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Illinois Private tours

Our most recommended Illinois Private tours

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 : The Field Museum Skip the Line 2H Guided Tour

3. Chicago : The Field Museum Skip the Line 2H Guided Tour

Meet your tourguide for a breathtaking 2-hour tour of the Field Museum, one of the most important museums in the world, part of the complex known as the Museum Campus in Chicago. A visit alone without a guide can be tiring because the museum's collection includes more than thirty million specimens. Some of the exhibits in the Field Museum include a large collection of dinosaur skeletons (including Sue, the largest and most complete skeleton of Tyrannosaurus rex currently known), a comprehensive exhibit on the evolution of the planet (spanning four billion years), extensive anthropological exhibits on the humanities and cultural sciences (including artifacts from ancient Egypt and pre-Columbian civilization, but also from the Pacific Northwest, the Pacific Islands, and Tibet), a large and diverse taxidermy collection (including large mammals such as two African elephants and several felines including Tsavo Lions from the 1996 film Shadow and Prey), and an exhibition on the ancient Americas with a large collection of Native American and Aztec artifacts.

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: Deep-Dish Pizza and Local Food Walking Tour

6. Chicago: Deep-Dish Pizza and Local Food Walking Tour

Immerse yourself in an exploration of Chicago’s outstanding food culture. Navigate through the Loop district, which is buzzing with activity, as your guide brings you straight to the vendors and restaurants they love most. Taste some of the local staples, including the world-famous deep dish pizza. Pass by iconic places like the Chicago Riverwalk and get to grips with the evolution of the city, as immigrants brought their culinary influence from all over the world. Get to know family shops owned for generations and learn the origins behind the Windy City's most beloved street eats. Enjoy a local street food staple, perhaps the famous Chicago-style hot dog or Italian beef sandwich. And, of course, a food tour of Chicago is not complete without a bite of the iconic deep-dish pizza. Try a slice and top it off with a traditional sweet treat for a complete foodie experience.

Chicago: Photo Shoot with a Private Vacation Photographer

7. 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: 2 Hour Family Walking Tour with Guide

8. 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. 

From O’Hare Airport to Chicago Private Sedan Transfer

9. From O’Hare Airport to Chicago Private Sedan Transfer

Whether you travel for business or leisure, enjoy the comfort of traveling worry-free from Chicago O'Hare Airport to Downtown. Your chauffeur will track your flight to ensure that they are there, ready, and waiting when you arrive. A tour operator will communicate with you through every step of your journey. Get picked up in the arrivals hall, where your chauffeur will be waiting with your name on a sign. Relax in a modern, luxury vehicle. Water will be waiting for you on board. Rest or work while your professional chauffeur gets you safely from O'Hare Airport to your hotel, office, or residence in Downtown Chicago.

Chicago: Architecture and Food Walking Tour with Tastings

10. Chicago: Architecture and Food Walking Tour with Tastings

Experience the best of Chicago on a guided walking tour that explores the city's architecture and food culture. Your 2-part walking tour begins by exploring the heart of Downtown Chicago. Join your guide as you discover the city's architectural highlights, both old and new. Admire views of the Chicago River, see Chicago's City Hall, the Wrigley Building, the Water Tower, Cloud Gate, and much more. Then, hit the Central Loop, where locals go to grab their favorite foods. Sample some of Chicago's famous fare and learn about the history behind street food staples in the Windy City. Let your local guide show you the how-tos (and how-not-tos) of legendary dishes, from deep dish pizza to sandwiches, to a loaded hot dog. Listen as they entertain you with fascinating stories of the everyday immigrant chefs and vendors responsible for Chicago's eclectic food scene. By the end of the tour, you'll have a deep appreciation for both the evolution of this city and the role food has played in the lives of its residents.

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What people are saying about Illinois

Overall rating

4.9 / 5

based on 93 reviews

A wonderful experience, thank you! We were lucky to have a perfect sunny, clear day, and a great pilot. Sara was very personable and explained things about the helicopter as well as giving us a fabulous tour over Chicago. Booking was easy and we were contacted prior to the flight with instructions on where to go and contact details.

Good location to pick up the bike, very close the the lake trail. No deposit taken which was good. Bike was in excellent condition and really good map provided. The staff handing out the bikes were great.

It was wonderful. Very kind guide and with lots of information about the architecture of the city. I highly recommend. It was a success

Everything went great. Very nice and helpful people. Our pilot was great.

The views and the experience alone makes it worth it!