Chicago · CHICAGO SIGHTSEEING BUS & DRIVING TOURS
A guided ride is the fastest way to join up neighborhoods that are miles apart. These 15 cover the crime and mob routes, the general sightseeing loops and the small-group minibuses, with prices and how often you get out.
Explore Chicago’s mob past by coach, with Al Capone sites, the Biograph Theatre, St. Valentine’s Day Massacre site, and Nitti’s vault.
“Great tour guide! Windows of bus were fogged, couldn’t see anything but stories were great! Good length but they need to fix the windows in winter with fogging!”
Explore Chicago mob history by bus, from the St. Valentine’s Day Massacre site to Dillinger’s final steps, with live stories and crime artifacts.
“Jay was a great tour guide! Really informative! Really enjoyed the tour!! The bus was quite loud and squeaky and it was hard to hear even with her speaker on full volume!”
See Chicago’s skyline, landmarks, parks, and neighborhoods on a two-hour minibus tour with live stories and four photo stops.
“great way to see the city, it felt like a private tour! our guide was very knowledgeable, friendly, & fun!”
Ride Chicago’s Prohibition-style Barrel Bus to three craft breweries for tastings, brewery stories, and a relaxed half-day without driving.
“Fun bus, fun talking to all of your fellow travelers. Each stop was a different experience but you feel welcomed and wanted at each place. They knew we were coming and were ready for the group to walk in. Very fun afternoon.”
Explore Chicago’s Prohibition past at three or four speakeasies on a lively walking or neighborhood bus tour with drinks extra.
“Amazing historical and highly entertaining tour of Chicagos dark past! Our tour guide Jonathan was absolutely spectacular and his commentary flowed effortlessly as well did the booze at each of the fine establishments we visited throughout the city. By far the best tour and guide in Chicago. We plan on taking this again and will bring family and friends anytime they visit the city.”
Review of Chicago’s small-group driving tour, architecture cruise, Cloud Gate, Skydeck, hotel pickup, costs, timing, and practical tips.
“Joe was an outstanding guide and host. Took great care of us and was extremely knowledgeable about the city’s food, history, architecture, film scenes, etc. Architecture tour on the river was very entertaining and informative.”
Explore Chicago’s darkest stories by bus, from the Devil Baby and Al Capone to haunted theaters, cemeteries, and ghost-hunting tools.
“The bus never showed up very 😡 we were looking forward to a good time and was very disappointed. Very unprofessional and having a hard time recovering my money”
See Chicago’s key sights by climate-controlled minibus, with photo stops and an optional 75-minute architecture cruise on the river.
“Informative as well as humorous - good driver - good way to see downtown highlights as well as the nice area near Lincoln Park. Highly recommend.”
See Chicago by river and open-top bus over two days, with skyline views, live architecture commentary, flexible stops, and 20% savings.
“Bus driver took or drop us off at Alder Planetrium. We walked to the door and the planetarium was closed ( 12 noon) not open on that day. But the bus driver had already left and the next one was for another 30 mins. We ended up taking a public transportation to go back to our Stop #1 because we still have to drive to ORD for our afternoon flight. Terrible experience!”
See Chicago at night from Willis Tower, the Ledge, and a skyline cruise, with downtown pickup and a small-group guide.
“Organisation désastreuse. Visite prévue de la rivière chicago annulée car le guide s est trompé. Remplace par 1 visite sur le lac non programmé fait en dernier minute et sur 1 créneau horaire en dehors du créneau horaire prévu. Des allés retours pour pallier cette incompétence et cette désorganisation qui nous ont fait perdre notre soirée.”
Explore Chicago gangster lore, ghost stories, Frank Nitti’s vault, Death Alley, and Loop landmarks from a comfortable tour bus for $49.
“The tour guide was very informative. Very sweet. It was a fun and amazing experience. Glad we had this opportunity. Everything was timed perfectly.”
See Chicago lit up at night with Skydeck, a river cruise, Cloud Gate, and a private-style driving tour for up to seven.
“The privacy of being taken around town. The boat ride was empty besides us. Probably could have done the two attractions separately just as easy. You can walk anywhere in Chicago with ease. Glad we did the boat ride and the observation deck!!”
See Chicago by open-top bus, then rise 1,000 feet at 360 CHICAGO with flexible two-day access and 20% savings.
“Complete and professional tour. It's a shame that French is not available.”
See Chicago by minivan and riverboat on a four-hour small-group tour with skyline views, architecture, Cloud Gate, and downtown pickup.
“Our guide was on top of his game and gave us a lot of unique facts about the city I didn’t know and I grew up in the state.”
See Wrigley Field, Millennium Park, Route 66, Lake Michigan, and more on a flexible private Chicago driving tour with hotel pickup.
“Deen was the best tour guide, very humble, jovial and very knowledgeable. He got stuck in traffic but not only informed us well in advance but also gave us more than extra time to visit places and made our day. We highly recommend Deen!”
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