Chicago - Girls On The Town

Through a happy coincidence, I, ten years removed from living in Chicago, and my Boston roommate Jen landed at O'Hare within a day of each other, to impose on our friend Erika's hospitality and explore the city in between Jen's grad school interviews, Erika's work schedule and my (gasp!) ten-year high school reunion. The three of us got to know each other in our goth club days, and as befitting smarty arty girls, we've got good jobs working in high-prestige/low-pay creative fields (publishing, design, architecture) so live for the cheap-yet-fabulous treasures that are in such abundance in Chicago.

From our home base, Erika's South Loop digs, we ranged North, West, and down the block, in search of good food at (mostly) reasonable prices, theatrical late-night fun that didn't involve cheeseball nightclub bump-and-grind ('cause we're so over that scene) and the perfect view of that iconic skyline. (Hint: Skip the Sears Tower and get yourself to a couple of well-placed El platforms.) Shopping too, of course: Jen was in need of punk show-worthy boots, I needed to outfit myself for the big reunion, and Erika was happy to be the devil on our shoulders, encouraging those sensible splurges that always require a second opinion.

Quick Tips:

Chicago offers plenty to do and see within a few blocks of your Loop hotel: world-class museums, jaw-dropping architecture, more restaurants than you could ever eat at and, of course, enough high-end shopping to bankrupt Paris Hilton. But you'd be doing yourself a disservice by limiting your Chicago experience to Michigan Avenue and Navy Pier. The Chicago Transit Authority is happy to help you figure out how to get to any place in the city:
If you call 836-7000 from any Chicago area code, (312, 773, etc.), you can get door-to-door directions right from the source.

The best way to find out about goings-on is in the local alt weekly newspaper The Reader, which devotes one of its four sections to arts listings ranging from national tour stops at the United Center to off-the-cuff  shows at blink-and-you'll-miss-'em storefront theaters. The Reader also has plenty of restaurant listings and reviews, and Chicago is pleasantly free of the national chains that can rob big cities of any local character.

Make a point of stopping by the Chicago Cultural Center in the old public library building at 78 E. Washington in the Loop. It's just a few steps from the must-see Millennium Park (it's reflected in half the photos you'll see of The Bean) and there's a great Visitor Information Center on the ground floor - there you can find out about city-wide events and festivals (even in the darkest winter months, the Mayor's Office of Special Events has something going on), find out what exhibits are on at local museums, and pick up CTA maps. The building itself is worth a visit, especially the Tiffany stained glass dome on the top floor and ground-level art galleries. The cafe is a great place to grab some coffee and pore through the stack of brochures you just picked up, and your copy of this week's Reader.

Best Way To Get Around:

Chicago's layout, thanks to the fire that wrecked most of the city in 1871, is orderly, thoughtful (no perfectly East-West streets, to avoid total sun-blindness at dawn and dusk) and easy to navigate, no matter what mode of transportation you choose. The city is oriented around the intersection of State and Madison, and streets numbers increase from there, in all directions, to the edge of the city limits. Street signs at major intersections will not only give you street names, but numbers, so it's easy to tell how far you've gone in any direction. And if all else fails, there's a Great Lake over there to the East that'll help you orient yourself.

By Bike (Don't laugh!)
Chicago's got miles of beachfront bike paths, super-flat Midwestern topography, lots of wide streets that don't pinch cyclists between traffic and parked cars, and a ton of citywide infrastructure, including lots of bike racks in and around the Loop. If you're visiting during suitable weather, the only downside to exploring by bicycle is the sheer size of the city - more than 200 square miles in all. Cycling enthusiasts would do well to plan their trip to take advantage of the annual L.A.T.E. (Long After Twilight Ends) ride, a midnight-to-sunup 25 miles through car-free streets ending with breakfast in Grant Park.

By Bus or Train
Chicago's elevated train system (the El) is practically a tourist attraction in itself, and it covers most of the major areas of the city pretty effectively. What neighborhoods don't have a nearby El stop make up for it with bus service. There are fewer options late at night, but the Red and Blue lines run 24/7, and they'll get you between the Loop and some great nightlife spots, so don't despair, you New Yorkers. will get you an all-week train-and-bus pass - one of the best values in the city. Single rides cost .75-.00, depending on mode of transit and method of payment.

By Car
Do-able, certainly, but you might find yourself shut out of the best spots in the city for lack of parking at less-than-extortionate rates. A car is helpful if you're wary of public transit late at night, when there are fewer people around, or if you want to visit the 'burbs. If you're staying in the 'burbs (not recommended), your best bet is to drive to the nearest major CTA hub or Park'n'Ride.

Leona's is a local family-owned (and family-friendly) chain of restaurants in the Chicago area specializing in homestyle Italian cooking and pub food. Its menu and atmosphere are quintessentially Midwestern - generous portions, significant amounts of cheese, and friendly waitstaff who'll happily help you navigate the seemingly-overwhelming number of dining options. Even the menus are informal, descriptive, and humorous. (Have you ever been somewhere that had five varieties of garlic bread? The house "Kickass" garlic bread is your best bet - it may seem bare bones, but it'll keep you from filling up on bread and not having room for your giant bowl of pasta.)

Our group of three stopped in at the Lakeview location (near great shopping around Clark and Belmont and down the street from the Vic theater) for lunch, intending to fill up on starch before a long evening of bar-hopping. We ordered family-style, starting with garlic bread and massive mozzarella sticks, and splitting the Ravioli Duo (choose two fillings and two sauces from a list that yields a dozen or more combo options), and a mess of small dishes from the "Crazy Lena's Side Dishes" menu - sides are included with entrées but can be ordered a la carte as well. They're a great way to sample several dishes in a single meal and the best way to get a salad-soup-and-pasta multicourse meal without having to let out your belt a couple of notches halfway through dinner. We took a pass on alcohol (there's a short beer and wine list, and some locations have full-service bars) in favor of a round of Red Zinger Lemonades, served in bucket-sized tumblers with sugar-crusted rims.

A massive lunch for three, with soft drinks, came to just under $50 before tip. We skipped dinner altogether that evening, with not a single stomach grumble between the three of us. Though you'll hear other worthy names mentioned ahead of Leona's when you're looking for that famous Chicago-style deep dish pizza, Leona's makes them too, as well as a great crispy thin-crust variety. The pizza menu, too, has an insane number of choices - swap out tomato sauce for pesto if you're ordering thin-crust. I got a small thin crust with pesto sauce and black olives on our way out the door, just so I could snack on cold slices for the next couple of days.

The last of our party of three arrived at O'Hare well after the usual dinnertime window, when People morphs from a restaurant into a world music lounge and bar, but we decided to see if we could wrangle some tapas out of the all-but closed kitchen to go along with a generous pitcher of red sangria (around $20, easily split three ways, thick with tasty bits of green apple).

Anyone who's worked in restaurants knows that showing up when the kitchen's about to close will often get you the worst service any restaurant had to offer, but we were graciously accommodated by the waitstaff and the kitchen. Though we were given a somewhat truncated menu, there were plenty of both hot and cold tapas to choose from - we ordered Hongos Jerez, Spanish tortilla (which came with a fantastic aioli) and something involving steak which the meat eaters raved about.

When we arrived, a live three-piece jazz ensemble was playing a set - good music, but at a volume that effectively killed conversation. As the first pitcher of sangria gave way to the second, the live music ended, the music switched over to Radiohead, the tables emptied out (except for ours - we were allowed to linger in peace, even when our waiter's shift ended and he handed us over to his replacement) and the bar filled up. We could have easily gone for a third pitcher, but we were still hauling luggage along with us, and had a bit of a trek on the Blue Line before getting home. This shortened evening was our first in Chicago, and set the perfect tone for the rest of our trip.

I don't, as a rule, wait in line for Sunday brunch. The Bongo Room just may be worth it, though, and you can avoid the worst of the wait by visiting on a weekday or showing up early to beat the hangover crowd. The most elaborated items on the brunch menu are only served on the weekends, but the daily breakfast menu offers plenty to choose from, and avoiding the line is absolutely worth it.

The Bongo Room is located near Ground Zero of Wicker Park, one of Chicago's most hipster-dense neighborhoods crammed with boutique shopping, see-and-be-seen coffee shops, and over-designed restaurants. If you do arrive during peak brunch hours, add your name to the list and kill time in Reckless Records, or Myopic Books, or any of the other nearby shops. The hours (yeah, it could easily be that long) will fly by.

When you are finally seated (I'm serious - don't say you weren't warned about that wait), it'll be in a bright open space with cheerful green walls that feels like early spring no matter how lousy the weather outside. The tables at the back of the room are on a slight rise, great for the people-watching you'll want to do.

Once inside, you'll be confronted with the classic Brunch Dilemma: Sweet or Savory? The Bongo Room serves up excellent renditions of the standard eggs Benedict or Florentine, and a great avocado-heavy breakfast burrito, but most diners seem to zero in on the rotating menu of pancakes. These are no pedestrian pancake creations - the amateur-hour chocolate chip or blueberry you can find at any diner. They're banana-Heath bar, or key lime cheesecake flavored, and served doused in super-sweet syrupy toppings. Highly recommended for those sweet of tooth.

The Alley: a store named for its back entrance, a relic of the days when this was a single shop on the block, and not the hub of what's now called, unironically, the Alternative Shopping Complex. The Alley and its spin-offs set the tone for many nearby businesses, making the few blocks surrounding Clark and Belmont a must-visit destination for the subculturally-inclined. It can be hard to believe, leaning on the hearse parked outside Punkin' Donuts, that you're less than a mile from Wrigleyville and all it's sports bars but hey, Chicago is nothing if not a city of neighborhoods.

Folks of a certain age might call The Alley and its sister stores a Head Shop, but I call it one-stop shopping for all your scenester makeover needs: Body jewelry (and on-site piercing), Manic Panic, leather jackets (including iconic decommissioned Chicago cop coats - a perfect, though pricy, souvenir), more things with skulls on them than you can count, and a shoe section that yielded victory in Jen's years-long mission to find the perfect pair of punk rock boots. In fact, she found two pairs.

The buying of boots took us, quite literally, hours - trips to the window display to point out possible pairs, lots of walking around to test out heels, and a lot of buckling and unbuckling. Joe, the guy manning the shoe section that day, was astonishingly patient and helpful, and the rest of the staff were extremely friendly, as well - one clerk even helped us dig through a bin of refrigerator magnets, looking for something Erika had seen in the store more than a year earlier.

Once you've outfitted yourself adequately, the rest of the Alley shops will help you make sure nobody finds out you're a poseur: Augment the pricey Alley clothes with more affordable vintage from Jive Monkey, add some appropriate bling at the Silver District, redecorate your apartment from scratch at the Architectural Revolution, and make sure you're wearing the right stuff under your clothes with a swing through Taboo Tabou.

The Alley is located at the intersection of Clark and Belmont on the near north side of the city. It's easily accessible by El, a block from the Belmont stop on the Brown or Red line. If you must travel by car, take Lake Shore Drive to the Belmont exit, and head a mile west. Then drive around for hours looking for on-street parking. Take those tow-zone warning signs seriously.