Show some mercy to this Chicago visitor
I've been searching this board off and on for weeks, but my lack of knowledge about Chicago geography has been forcing me to find a good rec, find the address, Google map every restaurant in relation to our hotel and then figure out if public transportation is available and let me tell you, my progress is slow. And I'm running out of time!
We're staying at Club Quarters, which is at 111 W. Adams St, Saturday and Sunday night. (It's been labeled as "Loop" but then I see comments about South Loop, North Loop, etc and I don't know where it is in relation to that.)
No car, but we're fine walking a mile or two, and we're up for 30 minutes in public transportation.
So far booked:
Sunday brunch at Atwood Cafe (thanks to this board's rec)
Sunday dinner at Harry Caray's (thanks to this board's rect)
In search of:
1) restaurant for dinner near Trap Door Theatre (1566 W. Cortland Ave). Looking for a good deep dish pizza, OR good mom-and-pop italian OR a good diner OR a place for a great burger (regular burger, not those nouveau Kobe burgers or salmon burgers). A great Mexican place would be fine. Just really convenient to the Theatre, please!
2) Italian bakery- the kind where you buy cookies by the pound. On here I've seen and Google map'ed ones that were far from the Loop- are there any nearby our hotel?
I look forward to hearing your recommendations!
Some additional comments to help with your orientation...
As achoo (gezundheit!) mentioned, you're in the middle of the Loop, Chicago's old commercial downtown area with lots of office buildings. I disagree with the comment about dining; there are actually many excellent restaurants in all price ranges in the Loop itself, and even more in the immediately surrounding areas.
The Loop was named after the loop that the elevated trains make in the downtown area, and is generally applied to the entire area south and east of the Chicago River and north of Congress Avenue. The South Loop is the adjacent neighborhood south of the Loop, extending for maybe a mile and a half south. The West Loop is the adjacent neighborhood west of the Loop, extending for maybe a mile and a half west. There is no "North Loop" unless someone is referring to the northern part of the Loop itself; you are probably thinking of River North, which is the adjacent neighborhood north of the Loop, extending for maybe a mile north. The terms Michigan Avenue and Magnificent Mile are often used to refer to the area around Michigan Avenue from the river north to Oak Street. Streeterville is the area east of that stretch of Michigan Avenue.
For the best deep-dish pizza in Chicago, get the "stuffed" (double crust) pizza at Giordano's, which has a location at 223 W. Jackson, two blocks from your hotel.
There are many sandwich shops and delis (e.g. Au Bon Pain, Corner Bakery, etc), some of them carry-out only while others have seating, and of course there are also the usual fast food places. A few examples of affordable sit-down food in the Loop include pizza at Giordano's and Pizano's, inexpensive Italian food at Pompei and at the Village and Cantina, burgers and more elaborate food at Park Grill, Cajun breakfast and lunch at Heaven on Seven, and long-time favorites for traditional American fare (burgers, pizza, ribs) like Exchequer Pub and Miller's Pub. Furthermore, one of the biggest bargains in the Loop is lunch at nicer restaurants like Vivere, Custom House, and Blackbird, which can be exceedingly affordable at a fraction of their dinner prices. Not to mention the proximity of affordable food nearby in Greektown, Chinatown, the South Loop (Hackney's), etc.
Convenient to the theatre could be tricky. Bucktown has become more upscale in past years so it could be hard to find what your looking for.
Club Lucky is close but I think the food is mediocre and overpriced ($15.00 plates of pasta).
I would walk down to Pequods for pizza. Head north on Ashland. Take a right on Webster and it will be on the NE corner of Webster and Clybourn (2207 North Clybourn). I would guess it's about a half mile.
I know your not looking for upscale but Jane's is located just a couple doors down (maybe next door). They have a fantastic burger. Their sirloin burger comes with bacon and cheese, a side of mashed potatoes, and a small salad for $11.00.
If you're going to be at the Trap Door Theater on Cortland, the closes recommendation I have is Jane's at 1655 W. Cortland. Here's the Website: www.janesrestaurant.com. The food is light; the atmosphere charming. You could walk up Cortland to Damen and turn left (south) and come across Hot Chocolate www.hotchocolatechicago.com which is well worth your time. They specialize in fabulous deserts, but the savory options are also very good.
Someone else mentioned LaGuardia on Armitage which is a bit further north and west. It's loud, fun and the food is good, but it's Cuban, not Mexican.
There's also Club Lucky on Wabansia, a couple blocks south and a couple blocks west of where you will be. It's decent Italian. Always crowded. www.clubluckychicago.com/
Armitage and Halsted is a pretty good trek from where you will be so, unless you plan to take a taxi, Minnie's might not be right for you. Honey One, mentioned by someone else is quite a bit west and, while many love the bbq, it has NO atmosphere.
The closest Italian Bakery that I can think of is D'Amato's Bakery which a bit of a hike from the loop, but they do have a big case full of excellent by the pound Italian Cookies, just like you ask for. Also next door to a great little independent Italian grocery called Bari Foods (same owner as D'Amatos and also known for having some of the best Italina Sbus in town). Its also across the street from an excellent higher-end restaurant called the May Street Market. Or a few blocks away from the more casual but also excellent Coal Fire Pizza. Both in fact are better than Lou's or Atwood IMO.
Note - Coal Fire is not traditional Chicago Style Pizza - its similar to more traditional Italian style pizza, but cooked in a coal/wood burning oven.
As far as the Trap theater is concerned, all that really comes to mind is a mile to the west of the Trap you will find Honey One - one of the best Barbecue joints in town.
All of which is a little off your planned agenda, but I thought I'd give you a few different ideas.
D'Amatos Bakery/Bari Foods - 1124 W Grand Avenue.
Coal Fire: http://lthforum.com/bb/viewtopic.php?t=12492)
(FYI, the service problems have cleared up since it first opened and got swamped
Since no one has chimed in: this may be of some help.
Lots of Mexican in the area. La Guardia on Armitage is nice(about 4 blocks N) I don't think there are any deep dish places nearby. I left Bucktown so long ago, I am not sure what's good anymore, except for Bongo Room.
http://www.chowhound.com/topics/372142 for cookies-up North, but from what I have read-well worth it. Plus it's in Andersonville-nice resto's, nice little shops. Italian, Middle Eastern, American, Swedish. I really don't think there are any italian cookie shops downtown-anywhere.
You are SMACK DAB in the middle of the Loop, so either North or South is convenient. Madison Avenue is the very center. The Central Loop unfortunately is lacking in good casual restaurants, especially on weekends since it is a mostly business district, but not too far away, there are lots of good choices. For burgers, I like Hop Haus at 646 N Franklin- just walk west to Franklin and head North- it's very walkable. It looks like a sports bar, but the burgers are really good! The art gallery district of River North is nearby. In the same vicinity, my favorite pizza (better than the usual suggestions) is Lou Malnatti's at 439 N. Wells. Again just walk west to Wells and head north. For Mexican, Frontera Grill, also nearby at 445 N. Clark is very good. It's always jammed, but you can usually get a bar seat at the rear of the restaurant and it's a more entertaining spot anyway. The Trap Door Theatre location is in a more "no man's land" location, but if you take the El to the Armitage Avenue stop, there are lots of choices on Armitage. That isn't too far from the theatre on Cortland. At the corner of Armitage and Halsted is a fun (trendy, but very delicious) hamburger place called Minnie's. It would be a good pre-theatre stop and then you can stroll west on Armitage and enjoy the neighborhood on your way to the theatre. I'd be happy to give you some alternate dinner and brunch ideas in the Loop that I like better than Atwood and Harry Caray's, if you're interested.