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    ChicaGo By Boat

    4.7 (13 reviews)
    Closed 9:00 am - 10:00 pm

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    Another perfectly relaxing skyline sail w/ChicaGo by Boat! We love sailing with Capt. Conway w/friends dates & family. Thanks & fair winds!
    Linda D.

    Trust Capt, Conway and ChicaGo By Boat for all of your sailing needs! Sailing is kind of my thing. There's nothing like relaxing out on the water with friends as we enjoy the inspiring views of Chicago. I'm not talking about a booze cruise. Sure, you can find those all over town. My first summer in Chicago I met friends with sailboats and was converted from the idea of a booze cruise to the perfect floating patios with close friends and instead of crowds. Ahoy! Enter ChicaGo By Boat. I first went sailing on a semi-private charter with a visiting friend: It's a fine way to mingle and take in Chicago from Lake Michigan. It's also an excellent intro to sailing. I was invited me to try a private charter. Fortunately I knew of some friends who would join me. The owner Captain Conway always make me and my guests feel like VIP's from booking to boarding to disembarking. They're very professional, responsive and flexible. Whenever there's a weather concern they've called ahead and communicated to give us the latest details before heading to Burnham Harbor. Captain Conway is very welcoming so it's more like entertaining and sailing with friend, than a generic charter or a set tour around the pier. He works with all levels of comfort with water, sailing and athleticism. Conway also has some entertaining stories of people places things that have come up under sail. Sporty, lively and heeling? Check. Relaxing and enjoying the skyline views? Absolutely! BYO summer menu with paired beverages and tastings? They've become a stellar go-to summer choice. Summer birthdays aboard Nightswimming? Certainly a luxury sailing vessel and first class event! They have several ways to let party hosts relax and lighten the load. When we have a group of 6 we can get an extra crew member to help. There's bottled water for us as well as a refrigerator, ice and plastic drink ware. Have a VIP, corporate client or the need to sail from DuSable Harbor or Belmont? Captain Conway and his team have always been able to help! With this relaxed and professional vibe everyone is instantly at ease and guests ask when we can sail next. Sometimes my guests and I enjoy a cocktail skyline sail, other times it's water, Pellegrino and an athletic day finding the best wind. Plus, the wind and the waves conjure up an ideal mix so it's like a built in spa day! And, it's wonderful to see more social media support for sailing. Thanks for everything Captain Conway! Sailing in these conditions again? YES, please!

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    Review Highlights - ChicaGo By Boat

    I couldn't ask for a better experience to bring visiting friends and family to show off the Chicago skyline and Lake Michigan.

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    Chicago Architecture Center

    Chicago Architecture Center

    (811 reviews)

    The Loop

    Chicago Walking Tour - Elevated Architecture Downtown 'L' Train…read moreWe have previously taken the CAC boat tour and one of the surface walking tours (both of which were great), but this time we wanted something with a slightly different perspective while staying downtown. We chose the Elevated Architecture Downtown 'L' Train tour led by Andrew, our CAC docent. As no one else had signed up for the tour that morning, it became a private tour. Andrew was not only very knowledgeable about the architecture and friendly, but also, given that he works in planning at the Chicago Metro, was able to take us on an even deeper dive concerning the "L", its history, and some of the current challenges. As we were about 35' about street level for the tour, we were also treated to a different perspective of the building and their design/decoration, something that cannot be readily observed from street level. Thans again to Andrew for an information and entertaining tour above the streets of downtown Chicago-truly a unique experience.

    If you're in Chiago you have to do the Architecture tour at least once. If you're in Chicago…read moreduring the Summer as I was you can seek sanctuary in the air conditioned lower level. I wish the audio was a little bit louder on that level due to the sound of the fans and people talking. If you like my reviews, consider "following" my profile for reviews all across the SF Bay Area . Why "follow" someone? It causes the person you follow's reviews to tier to top when you pull up a business. I find this very handy when researching venues. Rod's Review grading scale explained. Essentially I personally base it on the likelihood of a return visit and I try to be stingy with 5 star reviews since they should be "special" in my eyes. Price/Value also play a role obviously but there are $ and $$$$ littered across my grading scale. 5 stars - "I'll go out of my way" (approx 6 % of my reviews) 4 stars- "If I was in the area I'd go here and would recommend", (approx 38% of my reviews) 3 stars "Maybe if was nearby", (approx 37% of my reviews) 2 stars -"Would likely not return, Only if you want to go", (approx 16% of my reviews) 1 star -"No thanks, even if I was hungry", (approx. 3 % of my reviews)

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

    Chicago Architecture Center

    (559 reviews)

    $

    The Loop

    Took the Art Deco tour yesterday, what a great way to learn about some of the history of Chicago as…read morewell as the gorgeous buildings!! Our guide was knowledgeable and kept the tour interesting. Unfortunately I flew out yesterday afterwards, but will definitely be back to check out the Center as well.

    This is a rather small museum and when I was there there was like two exhibits to check out. The…read morefirst floor is 1/3rd gift shop 2/3 the Chicago exhibit. This exhibit has a cool model of the city and interactive screen that you can highlight different buildings. It's really amazing. However, there's multiple computers and if there's a crowd, as soon as you highlight the building you want someone else highlights the building they want and becomes really hard to really take it all in. There's a small series of panels on Transit orientated development which I really enjoyed. I'm not sure if those are always there or just currently there. They seemed rather new. There was also a piece on regular field with a model of the stadium and some interactive stuff to play with with a scoreboard. Overall the first floor was pretty good. Second floor is where I disappointment kind of hit. I guess they were in the middle of changing exhibits so there was only a small section to see and that exhibit didn't really resonate with me and didn't flow very well. It's worth checking out, especially if you have some sort of discount tickets like I did.

    Chicago River Boat Architecture Tours - Our boat

    Chicago River Boat Architecture Tours

    (281 reviews)

    Near North Side

    Every person I asked for a suggestion about what to do when in the city and everyone said to take…read morean architecture tour. They were right. I paid for the Gropuon which made our tickets half price. The one thing Is will say is that the parking directions for were confusing to me - I could have parked much closer but ended up going to the wrong location. This was something the tickets warned about but I just didn't figure it out. There was a bar and food on board but I didn't partake. We decided to do the nighttime tour per the suggestion of those who told me about the tour and I'm happy to have done so. The buildings were so beautiful and the lights were great. Next visit I will try the day time tour. It was an excellent way to spend 90 minutes and learn some really cool facts about a great city. I highly recommend it to anyone visiting Chicago.

    Chicago riverboat architectural historical tour on main branch of river. Time to cruise…read more Nonstop 90 minutes. Talk about the architectural sky scraper wonders. foremost. Mind blowing enormously tall. Alot of humor and details on rental price @$400,000 a year. Famous people like Barack Obama and Oprah Winfrey lived here. Willis seats tower 100 stories tall 1,052 in the Windy City Sky! It's the tallest! there are 37 drawbridges on the main branch river. That's all the facts in my head could remember. The river is alive! The buildings taller than Sequoia redwood trees or Oregon Douglas Fir. Glass, concrete and steel in assorted shapes - seemingly alive like a living tree. I feel the energy of the river and the buildings standing tall. Worth the moolah.

    ChicaGo By Boat - boatcharters - Updated May 2026

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