Sally was phenomenal. She brought the Art Institute to life. Throughly enjoyed her tour and would highly recommend it.

Art Institute of Chicago Tour with Skip-the-Line Tickets
Showcasing iconic highlights and uncovering unexpected delights










From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.
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Art Institute of Chicago
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English-speaking expert guideTours led in English, offering you unbroken understanding throughout.
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Intentionally sized groupsA smaller group means more time for conversations and questions.
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Tickets and entrance feesAll entry tickets included (unless clearly stated otherwise).
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HeadsetsHeadsets are included on tours that need them, so every word can be heard.
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GratuitiesWe encourage tipping as a way to thank your guide after your experience.
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Food and drinkRefreshments are only included during a tour when clearly noted.
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Transportation to and from the meeting pointUnless noted, pre- and post-tour transport isn’t included - this service can be added by request.
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Hotel pickup or drop-offUnless noted, travel to or from accommodation isn’t included - this service can be added by request.
Make the Most of Your Tour
Some helpful advice for getting the most from your experience, from practical prep to small on-the-day tips.
- Wear comfortable footwear
- Check the weather and dress appropriately
- Bring a bottle of water (no glass)
- Feel free to ask your Expert anything
- Bring firearms or weapons
- Bring sharp objects (e.g. knives, swiss army knives, switchblades, hiking sticks)
- Dress inappropriately to enter religious sites or sacred monuments
Don’t just take our word for it
Our experience with Context Travel at the Art Institute of Chicago was outstanding, and much of that was due to our exceptional guide, Sarah Bond. From the very beginning, Sarah was gracious and understanding when our group arrived later than planned. Traveling with my elderly parents can present unique challenges, and Sarah immediately put everyone at ease. She was incredibly patient, accommodating their slower pace, ensuring we used elevators when needed, and allowing time for periodic rests without ever making us feel rushed. What truly set Sarah apart was her knowledge and ability to engage everyone in our group. She connected wonderfully with my parents, making them feel comfortable and included throughout the tour. Her knowledge of the museum was extraordinary, but even more impressive was her talent for bringing the artwork and history to life through engaging stories and insightful commentary. The skip-the-line access was valuable, but Sarah's expertise and kindness transformed the experience into something truly memorable. She led one of the most spectacular museum tours we have ever taken. We left with a deeper appreciation of the Art Institute and wonderful memories of our time together as a family. I would highly recommend Context Travel and, if possible, specifically request Sarah Bond. She is a remarkable guide and made our visit unforgettable.
Sarah did an exceptional job crafting a tour that fit our unique interests. With my own background as an art teacher, I was interested in seeing artwork that was off the beaten path. Sarah was both knowledgeable and approachable, eager to discuss shared observations and explore interesting tangents. I was delighted to spend time with the works she chose and learn more about how they fit in the broader historical context. The three hours flew by!
Let Your Curiosity Shape Your Journey
Join passionate experts on intimate walking tours that reveal a city’s unique stories, spark conversations, and leave you seeing the world—and yourself—a little differently.
Structured, never scripted
Your interests guide your Expert, leading to stories and perspectives that matter to you.
Crafted for conversation
With ten or fewer guests, ask questions, engage with your Expert, and fully immerse yourself.
Experts, not guides
Explore with 1,200+ Experts—from historians and architects to archaeologists and chefs.





