Chicago Night Crimes Tour by Bus

★★★★★ 4.8 (519 traveller reviews)

By bus, stops on footLeaves at 7:30pmA live guide163 E. Pearson St

Two to two and a half hours on a bus from Pearson Street, off the Magnificent Mile, leaving at 7:30pm. A live guide tells the stories of the gangsters of the Prohibition era on the way, and you get off at five stops, including an old theater under its lit marquee. It is the only evening here spent on land, and the highest rated of all.

Hours, prices and access verified by the Chicago Night Tours team — last checked 2026-09-27.

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Two hours, five stops, one storyteller at the front

7:30pm outside 163 E. Pearson

The bus picks up outside 163 E. Pearson Street, on the southeast side of Pearson and Michigan Avenue. Look for the guide at the bus. Check in at least 15 minutes early: the bus leaves on time, and you cannot join after it has gone. There is no office on site. If you do not see the bus ten minutes before the start, call the number on your ticket.

Chicago Crime Tours runs this evening at 7:30pm on select weekdays, so the dates you can book are the ones it shows. Seating is first come, first served, and seats together are not promised. The pickup is a short walk from the river docks; it is on the meeting-point map with the other starts.

Capone, Nitti, Moran and Dillinger

This is Chicago's criminal past, told where it happened. The guide follows Al Capone, Frank Nitti, Bugs Moran, Dean O'Banion and John Dillinger through the city, with the beer wars of the Prohibition era at the centre of it. Between stops the bus plays historic video footage. You also pass the former site of the St. Valentine's Day Massacre.

Travellers keep coming back to the same point: the stops tie to the stories. You are not looking at a building and hearing a date; you are standing where a named man did a named thing. One traveller came on a colleague's word from Ireland; another said the drive through the neighbourhoods was as good as the crime history.

Off the bus where the stories happened

You get off five times, for five to fifteen minutes each. The first is the operator's own mini mob and gangster museum, about 15 minutes, and its entry is in the fare. Later you stop at the Biograph Theater for about ten minutes, under its lit marquee, then at 35 E. Wacker Drive, at Harry Caray's and at Holy Name Cathedral. The bus passes the Water Tower, Lincoln Park and North Avenue Beach on the way.

The whole route takes you through six neighbourhoods and ends back on Pearson Street. The river between stops is the same one the cruises use; how the two kinds of evening compare is on the night tour options page.

The mini mob museum and the crime quiz

Your fare also buys a few things other evenings do not. There is the museum stop, a souvenir brochure and an exclusive crime quiz, plus a profile of a personality from the Prohibition era. You can keep the brochure. There are no translations, audio guides or headphones, and the operator asks that nobody talks or translates on the bus while the guide is speaking.

Is 7:30pm dark?

It depends on the month, and it matters for a tour of dark stories. At 7:30pm it is dark from October to February, dusk in September and March, and daylight from April to August. In mid-June the sun is up for another hour after you leave.

Times are the U.S. Naval Observatory's for the Michigan Avenue Bridge in 2026. The stops on the later half of the evening are after dark in every month but high summer. More on the season is in Chicago weather at night.

Your evening, stop by stop

1. 7:15pm. Check in with the guide at the bus outside 163 E. Pearson St.
2. 7:30pm. The bus leaves, on time, with the guide at the front.
3. The mob museum. About 15 minutes off the bus; entry is in the fare.
4. Further north. Past the massacre site, then about ten minutes at the old theater.
5. Downtown. Short stops at 35 E. Wacker Drive and Harry Caray's.
6. Holy Name Cathedral. The last stop, about five minutes.
7. About 9:30 to 10pm. Back on Pearson Street, two to two and a half hours later.

Who this suits, and who should book something else

What $55 covers, and what it leaves out

Know before you go

• Check in 15 minutes early. The bus leaves at 7:30pm and does not wait.
• Use a restroom first. There are no restroom breaks during the tour.
• Eat before. There is no eating or drinking on the bus.
• Steps up, no lift. Some stops have stairs, and there is little room for a folded chair.
• Tip in cash or Venmo. About $5 a person is suggested, and it is not in the fare.
• English only. No translations, audio guides or headphones, and no translating aloud on the bus.

What travellers said back on Pearson Street

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Frequently asked questions