Chicago has forged its fame as a great group city in a variety of ways, from its sensational off-site venues to dazzling nightlife and world-class cuisine. Its culture can match practically any metropolis, and the city’s hotel variety and breadth is almost staggering.
It’s no big surprise then that a host of superb outdoor settings and experiences can get lost in the Chicago shuffle; but for planners and groups seeking alfresco escapes, the locale is, well, a breath of fresh air.
“From our 26 miles of lakefront, to picturesque parks and high-energy music festivals, Chicago truly is unparalleled when it comes to outdoor entertainment options as a destination,” says Marc Anderson, chief sales officer of Choose Chicago, adding that its wealth of impressive tour companies is another source of local pride.
Here’s a look at some of the very best Windy City selections for outdoor excitement.
SMOOTH SEGWAYS
For newbies to the world of Segway fun, the zippy stand-up scooters can be mastered in less than 10 minutes and transform your typical humdrum hike into a memorable meander.
“For two hours, the participants of our tours are completely engaged in an interactive experience. They glide for eight miles seeing the best sightseeing Chicago has to offer,” says Timmie Cortina, ‘CEO of Fun’ for Absolutely Chicago Segway Tours. “They are informed about the history, architecture, art installations, landscape and fun stories, which make our city the best.”
Cortina adds that Absolutely Chicago will customize its tours to suit any group, and that his company actually operates the outings year-round, though in winter, of course, they are contingent upon the weather.
LIKEABLE BIKING
Chicago is actually considered one of the better biking metropolises in the U.S., and one of the most reliable ways for groups to cycle the Windy City is via Bobby’s Bike Hike, which has been in biz since 2002 and offers hiking tours as well.
The outfitter can handle groups of practically any size and offers an array of outings with different themes to suit plenty of personalities. Examples include a Lakefront Neighborhoods tour cruising by city parks and ornate mansions, a Bikes, Bites and Brews outing focusing on some favorite local flavors, and even a City Lights at Night adventure exploring some hot nightspots.
Bobby’s also partakes in some special events, giving groups the chance to join up with Critical Mass Chicago, bike the Chicago Marathon and even get their group groove on during Lollapalooza.
WATER YOU WAITING FOR?
One of the most memorable perspectives of the city is surely aboard one of the luxury yachts operated by First Lady Cruises. While the company offers numerous private event options and other possibilities, the outings focused on the city’s awe-inspiring architecture are definite favorites.
“Daytime or evening cruises with fresh-air upper decks and Chicago’s world-famous skyline as a breathtaking backdrop combine for a fun and memorable event aboard one of our private cruising yachts,” says Holly Agra, president and CEO of Chicago’s First Lady Cruises. “Luxurious interior salons with full-service bars, gourmet catering, river and lake route choices and optional architecture commentary by a Chicago Architecture Foundation docent create a one-of-a-kind party atmosphere.”
First Lady boasts a fleet of six vessels and can host groups of up to 250 for an unforgettable foray.
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For a completely different water-bound escape—one fit for adrenaline junkie attendees—consider the Seadog Lakefront Speedboat Tours at Navy Pier, offering a host of outings, including the Extreme Thrill Ride aboard the Seadog Extreme. Attendees will laugh and scream as the vessel tops out at speeds of 45 mph and undergoes breathtaking 360-degree spins.
For an active group, planners can check out Chicago Water Sport Rentals, based out of the 31st Street Harbor, an attractive expanse of beachfront, marina slips and plenty of lush plant life. Doings range from low-key kayaking and paddle-boarding to making a real splash with Jet Skis and Flyboards.
PLACES IN THE SUN
Chicago has all manner of outdoor settings for group affairs, from watching Major League Baseball at Wrigley Field or U.S Cellular Field (formerly Comiskey) to exploring the numerous city parks. Millennium Park, a 24-acre oasis by the Loop neighborhood, is a particular favorite and offers free concerts and other events at its Jay Pritzker Pavilion during the summer.
For a sun-soaked lunch affair, the nearby Park Grill at Millennium Park, with its outdoor Plaza, presents the city’s largest alfresco dining option and offers more than just fresh air and tasty fare.
“The Plaza at Millennium Park serves as the gateway to the Chicago culinary and cultural experience,” says Eddie Velazquez, the establishment’s director of business development. “All summer, visitors enjoy alfresco dining along Michigan Avenue beneath the glistening Cloud Gate [metal statue]. Featuring local live music and food events, the Plaza at Millennium Park offers a memorable Chicago summer experience.”
Velazquez adds that the prominent patio typically makes its seasonal debut around May 15 and stays open until the Chicago Marathon. It features live tunes about two to five times weekly and can host up to about 1,000 attendees reception-style.
Another awesome alfresco dining option can be found at the Art Institute of Chicago’s Terzo Piano, with elegant Italian fare and terrace seating. And a fabulous fresh-air feast can also be enjoyed at the Trump Hotel Chicago’s Terrace at Trump, a regal rooftop restaurant serving up seasonal summer fare and breathtaking vistas.
Planners searching for a spectacular event venue with a vista will be blown away by The Crown at Tribune Tower, a dramatically set space between the flying buttresses of the elegant neo-Gothic edifice. The one-of-a-kind setting can host unforgettable affairs of up to 150 for a reception and showcases 360-degree panoramas.
TOUR-IST ATTRACTIONS
Chicago shows off a gamut of organized tours that get attendees outside for the most part, though many also make indoor stops.
Chicago Food Planet Tours explore some offbeat neighborhoods, strolling between specialty foodie purveyors, local ethnic eateries and iconic restaurants. History on Tap explores the city’s yesteryear through some of its classic saloons. And the Chicago Film Tour is a whirlwind excursion highlighting the Windy City’s cinematic past, seeing 30 filming locales for movies such as Ferris Bueller’s Day Off and The Blues Brothers.
For the cultural crowd, or a group already quite familiar with Chicago, consider an outing with Chicago DeTours, with a focus on walking and bus tours highlighting culture and history. The company aims to explore the offbeat and uncharted, uncovering wonders that most residents haven’t even discovered. mf
