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Private Chicago Craft Beer and Pizza Tour

Private Tours Chicago
$129

Pair craft beer tastings at three of Chicago's finest breweries with a pizza dinner on this 4-hour tour in the Windy City. A guide leads your small group on a tour of the brewery scene in Chicago. Round-trip hotel transportation is included, leaving you only to worry about which beer to try first.

Chicago is home to many world-class craft breweries and you'll visit three of them on this private 4-hour evening tour, starting with hotel pickup. Your guide will work with your private party to choose the breweries you visit from a selection including Lagunitas, Revolution, Half Acre, Vice District, Motor Row, Sketchbook, Temperance, Atlas and Haymarket.

Get a look at a brewery production facility at your first stop and learn how the beer you are sipping is made. At each stop, you will have the option to sample three 5-ounce samples or sip a pint of your favorite style of suds.

Tasting fees are included along with a Chicago-style pizza dinner along the way. Your beer tour concludes with a convenient hotel drop-off.

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Private Chicago Mafia and Blues Evening Tour

Private Tours Chicago
$123

It isn't Chicago history without a dose of mafia intrigue — and some killer blues tunes, too. This lively and fascinating private tour sends you back to the Chicago of the 1920s, 1930s, and 1940s, when Prohibition was in effect, when Al Capone roamed the streets, and when live music had never been hotter. See the site of the St. Valentine's Day Massacre, visit a legendary bar, take in some performances and otherwise immerse yourself in the Windy City's edgy past.

After dark is the perfect time to discover into Chicago's notorious past. This private, 2.5-hour tour kicks off between 7:30pm-8pm (depending on the season). Your guide will meet you directly at your downtown Chicago accommodation, where you'll be picked up and transported around town in a comfortable, private vehicle. As you go, you'll travel back in time — metaphorically, at least — to the Chicago of the 1920s, 30s, and 40s.

The first stop that you'll visit on this evening outing is the Lincoln Park location of the 1929 St. Valentine's Day Massacre, an infamous episode from Chicago's Prohibition past. Your guide will give you historical context for the event, and will also explain how blues music was in fact used as a powerful tool to help the mafia grow in Chicago.

Next, you'll continue through the North Side, and will explore the nightlife that makes the area famous. Stop by a legendary bar formerly owned by mobster Al Capone. Purchase a drink, if you wish, and listen to some jazzy live music.

The night winds down with a short sightseeing drive, which will give you some of the best angles on Chicago's iconic skyline. After that, you'll be returned directly to your Chicago accommodation.

Tour attendees must be aged 21 or over; please bring a government-issued photo ID on the tour with you.

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Private Chicago North Shore Half-Day Tour

Private Tours Chicago
$180

Explore Chicago's famously affluent North Shore in style on this private, half-day tour. After you're picked up from your Chicago accommodation, you'll be whisked away on this scenic sightseeing tour, passing by historic mansions, pretty gardens, and beautiful views overlooking Lake Michigan. See sights ranging from the Northwestern University campus in Evanston to the Chicago Botanic Garden before heading back to the Windy City and being dropped off directly at your hotel.

This half-day outing from Chicago begins directly at your Windy City accommodation: your guide will pick you up in a comfortable, private vehicle at 9am, after which you'll be on your way. Your destination is the North Shore: one of the most affluent areas of the country, it's famous for its Lake Michigan views, its beauty, and its cultural pedigree.

On this tour, you'll get an up-close experience of the best that the North Shore has to offer. Visit lively downtown Evanston, where you'll see Northwestern University's campus, visit the home of former Vice President Charles Gates Dawes, and drop by the Shakespeare Garden.

Then, head to the Baha'i House of Worship in Wilmette, the oldest surviving Baha'i House of Worship in the world, and the only one in the whole of the United States. The temple is also an architectural marvel, with its elaborate carvings and lovely gardens.

On the half-day tour, you'll also venture to the Chicago Botanic Garden, one of the city's prettiest green spaces, where you'll have time at your leisure to wander the tranquil grounds. A tram tour is included in your visit to the Botanic Garden.

At the end of your stroll, you'll reconvene with your driver, who will take you back to Chicago and return you directly to your accommodation.

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Private Day Sailing Excursion on Lake Michigan

Private Tours Chicago
$390

Enjoy a private two-hour sailing experience for up to six people along Chicago's beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago's spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route.  Three departure times offered daily.  All charters are NON-SMOKING experiences.

The Experience

Come Sailing is Chicago's Premier Private Sailing Charter offering daily sailing charters, sunset sails, fireworks cruises, and customized sailing experiences.

During this two-hour private charter our experienced crew will treat you to a relaxing sail along Chicago's beautiful lakefront. Exclusively for you and your invited guests, no other passengers will be aboard. Feeling adventurous? Take a turn at the helm. Captain Mike and his crew will be there to ensure a safe and fun experience. Whatever your choice, these exclusive sailing charters are tailored to your preferences. Captain Mike's mission is to provide safe, enjoyable, customized sailing adventures for his customers. Come Sailing with Captain Mike. 

There's a refrigerator on board that you may use and a bag of ice will be supplied. Please avoid bringing glass containers if possible. Bring your camera, your sunglasses, some sunscreen, and don't forget to bring a Bluetooth device loaded with your favorite music. 

  • Private Sailing Charter, only you the your invited guests
  • Up to six passengers
  • Enjoy a relaxing sail along Chicago's beautiful lakefront
  • Captain Mike and his crew will be there to ensure a safe and fun experience
  • Captain services included with all charters
  • BYOB but please avoid bringing glass containers

See you on the water.

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Private Chicago Sunset Sail on Lake Michigan

Private Tours Chicago
$390

Enjoy a private two-hour sailing experience for up to six people along Chicago's beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago's spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route.  All charters are NON-SMOKING experiences.

The Experience

Come Sailing is Chicago's Premier Private Sailing Charter offering daily sailing charters, sunset sails, fireworks cruises, and customized sailing experiences.

During this two-hour private charter our experienced crew will treat you to a relaxing sail along Chicago's beautiful lakefront. Exclusively for you and your invited guests, no other passengers will be aboard. Feeling adventurous? Take a turn at the helm. Captain Mike and his crew will be there to ensure a safe and fun experience. Whatever your choice, these exclusive sailing charters are tailored to your preferences. Captain Mike's mission is to provide safe, enjoyable, customized sailing adventures for his customers. Come Sailing with Captain Mike. 

There's a refrigerator on board that you may use and a bag of ice will be supplied. Please avoid bringing glass containers if possible. Bring your camera, your sunglasses, some sunscreen, and don't forget to bring a Bluetooth device loaded with your favorite music. 

  • Private Sailing Charter, only you the your invited guests
  • Up to six passengers
  • Enjoy a relaxing sail along Chicago's beautiful lakefront
  • Captain Mike and his crew will be there to ensure a safe and fun experience
  • Captain services included with all charters
  • BYOB but please avoid bringing glass containers

See you on the water.

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Private Navy Pier Fireworks Sail in Chicago

Private Tours Chicago
$446

Enjoy a private two-hour sailing experience for up to six people along Chicago's beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago's spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route.  The unique view of the Navy Pier fireworks from the water is an unforgettable experience!  Offered Wednesday and Saturday evening in season.  All charters are NON-SMOKING experiences.

The Experience

Come Sailing is Chicago's Premier Private Sailing Charter offering daily sailing charters, sunset sails, fireworks cruises, and customized sailing experiences.

During this two-hour private charter our experienced crew will treat you to a relaxing sail along Chicago's beautiful lakefront. Exclusively for you and your invited guests, no other passengers will be aboard. Feeling adventurous? Take a turn at the helm. Captain Mike and his crew will be there to ensure a safe and fun experience. Whatever your choice, these exclusive sailing charters are tailored to your preferences. Captain Mike's mission is to provide safe, enjoyable, customized sailing adventures for his customers. Come Sailing with Captain Mike. 

There's a refrigerator on board that you may use and a bag of ice will be supplied. Please avoid bringing glass containers if possible. Bring your camera, your sunglasses, some sunscreen, and don't forget to bring a Bluetooth device loaded with your favorite music. 

  • Private Sailing Charter, only you the your invited guests
  • Up to six passengers
  • Enjoy a relaxing sail along Chicago's beautiful lakefront
  • Captain Mike and his crew will be there to ensure a safe and fun experience
  • Captain services included with all charters
  • BYOB but please avoid bringing glass containers
See you on the water.

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Private Morning Sail on Lake Michigan

Private Tours Chicago
$390

Enjoy a private two-hour sailing charter for up to six people along Chicago's beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago's spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route.  All charters are NON-SMOKING experiences.

The Experience

Come Sailing is Chicago's Premier Private Sailing Charter offering daily sailing charters, sunset sails, fireworks cruises, and customized sailing experiences.

During this two-hour private charter our experienced crew will treat you to a relaxing sail along Chicago's beautiful lakefront. Exclusively for you and your invited guests, no other passengers will be aboard. Feeling adventurous? Take a turn at the helm. Captain Mike and his crew will be there to ensure a safe and fun experience. Whatever your choice, these exclusive sailing charters are tailored to your preferences. Captain Mike's mission is to provide safe, enjoyable, customized sailing adventures for his customers. Come Sailing with Captain Mike. 

There's a refrigerator on board that you may use and a bag of ice will be supplied. Please avoid bringing glass containers if possible. Bring your camera, your sunglasses, some sunscreen, and don't forget to bring a Bluetooth device loaded with your favorite music. 

  • Private Sailing Charter, only you the your invited guests
  • Up to six passengers
  • Enjoy a relaxing sail along Chicago's beautiful lakefront
  • Captain Mike and his crew will be there to ensure a safe and fun experience
  • Captain services included with all charters
  • BYOB but please avoid bringing glass containers

See you on the water.

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Private Chicago Walking Tour: Historic Landmarks In Germantown

Private Tours Chicago
$42

Bring Your Camera!

Enjoy a private guided walking tour of what's now known as Lincoln Square, home to a traditional German dining hall, an annual German festival, old-fashioned shops and cobblestone streets. During this 2 hour tour, you'll stroll amongst the locals, checking out 8 public art displays, architecture, and historic landmarks while hearing lesser-known stories about the area. As you walk, you'll discover the cultural inheritance of this quaint North Side community while learning new facts about Chicago's history.


When you arrive at the designated meeting spot, you will be greeted by your friendly local tour guide, who will be wearing a t-shirt or holding a sign with our name and logo for easy recognition. You'll follow your private expert guide through this quaint Far North Side community known for offering one of the last remaining glimpses of "old Chicago." As you tour the neighborhood, you will learn about the cultural and historical significance of the area. Throughout your tour, your knowledgeable guide is at your service and available to answer questions about the area and provide recommendations for meals and activities after the tour. Your tour will conclude at the meeting location where your guide can provide directions if you need them.

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Private Chicago West Loop Lunch & Libations Food Tour

Private Tours Chicago
$125

Wear Your Walking Shoes & Bring Your Appetite!

On this three-hour guided walking tour, you'll discover some of the best locally owned restaurants that tend to fly under the radar unless you're truly in-the-know. You'll get to partake in multiple food and beverage samplings at four establishments, all adding up to one satisfying lunch. Between stops, your guide will share lesser-known facts about this iconic neighborhood. 

What To Expect

A welcome greeting - When you arrive at the designated meeting spot, you will be greeted by your friendly tour guide, who will be wearing a name badge for easy recognition. Your tour guide will check you in, discuss safety, and provide an overview of the tour schedule.

Delicious tastings - You will visit 4 locations and enjoy 6 food & 3 beverage samplings, while also learning about the culture and historical significance of the neighborhood. 3 stops are at sit down establishments, and all 4 stops have restrooms.

Local immersion - You will engage with local restaurant owners and staff, get a look behind the scenes, and eat amongst the locals. As you tour the neighborhood, you will learn about the cultural and historical significance of the area and uncover how this once under-the-radar neighborhood is becoming a well-known foodie paradise.

Great service - Our local tour guides and restaurant partners provide top notch service. You will dine at 3 full-service restaurants where you have a seat at the table. Your knowledgeable guide is at your service and available to answer questions about the area and provide recommendations. At your final stop, you are free to stay and shop local artisan purveyors. After the tour, your guide can provide directions if you need them.

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Private Street & Public Art Tour of Chicago's Pilsen Neighborhood

Private Tours Chicago
$42

Bring Your Camera!

Enjoy a private 2-hour art mural tour with your very own local guide. You'll see 8-10 lively public art pieces while exploring art, culture and Chicago history in the heart of the city! As you walk, your local guide will describe the themes and messages that inspired the public art pieces throughout this vibrant community.


When you arrive at the designated meeting spot, you will be greeted by your friendly local tour guide, who will be wearing a t-shirt or holding a sign with our name and logo for easy recognition. You'll follow your private expert guide through Chicago's most colorful, vibrant and diverse neighborhoods on this lively tour that showcases the best of Pilsen's public art pieces. As you tour the neighborhood, you will learn about the cultural and historical significance of the area and discover the creative spirit of local artists. Throughout your tour, your knowledgeable guide is at your service and available to answer questions about the area and provide recommendations for meals and activities after the tour. Your tour will conclude at the meeting location where your guide can provide directions if you need them.

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Private Chicago City Sights Helicopter Tour

Private Tours Chicago
$174
Discover all of Chicago's top sights from great heights on this private helicopter tour. Travel in a state-of-the-art helicopter for magnificent views of Lake Michigan and Chicago's famous architectural features such as Willis Tower, Navy Pier, Shedd Aquarium, Millennium Park, and Lincoln Park. Your private pilot provides expert commentary about the highlights you see, and happily answers any questions that you may have during the flight. Bonus:This flight accommodates a maximum of two people for the ultimate private getaway! Tour route is subject to change.

Make your way to Vertiport Chicago to meet your pilot. Step on board your state-of-the-art helicopter, buckle up and get ready to start your helicopter private tour for two.

Lift up into the air and admire the spectacular perspective on Lake Michigan, with Navy Pier and Lincoln Park along the shoreline. Your pilot points out iconic skyscrapers including Willis Tower (formerly Sears Tower), the John Hancock Building and Trump Tower. Fly past Chicago landmarks like Soldier's Field, United Center, the Lincoln Park Zoo, Grant Park, the Field Museum and Shedd Aquarium.

From the sky, get an amazing look at the beautiful architectural layout of Millennium Park, designed by world-famous architect Frank Gehry. Then gaze over the horizon at the seemingly infinite waters of Lake Michigan.

Your pilot provides expert commentary over the two-way audio headset, detailing the sights you pass. Feel free to ask any questions you may have throughout your private helicopter flight. Tour route is subject to change.

Be assured that your helicopter is climate-controlled, making this tour appropriate for any time of year. It's a Chicago experience that you're sure to remember!

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Private Speakeasy Pub Crawl in Chicago

Private Tours Chicago
$495

Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun night out on the town to celebrate life and your friends. Hosted by a local historian, dressed in period clothing, the tour makes stops at:

  • Al Capone's neighborhood
  • Old Chicago bars
  • Prohibition era establishments 

We transport you back in time to the 1920s, entering our venues through secret openings that really shed light on what the city was like 100-years ago. Relive the glamour of this time period while listening to stories of the rampant racketeering and bootlegging. If you're really feeling up to it, dress the part, too.

We'll visit old bars of Chicago, many preserved in original condition, that were open during prohibition in the 1920's. Enter by way of the “secret” entrance and enjoy one of the same cocktails ordered by the infamous Chicago gangsters & bank robbers at these venues nearly a century ago. Al Capone's personal favorite was “The South-side.” Relive the glamour of the 1920's while listening to stories of the rampant racketeering and bootlegging of the era. This tour will visit several of these historic venues still in operation as speakeasies today in and around the Chicagoland area. The tour guide will tell the history behind and make recommendations for prohibition era cocktails, but the price of food and/or drinks is not included in the price of the tour. Dress is fancy casual or… For fun, you are welcome to wear period clothing like your Guide.

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Private Haunted History of Chicago Ghost Tour

Private Tours Chicago
$495

Up for more of a spooky perspective of the Windy City? Boy, does it deliver. We have curated a unique and underground ghost tour, providing you with the rare opportunity to visit many of Chicago's notable haunted locations. 

  • Murder Castle: the hotel designed specifically for murdering people in the late 1800s by America's first mass serial killer: H.H. Holmes.
  • Death Alley: Peruse a haunting pathway where hundreds of theater patrons were stacked after perishing in the great fire at the Iroquois Theater
  • Old Congress Hotel: Once the full time residence of its former owner, Al Capone, there are ghosts and spirits that haunt the hallways of this famed location.

Different from other tours, our Haunted Chicago Tour is guided by a historian, providing insight into the historical events, information, persons, and rumors of the past. 

Visit the old site of the “Murder Castle”, the hotel designed specifically for murdering people in the late 1800s by America's first mass serial killer H.H. Holmes. There is also the creepy and infamously haunted “death alley” where the charred remains of hundreds of theater patrons were stacked after perishing in the great fire at the Iroquois Theater just to name a few. Patrons will also get to enter infamously haunted venues such as the old Congress Hotel, once the full time residence of its former owner Al Capone. This is not a theatrical tour, but rather a historian guided tour with historically documented tales of hauntings told in more of a “camp fire tale” fashion.

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VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

Private Tours Chicago
$124
See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted and quickly escorted up to the 103rd floor. After a crowd-free morning looking over the Windy City, take a narrated tour on a classic Chicago trolley that passes John Hancock Center, Field Museum and Millennium Park. Finish your comprehensive Chicago tour — available only through Viator — with an afternoon cruise on the Chicago River with a complimentary drink in hand, learning about the city's many distinctive skyscrapers from an architecture-savvy guide.

Your grand tour of Chicago begins at 108-story Willis (Sears) Tower, the second tallest building in the United States. Zip up to the 103rd floor for exclusive access to the Skydeck, a series of glass-enclosed balconies that protrude from the sides of the sleek skyscraper. You feel as if you're levitating above the city in these small cubes, designed with 15,000-pound (6,803-kg) glass panels and steel rivets. It's a feeling that attracts thousands of visitors a day.

With this Viator VIP, you arrive before normal operating hours to enjoy the coveted views some 1,353 feet (1,353 m) in the air without the crowds. During your visit, snap photos and listen to your included audio tour to learn facts and anecdotes about the city and its most famous sights as you mill around the Skydeck uninterrupted.

After an hour at Willis Tower, board a comfortable trolley to begin a 2-hour narrated tour of downtown Chicago. Your insider guide helps you get to know the history and culture of America's third-largest city. See the grand old 1920s-era buildings along La Salle Street in the city's financial district, where you'll make a stop for photos.

Continue on your tour, admiring both old and new architectural masterpieces such as the 19th-century Rookery Building, glass-and-steel skyscrapers by Mies Van Der Rohe, the corncob-shaped towers in Marina City, and famous sculptures by Picasso, Calder, Miró and Chagall, among other notable city landmarks.

Make a stop at Millennium Park to see Pritzker Pavilion, designed by Frank Gehry, before crossing the double-decker drawbridge over the Chicago River. Drive through the bustling Magnificent Mile area, admiring the John Hancock Center, Tribune Tower and Wrigley Building along the way. Pass Grant Park, Soldier Field and the world-renowned Field Museum of Natural History before a stop at Adler Planetarium. Here you can take a moment to delight in jaw-dropping views of the Chicago skyline from the shores of Lake Michigan.

Your trolley tour ends at the popular Navy Pier shopping and amusement area, where you can grab a bite to eat (own expense) and explore on your own for an hour. Then board your 1-hour cruise along the Chicago River narrated by an architecture expert. Learn how architecture flourished in the city after the Great Chicago Fire in 1871, and see more architectural landmarks including the Aon Center, the IBM Building and the distinctive Willis Tower, where you began your tour.

Finish your 5.5-hour VIP tour of Chicago in early afternoon at Navy Pier, where you can find plenty of attractions to entertain you for the rest of the day.