Chicago on Broadway at the Ambassador Theatre: Honest Broadway Guide

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Chicago opened on Broadway in 1996. It’s still running. It’s the longest-running American musical in Broadway history, and with Phantom closed, nothing currently running has lasted longer. It’s currently playing at the Ambassador Theatre in New York. Revivals on Broadway usually burn out within six months, but Chicago has occupied the Ambassador Theatre since 1996 without needing flashy pyrotechnics or automated stages. Now that The Phantom of the Opera has closed, it officially reigns as the longest-running open show on Broadway. But keeping a 30-year-old production fresh means knowing what you’re actually paying for. Over at Shows and Stay, the priority isn’t selling you generic Broadway nostalgia—it’s giving you a clean look at whether this stripped-down jazz staple fits your itinerary, which Ambassador seats avoid cramped sightlines, and how to plan the night without getting stung by Midtown markups.

Where the Ambassador Theatre Actually Is

219 West 49th Street. Between Broadway and Eighth Avenue. You’re two minutes from Times Square, tops.

It’s a small house — under 1,100 seats. Honestly, that works in your favor. There isn’t a seat back there that feels far from the stage. I’ve sat in the last row of the mezzanine at bigger theaters and squinted through half the show. Not an issue here.

Getting There Without Losing Your Mind

Take the N, Q, R, W to 49th Street, the 1 to 50th, or the C, E to 50th Street & 8th Avenue.

Skip the car. Seriously. Midtown parking during show hours is a nightmare, and it’s pricey on top of that. A cab works if you must, but you’ll probably sit in more traffic near Times Square than you would just walking from the subway.

Booking Chicago Broadway Tickets

Skip the hassle of waiting in unpredictable box-office queues along 49th Street or risking marked-up passes on shady secondary resale platforms. To lock in your seats with total peace of mind, book your verified digital tickets directly through Shows and Stay.

You get guaranteed seat assignments, real-time date availability, and instant mobile delivery straight to your phone—meaning you can bypass the box-office congestion on performance night and walk straight through the front doors.

Budget Tip: Midweek evening performances (Tuesday through Thursday) consistently offer significantly better pricing and broader seat selections than crowded Friday and Saturday time slots.

Weeknights are cheaper. Tuesday through Thursday, generally. If your trip has any flexibility, that’s where the savings are.

What the Chicago at Ambassador Theatre

The Chicago show at Ambassador Theatre clocks in around two hours and 25 minutes, one intermission. It’s set in 1920s Chicago, follows two women — Roxie Hart and Velma Kelly — both locked up for murder, both chasing fame instead of, you know, remorse.

There’s no big scenery here. The band sits on stage the entire time. That’s the whole point, actually. It’s stripped down to jazz, sharp choreography, and performers who can actually sell a number. That’s probably why it’s outlasted shows with way bigger budgets. It never needed the spectacle to begin with.

Chicago Broadway Cast

The chicago broadway cast turns over a lot, which makes sense after almost 30 years. Roxie, Velma, and Billy Flynn often get filled by recognizable names doing short runs, backed by a resident company that’s been doing this a while.

If seeing a particular actor is the reason you’re going, check before you buy. Call the box office or check the show’s site. Casting shifts happen without much warning sometimes, and nobody wants to find out the night of.

Hotels Near Chicago Broadway

Staying close matters more than people think, especially leaving a late show. For hotels near Chicago Broadway, focus on Times Square and Eighth Avenue.

Cheaper chains cluster along Eighth Avenue, roughly 45th to 50th Street. Times Square itself has the mid-range and higher-end options. Want it quieter? Head toward Ninth Avenue — still a ten-minute walk, but you lose some of the noise and chaos.

Anything within five blocks means you can just walk back after the show instead of fighting for a cab in Times Square.

A Few Things First-Timers Should Know

Nobody dresses up for Broadway anymore. Jeans are fine. Don’t overthink it.

Leave the big bag at the hotel. Security’s faster when you’re not carrying much — every theater checks bags now.

Eat before or after. There’s no real dinner inside, just intermission concessions. Grab something real near Times Square beforehand.