Good friend swears by Papa Milano's for food, but said the wine list is pretty limited.

Good value doesn't necessarily mean cheap. I can give you the names of a 1000 places that have inexpensive food. You just wouldn't want to eat there, I wager. Especially when you are on vacation!

Let's be honest here - and I sincerely hope you don't take this for rudeness, just honesty. If you are going to confine your dining to the more touristy areas and neighborhoods (Magnificent Mile, River North, the Loop, Streeterville, etc.), where you likely will be staying, you will find most entrees are going to be in the $15-25+ range. You might find some of lesser cost (such as vegetarian or meatless pasta), but it's unlikely that they would be your choices on the restaurant menu. And as for $20 bottles of wine at a restaurant in those areas, I doubt sincerely you'll find anything close to that price. Maybe some close to $40.

An option you do have is to go to a BYOB. Almost all are in the more outlying neighborhoods. Are you planning on getting CTA visitor's passes? That would be the most inexpensive manner in going there and back, although you'll have to calculate time in your schedule for the commuting there and back (at the very least an hour).

Another option you have is to make a picnic meal one evening, especially if you are going to a free concert at the Jay Pritzker Pavilion at Millennium Park. If so, you might look at one of the specialty stores such as Pastoral (in the Loop) or Fox and Obel (over near Navy Pier). As you can see from their websites, they have a variety of sandwiches, wines and even picnic baskets which will fit into your budget.

Neighborhoods: What I would suggest is that you take a look at the www.explorechicago.org website. There they have a section dedicated to the different neighborhoods. Take a look at the descriptions of them and decide which sound interesting to you. Then what I would suggest is that you go to the free Chicago Greeter Service and reserve your own personal tour for one of them. (I believe that you need to make several suggestions so it pays to do your homework ahead of time.) I'm going to give you a few to especially take a look at: Wicker Park/Bucktown; Lincoln Square (and perhaps evening entertainment at Old Town School of Folk Music) and maybe Andersonville; Old Town, the Gold Coast and Lincoln Park (near these two others).

Since there are so many options for restaurants, all over the city, it would be counterproductive to start mentioning options now, though. Once you decide on your neighborhood(s), let us know and then we can suggest others.

You're going to pay around $10 (or more) for each drink at the Signature Room at the John Hancock Center. You pay for the view, you know.

I enjoyed two delicious meals at Bella Bacino's at 75 East Wacker Drive, just off Michigan Av. by the river, when I was in Chicago a few years ago.

It's a friendly, cozy, reasonably priced Italian restaurant with a great menu. It's open for breakfast, lunch and dinner.

Bella Bacino's was nice for lunch. For Italian dinner, my friends took me to Volare on Grand about 2 blocks east of Michigan Ave. If I remember correctly, we paid $21 for Lasagna. The best I have ever had and I have been to some very high end italian. Miller's Pub on Wabash in the Loop was fun for lunch.

I'm sorry if I didn't understand your question above. Do you want recs for local chains, such as Bacinos, too?

google

heaven on seven

one of the best restaurants for its price I've ever been to
it's a little wacky but not stupid; excellent food with big portions. ribs are some of the best anywhere

WE loved Big Star in Wicker Park- easy to get to on the Blue Line (Damen)... great beer selection, unique tacos with a twist. We have heard that there are several other cool places in Wicker park to eat, but we didn't get to spend enough time there.

The Purple Pig on Michigan Ave was moderately priced and has a great wine selection. I'd recommend it as well, but it gets really crowded so go early or late. I don't think they take reservations, but they may.

Hope this helps!

One more thing- we found Lux Bar (the owners of Gibson's own this restaurant too) to be a lot more affordable than we had anticipated. The steaks may be out of your stated price range, but the burgers are AWESOME and they have several bottles of wine in your price range. Lux Bar is in the ritzy Gold Coast neighborhood, but it isn't exactly ritzy itself. Pretty cool vibe in the bar area. Service is very quick- they can turn some tables- but it isn't off-putting.

Thank you everyone!

I now have more details on where we’re staying, which is with a friend in Boystown.

Exiledprincess – you’re right, cheap and good value are very different and I’m looking for the latter. I’d rather not confine my dining to the touristy areas as much as possible, but recognize that might be unavoidable for lunch. I like the idea of picnics, or at the very least shopping for picnic basket fillers. Great idea! As for local chains, sure, if they’re really good.

Quite happy to spend $10+ per drink at Signature room since it’s all about the view.

Very much looking forward to the trip, thanks for your suggestions!

For good, cheap, Chicago-specific eats consider:

-Italian beef sandwiches: Mr. Beef and Al's #1 are both worthy. Get it with sweet peppers and spicy giardiniera, and have the sandwich dipped in au jus.

-deep dish pizza: Gino's East, Lou Malnati's, Pizzeria Uno or Due, and Giordano's (stuffed version) are good places for this.

-Chicago style hot dogs: Portillo's or Gold Coast Dogs are probably the best options if you don't have a car. If you do, consider Superdawg or Hot Doug's.

A little hole in the wall that Jay Leno likes. I have eaten there myself. http://www.urbanspoon.com/r/2/14900/restaurant/River-North/Mr-Beef-Chicago

My favorite Italian place in Chicago is Sapori Trattoria at 2701 N. Halsted, which happens to be near Boystown.

Their Cappellacci all'Aragosta is my favorite dish in the world, actually.

http://www.saporitrattoria.net/

It's a very small, intimate little place. We don't even live in Lakeview anymore and we still go there all the time.

One place I always hit in Chicago for lunch is the Sultan's Market in Wicker Park. You take the blue line two or three stops from Mich Ave and then just walk a few blocks. I had never had a Falafel Sandwich before going to this place. It was awesome! They also have great homemade humus and lentl soup. It is kind of a dive, but there is always a line. You will be under ten bucks for the meal per person.