What to do and see in Illinois, United States: The Best Private Tours

July 9, 2021 Frederic Celentano

Discover the best top things to do in Illinois, United States including Private Chicago Architecture Tour, Private Al Capone Gangster Tour in Chicago, Navy Pier Photo Shoot and Walking Tour, Chicago Riverwalk Photo Shoot and Walking Tour, Private Segway Tour of Chicago, Boston Walk Through History Private & All-Inclusive Tour, Private Frida & Friends tour in Pilsen, Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket, Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago, Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago.
Restaurants in Illinois

1. Private Chicago Architecture Tour

Chicago Private Tours and Productions
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5.0 based on 4 reviews

Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern skyscraper. Chicago is so renowned for architecture that it’s the most vertical metropolis from here to Hong Kong. On our Chicago Architecture Tour, we’ll stop at and discuss: • Sears “Willis” Tower • The John Hancock Building • Gothic gems • Magnificent Mile notable locations • Historic brownstones • The Frank Lloyd Wright homes of Oak Park We offer a uniquely added value opportunity to view not only the outside, but also explore the inside of many of these infamous buildings. Our tour will satisfy the architecture style and structural tastes of the most discerning traveling.

Inclusions: All taxes, fees and handling charges, Professional guide, Hotel pickup and drop-off, Private tour

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Reviewed By 768marthah

We took the private architecture tour of Chicago Private Tours and Productions on 11/22/19. Stevie did not disappoint. His depth of knowledge and storytelling ability made us feel like Al Capone himself was in the Empire room with us. We learned about the history and saw the interiors of the most amazing buildings while being driven to the curb by chauffeur Carmela. Learned about the history of skyscrapers, Union Stock Yard, the World’s Fair in 1893 and it was so interesting that I bought “The Devil and the White City” for the plane ride home. Stevie even added a quick stop at Harry Carey’s so we could see the secret underground tunnel to the courthouse - used at a time when corruption reigned in the city. This tour was my favorite part of the weekend in Chicago and I highly recommend.

2. Private Al Capone Gangster Tour in Chicago

Chicago Private Tours and Productions
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5.0 based on 2 reviews

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  Visit the old stomping grounds of: • Al Capone • John Dillinger • The Untouchables View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre. We bring Chicago’s true crime past to life before your very eyes.

Inclusions: Hotel pickup and drop-off, Transport by private vehicle

Exclusions: Gratuities

Reviewed By 768marthah

We took the private architecture tour of Chicago Private Tours and Productions on 11/22/19. Stevie did not disappoint. His depth of knowledge and storytelling ability made us feel like Al Capone himself was in the Empire room with us. We learned about the history and saw the interiors of the most amazing buildings while being driven to the curb by chauffeur Carmela. Learned about the history of skyscrapers, Union Stock Yard, the World’s Fair in 1893 and it was so interesting that I bought “The Devil and the White City” for the plane ride home. Stevie even added a quick stop at Harry Carey’s so we could see the secret underground tunnel to the courthouse - used at a time when corruption reigned in the city. This tour was my favorite part of the weekend in Chicago and I highly recommend.

700 E Grand Ave, Chicago, IL 60611, USA Wallflower Studios
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5.0 based on 1 reviews

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -1 or 2-hour private session with a professional, local photographer -High-resolution edited images delivered via a private online gallery within 24-48 hours

Inclusions: Private walking tour along Navy Pier and the surrounding area, Professional photographer to take pictures of you throughout the tour, Private online gallery of edited images from your shoot delivered within one to two days

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Reviewed By knowluck44

I can't say enough great things about this adventure! Andrea was amazing in showing us different areas of the park we never would have found on our own. She did a wonderful job of taking fun, candid photos and was very professional (she even carried our stuff for us!). The photos are really great and we were able to pick our favorites to keep, even the quirky ones! Andrea was also super flexible and helped us decide what places we wanted to see or spend more time in. It may seem expensive, but for the professional photos and personal tour of the park, it was well worth it. This was a really great way to get the best of both worlds! It's a lot of walking, so make sure to wear comfy shoes. Thank you, Andrea!

4. Chicago Riverwalk Photo Shoot and Walking Tour

North LaSalle Street & West Wacker Drive, N LaSalle St & W Wacker Dr, Chicago, IL 60601, USA Wallflower Studios
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5.0 based on 1 reviews

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -Your choice of a 30 minute or 1-hour private tour with a professional photographer -High-resolution edited images delivered via a private online gallery within 1-2 days -Enjoy unlimited access to your photos and download as many as you would like with no expiration date *not all stops may be included depending on the length of time you select.

Inclusions: Private walking tour along Chicago's Riverwalk and the surrounding area, Professional photographer to take pictures of you throughout the tour, Private online gallery of edited images from your shoot delivered within one to two days

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Reviewed By knowluck44

I can't say enough great things about this adventure! Andrea was amazing in showing us different areas of the park we never would have found on our own. She did a wonderful job of taking fun, candid photos and was very professional (she even carried our stuff for us!). The photos are really great and we were able to pick our favorites to keep, even the quirky ones! Andrea was also super flexible and helped us decide what places we wanted to see or spend more time in. It may seem expensive, but for the professional photos and personal tour of the park, it was well worth it. This was a really great way to get the best of both worlds! It's a lot of walking, so make sure to wear comfy shoes. Thank you, Andrea!

5. Private Segway Tour of Chicago

300 E Monroe St, Chicago, IL 60601, USA Absolutely Chicago Segway Tours
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5.0 based on 1 reviews

There's no better way to tour the world-class city of Chicago than on a Segway! On your very own private tour, we will cruise around the parks and along Michigan avenue and show you the best that Chicago has to offer. If you are passionate about history, architecture, hauntings, Al Capone, and gangster or more, just let us know! We will customize the tour to fit your interests!

Inclusions: Use of Segway, Helmet

Exclusions: Gratuity , Enterence into museums, We do not enter into buidlings on our outdoor adventure

Reviewed By 355ron

We were in Chicago just for the weekend from Michigan. We decided to do the 2 hour lakeside tour and are so glad we did. it's a great excursion and our 13 year olds loved it. Our tour guide Cedar was really knowledgable and a joy to be around.

6. Boston Walk Through History Private & All-Inclusive Tour

Tremont St opp Temple Pl, Boston, MA 02108, USA ForeverVacation Boston
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5.0 based on 1 reviews

Our Boston Walk Through History Tour will take you to the most historic spots in Boston in one day. If you are looking for a bit of delicious food, some great photos, and a ton of American History, then this is the tour for you. The morning will start with meeting with your friendly local guide. From there your tour will begin as you start your day walking through Boston and exploring the most historic landmarks in Boston. ==== Full schedule 9:00 AM- Meet your guide Park Street Station 9:15 AM- Arrive at Boston Common 9:30 AM- Arrive at Massachusetts State House 10:00 AM- Granary Burying Ground 10:20 AM- Mesmerizing Kings Chapel 10:45 AM- Learn about the Old South Meeting House 12:00 PM- Boston Massacre Site 12:15 PM- Lunch! 1:00 PM- Faneuil Hall Marketplace 1:30 PM- Go to Paul Revere's House 1:50 PM- The Old North Church 2:30 PM- Walk along Griffin’s Wharf 3:00 PM- Get dropped off by your guide at the Boston South Station

Inclusions: An Uber ride, English Speaking Tour Guide, All Fees and Taxes, Bottled water, Lunch

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Reviewed By Johnsavytravels6

Took this tour in early December as our last stop in the US. What a great tour and great food in Boston. Ask for Robin as your guide. She was so nice and answered all of our questions about Boston. Loved how this tour was private so we could go at our own pace. Highly recommend!

7. Private Frida & Friends tour in Pilsen

18th, Chicago, IL 60608, USA Chica-GO Off The Beaten Path Tours
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5.0 based on 2 reviews

Discover Pilsen and its local art, street art, food and people. We will visit a traditional bakery and taqueria and enjoy the art of many great local artists. And then there are the hundreds of cool murals in the neighborhood. We may even meet one of the street artists or stop by an artist studio (on request).

Inclusions: Masks and sanitizer are provided if needed

Exclusions: CTA tickets (please provide tickets yourself) , Gratuities

Reviewed By mdgnaperville

We had a wonderful walking tour with Leentje, partly in areas we knew, but never knew the great stories behind it, and partly in new areas. Although living close by, we learned so much, the kids of 11 and 9 asked so many questions, and loved the tour which had so many cool elements for them and us. Thank you so much Leentje!

8. Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL 60603, USA Babylon Tours Chicago
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5.0 based on 1 reviews

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Inclusions: Skip-the-Line Private Museum Tour , Professional Tour Guide Exclusively For You , Duration 2 - 2.5 Hours , Wheelchair Friendly, All Entrance Fees

Exclusions: Tour price does NOT include hotel pickup or drop-off (we recommend UBER or Taxi), Tour price does NOT include gratuities (optional)

9. Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Pioneer Court, Chicago, IL 60611, USA Chica-GO Off The Beaten Path Tours
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4.9 based on 11 reviews

Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch. Focus can be on public or street art, architecture, food, and much more!

Inclusions: CTPA Licensed Guide

Exclusions: Alcoholic Beverages, Lunch, Snacks

Reviewed By marjoleinf289

What a perfect way to spend an afternoon with friends and family - discovering a new neighborhood of Chicago, enjoying the local cuisine and learning from our favorite guide Leentje. At the end of the tour the group was unanimous: we are definitely signing up for another one!

10. Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Come Sailing, Inc., Monroe Harbor, Chicago, IL 60603, USA Come Sailing, Inc.
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4.9 based on 7 reviews

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.

Inclusions: Professional US Coast Guard licensed captain, Use of Bluetooth speakers, All applicable taxes

Exclusions: Gratuities, Food and Drinks, Parking

Reviewed By Alain7309

Thank you Mike for the nice ride on your beautiful boat. We had such a great time and fun ! Appreciate that we could take commands and enjoy the strong wind.

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