Surviving Chicago’s Market Days festival

This Saturday and Sunday, Chicago welcomes the largest street festival in the Midwest, Northalsted Market Days. It’s a two-day free-for-all of over 400 vendors, 40 concerts and drag shows, street food, booze . . . and lots and lots of half-naked men.

You see, Market Days takes place in Boystown, a stretch of Halsted Street in the Lakeview neighborhood that is home to the majority of the city’s gay bars and adult shops (plus plenty of trendy restaurants and unique boutiques for any orientation) and many of its gay residents. While the festival isn’t adults-only, you’ll definitely see some things you might have a hard time explaining to your kids (“Mommy, what’s a speculum?”).

While Market Days is predominantly a party – you’ll see more champagne-slushy stands and margarita vendors than anything else – it’s also a chance to support the local community. The money raised from the voluntary $7 donation goes to support the Northalsted Merchants Association that represents the local business owners. They also profit greatly from the event in the form of extra business during Market Days, both at their restaurants and at booths they operate at the fest. Need a new “special toy”, some knock-off designer sunglasses, a hammock for your backyard, a set of “pitcher” and “catcher” t-shirts, or maybe just an arm full of used books? Market Days has you covered with it’s eclectic collection of vendors. You’ll also find giveaways and contests; last year a friend of mine won two sets of round-trip tickets from Travelocity’s “cash-grab” booth.

If you get tired of sipping frozen cocktails, sampling from food stalls, checking out the merchandise and just taking in some of the more outlandish outfits (or lack thereof) worn by the crowd, you can head over to the concert stage where performers like En Vogue and Jody Watley will entertain, along with some local Chicago bands. For that you’ll have to pony up a bit more though. Wristbands to see the stage run from $30-$50 each.

Given the huge crowds and sensory overload you’ll experience at Market Days, the first time can be a bit overwhelming. Here are a few tips for survival.

Bring cash. In addition to the $7 donation fee, you’ll need it for any purchase you make from a vendor. There are ATM machines located around the route, but they often run out of money over the weekend.

Bring toilet paper and hand sanitizer. A few hundred thousand drunk people can really take their toll on the porta-potties. Come prepared. Most establishments along the route will not let you use their facilities unless you buy something.

Bring snacks and water. You aren’t supposed to bring booze into the fest (though it’s easy enough to sneak in) but you can bring in some water to stay hydrated and some healthy snacks to keep your strength up.

Wear closed-toe shoes. Especially as the night wears on, your chances of getting stepped on (or worse, stepping in something unsavory) increase.

Bring your cell phone if you plan to meet up with friends and make a plan to meet just inside or outside one of the entrances. Make a plan for if you get separated too. It’s easy to get distracted and wander off from your group.

Bring a camera. You’ll want to document this. Trust me.

Dress to impress. If you’re looking for a hook up, bring your A-game. You’ll have lots of competition. From skinny young guys in nothing but a pair of speedos and some feathery angel wings to older “bears” in full-on leather, you’ll see it all and if you want to stand out, you’ll need to make an effort.

Take public transportation. If you plan on drinking, and even if you don’t, taking the El (Belmont Red Line) or bus is the way to go. Cops are out in full force looking for drunk drivers, and parking around the fest is nearly impossible anyways.

Come with an open mind. Market Days is a party for sure. But it’s also a celebration, of love and acceptance. Everyone is happy and friendly. Whether you are gay or straight, male or female, you’ll be approached or maybe even propositioned, but either way you’ll have a great time.

Chicago bed and breakfasts offer a hotel alternative

When I travel outside of the US, I often try to stay at bed and breakfasts. I love the personal attention I get at a b&b. I like the inside tips I get from the owners, who are usually more than happy to sit and chat over a glass of wine and offer recommendations on where to go and what to see in their city. I prefer staying in one of a city’s neighborhoods, rather than downtown, so I can imagine what life would be like if I actually lived there. And I like feeling as though the owners really care that I am there, rather than that I am just one of the many faceless guests at a hotel. These b&bs tend to be simply decorated, with modern furnishings. They’re relaxed, informal places where I can just as easily make friends with fellow travelers as I can keep to myself and enjoy my privacy.

Unfortunately, it seems that in the states, b&bs are envisioned as places overtaken by calico and creaky antique furniture, where “wine and cheese” hour strikes fear in the heart at the thought of awkward, enforced socialization and boring conversation with the far too perky elderly innkeepers. And that may certainly be the case at many bed and breakfasts around the world. But fear not, if you’re planning a trip to Chicago there are several stylish, accommodating options for fun, relaxing b&b stays around the city. Here are just a few.

Ray’s Bucktown B&B
Ray’s garners stellar reviews on TripAdvisor and is perfectly located for anyone seeking to experience some of Chicago’s trendy nightlife. Ray’s is right in the heart of Bucktown, a young ‘hood full of bars, restaurants, and boutiques that is just over 10 minutes from downtown on the El. The b&b offers 10 rooms, most of which have pillow-top mattresses, TVs with DVD and TIVO, free wi-fi, and phones with free local and long-distance calls. Some rooms have en-suite bathrooms, and rooms in the “Annex” have access to a shared kitchen. There is a free cooked-to-order breakfast daily, free parking, free use of the house’s Mac computers, and a steam room and sauna. Rates are on par with most other Chicago hotels and range from $119-$199 a night, but taxes are only 11.9% (downtown hotel tax is $14.9%).


House 5836
House 5836, in the northern neighborhood of Andersonville, boasts “hip urban rooms” for $99-$179 dollars per night. The rooms are simpler, with just a bed and bathroom in most, but the house offers wi-fi throughout and the common living room has a plasma TV. A free continental breakfast is served daily and you can book in-room spa treatments. The house is located just off the Red Line, about 30 minutes north of downtown, in an area known for its excellent ethnic restaurants.

Old Chicago Inn
Cubs fans coming to Chicago for a game won’t find a more convenient place to stay than the Old Chicago Inn. Located in the heart of the Lakeview neighborhood, the Inn is just a few blocks from Wrigley Field and about 20 minutes from downtown Chicago. Rooms feature pillow-top mattresses, free wi-fi, exposed brick walls, and hardwood floors. Some have en-suite bathrooms. Guests can also enjoy free street parking, continental breakfast daily, complimentary dinner at nearby Trader Todd’s restaurant, and a free local gym membership during their stay. Rates range from $100-$210 per night.

Villa Toscana
Villa Toscana earns mixed reviews, but at $99-$159 a night, it might be worth taking a chance on. Located smack dab in the middle of trendy Boystown (a part of the north side’s Lakeview hood), it’s the perfect spot to crash after a wild day at the annual Pride Parade or Market Days (the Midwest’s largest street fest) celebrations, which both take place right out the front door along Halsted Street. If you’re more interested in tamer activities, you can hit the boutique shops and restaurants of Lakeview or ride the El train 25 minutes or so into downtown. Each of the seven rooms in the historic 19th century building is decorated in a different style, from the chic and sleek British Colonial to the colorful Moroccan, and offers private en-suite bathrooms and free wi-fi. A continental breakfast is served daily.