© 2012; 2009 Connecting: Solo Travel Network & Lucy Schneck. Information.
Note: This article is reproduced here for inspirational value alone and will not normally be updated.
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Chicago is My Kind of Town – A Solo Travel Report

Entertaining Summer Getaway for One

Text & Photos By Lucy Schneck

Buddy Guy shook his head and looked right past me toward the door of his dimly lit nightclub. I realized I'd have to buy something to get my picture Lucy Schneck and Buddy Guy at Legends Nightclub, Chicagotaken with the musician who is a pioneer of Chicago's fabled "West Side" sound. But I didn't mind; after all, "legends" don't spring from stupidity. That picture and the CD I picked are priceless souvenirs of a very special day I spent in the Windy City.

I'll never forget my visit to Buddy Guy's Legends, the landmark blues club on Chicago's South Side. It was July 2007, the eve of the Crossroads Guitar Festival. Buddy's performance would figure prominently in the star-studded lineup of this day-long musical extravaganza co-hosted by Eric Clapton and Chicago's own Bill Murray.

Chicago has always been a crossroads for legendary musicians. This city hosts so many special events and annual festivals, it's easy to create a sight and sound combo getaway all summer long.

Determined to be a part of the one-time-only Crossroads Festival, I scratched up a cheap flight through Travel Zoo and planned to see as much of the city as I could in a weekend.

The venue for the Crossroads Festival was Toyota Park (formerly Bridgeview Stadium) on the South Side, a jumping off distance from Midway Airport.

Although Midway is about 16 km from downtown attractions, staying in the area worked fine both for sightseeing and for getting to and from Toyota Park. I was happy with my digs at the Sleep Inn. As a woman traveling alone, I appreciated the 24-hour shuttle to the airport.

I had a Fodor's Chicago guidebook that contained Chicago Transit Authority (CTA) schedules and contacts for the PACE bus, which regularly shuttles fans back and forth between Midway Airport and the Stadium. No car needed!

The CTA's Orange Line goes directly between Midway and the "Loop," Chicago's downtown core, close to many of the city's famous landmarks. Chicago is renowned as much for its central role in the development of American architecture as it is for its place in musical lore.

Music, Art, and Architecture

Soon after arriving on Friday morning I headed, by subway, for Navy Pier. This lively gathering spot is a summer favorite on Lake Michigan filled with restaurants, shops, and rides, including a Ferris wheel commemorating one built when Chicago hosted the World's Columbia Exposition in 1893.

Architecture tours by boat depart from the Pier and cruise the Chicago River into the heart of the city. More inspiring than I expected, the hour-long tour provided fascinating insights into many landmark buildings at their various stages of construction.

Meanwhile, Cloud Gate Sculpture, Millennium Park, Chicagoa cloudy morning had morphed into sun-soaked clarity, perfect for strolling Millennium Park, a haven for jugglers, public entertainments, and more spectacular art and architecture. Cloud Gate, a fascinating elliptical sculpture, reflects the city skyline and compels visitors to venture underneath where they can look up and see themselves mirrored in its gleaming chrome curves.

Chicago's tallest building, the Sears Tower looms high overall, but I was most impressed with the sharpened angles of the Smurfit Stone building and the revolutionary Pritzker Pavilion. Designed by renowned architect Frank Gehry, the pavilion is a unique band shell of curved steel with a framework spray of audio speakers hovering strategically above the audience area.

Jay Pritzker Pavilion, Frank Gehryís conch-shaped band shell. Pritzker Pavilionís revolutionary outdoor sound system mimics indoor acoustics.

Next, I came across a free bus tour and hitched a ride along the Magnificent Mile, eight blocks of exclusive stores, boutiques, and hotels lining North Michigan Avenue.

After spending the day touring, wandering, and admiring Chicago's skyline, I was duly impressed with this city's grand design but footsore and ready to call it a day. I grabbed a bite to eat and made my way back to my hotel room to rest up for the main event, my first reason for coming to Chi Town.

Solo-Friendly Festival

The next day, I hitched a ride to the Toyota Park with fans I met at my hotel. The atmosphere among audience members was warm and convivial. Beers flowed freely, bought by anybody for anybody throughout the surprisingly orderly 12-hour affair that began at noon sharp.

Eric Clapton had personally invited performers like BB King, Willie Nelson, Albert Lee, Sheryl Crowe, Vince Gill, John Mayer, Stevie Winwood, and many others. At midnight Buddy Guy led the show's stupendous closing act, and an after-party followed at his club.

As I made for my hotel on one of the procession of free busses that transported concert-goers to key subway stops and downtown landmarks, I mused upon how satisfying these few days had been. It seemed to me that all the good forces of man and nature had cooperated on my behalf. No doubt about it. Chicago in summer is my kind of town.


Summer in Chicago

Following is a sample of annual summer events that combine nicely with sightseeing excursions and help make Chicago a best bet for an entertaining, activity-filled, solo getaway.

If You Go


Tourist Info.

Chicago Transit Authority: sightseeing guide, trip tools.


Sleep Inn, 6650 S Cicero Ave. Bedford Park IL 60638.


Chicago Greeter: Chicago Office of Tourism that matches visitors with a friendly, enthusiastic, and city-savvy local for an informal insider’s orientation to the city. Free.

Chicago Architecture Foundation Walking, bus, and boat cruises.

Shoreline Sightseeing: Architectural cruise, tour: Tickets. $24-28;

Buddy Guy’s Legends, 754 S Wabash Avenue, Chicago, IL, 60605.


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