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    O'leary's

    4.8 (5 reviews)
    Open • 9:00 am - 9:30 pm

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    Chicago Architecture Center - The new Chicago Architecture Center at 111 E. Wacker Dr!

    Chicago Architecture Center

    4.6(567 reviews)
    19.1 km•The Loop
    •$

    Almost everyone you meet in Chicago who loves their city will ask when you tell them you are…read morevisiting from out of town, "Have you done the architectural boat tour?" People in Amsterdam will also ask if you have done a canal boat tour - and you have to do these when you visit these cities. Our docent volunteer guide, Steve, was excellent. He was very personable and extremely knowledgeable about the city's riverside buildings and its history. The boat staff was also hardworking and ready to help with any issues, from getting a drink at the boat's downstairs bar to handing out covers when the rain hit us. For what we paid, the 1.5 hour tour was more than worth it. I recommend sitting at the top towards the back, as you don't have to crane your neck as much when he points out places of interest. This was a truly wonderful experience and I would do it again in a heartbeat.

    Not what I expected overall but it was still a very educational experience. Scoring tickets to…read moreChicago's Architecture Center through our hotel, we used the tickets as a good time filler. Not a must see or do attraction but a great day filler activity as you explore the city. Loved the wealth of information they offer as it's valuable to understand Chicagos importance from the ground up! I thought it would be more about highlighting the amazing architectural buildings around the city but nothing like that. It's was more about the environmental impact the city has and the hurdles when designing buildings around town. The staff were friendly at check in and provided great service overall as they were kind and helpful. Small center that you may explore at your own pace and may or may not be worth the admission price. But scoring free tickets it allowed us to be selective in our day or day plans to include the activity to pay it a visit!

    Photos
    Chicago Architecture Center - The Chicago City Model Experience is the star attraction in the Chicago Gallery, featuring more than 4,000 buildings & interactive elements.

    The Chicago City Model Experience is the star attraction in the Chicago Gallery, featuring more than 4,000 buildings & interactive elements.

    Chicago Architecture Center - The stunning Drake Family Skyscraper Gallery on the 2nd floor of the CAC.

    The stunning Drake Family Skyscraper Gallery on the 2nd floor of the CAC.

    Chicago Architecture Center - The Chicago Architecture Foundation River Cruise aboard Chicago's First Lady Cruises is consistently voted the #1 tour in Chicago.

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    The Chicago Architecture Foundation River Cruise aboard Chicago's First Lady Cruises is consistently voted the #1 tour in Chicago.

    Wendella Tours & Cruises - Chicago River Architecture Tour

    Wendella Tours & Cruises

    4.4(1.6k reviews)
    19.0 km•Near North Side

    We went on the architecture tour tonight. It was fun and informative. However, the amount of…read morespiders on the boat is ridiculous. When on the lower level you are hoping a spider isn't go to fall on you.

    We bought tickets for a Sunday morning cruise (depart 10am) online and when we departed the boat…read morewas half full on the top level. We were blessed with perfect sunny skies and temps around 68-70 degrees the whole time. Our small group took up the one back corner of the boat and had a great time. The boat took us out through the lock into the harbor and then out around the breakwater into the open lake, around the lighthouse and then back through the lock (about an hour) to a nice cruise down river (30 mins). We turned around where the main branches come together at a Y. Along the way we learned about the history of the City, the great fire, why the lock exists, some local neighborhood history, reverse flow/pollution of the river, lots of building info/architecture new and old and about the lake. The lock and lake part of the trip was fun for the kids. I would recommend this type of tour if you have children so it keeps them a little entertained instead of hearing about buildings for 90 mins. The bathroom on board was clean. The bar area downstairs looked good, but we didn't drink or buy snacks. We walked from our hotel so I can't help you with parking. It's a couple flights of steps down to get to the loading area for the boat and the same steps back up to street level when you leave the boat. Last thing, when we got off our boat the lines for all the boat companies were long. If you hate lines, get the boat tour done early!! Thanks guys!

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

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    The Barrel Run

    The Barrel Run

    4.9(130 reviews)
    18.9 km•River North, Near North Side
    •$$

    The Barrel Run provided an exceptional experience. For my sister's 40th birthday, we arranged a…read moreprivate Prohibition Tour, which proved to be truly remarkable. Our tour guide, David, was an outstanding narrator whose extensive knowledge offered many new insights, even for those in our large group who reside in the Chicago area. Furthermore, Denise, who served as the primary point of contact for scheduling, was excellent; her communication was consistently thorough. I highly recommend The Barrel Run for anyone seeking a unique and memorable event.

    If you're a craft beer fan this tour should be on your list of things to do if you're visiting…read moreChicago. You get to visit 3 breweries/brew pubs. I believe at least one of them you get a tour of, Revolution brewery was the one we got to tour. Our guide Ted was awesome, he gave us some history on the places we were going to visit along with some local Chicago history during the ride. The location were kept a surprise ahead of time so we didn't know where we were going until we got there. They do have a rotation of different breweries they tour so if you decided to go again you could possibly explore some new spots the next time around. The coolest part about the tour is the bus itself, just checkout the pictures. The seating layout makes for great interaction with the rest of the people on the tour. I happened to find out about The Barrel Run when I was looking up Chicago tours on YouTube & came across some video a couple named kovACTION made about 3 months ago. Right after watching that I knew I had to fit this in my schedule when I was in town.

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    The Barrel Run
    The Barrel Run
    The Barrel Run

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

    Chicago Detours

    4.9(273 reviews)
    18.0 km•River 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.

    Excursions Into the Unknown

    Excursions Into the Unknown

    5.0(1 review)
    8.8 km

    took this tour of northside ghosty locations yesterday with family and friends. this was the…read moresecond time we've gone on one of the tours having taken the southside tour last year. our guide, dale kascmarek is extremely knowledgeable and a great driver. he came to pick eleven of us up in a passenger van which is wired with speakers all the way in the back so he can be heard by everyone on his mic as he explained the locations and stories behind them. the tour usually take roughly four hours but last night took a little longer because we got stuck in city traffic a couple of times. he took us to the st valentine's day massacre site, graceland cemetery, rosehill cemetery robinson woods and other locations, each time giving us a full explanation of each place and the stories behind them. there were several spots where we could get out of the van and take pictures which was very cool. dale welcomes all questions and is friendly and accommodating. the only down side is that with the traffic and all, it did get a little long but that wasn't his fault. saturday night in the city is like that. i'd recommend the south side tour over the north side one though only because there are more "get off the bus" locations and just more locations in general. we're going again next year :) .

    From the owner: Excursions Into the Unknown is the perfect blend of spooky and history! We are a bus tour of…read morehaunted Chicagoland locations which has been successfully servicing customers since 1982. We offer custom tours for groups of 6 or more! Tours last between 3-4 hours and are conducted in various sized vehicles from a 15-passenger van, mini-buses to full-size motor coaches. All tours are personally conducted by the President of the Ghost Research Society, Dale Kaczmarek who has been researching and investigating the paranormal since 1975. We have conducted tours for libraries, park districts, senior clubs, civic organizations and individuals. We offer AAA Chicago Motor Club, Senior, group, CASH and Yelp discounts.

    Photos
    Excursions Into the Unknown - 95th & Kean Ave.

    95th & Kean Ave.

    Excursions Into the Unknown - German Church Road

    German Church Road

    Excursions Into the Unknown - Rialto Square Theater

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    Rialto Square Theater

    O'leary's - tours - Updated October 2026

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