Show Me Chicago
A city rich in history, diversity, and entertainment, experiencing the Windy City in just one trip or during one season is not possible—even with the tightest itinerary and most comprehensive guide books. To understand Chicago, you must meet the people who work there, live there, and call it home.
Especially for working families, vacation time is precious. Knowing many families look to the tourism industry during itinerary planning, site seeing is a popular way to navigate unfamiliar territory. To make the most of your Chicago experience, consider a tour or specialized sightseeing company. With options for walking, public transit, and private transportation, each company offers a different tour structure, flexibility, and cost. From individual tours to large groups and reunions, here are three of our favorites:
Walk Chicago Tours is a privately-owned walking tour company. Designed to appeal those visitors who are hoping to avoid large groups, rushed touring methods, inconvenient scheduling, and higher costs, Walk Chicago Tours is available year round and with 12 different published tours on their website.
If your children are inquisitive, a Walk Chicago Tour is a grand way to have an edu”cation”. Pulled directly from the Walk Chicago Tours website: “We are convinced that our tours are substantial educational experiences. They are walks through history, architecture, biography, geography, and legend. At the least, they have the equivalent educational value of a school field trip.” With a mission to enable visitors to see Chicago in all its grandness, feel its energy, and know its heart, each tour is lead by a knowledgeable and experienced guide who is skilled at unraveling the many layers of Chicago’s culture and history.
Walk Chicago Tours also offers private, personalized, and customized walking tours based on the needs of the group. At least one guide is provided for every ten walkers and the per/person tour price decreases as group grows in size. Downtown tours combine aspects of Public Art in the Loop, Loop Architecture & Pedway, Millennium Park, and Tiffany Glass in the Loop. Reservations are required at least 72 hours in advance and children under age 16 are half price. All tours are both wheelchair and stroller friendly.
A free service provided by the Chicago Office of Tourism, Chicago Greeter matches visitors with residents both enthusiastic and knowledgeable about their city. Free to groups of six or fewer people, anyone can register to spend between two to four hours with a greeter on any one of 25 Chicago neighborhoods and in 40 different interest areas (from fashion to public art and ethnic influence in the city). Available one time per Chicago stay, your greeter (a volunteer matched with your interest and fluent in your native tongue) will meet you at your hotel and show you the city. During the tour, the cost of public transportation is “on the city.”
Advanced reservations are required (7-10 business days) and greeters are available on the second day (or later) of your visit to the city. For visitors on a less certain schedule, consider InstaGreeter, a 60-minute walking visit available on a first-come first-serve basis on Friday, Saturday, and Sunday (10AM-4PM, Central Time). Visitors interested in an InstaGreeter tour should check in at the Chicago Cultural Center Visitor Information Center at 77 E. Randolph Street. Also check the Chicago Greeter website for seasonal tours available at the Millennium Park Welcome Center at 201 E. Randolph Street.
Between the Chicago River that divides it and Lake Michigan that surrounds it, there’s no disputing Chicago isn’t as much a water city as its coastal counterparts. Considered a rite of passage by many, a trip to Chicago isn’t complete until you see the city by boat. For over 70 years, Shoreline Sightseeing has been navigating the city’s waterways on one vessel or another.
Expanding to a full fleet of touring vessels and water taxis, cruise options include Lake Michigan, Architecture Cruises, Skyline Tours, and Fireworks Cruises. Cruise prices and times vary based on the time of year, day of the week, and length of tour (double check the cruise website or download the free Shoreline Sightseeing iPhone app—complete with boarding times and docking locations). Military in uniform or with I.D. ride free on the Lake Michigan Skyline Tours and water taxis, and only pay a child’s price for the Architecture tours. Another money-saving tip is to bookmark the Captain’s Blog for special events, news, and periodic contests and giveaways.