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    Chicago Private Tours

    5.0 (29 reviews)
    Closed 7:00 am - 11:00 pm

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    Natalia T.

    This was my third time in Chicago and I wish I'd done this tour during my first visit! The van they drive you in is spacious and clean. They show you everything you want to see and answer any questions you have. Very knowledgeable and accommodating. Todd was our guide and TJ was our driver. One of the best tours!

    What a perfect way to explore Chicago!! My husband and I enjoyed a beautiful afternoon touring the city and local breweries. The tour was highly customizable, with excellent service, and super knowledgeable guides! We started the tour not knowing much about the city and ended the tour in love with CHI. Plan to return for our next trip! Thank you!!

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    Review Highlights - Chicago Private Tours

    Matt has such extensive knowledge and gives such a detailed history of the city you cannot help but fall in love.

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    Wendella Tours & Cruises - Chicago River Architecture Tour

    Wendella Tours & Cruises

    4.4(1.6k reviews)
    0.7 miNear North Side

    I've been to Chicago many times, but never did the architectural boat tour thinking 'oh it's too…read moretouristy.' This time I gave in thinking the weather is nice and I want to do something relaxing. Wendella was highly ranked and a friend recommended them. I was bummed when I saw the 90 minute sunset tour was sold out. I saved $50. lol I was happy to find that they had a 45 minute tour at 8pm. This was actually perfect and for $28! I got to see a little bit of light when we boarded and the actual sun setting and views of the city in the dark. Very beautiful. The host tries to tell us history and be funny, but I think most were busy taking photos or just relaxing as a breeze hit. The ride is smooth so not to worry if you typically get motion sick. I felt fine. You may book tickets online and I'd show up by 7-7:15pm to get on the 8pm boat. The line gets long and if you want premium seating in the back or along the sides, then you want to be early. This 45 minute tour takes off a little bit further in than the 90 min one that has entry just off the bridge by Michigan Ave. Not sure if the boat had a restroom. Overall I'd budget about 2ish hours for this activity from the time waiting in line, cruise, and getting off the boat. Highly recommend!

    So many choices, lucked out with today's architectural tour with the amazing John narrating…read more Knowledgeable, comical, and personable, I learned an incredible amount of Chicago history and architecture while being entertained. Who knew? Plus over 75 photos!!! This is a MUST DO for visitors and locals alike !!! Thank you John!!

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    Wendella Tours & Cruises
    Wendella Tours & Cruises
    Wendella Tours & Cruises

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    Chicago Food & City Tours - Urban Belly caramelized chicken dumplings

    Chicago Food & City Tours

    4.8(691 reviews)
    0.7 miRiver East, Near North Side

    My 13 year old daughter and I enjoyed the Iconic Foods of Chicago tour yesterday. Our guide Lillian…read morewas fantastic! the food was all amazing and I especially enjoyed all of the history she shared about the foods and neighborhoods of Chicago. Highly recommend!

    Amazing amazing amazing! My best friend and I absolutely loved the "Yes Chef! Chicago: A Bear…read moreInspired Food Tour". Casey, our guide, was phenomenal. So fun and witty, and he really went above and beyond to make sure we had a great experience. All the places we visited were very special and iconic, including a bakery that's 115 years old and an ice cream shop that's 105 years old. It was really fun remembering where these places appeared in the show. Another perk of the tour was skipping lines and having special areas and service just for us. And not having to drive and look for parking. The air conditioned bus was lovely and comfortable, and it was fabulous to be driven around different neighborhoods. We went to so many great places and it's a fun way to get to know the city better. We ate so much good food!!! Italian beef sandwich, charcuterie, pepperoni pizza, hot fudge sundae, strawberry donut and more. Great drinks too! Beer and cocktails, or soda. I didn't need to eat for the rest of the day! Everything was delicious! I highly recommend this tour! It was exceptional and worth every penny.

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    Chicago Food & City Tours - Mr. Beef beef sandwich with hot peppers

    Mr. Beef beef sandwich with hot peppers

    Chicago Food & City Tours - Pizza Lobo pepperoni pizza

    Pizza Lobo pepperoni pizza

    Chicago Food & City Tours - Our tour guide in a local temple.

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    Our tour guide in a local temple.

    Chicago Detours - Beyond dates and names of architects, we dig into the ways in which we interact with architecture.

    Chicago Detours

    4.9(272 reviews)
    1.3 miRiver West, Noble Square, West Town

    During Parents' Weekend at the University of Chicago, the university offered tours of the…read moreneighborhood through Chicago Detours. My wife did this tour a couple years ago and highly recommended it, but I wasn't especially interested because I had also gone to school here and figured I knew enough about Hyde Park already. However, she insisted that it would be worth our while and so I agreed to climb on the bus. And it was the absolutely right decision, because the tour was excellent. In fact, it wasn't just a tour of Hyde Park. It included the surrounding neighborhoods of Washington Park, Kenwood, Jackson Park, and Woodlawn. Since this was a UChicago sponsored event much of the information related to the University's investment and involvement in the area. Our tour guide and founder of Chicago Detours, Amanda, is herself a graduate of UChicago and thus she had some additional insight into the relationship with the community. Though the 75-minute tour felt a little slow-going at times, there was much to learn about the vibrant but sometimes troubled history of the area. Amanda has tremendous knowledge and the excursion was both fascinating and entertaining. I can imagine that Chicago Detours would have equally interesting tours of other neighborhoods in this diverse city.

    Virtual tours are such a cool thing to do right now. I attended a Yelp Elite event that was a…read morevirtual food tour of Chicago. It was incredibly informative and a good balance of history and current trends. Looking forward to attending more virtual tours, like the World's Fair and the Cruise From Your Couch Boat Tour. I loved seeing the pictures of the in-person tours and can't wait to attend some of those too.

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    Chicago Detours - On an architecture tour, you'll venture into spaces many locals don't know

    On an architecture tour, you'll venture into spaces many locals don't know

    Chicago Detours - Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

    Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

    Chicago Detours - Historic Walking Tour with Bars- drink, learn, eat, explore.

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    Historic Walking Tour with Bars- drink, learn, eat, explore.

    Shoreline Sightseeing - Chicago Fire Department near Navy Pier

    Shoreline Sightseeing

    4.7(1.9k reviews)
    1.0 miNear North Side

    This tour was on the top 10 list of our things to do in Chicago. I researched all the boat…read morecompanies that offered the Chicago architecture boat cruises and Shoreline Sightseeing came out hands down #1 for us in tour length, type of cruises, accessibility and in price for what you got. Best deal. Our tour guide was happy, energetic, and very knowledgeable about Chicago because he was born and raised there. We chose the 75 minute, 4pm Chicago River tour and it covered a lot! We never lost interest and learned about Chicago's history. It is well worth it! Our Architecture River Tour boat departed from the dock at Navy Pier. We learned that their boats are the most accessible at this location. Their boats can accommodate wheelchairs up to 30-inches wide. Your wheelchair must be able to navigate a ramp with a 2-inch step at one end. I needed one that was kind to my knees. Best to call them for more details. They were very helpful whenever we called them. Their boats are both double-decker and single-level boats, and there is generally no protection from the sun, rain, or wind. There is a small bar on the main level. Restrooms are located on the lower deck, which is accessible only via stairs from the upper deck. Enjoy! It's amazing!

    Sam S was a great tour guide!…read more Awesome tour! Great info, lovely views! The boat was large, comfy, onboard restrooms and bar.

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    Shoreline Sightseeing - The Chicago Architecture Tour boat cruise was amazing!

    The Chicago Architecture Tour boat cruise was amazing!

    Shoreline Sightseeing - Top deck - guide Joe

    Top deck - guide Joe

    Shoreline Sightseeing - Merchandise mart

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    Merchandise mart

    Chicago Private Tours - tours - Updated August 2026

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