Chicago's Original Gangster Tour by Bus
The only tour with raffles and prizes included.
4.6 ★ · 174 reviews · 1 h 45 min
Includes Raffles and Prizes
Chicago · Illinois, United States
From $10 shuttles to $539 private tours, Chicago bus tours fit every style and budget.
Bus tours are a major way to see Chicago, with 85 options—16% of all tours sold in the city. They cover everything from gangster history and pizza tastings to architecture and TV locations. Bus tours appeal to visitors who want to cover a lot of ground, avoid walking, or get a themed introduction to the city’s highlights.
Most travelers choose these tours for their convenience and variety: the most-reviewed bus tour has over 3,500 ratings, and 88% of all bus tours are rated 4 stars or better. Whether you want a quick city overview, an in-depth private experience, or a themed adventure, there’s a bus tour at nearly every price point.
Bus tours are one of the most diverse and popular categories in Chicago, with 85 products available. They make up 16% of everything on offer in the city, second only to walking tours. Prices range from $10 for a basic shuttle to $539 for a private custom tour, with a median starting price of $188—much higher than the $94 median across all Chicago tours.
Most bus tours cluster at the two ends of the price spectrum: 22 are under $60, but 37 cost over $250. The jump in price is often tied to private or small-group formats, while classic sightseeing and themed tours tend to be much more affordable. Compared to walking, food, or cultural tours (all with $63 medians), bus tours are a bigger investment but offer more comfort, coverage, and sometimes exclusive access.
If you want to see the city without the hassle of public transit or long walks, bus tours are the most efficient way to cover Chicago’s top sights, especially for families or groups with limited time.
The right Chicago bus tour depends on your interests, budget, and how you like to explore. For the most affordable options, look for classic sightseeing or themed group tours: you’ll find several under $60, including the well-known crime and mob tours and the hop-on hop-off circuit. These are ideal for first-time visitors who want a narrated overview and the flexibility to explore at their own pace.
If you want more depth or a specific theme, mid-range tours ($60–$120) often include extras like food tastings or longer routes. The Chicago Pizza Tour, for example, combines bus transport with stops at several pizzerias and is consistently praised for its knowledgeable guides and generous tastings. Small-group minibus tours in this bracket tend to get higher ratings for comfort, guide quality, and the chance to stop for photos.
Private and custom tours, priced from $199 to $539, are the most expensive but offer a tailored experience with hotel pickup, flexibility on stops, and a dedicated guide. These are best for families, small groups, or anyone wanting a personalized itinerary. Reviews highlight the convenience and depth of information, though some travelers wish for more input on the route or deeper expertise from guides.
Across the category, the best-rated tours share knowledgeable, engaging guides and a balance of storytelling with stops for photos or exploration. However, about 12% of bus tours are rated below 4 stars. Common complaints include uncomfortable seating on older buses, tours that drive by rather than stop at key sights, and inconsistent guide quality. Some travelers also mention confusion about pickup locations or disappointment when tours don’t match their expectations for interactivity or access.
The only tour with raffles and prizes included.
4.6 ★ · 174 reviews · 1 h 45 min
Includes Raffles and Prizes
Offers the most interactive crime-themed extras and has far more reviews than the others.
4.6 ★ · 3,531 reviews · 1 h 30 min
Includes Prohibition Era personality profile · Exclusive crime trivia quiz · Mini mob and gangster museum
The only tour where you can hop on and off at multiple stops, but has a lower rating than most.
3.9 ★ · 2,387 reviews · 2 h
Includes Hop-on Hop-off Sightseeing Tour by Open-top Bus · Enclosed/Climate Controlled Lower Deck, Top Deck Open · Big Bus Tours app (ticket storage, live tracking and ticket activation)
The only tour with an optional architecture river cruise included.
4.8 ★ · 735 reviews · 2 h
Includes Local guide · Three photo stops · Transport by 13-passenger, air-conditioned minibus
Includes the most photo stops among the city minibus tours.
4.9 ★ · 641 reviews · 2 h
Includes Transport by 13-passenger, air-conditioned minibus · Four photo stops
The only crime tour offered at night, but costs more than the daytime options.
4.8 ★ · 513 reviews · 2 h
Includes Prohibition Era personality profile · Mini mob and gangster museum · Inclusions are subject to availability.
The only tour that includes multiple pizza tastings, but is nearly double the price of the others.
4.9 ★ · 482 reviews · 3 h 30 min
Includes Local guide · Four slices of pizza · Transport by bus
The only private tour for up to five people with hotel pick up, but at a much higher total cost.
4.9 ★ · 207 reviews · 3 h
Includes Private transportation · Local guide · Professional guide
Sold by Viator. Prices and review counts checked on 09/09/2026.
Yes, most bus tours are family-friendly and cover major sights. Some themed tours, like gangster or pizza tours, are especially popular with kids and teens.
Most group tours last 90 to 120 minutes, while private and specialty tours can run up to 3 or 4 hours.
Many mid-range and private tours include several photo stops. Some cheaper or themed tours may only drive by key sights.
Private tours cost much more but offer hotel pickup, custom routes, and a dedicated guide. They suit travelers who want a tailored experience and more flexibility.
They offer flexible sightseeing, but reviews mention unclear stop locations and inconsistent service. Check the route and schedule before booking.
Pick based on your interests: crime tours focus on history and stories, food tours include tastings, and city highlights tours cover the most landmarks.
Booking is handled by Viator, part of TripAdvisor. Live prices, free cancellation on most.