Wait, for realsies? I had no idea.

Why would food trucks want to set up outside the Loop/River North? That's where the customers are. Six Corners, sure. Other late night hotspots like around Halsted/Diversey, etc. (and it would be such a shame if people stopped going to Weiner Circle at 2am).

Speaking of night markets:
http://www.uptownupdate.com/2013/05/n...

That these are happening on a week night is a little odd -- I would expect a weekend night to get much more traffic -- but I'm still pretty curious just the same.

There's a one-off, mom and pop place left in the Loop/River North that offers cheap/affordable & quick lunches to go? Cafecito comes to mind but I otherwise can't think of anything and I would sincerely love to know about other, similar places.

The last time I was in DC, I saw 2-3 trucks parked in front of a Cosi. The Cosi was packed. The trucks had healthy lines. Would Cosi have been more crowded had the trucks not been there? No way to tell.

If I recall, one of the more vocal/oft quoted opponents of a liberal approach to managing food trucks owns Trattoria No. 10. Personally, I am baffled that he would see a food truck as a threat to his brick and mortar operation -- they serve very different audiences. When lunch time rolls around, I do not ask myself, "What will I eat today? A $20 plate of pasta or a $7 order of Jerk chicken wings?"

I would love it if a decent food truck parked near my office in River North. I stick to Chipotle, Potbelly - maybe Hannah's Bretzel and... it gets old. But I'm also not willing to pay for a plate of food cooked and packaged offsite hours earlier. I hope that Jerk312 does well and encourages additional, high-quality trucks that cook food to order.

To get a healthy food truck going, you need to be in a high-density area -- ie. the Loop/River North. Unfortunately, a few well-connected business owners lost their damn minds and convinced the city council to pass a horrible bill that over-regulates food trucks.

I believe there is only one food truck in Chicago that actually cooks its food to order, Jerk (http://www.jerk312.com/). Other food trucks, like the Southern's Mac 'n Cheese truck, prepare food offsite and keep it warm on the truck. You can thank mystifyingly onerous food truck regulations for preventing a decent food truck culture in the city.

In other words, I wouldn't go out of your way to eat from a food truck here in Chicago.

I completely agree re Big Star. It's still great for drinks and people-watching and the food is certainly fine (but not great). I'd suggest Takito next time you're in town -- a few blocks south on Damen, it's another fancy taco place, but perhaps a half-step up from Antique Taco (ie. Takito has table service).
http://www.takitokitchen.com/

L'Patron, in Logan Square, is the next great thing for hole-in-the-wall taquerias.

Fat Rice and Masa Azul, though not taco-centric (the former not at all) are well worth trying, as well. Mott St., a new concept from the team behind Ruxbin, will be open in a few weeks and I have high expectations. They'll be at 1401 N. Ashland and their menu will be late-night street-food-style snacks. Their bar program will be run by a Longman & Eagle vet.

They don't sell slices - only whole pies (and I completely agree, Coalfire is wonderful). The only place I can think of that approaches "NY style" would be Santullo's, in Wicker Park. But I've found the quality to be pretty spotty when ordering by the slice (whole pies are great). Also, I'd just as soon walk ~150' to the East and eat at Piece (which is New Haven style -- also not available in slices, though you can get a killer individual-sized portion until 5pm; their beer is very good, too).

Unless something has changed radically, Schwa has about 4 staff members. Total. So they clean, answer food, prep for dinner service, serve dinner and clean again. How do they decide if they can answer the phone? If they don't have anything else to do and/or if they feel like it? And I don't mean that in any sort of snotty/snide manner but just to let you know why there's no one dedicated to reservations. Which, for some, is part of the charm.

Have you looked at El Ideas? It's another small BYO restaurant with a lot of interaction with the staff. Biggest difference is that you can probably get an answer from them sooner rather than later. Even at this point, there still might be a seat available so don't hesitate to email/call.

Merkay, above, gave some good choices for Andersonville -- I would continue North along Clark Street all the way to Norse Bar, though.

Hamburger Mary's makes its own beer but I've never been impressed.

I just want to echo BSpar's suggestion for Longman & Eagle for a place to stay. Rooms are very comfortable and stylish and well-located, in terms of dining/drinking/public transportation. Not to mention the fact that Longman & Eagle is precisely the kind of bar where you can talk to bartenders and regulars while enjoying one of the best bar programs in the city (and the food is pretty good, too).

If you're in town for so long, I'd consider splitting your stay between L&E and the other hotel you've found. You'll get a vastly different experience staying in Logan Square (the neighborhood where you can find L&E) compared to downtown. Longman puts you within spitting distance of a host of great options:
Lula (restaurant)
Scofflaw (more bar than restaurant but the food is still great)
Yusho (restaurant with a small bar area)
Fat Rice (restaurant)
Helen's Two Way (dive bar)
Whirlaway (dive bar)
The Owl (dive-ish bar)
Cole's (dive-ish bar)
Revolution (brewpub with great food)
Billy Sunday (cocktail bar)

And then you're just a short L ride to Wicker Park/Bucktown which is another great neighborhood, as well.

The Bucktown/Wicker Park area is probably a good place to start (with a foray into Logan Square, too). Just spitballing here but this could be one route:
Revolution Brewpub (great food, too)
Map Room (no food, though you can bring it in; cash only)
Piece (food menu largely limited to pizza)
SmallBar (Division Street) (food is over-priced)
Jerry's (Wicker Park) (food is okay, at best)
Bangers & Lace (food is good but limited to sausages in various forms)

Revolution to Map Room may be a longer walk than what many consider "walking distance" but Revolution is, I think, about the most consistent brewery in the city right now and shouldn't be missed.

Or there's the Roscoe Village/North Center areas:
Northdown (solid bar food, nothing crazy or terribly innovative)
The Green Lady (no food, though you can bring it in)
Half Acre Tap Room (no food, though you can bring it in)
Bad Apple (great burgers, especially if you like them over-loaded with assorted toppings)
Fountainhead (they just brought in a new chef so I can't speak to what the food will be like; they have a killer rooftop deck)

With this list, Green Lady to Half Acre is probably more than walking distance. The Brown line (Paulina to Irving Park) wouldn't take long or it would be a cheap cab ride. Half Acre's Tap Room is a fun place and they offer all beers in a variety of sizes, making it easy to sample a variety of what's on tap (most of which will not be found anywhere else in the city)

Lincoln Park could work well, too:
Whole Foods (Kingbury St. location) (yes, it's a Whole Foods, but they have a craft beer bar in-store and it's often as good, if not better, as any other bar in the city)
Goose Island (Clybourn brewpub) (skip the food; the beer can be hit or miss, so stick to a flight or two and appreciate what they're aiming for even if they don't stick the landing, so to speak)
Local Option (food is okay; beer list is great; don't expect good service)
Beer Bistro North (formerly part of the SmallBar family, the beer list is still very respectable but the food won't blow you away)

As with all of the options above, just be sure to check hours first -- some don't open until the late afternoon, others are closed on certain days, etc.

I think The Bristol is very good and it's in a great neighborhood for eating/drinking (and shopping, for that matter). Dinner at The Bristol followed (or preceded!) by cocktails at the Violet Hour (very chill cocktail lounge) or even Big Star (very lively pseudo-country western taco joint with amazing whiskey and tequila drinks) would be a great evening.

The Publican is easily one of my favorite restaurants in the city. While the meat dishes are often very hearty and rich, the seafood options are great, too. The whole place reminds me of European beer halls and brasseries and their menu that highlights the best the Midwest has to offer.

I could be wrong, but I don't think The Purple Pig has a separate brunch menu. They open at 11:30am and serve the same menu until the kitchen closes (again, I could be wrong - I'm usually there for an early dinner after work and stay away on weekends). Are you asking about brunch at the Publican? They accept reservations for brunch so waiting shouldn't necessarily be an issue.

The only rooftop spot I can think of at the moment is at Fountainhead, just under a mile away. The general atmosphere is pub-like, but it's definitely more upscale than most other pubs (Irish, faux-Irish, etc) I've seen in the city. I don't know when the rooftop bar opens for the season, however.

http://fountainheadchicago.com/
1970 W Montrose Ave
773.697.8204

I think jbontario is pretty spot-on, but as far as Rossi's - it's not the biggest bar, but it's comfortable and welcoming enough. There's a fair amount of suits and ties after 5 (and sometimes around lunch time).

Miller's Pub, in the Loop, would probably suit your needs pretty well, too.

And not to give you even more outside reading materials, but the local alt weekly has a pretty good guide to drinking in Chicago (organized by neighborhood and type): http://www.chicagoreader.com/chicago/...

Agreed about Dragon Ranch -- Smoque is a much better alternative for BBQ. But if you're going to be in the River North area, Bub City (next to Dragon Ranch) wouldn't be a bad idea. It's a bit gimmicky (lots of Southern-fried kitsch) but it's a lively, fun atmosphere with respectable BBQ. Maybe the bar downstairs will be open by the time of your visit, Three Dots & A Dash. It's going to be a Tiki bar (without the irony) from one of the city's best bartenders. It should be a good time.

Irazu is all right. It's fine if you're in the area, but I wouldn't consider it destination-worthy. They are BYO (and there's a decent wine store across the street, too). A few blocks to the Northwest is a place called Belly Shack -- Puerto Rican/Korean, broadly speaking, Just as casual as Irazu and they are also BYO (you can also order food to go and bring it into the bar next door, Green Eye, which is a decent dive-ish bar with good beer and cheap shots of whiskey).

For one of your other dinners, I'd take a look at Nightwood, in Pilsen. It's one of the best farm-to-table restaurants in the city (though it's more casual than, say, Naha or even North Pond) while still being very chic. The Skylark is next door, one of the best dive bars in the city (they are also known for their tater tots).

Another strong suit here in Chicago is Thai food. Aroy Thai is a favorite of mine (ask for the Thai Classics menu if they don't provide it), but there are other options, as well (Sticky Rice and TAC Quick come immediately to mind - it might depend on how far you want to travel).

Broadly speaking, I think you'll find some of the better dive bars in the Wicker Park/Bucktown/Logan Square neighborhoods (home to Bristol and Yusho). Also some of the better cocktail destinations (The Whistler and Violet Hour come to mind). Big Star is great for people-watching and cheap whiskey drinks (their tacos are good, too).

Andersonville is a fun neighborhood, too, and since you'll be in town for so long it might be worth the trip (ti's about ~8 miles north of downtown, accessible via the red line but it's not a short trip). Big Jones is great for Southern/coastal/low country cooking (and bourbon). Not far from them is a great bar, Simon's (look for the neon fish), as well as one of the best beer bars in Chicago (Hopleaf - they also serve up pretty good, Belgian-ish food). If you're a fan of gin, Vincent is close, too - one of the new places where you get a decent glass of genever and a plate of herring (if that's your thing).

Camusman mentioned it above, but if you really want pork, consider the Publican. I don't love it for dining solo (you get seated at a cramped bar-type area) but they are known (rightfully) for their pork. While they are also known for their beer program, the wine and cocktail options are very good, as well.

For solo dining, I love avec. It's not hard to get a seat at their bar and you get to enjoy the goings-on in their open kitchen. Many plates are available as half-portions, even if the menu doesn't explicitly say so. They aren't quite as pork focused as the Publican but there should be some options to satiate your hunger for pork.

Frontera (and Bayless' other restaurants) are closed on Sundays and Mondays.

I was about to suggest the Publican myself by kathryn beat me to it! They open for brunch at 10am and accept reservations. Personally, I'd pick a somewhat later time, order a lot of food, and I'd be set for the afternoon.

True, but it's only one variety of Dark Matter's coffee at Do-Rite -- their Do-Rite blend (which is very good, don't get me wrong!). You can buy a pound of that blend to go but the mark up is really high (and may not be worth it). Also, Do-Rite doesn't have much in the way of seating. About 6 2-tops outside but if the weather is uncooperative... Just so you aren't expecting a cafe or anything.

But Intelligentsia is very much a cafe - a fair amount of seating, a small selection of pastries, lots of coffee (and tea) options (as well as several options as to how to brew the coffee (Chemx, pour over, French press, etc)).

I would take a look at Big Jones. Great food, great room -- they also accept reservations. Brunch menu here: http://www.bigjoneschicago.com/brunch...

I think Smoque is my overall favorite and it is very convenient via the city's Blue line (Irving Park stop). They're also BYO. They tend to be very crowded, as mentioned, but the staff is good about managing the line and tables; they won't let you order until you have a seat, so at least you won't be standing around with a tray of bbq and no way to really eat it.

Lillie's Q, in Bucktown/Wicker Park, is also very good. Their tri-tip, in particular, is a stand-out and the smoked fried chicken, too. More of a restaurant than a shack, they're pretty close to the Damen blue line stop. They recently started selling food at the city's French Market in the West Loop. The hours and menu are a little more limited, but it might be convenient for you if you're downtown.

http://lilliesq.com/
http://lilliesq.com/frenchmarket.htm

If you don't mind a cab ride or a L ride, I'd look at some options in the Logan Square/Avondale areas. Yusho and Fat Rice are great for small plates, though Yusho has a much stronger beverage program and accepts reservations. Yusho is yakitori-ish, though the menu doesn't limit itself to Japanese ingredients/preparations. Fat Rice is Portuguese, Chicago's first, and really nails the wide-ranging flavors and techniques you would expect from a one-time colonial superpower. They opened up pretty recently and are already one of my favorite restaurants.

Longman & Eagle is another option. The menu is pretty wide-ranging and not dissimilar to Publican. L&E doesn't accept reservations and waits for a table can run long - fortunately, they have an excellent beverage program, including one of the more exhaustive selections of bourbon.

Just to the west is Scofflaw. Known primarily for cocktails, the food menu is also really good. Though as kathryn suggests, great cocktails and food alone may not be a huge draw for you. But if you're in the Logan Square area already, it would make for a great stop.

In Hyde Park, there really aren't many places I'd recommend. The only bar worth going to is Jimmy's (aka the Woodlawn Tap; 1172 E. 55th St.). It's a total dive, in every sense of the word, but it's where professors, students and Hyde Park residents have been going for years and years.

http://yusho-chicago.com/
http://www.eatfatrice.com/index2.php#slide-main
http://www.longmanandeagle.com/

As often as I eat at L&E, I've actually never done brunch -- precisely because they don't take reservations and unless you go when they open or right before the brunch menu ends, wait times can easily be 60 minutes and up (though it's possible to grab a seat at the bar more quickly - that gets much more difficult the more people there are in your party).

But here's an alternative idea -- have you considered The Publican? The menus at both restaurants have a certain sympatico and The Publican accepts reservations (and it's much closer to the Loop). Brunches at The Publican rank as among my all time favorites.

To save you some (potential) disappointment, you won't find any happy hour specials for drinks in Chicago -- they're not allowed. Some places may offer all-day drink specials and/or happy hour specials on food, though they're not as common as they once were.

I think the Publican could work well for a drink or two with some snacks (they also have a killer oyster menu). If you get there on the early side, you will probably find it to be less crowded and (potentially) more enjoyable. This is their 'afternoon' menu (dinner service starts at 5pm, I believe): http://thepublicanrestaurant.com/uplo...

The first place that comes to mind is Bar Deville, in the Ukranian Village: http://bardeville.com/ . Very talented bartenders, comfortable bar (which will get crowded and perhaps less comfortable as the night wears on), close to plenty of other dining/drinking options (Bar Deville does not have a kitchen).

Scofflaw, just to the west of Logan Square, might work, as well. The location is a little more out of the way but they can still fill up quickly on weekends. Until then, though, great staff, great drinks, great atmosphere. http://scofflawchicago.com/

Are you looking for bars in a specific part of town? That might make it easier to offer up other suggestions. I suspect the bigger challenge is finding a place that is cozy and low-key. Most of the other bars with a great cocktail program that come to mind skew towards more crowded/hipster-ish.

Indeed I am being serious! SERIOUSLY!

To elaborate -- Chef Bower is putting out some of the best food in Chicago these days. There was a sweetbreads dish a few months back that was a game-changer for me. Best preparation I've ever had. His pasta dishes are very strong and the introduction of salumi plates was one of the best things to happen to avec in years.

Also, the chairs/noise issues are obviously not so universally reviled or the restaurant would have closed years ago. Apparently they must be doing something right all these years.

I think a great option would be avec, just west of the Loop. There's a bar with a nice view of the open kitchen -- bartenders are always very friendly and knowledgeable about the menu and the large wine list. The menu is Mediterranean-ish, with a large focus on seasonality and simple preparations. Don't hesitate to ask about half-plates, even if the menu doesn't explicitly mention the possibility.

avec is often very busy and they don't take reservations, however. I wouldn't necessarily go there on a Friday night (unless you go pretty early) but I've rarely had issues on weeknights. They are also open on Mondays, which is when many restaurants might be closed. Some say the restaurant is too loud and the barseats too uncomfortable (I wouldn't say either) - your mileage may vary.

One of my favorite places for lunch is Big Jones, located in the Andersonville neighborhood. It is about 8 miles from the Loop, but is well served by public transportation. Great Southern/low country food with excellent ingredients. They offer a 'Boarding House Lunch' special that's a real steal.

Andersonville is a great neighborhood for walking around and shopping. Be sure to check out The Galleria - a mini-mall of sorts, with ~90 stalls by local artists/jewelers/print makers, etc.

As others have mentioned, Publican has a really strong seafood program. Half of their menu is devoted to seafood (raw and cooked). Do they "specialize" in seafood? Only as far as they "specialize" in pork. Which is to say, they "specialize" in great food, plain and simple.

I once got into a counting contest with a poster on these boards about how many seafood dishes they had versus other types of plates. It was then, and remains, utterly beside the point. They "specialize" in great food.

I really wouldn't consider The Gage to be in the same league. The menu is pretty pedestrian, albeit tasty enough. The beer list is forgettable. The Publican is a great 'brasserie by way of the Midwest' sort of place. Avec would be worth considering, too (the new chef is nailing it, week in and week out), though they don't accept reservations and you can expect long waits at peak times (so go early or go late) and unless you sit at the bar, you might be sitting next to strangers at communal tables.

I would also strongly recommend Nightwood.