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    Strayboots

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

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    Museum Hack - LGBTQ+ friendly tours.

    Museum Hack

    5.0(5 reviews)
    1.3 miThe Loop

    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
    Museum Hack - Fun group activity at the museum

    Fun group activity at the museum

    Museum Hack - Unique group activity.

    Unique group activity.

    Museum Hack - Selfie time.

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    Selfie time.

    Shoreline Sightseeing - Top deck - guide Joe

    Shoreline Sightseeing

    4.7(1.9k reviews)
    0.3 miNear North Side

    Loved it! This boat tour was my favorite part of our trip!! The boat had plenty of room. Some…read moreseating was protected from the sun with an overhang and a bar. It also had an open area with bench seats that had a good amount of lean, so that you can see the highest points. The guide was awesome. I learned a lot about Chicago's history and architecture trends over the years. A lot of the buildings "front" side faces the river, so the view is very different from the boat. The boat ride was smooth with great views. I highly recommend!!!

    Just did the 60-minute architectural river tour departing from Navy Pier this past weekend and it…read morewas a fantastic experience. Our guide Ruby was awesome - engaging and funny with a perfect mix of architectural history and fun facts that kept everyone entertained. Right before docking at the end of the tour, the captain turned the boat toward the river entrance for a minute so everyone could take photos in front of the skyline, which was a nice touch. The biggest selling point for me was that all of Shoreline's tours are dog-friendly. I brought my pup Shadow along and they even gave her a treat as we were boarding. A couple tips: getting your tickets on Groupon will save you a couple bucks off retail, and bring your own water if it's a hot day - beverages on the boat are pricey. Great guide, amazing views, and pet-friendly. Highly recommend!

    Photos
    Shoreline Sightseeing - Merchandise mart

    Merchandise mart

    Shoreline Sightseeing - View of (former) Sears Tower  See the Chicago's architectural landmarks on this relaxing river tour

    View of (former) Sears Tower See the Chicago's architectural landmarks on this relaxing river tour

    Shoreline Sightseeing - 07.03.25 Navy Pier [Lake Michigan Skyline Cruise in Chicago]

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    07.03.25 Navy Pier [Lake Michigan Skyline Cruise in Chicago]

    Museum of Contemporary Art - Chicago - Restaurant

    Museum of Contemporary Art - Chicago

    3.9(625 reviews)
    0.9 miStreeterville, Near North Side
    $$

    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!

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    Museum of Contemporary Art - Chicago - Takashi Murakami

    Takashi Murakami

    Museum of Contemporary Art - Chicago - Outside

    Outside

    Museum of Contemporary Art - Chicago

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    The Art Institute of Chicago - Adult ticket $32

    The Art Institute of Chicago

    4.7(2.5k reviews)
    1.2 miThe Loop

    How lucky are we to live in a city that house the incredible, iconic, and historic artwork that…read morefinds a home within The Art Institute of Chicago. I've been here many-a-time throughout my years. Some highlights include: Georgia O'Keefe's NYC series and Henry Matisse's Jazz cutouts. Come here to see other classics such as American Gothic, Nighthawks, and A Sunday on La Grande Jatte. You can spend a full day here, so plan accordingly. Also, if you live in Chicago or Illinois, consult your public library for free passes!

    The decision to go to Chicago meant that I immediately began looking up landmarks from movies that…read moreI love, so obviously we had to make a trip to The Art Institute of Chicago. And was it incredible to stand in front of A Sunday on La Grande Jatte after watching Ferris Bueller for decades? Of course. It was an awe-inspiring experience that gave me literal goosebumps and even got me a little emotional. But the rest of The Art Institute is incredible, too. We barely scratched the surface and yet managed to see several iconic paintings -- including American Gothic and that famous Van Gogh self-portrait. Obviously we should've planned more than a couple of hours in the place. I feel like you could spend a week wandering around the place and you'd still feel like you hadn't seen everything. I really can't wait to go back someday.

    Photos
    The Art Institute of Chicago - Members lounge is worth the investment- even for an out of towners! Free coffee, tea, views, bathroom

    Members lounge is worth the investment- even for an out of towners! Free coffee, tea, views, bathroom

    The Art Institute of Chicago - Sculpture

    Sculpture

    The Art Institute of Chicago - The Art Institute of Chicago is now open on Wednesdays.

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    The Art Institute of Chicago is now open on Wednesdays.

    Navy Pier - 07.03.25 Navy Pier Store

    Navy Pier

    3.5(1.5k reviews)
    0.0 miNear North Side

    One of the highlights of any trip to Chicago is a visit to Navy Pier--a destination where history,…read moreculture, and entertainment come together along the shores of Lake Michigan. Originally designed by architect Charles Sumner Frost, the pier opened in 1916 as Municipal Pier. Built at a cost of $4.5 million atop 20,000 timber pilings imported from Oregon, its design was inspired by Daniel Burnham's visionary Plan of Chicago. It was intended to serve as both a shipping hub and a recreational centerpiece for the city. In 1927, the pier was renamed Navy Pier to honor the naval personnel stationed there during World War I. During both world wars, it played a significant role in military operations--housing barracks, a Red Cross station, and training facilities. In World War II alone, more than 60,000 service members trained here, including 15,000 pilots. In a fascinating and little-known chapter, converted Great Lakes steamers were used as makeshift aircraft carriers; many training mishaps sent planes to the bottom of Lake Michigan, where they still rest today. After the war, the pier entered a new phase. In 1946, it temporarily became home to what is now the University of Illinois Chicago, serving returning veterans on the GI Bill. Over the decades, Navy Pier continued to evolve--from hosting the massive SS Aquarama passenger ship in the 1950s to welcoming Queen Elizabeth II during her 1959 goodwill visit marking the opening of the St. Lawrence Seaway. It was designated a Chicago Landmark in 1977 and underwent major renovations in 1994. Since 2011, it has operated as a nonprofit dedicated to public programming and community engagement. Today, Navy Pier remains one of Chicago's most beloved attractions, offering something for everyone. A standout experience is the Centennial Wheel, which provides breathtaking panoramic views of the skyline and Lake Michigan. The ride is both relaxing and exhilarating--a must-do while visiting. There's no shortage of things to see and do. Families will enjoy the Chicago Children's Museum, while theater lovers can catch a performance at the Chicago Shakespeare Theater. From immersive film experiences to classic amusements like the carousel, the pier offers entertainment for all ages. Dining options are just as diverse, with everything from casual bites to full-service restaurants serving seafood, pizza, and international cuisine--there's truly something for every taste. Whether you're taking a leisurely stroll, enjoying the lakefront views, or spending the day exploring its many attractions, Navy Pier is a wonderful place to relax and soak in the energy of the city. Its blend of history, scenery, and entertainment makes it an unforgettable destination for both locals and visitors. My visit left me with lasting memories, and I can't wait to return to this iconic gem in the heart of the Windy City.

    Overall okay experience, more like a 3 star visit for me. The location itself is obviously iconic,…read moreright on the lake with nice views of the skyline and water. There's lots to see and do in theory, from restaurants to attractions to walking area. Definitely has that classic Chicago tourist energy. My experience felt pretty limited since I didn't really get to explore the whole pier. I mostly stayed in a smaller area so it didn't feel like the full experience everyone talks about. What I did see was fine but nothing really stood out in a memorable way during the visiy. It also felt a bit hectic which made it harder to casually just walk around the area to enjoy it at my own pace. I mean, it's a well0known spot and I would definitely come again.

    Photos
    Navy Pier - 07.03.25 events, culture, dining, shopping

    07.03.25 events, culture, dining, shopping

    Navy Pier - 07.03.25 shopping and dining

    07.03.25 shopping and dining

    Navy Pier - Ferris wheel and carousel

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    Ferris wheel and carousel

    Strayboots - scavengerhunts - Updated June 2026

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