Unusual Tours in Chicago

Everyone knows about the architecture cruise, the double-decker buses and the bike tours, and our sightseeing tours in Chicago page covers those. This page is for the second trip, or the traveler who'd rather stand in a cemetery or on an 'L' platform than sit on a boat. A lot has changed since we first wrote it. When we checked every operator in September 2026, the pizza, chocolate, blues club, Boystown and "Weird Chicago" tours on the old list had either closed or stopped offering public tours, so they're gone. Here's what's still running. Prices come from each company's site in September 2026 and will creep up, so treat them as a guide.

Gangsters, crime and ghosts

Chicago has been selling its Prohibition-era reputation to visitors for decades, and two bus companies do it well. Both visit the St. Valentine's Day Massacre site on the North Side, the Biograph Theater, where the FBI caught up with John Dillinger, and Holy Name Cathedral.

Chicago Crime Tours

Chicago Crime Tours is locally owned and leans toward history, with historic video footage on the bus, photo stops at crime scenes across six neighborhoods and stories of Capone, Nitti, Dillinger and H.H. Holmes. The daytime tour lasts 1.5 to 2 hours and starts at $42. The longer Night Crimes Tour leaves at 7:30pm, runs 2 to 2.5 hours and starts at $47. Both pick up outside 163 E. Pearson St., at the southeast corner of Michigan Avenue and Pearson, near the Water Tower. The company recommends it for kids 10 and up, and tours often sell out, so book ahead.

Untouchable Tours

Untouchable Tours bills itself as Chicago's original gangster tour, and it was on our list back in 2010. The difference is the guides, who are actors playing 1920s gangsters, so it's more of a show. There are prizes at the end. The tour runs about 1.5 to 2 hours on a climate-controlled bus, starts at $45, with a discount for kids 12 and under, and picks up on Clark Street between Ohio and Ontario in River North. Get there 10 minutes early. The bus leaves on time.

Chicago Hauntings

The ghost tour with the best pedigree is the Original Chicago Hauntings Ghost Tour, founded by Ursula Bielski, a ghostlore historian who has written several books on haunted Chicago. It's a three-hour narrated coach tour with stops to get off, and it covers the site of the 1915 Eastland disaster on the Chicago River, the alley behind the old Iroquois Theater (now the Nederlander), where hundreds died in a 1903 fire, the St. Valentine's Day Massacre site and the Resurrection Mary legend. It leaves on Saturdays at 7pm from the Congress Lounge bar inside the Congress Plaza Hotel at 520 S. Michigan Ave. Tickets run about $57, and the tour is for ages 13 and up. The coach isn't wheelchair friendly, and sales are final.

Cemeteries

This sounds grim, and it's one of the best afternoons you can have in the city. The Chicago Architecture Center sends its trained docents into the city's old cemeteries, where the monuments were designed by some of the same people who built downtown. Every CAC walking tour ticket also gets you into the center at 111 E. Wacker Dr. within seven days.

Start with Graceland Cemetery, in Uptown, a short walk north of Wrigley Field. The two-hour walk covers Daniel Burnham, Potter Palmer, George Pullman, Marshall Field and the architects Louis Sullivan and Mies van der Rohe, plus Sullivan's Getty Tomb and sculpture by Lorado Taft and Daniel Chester French. The same cemetery hosts Graceland Cemetery: Women of Influence, one of the few tours from our original list that's still running. It's two hours on the women who shaped early Chicago, from Underground Railroad activists to the founders of the juvenile court system and Kate Warne, the Pinkerton detective who helped foil a plot to kill Abraham Lincoln. You'll also stop at the graves of pioneer Juliette Kinzie, architect Marion Mahony Griffin, dancer Ruth Page and Katharine Dexter McCormick. Both tours meet at the main gate, 4001 N. Clark St. at Irving Park Road, and involve two hours on paths that can be uneven. The Red Line's Sheridan stop is the nearest 'L' station.

The CAC also runs cemetery tours at Rosehill (the Civil War), Oak Woods on the South Side (from the Civil War to civil rights), Bohemian National and Lake Forest. Check the center's calendar, since not every tour runs every month.

Architecture from odd angles

The 'L' tour. The CAC's Elevated Architecture: Downtown 'L' Train is the center's most comprehensive Loop tour and takes you up to the platforms, where you see details that people on the sidewalk miss. Don't expect a train ride. Only about 15 minutes of the two hours is on a train, and the rest is on platforms and walking between them, so it isn't accessible and involves plenty of stairs. It meets at the center at 111 E. Wacker. If you'd rather do it yourself, ride the Brown Line around the Loop with a $5 CTA day pass.

The Board of Trade. The old version of this page promised a look down at the trading floor from an observation deck. Today's tour is about the building instead. The CAC's one-hour Chicago Board of Trade Building tour takes you inside the 1930 Art Deco tower by Holabird and Root at the foot of LaSalle Street, including its lobby and the traders' vault, and compares it with the 1982 and 1997 additions. It meets in the lobby at 141 W. Jackson Blvd. It's a CAC Select tour, free for members at the Dual level and above.

The Pedway. In January, the best tour in the city is underground. The CAC's Pedway tour is covered on our sightseeing tours page.

Money

Steps from the Board of Trade, the Federal Reserve Bank of Chicago's Money Museum is on the first floor at 230 S. LaSalle St., at Jackson. Entry is free and you can just walk in, and only groups of 15 or more need to book. You can try spotting counterfeit bills, see what a million dollars looks like and look at rare currency. It's open Monday to Friday from 10am to 5pm, but it closes on Federal Reserve holidays and sometimes keeps short hours, so check the site. Pair it with the Board of Trade tour for a cheap morning on LaSalle Street.

Hot dogs

The Vienna Beef factory tour on our old list is gone. Vienna moved production from Bucktown to Bridgeport in 2015 and doesn't advertise public tours. If you want to go deeper, Vienna runs Hot Dog University, a course for people who want to open their own hot dog cart or stand. It's aimed at would-be vendors and there's tuition, but it's the closest thing to a look behind the counter. For the rest of the story, and where to eat one, see our page on Chicago-style hot dogs.

For other food tours, Chicago Food & City Tours (formerly Chicago Food Planet) is still going, with neighborhood walks in Pilsen, Chinatown and the West Loop and one inspired by The Bear. Details are on our sightseeing tours page. For deep dish without a guide, see pizza in Chicago.

What happened to the rest

• Second City Pizza Tours, Chicago Chocolate Tours and Weird Chicago Tours no longer run public tours. The pizza tour's website is gone, the old Chicago Chocolate Tours address now points to its founder's personal site, and the Weird Chicago website has expired.
• Chicago Dine-Around still exists but now does private corporate events only.
• The Chicago Blues Tour and Chicago Elevated's Boystown walk have gone quiet online, so we dropped them. For live blues, go straight to the blues and jazz clubs. The neighborhood the Boystown tour covered now goes by Northalsted, and our gay Chicago page has more.
• Wrigley Field tours are still running and are covered on our Chicago Cubs games page.

If you'd rather have a local show you around for nothing, the free Chicago Greeter program pairs you with a volunteer for a neighborhood of your choice, if you book a couple of weeks ahead.

Photo by southie3