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    Strayboots

    3.8 (13 reviews)
    Closed 10:00 am - 10:00 pm

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    Museum Hack

    Museum Hack

    5.0
    (6 reviews)
    1.3 mi

    Wow, what a great experience. We stumbled on this unique tour while looking for things to do in…read moreChicago. I've been to the Art Institute many times, but this was a completely different experience and well worth the price. Museum Hack offers unique tours of museums with the goal of making the experience both entertaining and informative. Our guide, Colin, took us around and showcased several pieces of art by telling us the stories behind the works. This really brought the art to life for us. His tour was informative and fun. It was also interactive. We were joined by a drag artist about halfway through the tour and that was a really interesting experience. They took us to several of their favorite pieces and talked about how the art they chose fit in to their experience as a drag performer. It was fascinating. We were lucky because we were the only 2 slots booked for our tour. The maximum group size is 10 and the minimum is 2. This meant we got a really personal experience with our guide. A tour like this will really help you see the museum in a new way. It's pricey, but worth it. Museum admission is included in the package and at least on our tour we did not meet at the main entrance. We entered by the modern art wing. I really have nothing but good things to say about the tour and our guide. He kept us informed leading up to the tour and kept us entertained during the tour.

    Had a great time with Museum Hack and their team. Colin was a great rep and show our management…read moreteam an exciting and educational time. Was a great experience and would recommend to anyone.

    Photos
    Fun group activity at the museum
    Fun group activity at the museum
    Unique group activity.
    Unique group activity.
    Selfie time.

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    Selfie time.
    Shoreline Sightseeing

    Shoreline Sightseeing

    4.7
    (1.9k reviews)
    0.3 mi

    Eric was a very good speaker and staff war very nice, the entire thing was very informative thank…read moreyou guys so much!

    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!

    Photos
    The Chicago Architecture Tour boat cruise was amazing!
    The Chicago Architecture Tour boat cruise was amazing!
    Top deck - guide Joe
    Top deck - guide Joe
    Merchandise mart

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    Merchandise mart
    Chicago Dine-Around

    Chicago Dine-Around

    4.8
    (66 reviews)
    1.4 mi
    Private events
    Large group friendly

    We hosted our Toronto team in Chicago for the first time and used Chicago Dine Around to help plan…read moreour team event. Working with Brandon was absolutely fantastic from start to finish. He made the entire process incredibly easy and stress-free. We chose the Private Architectural Boat Tour, and the Chicago Dine Around team went above and beyond to ensure everything was perfect. They even arranged for us to tour the boat beforehand so we could confidently select the right experience for our group. For lunch, they seamlessly accommodated all dietary restrictions and preferences, making coordination effortless. Every detail was handled professionally, allowing us to focus on enjoying the event. The feedback from our team was overwhelmingly positive. Many team members said it was one of the best company events we've had to date. Even our Chicago-based employees, who are very familiar with the city, thoroughly enjoyed the tour and experience. I highly recommend Chicago Dine Around for anyone planning a corporate event or group outing. Their attention to detail, outstanding customer service, and local expertise made our event a huge success.

    I worked with Brandon at Chicago Dine Around to plan a dinner and Casino night for my company…read moreouting. Brandon was amazing and incredibly helpful and responsive! At the venue, Genesis was the event coordinator for the evening. She made sure everything flowed seamlessly and helped me enjoy the outing stress free! Both our game dealers (John and Ivan) were very knowledgeable and fun! They helped teach many of us how to play roulette and blackjack and were patient with us throughout the games! I would highly recommend Chicago Dine Around and we will absolutely return to book other events!

    Photos
    Interactive Culinary Experience (Stuffed Pizza)
    Interactive Culinary Experience (Stuffed Pizza)
    Interactive Culinary Experience (Stuffed Pizza)
    Interactive Culinary Experience (Stuffed Pizza)
    Interactive Culinary Experience (Stuffed Pizza)

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    Interactive Culinary Experience (Stuffed Pizza)
    Museum of Contemporary Art - Chicago

    Museum of Contemporary Art - Chicago

    3.9
    (628 reviews)
    0.9 mi
    $$

    Finally visited this River North museum during my return to Chicago. Since I wasn't a CHI/IL…read moreresident, the adult ticket price was $22, however you can also opt for the Pay As You Wish option, which is essentially Suggested Donation. While the museum is 4 floors, the exhibits weren't as plentiful. The 1st floor is basically their cafe. The 2nd and 4th floors are prob the floors with more artwork. The 3rd fl felt like an "in-between" floor. Thankfully, the Yoko Ono exhibit was on display, which featured several interactive activations, like a Wish Tree or writing on a wall, which were fun. Their Museum Shop also spans from floors 1-2. I wouldn't say that this museum has the popular artists. The overall artworks are a mix of abstract, photography, and mixed media. I wouldn't recommend it as a "Must See" for tourists, personally. However, I'm an art enthusiast and still thought it was a decent museum to walk through. Perhaps opt for the Suggested Donation for this one.

    I loved my experience! I really appreciate the free Tuesday nights for Illinois residents. That's…read moresuch a treat! Beautiful museum with multiple floors, excellent customer service, plenty of comfortable seating, cool gift shop, and a cafe and restaurant too. It has everything I need! The vibes are good here. I enjoyed all the floors and saw an impressive variety of art. I also wanted to see the Yoko Ono exhibit and I really enjoyed it. I appreciated how interactive it was. There were a few writing stations with activities, such as writing about your mom and taping it to the wall, and writing a wish on a tag and tying it to the wish tree. One room was blue and there were blue markers available and people were encouraged to add to it. Fabulous venue!

    Photos
    Takashi Murakami
    Takashi Murakami
    Outside
    Outside
    Museum of Contemporary Art - Chicago

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    Navy Pier

    Navy Pier

    3.5
    (1.5k reviews)
    0.0 mi

    It is easy to find the Navy Pier from most of the Chicago Riverfront because of the giant Ferris…read moreWheel, which stands out noticeably. We were told by several Chicagoans to go to the Navy Pier because there were also many restaurants and shops to enjoy. We actually went to the Navy Pier twice. Our main reason to go there was because that is where Shoreline Sightseeing boat cruises is located. We had booked a Chicago Architecture Boat Cruise thru them which was an exciting Chicago tour thing to do. We got there early and did some sightseeing and went on the ferris wheel. The Chicago Children's Museum was great for families and the shopping mall was really cool because it also has a Giordano's Deep Dish Pizza parlor! How lucky can you get! A really fun place to go. At the end of the pier is the Beer Garden, where you can sit and enjoy the spectacular view of the Chicago Skyline and a beautiful sunset. You can take the Big Bus Tour and get off at stop #8 at the Navy Pier, which is what we did. Have fun!

    Definitely a hot spot for tourists which can make it overlooked by locals, but there are some great…read moreaspects of Navy Pier that deserve to be highlighted. The first being, for how busy it is, it's always clean! Its huge and can get busy, but the grounds crew do an incredible job keeping up with the crowds. There is also so. much. to do here!! Rides, restaurants, museums, shows, live music, and so much more!! Navy Pier is bursting at the seams with activities for the entire city to take advantage of. Dinner, a boat ride, and fireworks at the beer garden make for a perfect evening or date night. If you've got kids, the Children's Museum is plopped right there on the pier and is really wonderful! There is a lot to do for children and adults alike, and I think it's worth a visit at least once a year. If you're a local and have been avoiding Navy Pier, give it a shot. I think you'll be pleasantly surprised!

    Photos
    07.03.25 events, culture, dining, shopping
    07.03.25 events, culture, dining, shopping
    07.03.25 shopping and dining
    07.03.25 shopping and dining
    View from Navy Pier!

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    View from Navy Pier!

    Strayboots - scavengerhunts - Updated August 2026

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