Tours and Trips in Chicago

Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide for 2 hours as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.

Stroll through Chicago's winter streets, lit up for the holidays, on this 3-hour walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows at Macy's, and ice skating at Millennium Park. Follow your local guide on a walk down festively decorated State Street and sample generous tastes of classic Chicago foods and holiday treats. Seasonal craft beer tastings will help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.

Explore the past and present of two Chicago neighborhoods on this guided, 2.5-hour walking tour. Visit Wicker Park, once infamous as a home for gang bangers, drug addicts and prostitutes, it's now widely considered one of the trendiest neighborhoods in America. Then walk through the West Town district of Noble Square, formerly known as 'Old Polonia.' Along the way, see many popular points of interest and enjoy food tastings at some of the area's best eateries.

You and a guest will soar above Chicago's skyscapers, shoreline and iconic sights on a private, 15-minute helicopter tour of the city. Communicate with your personal pilot through a two-way headset, and personalize your flight to your interests. Capture extraordinary aerial images of the city scape as you fly past Lincoln Park and Lake Michigan, then spot Willis Tower, the John Hancock Building and the gleaming Trump Tower. Bank high above Millennium Park and enjoy views of the Windy City from the comfort of a climate-controlled private helicopter. Tour route is subject to change.

Enjoy a thrilling tournament and a sumptuous royal banquet with tickets to Medieval Times Chicago and spend an evening in a castle lined with armor, artifacts and coats of arms. Take in show-stopping displays of falconry and horsemanship as you linger over a four-course meal served by medieval staff. Listen to hooves pounding in the Grand Ceremonial Arena, cheer for your knight through a series of jousting matches, then see Queen Maria Isabella crown the evening's champion with plenty of pomp and fanfare.

The Museum of Science and Industry Chicago is the largest science museum in the country.  Housed in the only remaining building from the 1893 World's Fair, MSI is a Chicago must-see!  You'll experience 14 acres of hands-on exhibits and have the chance to stand before a 40-foot tornado; take a run in a human-sized hamster wheel; navigate through a mirror maze; board a 727 hanging from the ceiling; transmit your pulse to a 13-foot, 3-D beating heart; and much more!

See Chicago your way on this private guided tour. Up to 12 passengers can take part in this tour that features the parts of Chicago that you are most interested in. Your driver will take you to select points of interest, while your guide fills you in on the history and insider information of the sights--all at your speed, according to your preferences.

Get an insider's look at the Windy City's most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city's top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.

One of the country's largest science museums, the Museum of Science and Industry is a popular Chicago highlight. Home to 14 acres of interactive activities, exhibitions, and games, the museum is an entertaining destination for visitors of all ages. Save yourself any hassle by booking your admission in advance. Your tickets also entitle you to attend one film at the on-site Giant Dome Theater, where a five-story screen and state-of-the-art laser projection system make for an exceptional movie-watching experience.

Bring the kids to  LEGOLAND® Discovery Center in Schaumburg for a day of brick-building adventure. With 30,000-square-feet of space this family-friendly attraction has activities for everyone: from an interactive pirate-themed playland to a factory tour where you can actually see how LEGO bricks are made. There's even a mini replica of famous Chi-town landmarks made from nearly 2-million LEGO pieces.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you'll step back to the roaring 20's, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Sample craft beer at several locally owned Chicago establishments during a 3-hour guided walking tour. Explore the Bucktown and Wicker Park neighborhoods on foot, stopping to learn about the city's historical architecture along the way. Visit bars dating back to the 19th century and enjoy tastings equal to four beers - with the option to book the tour without beer tastings, if you wish. Bonus: pair your brews with a Chicago-style hot dog!

When it's time to refuel in the Windy City, stop into Hard Rock Cafe Chicago for a tasty, filling, and enjoyable meal of classic American fare. Choose from a 2- or 3-course menu that's themed on musical styles all served with dessert and a drink. When ordering from this popular prix-fixe menu, entrees include salmon, steak, chicken, or a half-rack of hickory smoked ribs, and once you've enjoyed each succulent bite, stick around to explore the collection of music-themed memorabilia.

Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city's most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.

Explore the affluent North Shore of Chicago on this guided, half-day sightseeing tour. Enjoy a scenic ride along Lake Michigan, passing by four cities, plus majestic mansions and historic American homes. Stop in downtown Evanston, with a visit to the Shakespeare Garden and the campus of Northwestern University. See other popular locations like Rogers Park, Loyola University, the Bahai House of Worship, the Chicago Botanic Garden and much more. All entrance fees plus a Chicago hotel pickup and drop-off are included.

Travel back in time to the 1920s, when Chicago was a prohibition era hub for lively speakeasies. Your guide, a local historian in period dress, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone. Order prohibition era cocktails (additional cost) and listen to stories about bootlegging and racketeering in 1920s Chicago. Guests are welcome to come in period dress.

Get a taste of Chicago's best Italian food on this guided, 2.5-hour culinary walking tour. Join an expert foodie guide on a leisurely stroll through the vibrant Magnificent Mile and Gold Coast districts, home of the Chicago Italian beef sandwich, deep-dish pizza and much more. Visit restaurants like Al's Beef, known for overstuffed Italian beef sandwiches and hot dogs; Uno Pizzeria and Grill, the original home of the deep-dish pizza and Portillo's, for the best meatball sub in the city. All food tastings and any necessary entrance fees are included.

Experience Chicago with a private guide and seperate driver in a luxury SUV. The tour is fully customizable with different itineraries to suit your tastes and interests. Visit Wrigley Field, peruse Fulton Market, and bring your camera for famous skyline views. Then get of the beaten path and venture into local neighborhoods. This tour is ideal for visitors who value privacy and who are looking for a personalized experience.

Explore stunning, trend-setting Chicago at your own pace - and in your own language. Choose from Arabic, French, Mandarin, Russian, and more, and get personalized attention from your own multilingual guide. Build your own itinerary using a tailor-made list of stops - from Lake Shore Drive and Millennium Park to under-the-radar local neighborhoods - and customize your own sightseeing trip just as you like it.

Chicago's mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you'll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You'll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine's Day Massacre.