Location: Chicago
Top Things to do in Chicago
10 Private Tours in Chicago That You Shouldn't Miss
The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago
1. Private Chicago Architecture Tour
Overall Ratings
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
Exclusions:
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
Overall Ratings
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.
3. Millennium Park Photo Shoot and Walking Tour
Overall Ratings
5.0 based on 3 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, 1-hour, or 2-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. *Due to COVID restrictions, some stops may be not be accessible
Inclusions: Private walking tour throughout Millennium Park, Professional photographer to take pictures of you throughout the tour, Private online gallery of your edited images delivered within one to two days
Exclusions:
Reviewed By FleuroNZ
Amazing photos! We had a family shoot including a 2&3yr old Andrea made it so easy as we’re not the most relaxed in front of the camera but we all felt at ease and had a great time. She was great with the kids and had all the tricks to get the kids attention and smiling. The end result is lots of wonderful photos to remember our trip by. We wouldn’t hesitate in recommending Andrea!!
4. Navy Pier Photo Shoot and Walking Tour
Overall Ratings
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
Exclusions:
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 Secret Food Tour of Chicago
Overall Ratings
5.0 based on 2 reviews
We are Chi-Town foodies of the first order, and we're so excited to share with you all the culinary delights this historic Midwestern city has to offer. There is so much to share about Chicago: historic enclaves, stunning architecture, an extensive collection of publicly displayed civic artwork, and a culinary style steeped in history. We will discover each facet of this unique city as we eat and explore Chicago's Loop District. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!
Inclusions: Lunch
Exclusions:
Reviewed By CrackheadRecords
What a fun time! My tour was on Sat Oct 17th, shortly before Chicago shut down indoor dining again. My guide Denise was so lovely and I couldn’t have had a better time! We started out at Gino’s East for deep dish pizza, Italian beef and Al Capone’s drink at Italian Village as well as hot dogs (without ketchup) at Luke’s! In between restaurants, I had a history and pop culture lesson from around The Loop with sites such a the Flamingo, Picasso’s Maquette as well as a mural by Marc Chagal. For coming when Chicago was partially shut down, Denise certainly made this an unforgettable experience!
6. Chicago Riverwalk Photo Shoot and Walking Tour
Overall Ratings
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
Exclusions:
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!
7. Private Segway Tour of Chicago
Overall Ratings
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.
8. Boston Walk Through History Private & All-Inclusive Tour
Overall Ratings
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
Exclusions:
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!
9. Private Frida & Friends tour in Pilsen
Overall Ratings
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!
10. Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket
Overall Ratings
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)
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