Descending from the L staircase at Madison, you'll drop into a noisy hub of jewelers, diamond stores and watch repair shops at every turn. You will find, beyond the jewelry storefronts and urban malls, are a range of some expected chain stores as well as one-of-a-kind eateries and artist cafes. As always, the Madison stop proves that Chicago likes to mix things up between gritty and glam.
Best of the nightlife
14 Karat Lounge
A good Loop bar is a hard gem to unearth. Due to the few hours of business they get from the average working stiffs in the area, most bars in the Loop either pour on the swank and make themselves a destination, or just roll with the punches and have a group of regulars to keep things running. The 14 Karat Lounge (otherwise known as the front part of Ada's Deli) seems to have the latter down, but in reality there are several types of guests who consistently patronize the bar: five o'clock party animals, School of the Art Institute students coming in from across the street, and older couples/singles who look like they've wandered in for the soup at Ada's and got just a little distracted on the way back to the restaurant. They all manage to squeeze in thanks to the unique question-mark shape of the bar, which lets everyone have some group space without sacrificing the overall pleasantness of a room full of happy bar-chatter.
Good for groups
Big Downtown
For diners nostalgic for Chicago's bluesy past, The Big Downtown Chicago is the best spot to reminisce about the good old days. So don your fedora and plop down at the bar for one of The Big Downtown's gargantuan diablo burgers, layered with jack cheese, guacamole, bacon and the secret diablo sauce. Not in the mood for burgers? No sweat, there are lots of possible substitutions, like a turkey or corned beef reuben, a chicken breast sandwich dripping with Boursin cheese or a barbeque chicken pizza. You can't find any sharks in Lake Michigan, but you can eat one, or at least a part of one, with asparagus, risotto and carrots in an apricot vinaigrette. Other options that you can't catch from Montrose harbor include crab-stuffed prawns, chipotle pasta with scallops and lobster cakes. The entrees aren't as expensive as a fishing boat, but they are a bit pricey. Sandwiches run from $10-$13, while entrees start at around $15 and top off at $30.
Cheap Eats
Oasis Cafe
Be careful not to miss the little knee-height sign propped on the sidewalk outside the Wabash Jewelers Mall directing you indoors to the Oasis Cafe. Even once inside and among the bustling jewelry crowd and rows of vendors, I felt completely baffled about where or why this Middle Eastern lunchtime favorite existed among the sales of diamonds and gold. Following my gut, I walked directly to the back room to find satisfied eaters in conversation or happily alone, apparently not baffled at all.
Where to chill
Pittsfield Cafe
A visit to the historic Pittsfield Building, built in 1927, and its first-floor deli and cafe by the same name may surprise you with its elaborate five-story atrium and Spanish Gothic Revival details. While you may not expect to find a simple sandwich in typical diner fashion, you'll stumble upon exactly that once you pass through the rich marble and bronze accents in the building's main entrance and atrium. Be warned, though; you'll spend between $8 and $10 for a sandwich with (amazing) seasoned fries.
In-the-know spot
My Thai
A favorite for nearby museum-goers from The Art Institute, My Thai is great Thai. Served with Jasmine rice, the entrees run from $6 to $8 and include the standard favorites of ginger chicken, panang curry and pad Thai. Often busy with the lunchtime work crowd, you may want to try My Thai for take-out on movie nights during the Chicago Outdoor Film Festival at Grant Park. Bring your own blanket and beer and order up several appetizers such as cucumber salad, fried tofu, spring rolls and chicken satay to create your Thai picnic, keeping you healthy and happy while watching "Sunset Boulevard" at sunset.
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