EMPIRE OF SPIRITS
Supply & Demand in Chicago’s Mob Era
September 3-7, 2026 | The Drake Hotel, Chicago
Limited to 20 Guests | Hosted by Birdie’s Excursions | Powered by FORA Travel
Long before the skyline glittered and the river ran green each March, Chicago was a city built on deals. Railroads, stockyards, whiskey, labor, jazz, and ambition all moved through the same restless machine.
During Prohibition, that machine simply found new routes.
Speakeasies thrived behind unmarked doors. Music poured out of smoky rooms. Fortunes changed hands over steak dinners and quiet handshakes. And somewhere between the lakefront wind and the glow of a midnight bar, the city learned how to turn vice into legend.
Chicago has always run on appetite.
For four nights over Labor Day weekend 2026, a small group of travelers will settle into the historic Drake Hotel and explore Chicago through the stories, flavors, and hidden corners that shaped its most intoxicating era.
Empire of Spirits is your invitation into that world.
This isn’t a checklist trip.
It’s a hosted experience designed for connection, curiosity, and the kind of memories that feel slightly impossible when you try to explain them later.
Think velvet dinners, river cruises through architectural canyons, late-night jazz, neighborhood discoveries, and just enough independent time to wander wherever the city pulls you.
Once you arrive, everything is taken care of.
All you need to do is show up ready to step inside the story.
The Experience:
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Arrive at the Drake
Spend the afternoon enjoying the lakefront, exploring, or just resting
Meet your new flock at our evening welcome reception
Optional late-night cocktail outing
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Early morning leisure time
Hosted Prohibition / mob era tour
Independent lunch and afternoon free time
Evening signature group dinner (formal/semi-formal)
After-dinner jazz club and speakeasy outing
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Early morning leisure time
Riverboat Architecture tour
Independent lunch and afternoon free time
Casual dinner
Optional hosted excursion
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Early morning leisure time
Brunch
Cultural nighborhood experience
Independent lunch and afternoon time
Final group dinner at one of Chicago’s most iconic casual restaurants
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Light breakfast and coffee
Hugs and “until next times”
Scheduled departure transfers
Your package includes:
4 Nights at The Drake Hotel
4 nights at Chicago’s Iconic Drake Hotel in your elegant King or dual Euro Twin room overlooking the sparkling shores of Lake Michigan.
Suite upgrades available.
Rates based on double occupancy
Welcome Reception
Meet your hosts and fellow explorers, enjoy beverages and hors d'oeuvres, and immerse in The Drake’s historical elegance.
Chicago’s most fascinating story has just begun.
Food, 2 drinks per guest included
Chicago Architecture Riverboat Tour
Explore Chicago from the water on a guided architecture cruise, where the city’s towering skyline reflects an era driven by ambition, rapid growth, and the forces of supply and demand that shaped its underground economy.
Admission, tour, and transportation included
The Untouchables Private Tour
Go beyond the headlines on a private tour through Prohibition-era Chicago, where rival empires, secret operations, and larger-than-life figures shaped the city’s most notorious chapter.
Tour and private group transportation included
Gene and Georgetti Private Dining
Dine like Chicago’s power players at Gene & Georgetti, the city’s oldest steakhouse, where deals were made, alliances were forged, and reputations were built behind closed doors. Enjoy a private dinner in The Library, reserved exclusively for your group.
Dinner, 2 drinks per guest, transportation included
Chicago Speakeasy Experience
Savor the kind of hidden nightlife that thrived during Prohibition, where demand never disappeared… it just moved underground. Discover Chicago’s modern speakeasies, where secrecy and sophistication still linger.
Cover, two cocktails per guest, and transportation included
Classic Chicago Deep Dish Experience at Lou Malnati’s
Indulge in Chicago’s most iconic dish at Lou Malnati’s, where deep dish pizza is served the way the city intended—rich, hearty, and unapologetically satisfying.
Dinner and transportation included
Hosted by Founders Carla and Lee Rowley
We’re your hosts throughout the experience - guiding, coordinating, and ensuring everything runs seamlessly so you can simply enjoy the moment. We’re a bit eccentric. You’re welcome to be, too.
Stories, recommendations, and well-placed surprises included.
Every Detail, Thoughtfully Handled
From reservations and transportation to timing and coordination, every detail is carefully managed so you can simply relax and enjoy the experience.
All post-flight logistics included.
Pricing:
All prices are based on double occupancy. Limit 20 guests.
Founder’s Flock: $3,497 Per Guest
Through July 1, 2026
Due today: $500
Due on July 1: $2,167
Due at hotel upon arrival: $830
Standard Rate: $3,997 Per Guest
After July 1, 2026
Due at booking: $3,167
Due at hotel upon arrival: $830
Upgrade to Founder’s Reserve
Through July 1, 2026
Want to secure your place and settle everything upfront?
Guests who choose to pay in full are welcomed into Founder’s Reserve - a limited tier for those who commit early and experience the city on their own terms.
As part of Founder’s Reserve, you’ll receive a complimentary Chicago CityPASS® for each guest, giving you access to some of the city’s most iconic attractions during your free time.
Your CityPASS® includes:
Shedd Aquarium
Skydeck Chicago
Plus your choice of 3:
Field Museum
360 Chicago Observation Deck
Griffin Museum of Science and Industry
Art Institute of Chicago
Adler Planetarium
A little more freedom, built in.
We’ve intentionally left space in your itinerary—so whether you want to explore more of the city, revisit a favorite spot, or simply wander, your CityPASS makes it easy to do Chicago your way.
Who is this for?
Empire of Spirits isn’t for everyone. If your idea of a vacation is lounging on beach or catching a “highlights” tour, this probably isn’t going to be much fun for you.
Empire of Spirits is for curious people who delight in savoring the details, but not in managing them.
It’s for folks who look beyond the lip gloss to see what makes cities - and people - tick.
And it’s for travelers who wish they could find more of their people.
If you’re intrigued by Prohibition-era Chicago and think it would be fun to explore the city with new friends (and a couple of quirky-but-oddly-responsible hosts), we’d love for you to join us!
Meet your hosts:
Hi. We’re Carla and Lee Rowley.
For the past 26 years, we’ve been traveling together and learning what separates a forgettable trip from an experience that actually stays with you.
Our first vacation was a budget Bahamas getaway in our 20s - complete with aggressive timeshare pitches, Spring Break chaos, and getting lost more than once. It was equal parts stressful and educational.
That experience shaped how we travel today.
We design and host once-in-a-lifetime trips for people who want more from a vacation than a sunburn and a hangover.
We’re not for everybody. And we quite like it that way.
Frequently Asked Questions
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In a word: Depth.
A business owner once told us, “We just sell what people settle for.”I’m not sure which of us cringed harder.
We’re not about “settling.” We prefer creating flawless, engaging experiences that no one else offers.
The kind that makes you wonder why someone didn’t think of this before.
We’re not for everyone. And honestly, we prefer it that way. -
Empire of Spirits is a 5-day, 4-night, group-enhanced journey through one of Chicago’s most notorious - and fascinating - chapters.
It’s for people who want depth, not just another throwaway trip.
Each day, we’ll immerse in the scenes, stories, and streets where Prohibition reshaped a city - leaving the door open for organized crime.
You’ll dine like mob bosses, ponder secrets whispered in scarlet speakeasies, and discover the true personality of a city whose past won’t stay buried.
When you get home, you’ll have more than a souvenir mug - you’ll have stories and new friends that just might outlast your luggage. -
Empire of Spirits is a “group-enhanced” experience that combines the flexibility of independent travel with the support and peace of mind of group travel.
Each day, we’ll join for at least one excursion or experience: The Untouchables tour, a riverboat architecture tour, private dining at the city’s oldest steakhouse, just to name a few.
But you’ll have independent time each day to explore Chicago on your own, take in an exclusive experience, or just relax between outings.
And you can always connect with us and your fellow explorers through FlockTalk, our private small group mobile hub!If you’re not into an excursion or you’re excited about something not on the itinerary, we’ll do our best to tailor your experience.
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The “Founder’s Flock” rate, valid until July 1, 2026, is $3,497 per guest.
If spots are available after July 1, the Standard Rate of $3,997 per guest will apply.
We’d rather overdeliver than underwhelm, so we’ll do our best to delight you with swag, prizes, and extras along the way.
We do have a few premium enhancements you can add to complete your experience. We can also arrange special tours, shows, and experiences just for you - perfect for those times between group experiences. -
Every reservation includes:
4 nights at The Drake Hotel, King or 2 Euro Twin room (double occupancy)
Private welcome reception
The Untouchables private mob tour
Riverboat architecture tour
Dinner at Gene and Georgetti
Dinner at Lou Malnati’s
Chicago speakeasy experience
Transportation to all group tours
All logistics thoughtfully handled
Swag, prizes, and extras!
Two professional-but-quirky hosts throughout
Access to hosts, guests, itinerary, special giveaways, and more on FlockTalk before and throughout the event
The following items are not included in the base price:1. Airfare
We’ve discovered that flight preferences are deeply personal, so many guests choose to arrange their own flights.If you would like us to handle your flights, just let us know!
2. Meals not specifically listed.
3) Breakout experiences
Tickets, transportation, and other costs of breakout experiences are not included.
4) Shopping, souvenirs, etc. outside of designated swag
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Yes, you absolutely can! If you want, we’ll even send you our contact list so you can plan a Labor Day Prohibition-themed cultural tour of Chicago all by yourself.
But it’s like saying a steak from the supermarket should cost the same as a steak at Gene and Georgetti.
Nothing wrong with a home-cooked steak. But you won’t still be talking about it a decade from now.Empire of Spirits is a completely hosted and managed experience where the people you travel with are as fascinating as the destination.
And since we love to chat with locals wherever we go, we have access to exclusive surprises you won’t find on big bus tours.
It’s not how the average person gets to experience Chicago.But you can.
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Click the “Reserve Your Place” button and follow the checkout process to complete your reservation and deposit payment.
A deposit of $500 per guest is due at the time of booking, with the remainder (minus hotel) due on July 1.
Or choose “Upgrade to Founder’s Reserve” to pay your Birdie’s balance in full before July 1 and get a Chicago CityPASS ® ($144 value) per guest - on us.
Reservations made after July 1 require payment in full, and do not qualify for the CityPASS ® bonus.
Payment can be made with any major credit/debit card or ACH. -
We designed Empire of Spirits around how we like to travel - with structure, but not stress.
The pacing is thoughtful, varied, and flexible enough that vacation actually feels like vacation. Each day features group experiences and independent time so you feel supported, not herded.
Also, we’re not in our 20s anymore, so “breakneck pace” really isn’t our thing. If you’re comfortable with short walking tours and mild-to-moderate activity, you’ll be fine. -
All reservations are fully refundable within 14 days of initial payment.
For added protection, we can provide trip insurance at a nominal extra cost. Your concierge can explain coverage and cost details to help you decide if this is right for you. -
No problem! Here’s how to contact us with questions:
Email:concierge@birdiesexcursions.com
Phone:
(614) 585-6347