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Have dice, will travel

We devise a game that asks: Can our writer really go last minute—and, more important, can he really let himself go?
Image: Chicago
Unwind by seeing Second City's iconsGetty Images
/ Source: Arthur Frommer's Budget Travel

A roll of a die sent me to Chicago. In a quest that was one part journalistic inquiry, one part sadistic lab experiment, the editors of Budget Travel summoned me to their offices with a packed suitcase and handed me a clear mission: Find six of the Internet’s best last-minute travel offerings, assign each one a number, roll a die, and go.

Scoring deals was the easy part: Site59, for example, was selling round-trip airfare from New York City to Miami, plus two nights at the Franklin Hotel in South Beach, for $350. And it also had round-trip airfare to London—plus two nights in a West End hotel—for an amazing $257 (including taxes). If only I’d rolled a 1 or a 2.

Hotwire’s “Weekender” found me a two-night trip to Madison, Wis., for $302 (just roll a 3), and Priceline could get me to New Orleans (if I rolled a 4). Taking up the number 5 spot was Digital City, which located a sale to Los Angeles for $178.

Number 6 was Continental’s $109 round trip to Chicago, through the alerts on Smarter Living. Priceline rejected my bids for a hotel there at $85 a night, but Hot Rooms, a Chicago-specific last-minute site, got me a room in a three-star hotel—the Congress Plaza—for $99 a night. The Windy City weekend total: $307. Thanks to that lucky roll—6!—that’s where I was headed.

And then…dread. To be honest, I’m not the most spontaneous person in the world. My idea of impetuousness is to buy a pack of gum as I’m checking out at the supermarket. When traveling, I plan everything in advance, from where I’m going to eat breakfast to which museums I’ll peruse (and which ones I won’t because they’re not near where I want to eat lunch) to making sure the hotel is accessible to the airport (and near dinner). On this spur-of-the-moment trip, could I truly let go? Could a kind of travel Zen overcome my need for control? And, most important, could I just have a fun weekend?

I started answering that question by grabbing a cup of coffee and wandering over to the Art Institute to listen to four kids bang on huge pickle containers. Suddenly I was overcome by the need to make plans. Although I’ve learned that spontaneous, random conversations with strangers can only lead to long, dull conversations with strangers, I chatted up people for tips on how to spend the rest of the day. As it happened, the city was sponsoring a screening of Psycho at the newly rebuilt Soldier Field for just $2. Score one for spontaneity.

Of course, in Chicago, Mother Nature has an equally impetuous side. By the time the movie started, the temperature had dropped. I did get to see Janet Leigh in a bra and panties in the opening scene, but by the time she was getting stabbed in the shower, I was having a burger and a $7 pitcher of beer indoors at Boston Blackies, north of the Loop. Yet the thrill of watching a film in a Chicago landmark lingered longer than the chill.

A conversation with a stranger at Blackies yielded a tip about a brunch place in Bucktown,  the Bongo Room. Forget spontaneity, I was told; for salmon eggs Benedict this good, you’ve got to plan ahead. The next morning found me in line at 8:30 a.m.—but I was first.

After buying a handmade belt for my wife at Hanger 18, a hip Roscoe Village store, I chewed the fat with a local named Rindy. (What kind of name is that? “I tell everyone, ‘That’s Cindy with an r,’ but then they call me Crindy.”) I explained to her about my attempt to “let go” after my fateful roll of the die and how my urge to preplan sometimes got in the way. Rindy was my opposite. When she needs a vacation, she just hops in the car and drives. Once, she ended up in southern Illinois. Another time, Wisconsin. She confessed that her spontaneity limits her: “I don’t see too much. I should probably plan ahead more.”

Maybe not. Now that I’ve tasted impromptu traveling, I understand the draw of Rindy’s road trips. Sure, I did plenty of aimless searching, but I also got to watch Janet Leigh on the big screen, eat a great brunch in a happening joint, and see one of America’s most beautiful cities.

The problem with going with the flow, of course, is that sometimes the flow goes somewhere you’d rather not. But, like unrequited love, it’s always better to have gone at all.

Chicago

  • Lodging: Congress Plaza Hotel 520 S. Michigan Ave., 800/635-1666, www.congresshotel.com
  • Shopping: Hanger 18 2040 W. Roscoe St., 773/529-3349
  • Activities: Art Institute of Chicago 111 S. Michigan Ave., 312/443-3600, admission $10, Tuesdays free, Soldier Field/ Chicago Park District 312/742-7529, www.chicagoparkdistrict.com
  • Food: Boston Blackies 164 E. Grand Ave., 312/938-8700, Bongo Room 1470 N. Mil-waukee Ave., 773/489-0690

—Gersh Kuntzman