Chicago
Private Experiences

Enter your dates to find available activities

Our most recommended Chicago Private Experiences

Chicago: 45-Minute Private Helicopter Flight for 1-3 People

1. Chicago: 45-Minute Private Helicopter Flight for 1-3 People

Enjoy spectacular views of Chicago from an MD500 helicopter. This helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumburg Regional Airport and see some of Chicago's highlights including the Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan with its beaches and picturesque shoreline. Also see the Chicago River, Grant Park, Millennium Park, Buckingham Fountain, and Museum Campus. Make sure you also look out for Wrigley Field, home to the Chicago Cubs, and the United Center, where the Chicago Bulls and Blackhawks both play. This is a private helicopter experience for 1 to 3 passengers. Travel in complete safety with a professional pilot who will provide you with live commentary through noise-canceling headphones. In the summertime, have the added thrill of the doors being able to be off during the flight.

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

2. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

Chicago: 2 Hour Family Walking Tour with Guide

3. Chicago: 2 Hour Family Walking Tour with Guide

Spend a family fun day out on this 2 hour guided walking tour, designed to suit all ages and interests. Meet your guide, then set off into Chicago’s bustling city streets where your sightseeing adventure begins. Along the way, visit some of the city’s most iconic sights and landmarks, and learn interesting facts and stories about Chicago’s history. Hear how Chicago got its name, and discover hidden secrets as you head off-the-beaten-path. The tour has an easy pace, and your professional guide ensures the whole family has fun. 

Chicago: Private Architecture Tour - 3 or 6 Hours

4. Chicago: Private Architecture Tour - 3 or 6 Hours

Start with pickup from your hotel and meet your local tour guide, an expert on the architecture of Chicago. Travel through the city in luxury private transportation to discover its rich architectural history. See famous buildings such as the Sears Tower, The John Hancock Building, and the Wrigley Building Discover Gothic gems along the Magnificent Mile, historic brownstones, and the Frank Lloyd Wright homes of Oak Park. Enjoy a unique added value opportunity to view not only the outside but the amazing hidden interior of many of the buildings on the tour. At your discretion, make numerous stops along the tour to go to the top of the sky decks of famous skyscrapers. Walk along the Chicago River and enter the inside of buildings designed by many famous architects. This tour has several different options. Enjoy the sites of the downtown Chicago area with its many skyscrapers, amazing interiors and great photo opportunities. You may also choose the Oak Park Frank Lloyd Wright Homes and Studio option in lieu of the downtown tour where you will have the opportunity to view the interior of his very first home and studio along with over two dozen of his original structures lining Forest Street in Oak Park anchored by Unity Temple, considered to be the world's first building of the modern architectural style. Each of the above separate options are 3 hours long. If you are to choose both options for a full 6-hour touring experience, enjoy a lunch stop at one of Chicago's many famous hot dog stands or deep-dish pizza joints.

Chicago: Private 3-Hour Al Capone Gangster Tour

5. Chicago: Private 3-Hour Al Capone Gangster Tour

Experience amazing stories of true crime coming to life on this three-hour private tour. Visit many of the old venues where gangsters used to operate, including old speakeasies and historic hotels. Your expert historian guide will accompany you and your private group in luxury accommodation to historically significant locations in the city. View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, and the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy guns. See the site of the infamous St. Valentine’s Day Massacre, and sit in Al Capone’s booth at the Green Mill. Finally, visit the location where Public Enemy #1 John Dillinger was assassinated by the FBI.

Chicago: Photo Shoot with a Private Vacation Photographer

6. Chicago: Photo Shoot with a Private Vacation Photographer

The tour provider will organize the locations for your photo shoot based on your own unique requirements, whether it be a family getaway, a romantic trip or a livelier one with friends.  Once the details are organized, you will receive confirmation of all the information you need, leaving you to simply meet the photographer on location in Chicago on the day and let them work their magic, capturing your travels in a contemporary and candid style of photography. Your Chicago vacation photographers are handpicked and highly experienced in addition to being local experts and will share their knowledge of the city with you like an old friend. Once your photo tour has finished, you will receive a link to your own personal online gallery (password protected) within 5 working days, containing your professionally edited images, all free to download. This photo tour will allow you to look back over your travels with fond memories, when all too often you are left with rusty memories of your journeys. Make sure that the next time you travel, you will have mementoes that will last a lifetime and beyond.

Chicago: Private Half-Day Highlights Tour with Hancock Tower

7. Chicago: Private Half-Day Highlights Tour with Hancock Tower

Explore Chicago, a vibrant metropolis packed with incredible history, architecture, and public art. Discover the third-largest city in the United States on a guided walking tour. Visit all of the city's major sights, such as the Magnificent Mile, Navy Pier, Millenium Park, and Hancock Tower. Listen to stories about Chicago life from a local and find out how the city earned its nicknames. Savor a slice of deep-dish pizza at the end of your tour before your guide drops you off at Hancock Tower. Enjoy 360-degree views of the city from the observation deck.

Frequently asked questions about Chicago Private Experiences

What are other things to do than Private Experiences that are worth visiting in Chicago?

The other unmissable things to do in Chicago are:

Other Sightseeing Options in Chicago

Want to discover all there is to do in Chicago? Click here for a full list.

What people are saying about Chicago

Overall rating

4.9 / 5

based on 93 reviews

Very informative, everything worked out wonderfully from pick up to the end. Very nice and very good guide, also nice and courteous driver, comfortable car. The tour itself has a strong focus on Lloyd Wright, but that's fitting in a city where he started, has been active, and where many of his homes stand. Overall excellent tour with insights we would never have had otherwise.

Kai was an excellent guide for our activity last night. She had so much knowledge of Chicago history and when we requested more of history/ gangster knowledge vs just the speak easy stops, she made a significant pivot to make our activity specific to our requests. Would highly recommend this tour and Kai!

Was a very exciting and thrilled ride...Especially with the doors off. It was a sunny day with great views of the city

They had great communication and the flight was AMAZING!!! Sara was an amazing pilot and we had a ton of fun!!

We loved it . Sara was excellent pilot! Unforgettable experience ❤️