Open House Chicago 2026 Best Buildings to Visit

My wife and I are taking our 14 year old son downtown for Open House Chicago on Saturday the 17th. We'll be taking the Metra into Ogilvie in the morning and have the whole day, but we only want to do one day this year. Last time we tried, we waited in line for the Kemper Building for over an hour and gave up. I'm trying to avoid a repeat of that. Is it worth waiting 2+ hours for the view from one of the supertalls on Wacker, or are we better off picking a neighborhood and exploring? My son is into architecture but will get bored fast in a long line. What are the sites with the best payoff for the wait time? Any non-obvious ones we should look at?

Honestly, skip the Loop on a Saturday. The lines are just brutal and you spend half your day on the pavement. My advice is to pick a neighborhood cluster. A few years ago we stuck to Uptown. We saw the Riviera Theatre, the Aragon Ballroom, and one of those old pre-war apartment buildings on Marine Drive. The longest we waited was maybe 30 minutes for the Riviera, and it felt like we saw a real part of the city's history, not just a corporate office with a good view.

I have to disagree a little. You are coming from the suburbs, you should see a skyscraper. The trick is to be strategic. Do not go to the famous ones that already have an observation deck. Pick a big bank building on LaSalle or a private club. Get there 30 minutes before it opens at 9am so you are in the first group. You get the amazing view, and then you are out by 10:30 and can hop on the L to spend the rest of the afternoon in a neighborhood. You can do both if you plan it right.

The private clubs can be a real letdown. We waited 90 minutes for one in the Gold Coast and they rushed us through two rooms and that was it. My best experience was focusing on the unique industrial sites. One year we went to a prop house for theaters over by Goose Island and another time a boat building workshop in Bridgeport. The lines are usually non-existent and your son would probably think seeing how stuff is actually made is way cooler than another fancy lobby.

The key is a solid walking plan. We always pick a theme. Last year was 'Gilded Age Gold Coast'. We started at the Three Arts Club and worked our way through the surrounding mansions. It was all walkable. Make sure to check the OHC app for each location before you go. Some don't allow photography and, more importantly, many of the smaller neighborhood spots do not have public restrooms. You have to plan your coffee stops strategically.

The Uptown sites are great and very easy to get to. The Riviera, Aragon, and Green Mill are all right at the Lawrence Red Line stop. But just a heads up, the Green Mill line looks short but it takes forever because the place is tiny. The Riviera and Aragon are huge so the lines move much faster. You can see both of those and then walk south on Kenmore or Sheridan to see some beautiful historic apartment lobbies in Buena Park without any wait.

This is all fantastic advice, thank you everyone. The tip about the restroom availability is a life saver, I would not have thought of that. Based on this, we're ditching the Loop idea. We're going to take the Red Line up to Lawrence and do the Uptown theaters and the Buena Park walk that Beth mentioned. The industrial sites are a great backup plan if the crowds are worse than we expect. Much appreciated.