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6 Tours First-Time Chicago Visitors Should Experience

Sail, ride and walk your way through the Windy City.

U.S. News & World Report

6 Tours First-Time Chicago Visitors Should Experience

18 Street Bridge, St. Charles Air Line Bridge, Chicago, Illinois.

Experience all that Chicago has to offer.(Getty Images)

Guided experiences are as diverse as Chicago's attractions, parks, restaurants and neighborhoods. U.S. News asked local experts for their take on the best tours the city has to offer. Here's what they said.

By Boat

Tall Ship Windy offers several kinds of tours to suit visitors of all ages.(Courtesy of Tall Ship Windy)

Water has shaped Chicago since its frontier beginnings when, in 1803, Fort Dearborn first stood at the confluence of the Chicago River and Lake Michigan, now Michigan Avenue. Today, scenic boat tours cruising the lakefront and river give visitors essential insight into the city’s identity.

“Seasonal Chicago River architecture boat tours through the canyon of landmark skyscrapers is a tradition for Chicagoans, and an absolute must for first-time visitors,” says Steve Grillo, head concierge at The Peninsula Chicago.

The Chicago Architecture Foundation partnered with Chicago’s First Lady Cruises to provide in-depth explanations of architectural styles represented by more than 50 riverbank buildings and bridges. Tours cost $46 for adults. Affiliated with the Chicago History Museum, Chicago Line Cruises also covers buildings’ architecture anchored by historic stories about the city’s development. The 90-minute Chicago History Cruise costs $43 for adults.

“Chicago is designed around its waterways and parks, so it’s important to experience the city through them first,” says Michael Kelly, general superintendent and CEO of the Chicago Park District. “Lake Michigan’s sheer size just blows first-time visitors’ minds, some comparing it to an ocean and our foreign visitors calling it a sea.”

Lake Michigan architecture cruises and leisurely dinner cruises operate year-round. Families love the seasonal Great Lakes pirate-themed schooner sails aboard Tall Ship Windy ($30 for adults), and the wild, wet thrill rides on speedboat Seadog ($31.95 for adults). Active options are Kayak Chicago’s guided paddle architecture tour or the lake paddle tour; each tour costs $69.

By Bus

Big Bus Chicago.(Courtesy of Big Bus Chicago)

Bus tours cover a lot of territory, efficiently highlighting top city attractions, including the John Hancock Center, The Magnificent Mile, Navy Pier, Millennium Park, the Art Institute of Chicago, Museum Campus and Willis Tower.

“I’m a big fan of these informative tours because when I moved to Chicago from overseas, they were the best way for me to learn about the city quickly,” says Onal Kucuk, general manager of Hotel Lincoln.

Gray Line Chicago tours offer comprehensive two- to four-hour excursions, from $29, as well as a shorter holiday lights tour during the Christmas season. See It All Tours takes small groups for two-hour guided tours in comfy minibuses for $35.

Chicago Trolley & Double Decker Co. and Big Bus Chicago offer flexible tour-transportation options that allow visitors to hop on or off at different points of interest.

Waldorf Astoria Chicago concierge Judson Corrie says, “Purchase a one-, two- or three-day Big Bus ticket to explore the city at your pace. A guide onboard provides an entertaining fact-based tour.”

Open rooftop Big Buses circulate among 14 downtown stops. Valid for six months, one-day passes are $36, and children younger than 4 ride free. Free Spanish language pre-recorded tour headsets are available on some buses.

By Helicopter

The Chicago Helicopter Experience looping above the lakefront provides the ultimate city overview. From above, visitors easily see Lake Michigan’s vastness and Chicago’s expansive parks and boulevards system first envisioned in architect Daniel Burnham’s 1909 Plan of Chicago. During the 15-minute tours, the pilot points out famous landmarks and relays Chicago history. In summer, choppers hover over Navy Pier during fireworks displays.

Flights start at $148 a person and run year-round.

On Wheels

Bobby's Bike Hike Chicago.(Courtesy of Bobby's Bike Hike Chicago)

Chicago has more than 200 miles of on-street bikeways connecting neighborhoods, parks and beaches. The roughly 18-mile paved Lakefront Trail threads along Lake Michigan’s shore. It’s part of the tour routes that Bobby’s Bike Hike and Bike and Roll take. Rent bikes, or take seasonal tours starting at around $40 for adults.

“You’re never too old to ride a Segway, ever,” says Tim Batchelder, head concierge for The Talbott Hotel.

First-time visitors enjoy Absolutely Chicago Segway Tour's two-hour lakefront architectural tour, which costs $65.

Pedal like a local through Chicago neighborhoods on the new The 606 trail. Kelly says, “We transformed an abandoned railroad track into an elevated park along a 2.7-mile, paved thoroughfare linking the Wicker Park, Bucktown, Logan Square and Humboldt Park neighborhoods.” There’s multiple Divvy bike-share stations at trail access ramps. A 24-hour pass for unlimited 30-minute rides is $9.95.

On Foot

Here’s some of Chicago’s most popular guided walking tours:

  • Free Chicago Greeter tours led by local volunteers are designed around 40 special interests and wander through 25 neighborhoods. Offered in more than a dozen languages, the two- to four-hour walks require advance online registration. But, not so for the one-hour InstaGreeter free, year-round tours of the Loop and seasonal strolls through Millennium Park. “Causal and low-key, these tours are like having a friend or family member show you around town,” says head concierge Mark Roberts of Thompson Chicago.
  • For architecture buffs: The Chicago Architecture Foundation’s more than 85 tours explore the city’s architectural legacy and evolution exhibited in its skyscrapers, landmark buildings, interior decors, outdoor sculptures and parks. Led by highly trained volunteer docents, tours start at $15. Guided foreign-language tours are offered, and some are self-guided audio headset tours. The Chicago Athletic Association showcases the 1890 hotel’s influence in Chicago sports history through the concierge-led free public tours at 2 p.m., Monday through Saturday.
  • For art lovers: Stroll through galleries in Chicago’s largest arts district River North on the free Chicago Gallery News tour held Saturdays year-round. Docents explain the workmanship in the world’s largest Louis Comfort Tiffany stained-glass dome crowning the landmark 1897 Chicago Cultural Center during free tours Wednesday through Saturday at 1:15 p.m.
  • For foodies: Join the Chicago Food Planet tours tasting their way through the Gold Coast, Old Town, Bucktown, Wicker Park, Lincoln Park and Chinatown neighborhoods from March through November. Most tickets range from $42 to $59. Hop on the giant barrel-shaped bus for The Barrel Run craft brewery and distillery tasting tours. Tickets cost $65.

On Your Terms

For those who want to experience the city their way with a guide in a chauffeured luxury vehicle, there’s Chicago Private Tours. Experiences priced by group size start at $319 for one to five guests.

Concierge Supervisor Bernard Runo of Sofitel Chicago Magnificent Mile says, “The tours are customized to visitors’ interests, and guides are fluent in several languages.”

To experience more of what Chicago has to offer, check out the U.S. News Travel guide.

Corrected on March 1, 2017: A previous version of this story misspelled Bobby’s Bike Hike.

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