Frankly, you’re either one of those people who likes to look over the edge or you’re not – there’s really no in-between. You either press your forehead against the window of the skyscraper to stare straight down or you stand a safe two feet back and admire the vistas from a far more reasonable position.

Aimed squarely at those visitors leaving their headprints on the glass of the Willis Tower, the Ledge at Skydeck takes that impulse one step further, so to speak. Thanks to some architectural wizardry, sightseeing daredevils no longer need to stop at the rail of the 103rd floor perch, but instead can continue out into one of the glass-encased pods protruding from the Skydeck wall on the west side of the building to get a true 360-degree view – including the people and traffic going about their business a stomach-turning 1,353-feet directly below.

In addition to the panoramic viewing platform, the Skydeck also features a variety of interactive and educational exhibits highlighting some of the most noteworthy civic and cultural touchstones in the city’s rich history. But despite the generally stunning views and the compelling story of Chicago and its citizens, don’t be surprised if most of the chatter among your fellow passengers on the high-speed elevator trip back to street level centers on the fascination of living on the Ledge.             

Back down on terra firma, get another view of the Chicago River from the far less harrowing perspective of the outdoor patio at nearby Rivers, where you can rub elbows with the decompressing financial pros and sample a wide-ranging menu of American favorites while watching the passing tour boats and gazing at the buildings – this time from the ground up. 30 S. Wacker Drive. 312/559-1515.

As third-generation owners of Mercury, Chicago’s Skyline Cruiseline, which is celebrating its 76th season, Bob and Holly Agra know a thing or two about Chicago’s waterways. In fact, you would be hard-pressed to find a more entertaining way to spend your time in the Windy City than aboard one of Mercury’s fun, family-friendly cruises. 312/332-1353.

If luxury is more your speed, opt for one of the company’s Chicago's First Lady Cruises. The official vessels for The Chicago Architecture Foundation, the elegantly-appointed 1920s-style yachts offer comfortable open-air and air-conditioned seating for the 90-minute river cruise showcasing more than 53 historic and architecturally significant sites. Test out the waters aboard the company’s newest and largest addition, Chicago’s Leading Lady. The $3.2 million 98-foot steel vessel joins sister yachts, Chicago’s First Lady, Chicago’s Little Lady and Chicago’s Fair Lady. All cruises depart from Michigan Avenue and Lower Wacker Drive on Chicago's Riverwalk. 800/982-2787.

This weekend brings two world-class art festivals - just two blocks apart. Produced by the nation’s leading festival promoter Howard Alan Events, the 20th Annual Chicago Tribune North Michigan Avenue Art Festival is consistently voted one of the top 100 outdoor juried art festivals in the country by Sunshine Artist magazine. This wildly popular three-day event, running July 8th-10th, features 200 of the country’s leading artists who will line North Michigan Avenue, opposite the Wrigley building, along the Chicago River. All artists will be present for the duration of the festival. For additional information visit www.artfestival.com or 561/746-6615.

Two blocks away, the Gold Coast Art Fair at Grant Park is the third oldest and by far one of the most well attended art festivals in Chicago. Free and open to the public, the Gold Coast Art Fair showcases the work of more than 350 juried artists from around the world with prices ranging $25 to $25,000. An exciting addition to this year’s festival is the Glunz Family Wine & Beer Garden, which will be serving beer, wine and sangria throughout the festival weekend!  A portion of proceeds from the Wine & Beer Garden benefits the Chicago Special Olympics.  Incredible artwork and demos, live music, great food, fun activities for kids, and speed-dating from exhibiting and visiting artists make this a destination for all! Located at Grant Park’s Butler Field at the corner of Monroe and Lake Shore. Drive. Open July 9th-10th from 9am-7pm. For more info, visit www.gcartfair.com.