5 Must-Do Things in Chicago, Illinois (Updated 2026)

Chicago doesn’t just sit quietly on Lake Michigan; it hums. The city moves with energy, layering culture, food, art, and a kind of Midwestern hospitality that feels instantly grounding. Whether you’re here for a weekend or setting up camp for a while, there are certain experiences that just belong on your list. And yes, one of them involves a robot.

1. Try a Robot Massage with Aescape

If you think “robot massage” sounds futuristic, that’s because it is. Chicago is one of the cities where you can step into an Aescape massage and have a self-guided massage session unlike anything you’ve experienced before.

The setting is private, solo, and judgment-free; you’re in complete control of your session. It’s about offering an option where you can ease tension, calm your system, and reset on your own terms.

2. Walk the Chicago Riverwalk

It’s not just a walkway, it’s an open-air living room. Grab a coffee, people-watch, rent a kayak, or just sit and let the skyline show off. The mix of water, architecture, and constant buzz makes it feel like the city’s heartbeat.

3. Take in Art at the Art Institute of Chicago

This isn’t your average museum stop. The Art Institute houses everything from ancient pieces to modern design, and standing in front of works like American Gothic is surprisingly emotional. Even if you’re “not a museum person,” this place has a way of pulling you in.

4. Catch the View from 360 Chicago

Yes, it’s touristy, but you’ll thank yourself when you’re 1,000 feet up, staring out at Lake Michigan like it’s an ocean. The best time? Sunset, when the city lights up and you feel small in the most wonderful way.

5. Eat Your Way Through a Food Tour

Chicago takes food seriously, but not in a pretentious way. Think deep dish pizza that requires a fork, hot dogs with “rules,” and neighborhoods with flavors that reflect the whole world. A guided food tour is the quickest way to taste the city’s soul.

Chicago, in 2026, is equal parts classic and forward-thinking. You can watch a Monet, eat a pizza the size of your head, and then go let a robot help your body reset, all in the same day. And that mix? That’s Chicago magic.

Let us know you enjoyed this read by booking a massage and using code BLOG for $10 off your first session (30 minutes and up!). Wanna share your thoughts? We’d love to hear from you. Give us a shout at @LetsAescape on social!