Slideshow: A Whirlwind Eating Tour of Chicago: 9 Restaurants and 16 Dishes

Hoosier Sugar Cream Pie at Hoosier Mama Pie ($5/slice with a cup of coffee; $20 whole pie)
Hoosier Sugar Cream Pie at Hoosier Mama Pie ($5/slice with a cup of coffee; $20 whole pie)

The first thing I did after eating a slice of Hoosier Mama's sugar cream pie was buy another for the road. The filling was luscious and pudding-like with milky butterscotch flavor (no doubt, from the brown sugar and vanilla paste) and the crust was all butter. I thought fruit pies were my favorite, but this one might have changed my mind.

Hoosier Mama Pie Company, 1618 1/2 W Chicago Avenue, Chicago, Illinois (map); 312-243-4846; hoosiermamapie.com

Biscuit with Jam and Butter at Bang Bang Pie Shop ($5 with a coffee)
Biscuit with Jam and Butter at Bang Bang Pie Shop ($5 with a coffee)

It's hard to think that Bang Bang could make anything as good as their pie, but the biscuits are pretty incredible: shamefully buttery, moist and tender with a crisp crust, and served with as many different flavors of the homemade jams and compound butters as you like (don't miss the blueberry-lavender preserves). Alternatively, order it with local smoked ham or candied bacon.

Bang Bang Pie Shop, 2051 N California Ave, Chicago, Illinois 60647 (map); 773-276-8888; bangbangpie.com

Chocolate Cloud Pie at Bang Bang Pie Shop ($5 per slice; $26 whole pie)
Chocolate Cloud Pie at Bang Bang Pie Shop ($5 per slice; $26 whole pie)

Decadent but light, not too sweet, and held together with a lard-butter crust. Perfect.

Bang Bang Pie Shop, 2051 N California Ave, Chicago, Illinois 60647 (map); 773-276-8888; bangbangpie.com

Kao Soy at Andy's Thai Kitchen ($8.50)
Kao Soy at Andy's Thai Kitchen ($8.50)

Successful combination of authentic flavors and nice-to-eat (if slightly bland) pieces of chicken (read: no gnarly bones or gaminess). Pickled mustard greens were good and pickle-y, coconut milk broth was rich and heady, and noodles were crisp and also springy—just the way kao soy should be.

Andy's Thai Kitchen, 946 W. Wellington Avenue, Chicago, Illinois 60657 (map); 773-549-7821; andysthaikitchen.com

Hibiscus-Lemongrass Agua Fresca at Xoco ($2.50)
Hibiscus-Lemongrass Agua Fresca at Xoco ($2.50)

If a sip of this agua fresca had been my only sample of XOCO, I still would happily go back every day. Concentrated, tangy, sweet, and incredibly refreshing, this was one of the best drinks I've ever had.

XOCO, 449 N Clark Street, Chicago, Illinois 60654 (map); 312-334-3688; rickbayless.com/restaurants/xoco.html

Ahogada at Xoco ($10)
Ahogada at Xoco ($10)

I wasn't sure what made this a dine-in-only sandwich until it landed in front of me. What comes between the crusty bread is simple: moist shreds of carnitas, pickled onions, and an arbol chile sauce. But the flavors are bold, and since the cut sides sit face down in a heady tomato sauce, each bite is literally soaked in savory pork and tomato juices. A truly spectacular sandwich.

XOCO, 449 N Clark Street, Chicago, Illinois 60654 (map); 312-334-3688; rickbayless.com/restaurants/xoco.html

Chorizo-Stuffed Medjool Dates at Avec ($12)
Chorizo-Stuffed Medjool Dates at Avec ($12)

Definitely the largest stuffed dates I've ever had, and among the tastiest as well: smoky, sweet, and tangy. Given the number of orders going to other tables (and the fact that they sell the dates for a buck a piece at Publican Quality Meats butcher counter), I'd say it's one of the most popular dishes the kitchen makes.

Avec, 615 W Randolph Street, Chicago, Illinois 60661 (map); 312-377-2002; avecrestaurant.com

Barbequed Octopus at Avec ($16)
Barbequed Octopus at Avec ($16)

No kidding on the "barbecue" here; this tentacle was good and charred, especially at the tip. But amazing, it was tender, almost creamy inside, and the buttery polenta and cool, crisp kohlrabi made ideal contrasts.

Avec, 615 W Randolph Street, Chicago, Illinois 60661 (map); 312-377-2002; avecrestaurant.com

Sauteed Green Beans at Girl and the Goat ($9)
Sauteed Green Beans at Girl and the Goat ($9)

Yeah, they're salty, but they're crisp-tender and the combination of creamy fish sauce vinaigrette and cashews is just tasty.

Girl and the Goat, 809 W Randolph Street, Chicago, Illinois 60607 (map); 312-492-6262; girlandthegoat.com

Wood-Fired Chicken at Girl and the Goat ($23)
Wood-Fired Chicken at Girl and the Goat ($23)

I would order this again for the bread alone. The grilled naan was more pliable and tender than most traditional Indian restaurant versions, and (like everything else from Izard's kitchen) generously seasoned. It was great for mopping up the tangy yuzu harissa and chicken jus.

Girl and the Goat, 809 W Randolph Street, Chicago, Illinois 60607 (map); 312-492-6262; girlandthegoat.com

Pan Pizza at Pequod's Pizza ($6.95-$17.50, depending on size)
Pan Pizza at Pequod's Pizza ($6.95-$17.50, depending on size)

There was no shortage of pan pizza places to check out, and this one didn't disappoint. Pequod's was exactly what I hoped my Chicago pizza experience would be: a boisterous Blackhawks bar with nice people and good food. They're known for their caramelized cheese crust, which was rich, salty, and crisp—all pluses, especially when there's so much tender interior dough in a pan pie. Extra cheese and extra sauce were good advice, as were the meatballs.

Pequod's Pizza, 2207 N Clybourn Avenue, Chicago, Illinois 60614 (map); 773-327-1512; pequodspizza.com

Butcher's Cold Charcuterie Plate at Publican Quality Meats ($19 for 5 items)
Butcher's Cold Charcuterie Plate at Publican Quality Meats ($19 for 5 items)

One of my favorite—and most surprising—meals in Chicago. Favorite because the execution quality was so high. I still can't decide which of the items I liked best: harissa and prune pork pate, beer salami, pork and duck rillettes, spicy and creamy-textured ndjua (spreadable pork sausage), or the delicate corned beef tongue. Surprising because I ended up having lunch with a total stranger; we both admired what the other was eating (she had the hot charcuterie plate—highly recommend) and decided to share.

Publican Quality Meats, 825 W Fulton Market Street, Chicago, Illinois 60607 (map); 312-445-8977; publicanqualitymeats.com