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Comedy and Craft Beer Tour of Old Town

Booze Tour Chicago
$62

No matter the season, the weather, or the political climate, The Windy City has two unparalleled passions: beer and improv comedy. For over a century, Chicago has been churning out some of America's all-time favorite comics and brews.

Try a variety of tasty local craft beers at several iconic Old Town bars, then stroll down Wells Street and learn all about Chicago's improv and sketch comedy history.

The Old Town Comedy and Craft Beer walking tour is perfect for friends, birthday parties, bachelor/bachelorette parties, guys' or girls' weekends, couples, or anyone looking to have a good time!

Meet your guide at 2:30 just outside the famed Second City comedy club, where many of Saturday Night Live's greatest comedians got their start. Stroll to the Old Town Ale House and savor a local brew while reveling in the bar's rich history and atmosphere. Patrons have included Anthony Bourdain and Roger Ebert. Next, walk past Zanies comedy club where your guide will explain more of Chicago's rich comedy tradition. Stop at classic dive Burton Place for a "Chicago Handshake," a shot of an infamous local liqueur followed by an Old Style. Next, learn more about the colorful artists who used to populate Old Town, and walk to Old Town Pour House, featuring one of Chicago's largest beer selections. Sample a couple of local brews with a savory snack, and then walk further south past the charming boutiques and restaurants of Wells Street. Refresh yourself with another local pour at Declan's Irish Pub, and then finish the tour at Glunz Tavern, one of Chicago's oldest and most storied establishments.

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Chicago Prohibition Tour

Booze Tour Chicago
$45
Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the sale of alcohol was banned for more than a decade in the United States, and the subsequent popularity of illicit establishments where liquor, jazz, and mobsters ruled. An air-conditioned coach shuffles you from bar to bar, so feel free to buy a drink or two. This small-group tour, limited to 20 people, ensures a more customized experience with your guide.

Meet your guide at the Green Door Tavern to start the 3.5-hour journey to four historic Chicago speakeasies used during Prohibition that still operate today. Bring your government-issued ID, money to purchase drinks, and a camera for photo ops.

Travel by comfortable air-conditioned coach between stops, and learn about the 1920s cocktails typically found in each establishment. If you like what you see and hear, purchase signature drinks to taste for yourself. As you sip craft cocktails made by expert bartenders, your enthusiastic and knowledgeable guide explains the key players of Prohibition. Hear stories about the lawmakers and the lawbreakers, including Al Capone and other famous Chicago gangsters who became powerful during the dry years of Prohibition.

Each former speakeasy that you visit has a different character. Stops include a downtown tavern built in 1872 that is decorated with antiques and Americana collectibles that give it an old-school Chicago vibe. Then pull up a stool at a cocktail lounge in Wicker Park where great blues music pumps from an old jukebox. You'll also enjoy a neighborhood bar that claims to be the oldest and longest-running tavern in the Old Town district. Wrap up at a downtown restaurant rumored to be a favorite hangout of Al Capone where historic newspapers, photographs, and posters line the walls of the bar.

Your tour ends downtown in the Chicago Loop.

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Pioneers and Pints Beer Tour in Bucktown and Wicker Park

Booze Tour Chicago
$65
Discover Chicago's finest beer on this 3-hour walking tour of the Bucktown and Wicker Park neighborhoods. With a knowledgeable guide, learn about Chicago's history related to immigration and brewing — from the late 1600s to the present day — and visit bars, restaurants and other locally owned establishments to sample craft beer. You'll also enjoy a Chicago-style hotdog and get a look at some of the city's historical architecture. You can book this tour without the beer tastings, if you wish.

Meet your guide in the heart of the adjacent Bucktown and Wicker Park neighborhoods, and set off on your walking tour of the area's beer establishments.
During your 1-mile (1.6-km) walk, visit venues like a bar that dates back to the 1800s and features an impressive beer list and relaxed vibe where you can pair your beer tasting with a Chicago-style hotdog by a 60-year-old family-owned restaurant. Then, pop into an innovative space that combines a butcher shop, restaurant and bar, and a bar that combines craft beer with old school video games.

Visit a bar that doubled as 'Molly's' on the TV show Chicago Fire, and explore 'Beer Baron Row,' where a majority of the old German beer barons used to live in the late 1800s. While you walk, you'll also admire Chicago's famed architecture and hear stories from your guide about the area's immigration and brewery history, as well as the history of beer in general, which dates back some 10,000 years.

In total, your beer tastings add up to the approximate equivalent of four beers, from lagers to porters, many of which are Midwestern craft brews. The tour ends in the heart of Wicker Park, where you can continue to explore these neighborhoods on your own.

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Sin and Suds Beer Tour in the Loop and South Loop

Booze Tour Chicago
$62
Explore Chicago's Loop and South Loop neighborhoods located right downtown. You'll visit renowned neighborhood establishments, sample delicious beer, and learn how well beer pairs with Chicago's vice history - including gambling, saloons, crime bosses like Al Capone, and other nefarious activities in the 1800s and 1900s!

On this tour you will learn the basics of Chicago's vice history, all the way from the city's first vice district, the “Sands,” to the infamous levy district and the associated debauchery, to Capone and the mob. Explore the basics of different beer styles and beer's influence on criminal enterprises, especially during Prohibition.

We take great pride in visiting locally-owned establishments. These places not only provide friendly service, but they also have character and  are unique places that add to the neighborhoods.

First, we will visit an old Chicago bar and restaurant where Capone himself was known to hang out. Next, we will make a stop at one of the oldest bars in the city, started by a one of the many German immigrants that moved to Chicago, still holding liquor license No. 1 after Prohibition. After, we will stop by a blues club that was started by Buddy Guy, one of the ultimate legends in the business, and finally,  visit a new microbrewery that pays homage to Chicago's vice past.

Note that we will be making the following substitutions during the winter months to make the tour more weather appropriate and accommodate our vendors: 
December: First Draft will be subbed in for Berghoff
January: Brando's Speakeasy and First Draft will be subbed in for Buddy Guy's and Vice District
February-March: First Draft will be subbed in for Vice District
Please also note also that other food tastings will be subbed in for pizza in January-March. Other location substitutions are possible from time to time based on our vendor schedules.

As you can see, there is a lot that is offered on this tour – you'll learn about Chicago history, primarily as it relates to vice – and you'll be surprised by how many incredible stories we share. You'll taste delicious beer from visiting unique, local establishments, with great variety on both. You'll also walk and get a feel for these interesting neighborhoods – the Loop and South Loop are some of the oldest neighborhoods in the city, and we have no doubt that you'll want to explore the area even more.

Combining it all together with great people, including you, and it makes for an unforgettable experience. In short, our tour is a really unique experience that is fun and memorable.

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Bacon and Brewing Beer Tour in Lakeview and Lincoln Park

Booze Tour Chicago
$65
Sample local and international beer while exploring two iconic Chicago neighborhoods on this 3-hour walking tour. With an in-the-know guide, explore Lakeview and Lincoln Park, stopping at several bars and other venues for tastings of Midwestern craft brews, from porters to lagers, as well as some Irish Guinness. You'll toast Chicago's rich brewing heritage as you learn about its past and present beer culture and watch a home-brewing demo. Plus, enjoy three of your tastings with three different types of bacon.

Your walking tour begins at a local watering hole, where you'll meet your guide and enjoy your first beer tasting of the day.

Then continue your tour around the Lakeview and Lincoln Park neighborhoods, making your way to other locally owned, off-the-beaten-path establishments. As you walk, hear stories from your insider guide about Chicago's long history of brewing beer.

Pop into an Irish pub for a creamy pint of Guinness pulled just right by an expert barkeep. Head over to a beer-and-bacon bar to savor a variety of crispy bacon treats paired with your beer tasting. Meet the owner of a specialty beer and wine store, and hear about how he handpicks his collection. And stop by a microbrew pub before walking into a punk rock bar that was established before Prohibition and is known today for its eclectic beer selection and whiskeys.

You'll also have the chance to watch a home-brewing demonstration, learning about different beer styles as you take in the aromatic hops and barley. When your tour ends, you'll have plenty of new knowledge about some of Chicago's best places to find a great pint.

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Fox River Wine Country with Gourmet Lunch

Booze Tour Chicago
$159

Just west of downtown Chicago lie the charming old towns of the scenic Fox River Valley. An experienced winemaker guide accompanies you to three tasting rooms featuring wines made from grapes grown in the unique ‘terroir' of Illinois and other Midwest states. Sample up to seven wines at each stop and enjoy a gourmet lunch. At the conclusion of the tour, you can be dropped off at select Chicago hotels.

Meet at the InterContinental Chicago Magnificent Mile and settle aboard a 12-passenger, air-conditioned van with individual seating. You'll head out of downtown to the western suburbs of Naperville, Aurora, Geneva, and St. Charles for a full-day of wine tasting in the Fox River Valley.

Your guide — an experienced winemaker and licensed wine distributor who knows the winemakers at each of three wineries you will visit — shares intimate knowledge of the hybrid grapes that are used in the Midwest wine industry.

At each tasting room, receive up to seven tastings and spend 45 minutes learning about the wines that these wineries produce. A leisurely gourmet lunch is provided along the way; your small group can choose from a variety of cuisines.

Tasting fees, snacks, and bottled water are also included along with drop-off at your hotel.

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Duneland Wine Country with Gourmet Lunch

Booze Tour Chicago
$185

Just over the Illinois border along the southern tip of Lake Michigan lie the Indiana Dunes. In the charming villages that dot the area known as Duneland, you'll find artisan wineries featuring wines made from grapes grown in Indiana and other Midwest states. Let an experienced winemaker accompany you from downtown Chicago to three tasting rooms and provide insight about this unique terroir. Your full-day itinerary includes a luxurious lunch of contemporary, farm-fresh fare in Chesterton.

Meet at the InterContinental Chicago Magnificent Mile or receive pickup from your accommodation in the Chicago Loop. You'll depart for Duneland wine country towns located around the Indiana Dunes, just a stone's throw from downtown Chicago and roughly one hour from the Loop.

This full-day of wine tasting includes stops at three wineries where you'll learn from local winemakers about the hybrid grapes grown in the Midwest (tasting fees included). These wines have different aromas and flavor profiles from wines made in Europe and California, so both novices and aficionados will increase their knowledge of all things wine. Your guide is a licensed wine distributor who shares intimate knowledge of the area's wine industry.

A leisurely gourmet lunch with local farm ingredients is served in Chesterton, located in the heart of the Indiana Dunes National Lakeshore, before hotel drop-off in the late afternoon.

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SW Michigan Wine Country with Gourmet Lunch

Booze Tour Chicago
$185
Come explore wine country in the southwest Michigan, just a short journey from downtown Chicago. Discover what this region has to offer and experience wines that are food friendly and amazingly different than what you will taste in California or France. The private tours are perfect for both novice and experienced wine lovers who want to learn more about growing grapes in colder climates and the process of making wine from vine to glass.  The tours are hosted by a knowledgeable wine maker who will answer any questions along the way as you stop at three different wineries along with a gourmet lunch break. The tours include round trip transportation, all tasting fees, and lunch. If you have a larger group, a private pickup can be arranged. If you are staying in a downtown Loop hotel in Chicago, a pickup from your hotel can be arranged.

Start your day with a pick-up from your centrally located Chicago hotel. Take part in a departure toast then head out to visit three wineries for your day in wine country. As the day progresses, your guide will explain to you how grapes that have been cultivated for cold climates have a special character that cannot be found in other parts of the world. In between tastings, you will have the chance to enjoy a delicious 2-course gourmet lunch which is, of course, paired with wine.

Wineries you may choose from include:
Hickory Creek Winery; Lemon Creek Winery and Farmer's Market; Free Run Cellars; Round Barn Winery and Tasting Room; Butler Winery Tasting Room; Tabor Hill Tasting Room

At the end of your tour, your driver will bring you back to your hotel.

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Chicago Craft Brewery Barrel Bus Tour

Booze Tour Chicago
$78

There's never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect city for suds lovers. Visit four of its craft breweries on this all-inclusive, 4-hour tour, where you'll get to tour brewery production facilities and enjoy copious samples of local brews. To keep things interesting, you'll travel in a barrel-shaped bus. Morning and evening departure times are both available.

Chicago is a beer lover's town, and on this all-inclusive, 4-hour tour, you'll travel around the city in a quirky, barrel-shaped bus, sampling its many suds. Depart at either 11am, 7pm, or 8pm, and look forward to visiting four of the city's breweries.

As you drive around town, your guide will provide historical context for the city's recent craft beer resurgence, detailing the rise of its brewing industry in the 1800s, the fact that Chicago's first mayor opened a brewery, and the impact that Prohibition had on the fledgling industry.

You'll stop at four different breweries as part of this tour, from big names like Lagunitas to several of the city's smaller, upstart craft breweries. As you go, learn more about the science behind the brewing process, enjoy an informative tour of brewery production facilities, and get ready to do some sampling. Taste a number of different brews at each stop; you'll consume roughly 50 ounces of beer during the tour, which adds up to about four bottles' worth of suds.

Attendees must be 21 years of age and older to join the tour; please bring along your government-issued photo ID. The tour concludes at your original point of departure.

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Chicago Barrel Bus Craft Distillery Tour

Booze Tour Chicago
$78
Indulge in some of Chicago's uniquely crafted spirits on this all-inclusive distillery tour. Have samples at three local distilleries and tour one distilling production facility while being whisked around town in our one of a kind barrel bus. Our Prohibition-era experts will relive the trials and triumphs of the historical and modern day figures responsible for making Chicago one of the country's best destinations for fine liquors!

What better way to visit and taste at local craft distilleries than in a Prohibition-era styled barrel bus! Step on the bus through the speakeasy style, hidden vertical door to start your one of a kind Chicago Distillery Tour. As you are taken from distillery to distillery in this jitney, your guide will provide an entertaining and educational insight of Chicago's liquor industry originating in the 1800's. Hear stories of George Remus, the man who owned many of the distilleries across America during Prohibition. Learn about the affect that Prohibition laws had on Chicago, and how certain gangs were developed to facilitate the transport of illegal hooch. 

At each of the three distilleries you will receive samples of craft spirits ranging from whiskey to gin, apple brandy, vodka, and more. Enjoy approximately 9-12 samples of different flavors of craft spirits along the entire tour. Each location has its own unique flavors to offer, and sample types vary depending on the locations visited. As you stop at some large and small facilities, you can get the sense of what it was like to step in a distillery back before the 18th Amendment made booze illegal. On the production facility tour, learn the step by step procedures of distilling and the science behind the process.

Please bring your government issued photo ID. Your tour ends at the pickup location.