tonyg]

"La Scarola - West Town - Best Italian (hands down) in the City; probably a front, but who gives a damn with food this good"

Probably a front? Really? Please elaborate on what would cause you to draw this conclusion. That's a pretty bold speculation.

[dallarose23]

Best brunch- head to M Henry in Andersonville. You'll need to get there early-ish or risk waiting for a table, but it is worth it. Best brunch I've had in the city.