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Strayboots

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

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The Great Escape Room Chicago - Lobby

The Great Escape Room Chicago

4.5(95 reviews)
1.0 mi•Near North Side, River East

Environment: You need to take the elevator to go up and when you enter, you need to wait for them…read moreto open the door. The entrance is a bit small, especially if there are parties waiting or finishing. Staff: very friendly and humorous. They were very nice when we booked on the spot, helping us get started with the game, and during the game, too. Game: we just decided to try this place out with reservations at around 8pm we picked the poker one and I think they said that was a medium level or so. I'm not very good at these games but it was a very good experience. We asked for hints when needed and they provided subtle suggestions which made it more fun for us instead of being direct (they checked with us prior). I also appreciated them asking if we wanted pictures after playing and allowing us to be in the room for that. This escape room was simple, as in there were two rooms, we didn't have to crawl or go through a tone of rooms and such. BTW, with the 3 of us total, we escaped with about 7-9min left haha. I finally escaped an escape room! Also they have bathrooms and if we needed water or just a breather/destress, we were free to go out and do so which was thoughtful.

The games are so fun, and Lucia is an amazing game master…read more The facility is clean and have fun games.

Photos
The Great Escape Room Chicago - The President's Bunker

The President's Bunker

The Great Escape Room Chicago - Sherlock Holmes has enlisted your help in foiling Professor Moriarty's latest deadly scheme. Can you stop him in time?

Sherlock Holmes has enlisted your help in foiling Professor Moriarty's latest deadly scheme. Can you stop him in time?

The Great Escape Room Chicago - Tickets are purchased online at:  www.thegreatescaperoom.com

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Tickets are purchased online at: www.thegreatescaperoom.com

Museum Hack - LGBTQ+ friendly tours.

Museum Hack

5.0(6 reviews)
1.3 mi•The 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 - Chicago Fire Department near Navy Pier

Shoreline Sightseeing

4.7(1.9k reviews)
0.3 mi•Near North Side

A river tour is a must when visiting Chicago! We decided to do Shoreline Sightseeing, and it was…read moresuch a great experience. We were nervous because my mom gets motion sickness easily, and we weren't sure she'd be able to enjoy the tour. Thankfully, the water was calm enough, and she absolutely loved it! The views were beautiful, and we learned so many fun facts about the city along the way. Definitely recommend adding this to your Chicago itinerary!

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

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

Chicago Dine-Around - Interactive Culinary Experience (Stuffed Pizza)

Chicago Dine-Around

4.8(66 reviews)
1.4 mi•The Loop
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
Chicago Dine-Around - Interactive Culinary Experience (Stuffed Pizza)

Interactive Culinary Experience (Stuffed Pizza)

Chicago Dine-Around - Interactive Culinary Experience (Stuffed Pizza)

Interactive Culinary Experience (Stuffed Pizza)

Chicago Dine-Around - Interactive Culinary Experience (Stuffed Pizza)

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Interactive Culinary Experience (Stuffed Pizza)

The Art Institute of Chicago - Adult ticket $32

The Art Institute of Chicago

4.7(2.5k reviews)
1.2 mi•The Loop

Far from our first visit to The Art Institute, but every visit here is a wonder. It rivals The Met…read moreand MOMA in New York as a top American art museum. And it's so close to other attractions as well as hotels and restaurants downtown/in the Loop. You can even walk to Millennium Park across a bridge from the Modern Wing. The museum can get very crowded, and has 3 main levels, but note parts of the lower and 2nd level are not connected. We only had a few hours to spend here, so of course did some of the "greatest hits" by Seurat, van Gogh, O'Keefe, Wood, Hopper, Picasso, Monet, Renoir, Warhol, Pollock, etc. I am particularly fond of the Impressionists, and the Institute had quite a collection from this period. The biggest discovery for me were the Thorne Miniature Rooms on the lower level of the main building. These intricate miniature rooms were fascinating and impossibly detailed; I especially liked how there were other rooms/gardens visible beyond the main room, and how much attention was paid to the lighting, as if the sun was shining through a window or door. You can enter the museum off Michigan Ave or via the Modern Wing. There's a cafe and a snack bar, a seasonal garden bar, and a members-only rooftop bar in the Modern Wing. The bridge to Millennium Park is just outside the member's bar. Always a must visit in Chicago, continuously impressive.

The Art Institute of Chicago is a massive museum with really dope pieces all for the grand total of…read more$14 for general admission. In my opinion, this museum is way too vast to thoroughly experience it in one day. So, if you are short on time, like I was, map out your "must go to pieces" and hopefully, you would see some other gems on the way to your next "must see piece". This is definitely a museum that I would revisit. Thoroughly enjoyed.

Photos
The Art Institute of Chicago - Picasso

Picasso

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

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Sculpture

Chicago Trolley & Double Decker

Chicago Trolley & Double Decker

3.7(395 reviews)
0.6 mi•River East, Near North Side

Looking for something new and different to do on Black Friday we took…read morethe Holiday lights tour this year. We have a tremendous driver, he was a lot of fun and really made the night. The tour goes the Christkindlmarket market at Wrigley and then the zoolights at Lincoln park zoo. I wish we got to see more lights around the city, but I don't know how that would work. It was allot of fun anyway. we got to spend a good amount of time at each stop. In between on the drive our driver told some great stores, some history and sang Christmas carols. A fun thing to do even if your not a tourist but a local like us. Make be a new family tradition.

Worst Hop on Hop off bus experience of any city we've done (and, we've done a lot!) We bought a 3…read moreday pass so we could go to the Obama Presidential Center that was included. The ONLY bright side was an employee named, Bongi, who we encountered on Days 1 and 2 and she could not have been more friendly, professional and informative. After that it was all down hill. The regular bus route is crazy and takes you so far out of the way around the city that it's not practical to hop on and hop off. Secondly, it isn't narrated live, it's prerecorded so you have to use their ear buds. On day 3 NONE of the ports were working with the ear buds on the bus (see the picture with the driver in the window and tag on the front of the vus) but they still kept on going and even though everyonelet them know. On Day 2 the bus driver (the picture with his face in the rear view mirror) was so rude that he actually told an elderly couple after they boarded the bus, picked up a map and asked which number was a particular stop, said "you have a map, use it." We about fell out of our seats. Horrible, horrible, horrible waste of money. All the reviews we read never mentioned the narration wasn't done live, by a person on the bus like every other Hop on Hop off bus we've ever been on.

Photos
Chicago Trolley & Double Decker - Rude, rude, rude driver. See review

Rude, rude, rude driver. See review

Chicago Trolley & Double Decker - No sound on board. Told the driver and his assistant. They continued to pick up more unsuspecting passengers and taking their money

No sound on board. Told the driver and his assistant. They continued to pick up more unsuspecting passengers and taking their money

Chicago Trolley & Double Decker

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Strayboots - scavengerhunts - Updated November 2026

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