Entertainment Tour Party Bus in Chicago

What an entertainment tour is, and what it is not

Chicago exported improv comedy, electrified the blues and kept jazz rooms open through every change in fashion. An entertainment tour is a night built to sample that: two or three live performances in different rooms, with a hired vehicle connecting them so the group stays together and nobody drives.

It helps to be clear about what this page is not. If your night centers on a single headliner at an arena or amphitheater, you want our concert party bus guide. If the plan is comedy from start to finish, the comedy shows page goes into seating and two-show timing at Second City, Zanies and the rest. A seated play or musical with a fixed curtain belongs on the theater page. And if the music is incidental and the bars are the point, see bar crawls.

The entertainment tour sits between those. It is for the group with out-of-town guests who want "real Chicago," the fortieth birthday that would rather hear a band than stand in a club line, the company hosting clients who have already done the steakhouse dinner. The appeal is variety — a sketch revue, then a blues set, then a jazz trio at midnight — and the challenge is that every one of those rooms runs on its own schedule. The vehicle solves the geography; you still have to solve the clock, and that is what the rest of this page is about.

Blues, jazz and the rooms worth building a night around

For blues, two clubs carry most itineraries. Kingston Mines on Halsted in Lincoln Park runs two stages with bands alternating late into the night, which makes it forgiving — you can arrive mid-evening and still catch full sets. Buddy Guy's Legends on South Wabash in the South Loop is the better-known name, serves food and books both local and touring acts. Rosa's Lounge on West Armitage is smaller and more of a neighborhood room, a good pick for groups who want the less touristy version.

For jazz, the Green Mill in Uptown, at Broadway and Lawrence, is the one everybody asks about: a Prohibition-era cocktail lounge with a curved bar and booths. It is also small, and it has long operated on a first-come basis with a cover charge at the door. A group of eighteen should not expect to sit together, or necessarily to get in at peak hours — check the club's current policy and go early or late. Andy's Jazz Club on Hubbard in River North and the Jazz Showcase at Dearborn Station in Printers Row take reservations for many shows and handle groups more easily.

For rock and indie, the rooms are scattered: Metro in Wrigleyville, Schubas and Lincoln Hall in Lakeview and Lincoln Park, Thalia Hall in Pilsen, the Empty Bottle in Ukrainian Village, the Hideout near the river. These are ticketed shows with set times, so treat one as the anchor of the night and build lighter stops around it.

Routes that work: keep the map tight

The most common mistake on a multi-venue night is a route that looks fine on paper and spends ninety minutes in traffic. Chicago's entertainment rooms cluster, and good itineraries stay inside one or two clusters.

The North Side run. Start with a revue at The Second City in Old Town, ride ten minutes up Halsted to Kingston Mines, then continue north to the Green Mill in Uptown for the late set. All three sit along a rough north-south line, and each leg is short. This is the classic first-timer tour.

The downtown run. Dinner and an early jazz set at Andy's in River North, then down to Buddy Guy's Legends in the South Loop, with the Jazz Showcase in Printers Row a few blocks away as an alternative or a finale. Hotels are close, which makes this the natural choice for visiting clients and convention groups.

The indie run. A ticketed show at Thalia Hall in Pilsen or the Empty Bottle, bracketed by a drink before and late food after in the same neighborhood. One anchor, two soft stops.

What to avoid: zigzags such as South Loop to Uptown to Pilsen. Each cross-town leg on a Saturday night is twenty-five to forty minutes, and you will feel every one of them. Two venues done properly beats three done in a hurry; a full set, a drink and a relaxed exit take about ninety minutes per room. Sketch your draft in the trip duration estimator and see whether the hours add up before you buy a single ticket.

Tickets, covers and getting a group through the door

Transportation is the easy part of this night to arrange. Entry is the part that needs homework, because every room does it differently.

• Ticketed shows (Second City, Thalia Hall, Metro, most theater-style venues): buy for the whole group in one purchase if you can, and note whether seating is assigned or general admission.
• Reservation rooms (many supper-club-style jazz venues): reserve for your full headcount and ask about minimums, set times and whether the reservation covers one set or the whole evening.
• Cover-at-the-door clubs (several blues and jazz bars): bring cash as a backup, expect a line on weekends and ask whether the club will hold space for a group that calls ahead. Some will; some cannot.

Age limits matter more than people assume. Most music bars are 21 and over, with IDs checked at the door, while some ticketed venues admit younger guests for certain shows. One underage guest, or one adult who left an ID at home, can stall an entire stop. Confirm every venue's policy for your date.

Set times slip. Bands start late, encores run long, and a group that is enjoying itself will not want to leave mid-song. Put fifteen to twenty minutes of slack between stops, and have one person — not the guest of honor — own the schedule and stay in contact with the driver.

On board, alcohol is for guests 21 and over only, where the vehicle's policy allows it. Drinks at three venues add up quickly, so treat the rides as the place for water.

Picking the vehicle and the night

Entertainment tours draw mid-size groups. Across all inquiries in our booking network, 49% were for 11 to 20 passengers and another 28% were for ten or fewer, and this occasion sits squarely in that range: big enough to be a party, small enough to get into a jazz club.

For eight to fourteen people, a 14 passenger limo Sprinter is hard to beat. It loads quickly at tight curbs on Halsted, Broadway and Hubbard, and the cabin is social without being a nightclub. For fifteen to twenty, a 20 passenger party bus gives everyone room, and a 20 passenger Hummer limo is the showier alternative for a milestone birthday. Client-hosting groups who want a quieter, business-appropriate ride should look at a 12 passenger executive Sprinter van. What each vehicle carries on board differs, and the written quote lists what is included with the one assigned to you.

Think hard before going bigger than twenty. The vehicle will be fine; the venues will not. Small music rooms cannot absorb thirty people arriving at once, and you will spend the night split across a room or waiting on the sidewalk.

As for the night: 81% of all inquiries in our network ask for a Friday or Saturday, yet blues and jazz clubs book strong acts all week. A Thursday tour means shorter lines, easier group entry and more vehicle choice. Plan a few weeks ahead so ticketed shows do not sell out from under you, and use the budget calculator to total transportation alongside tickets and covers per person.