Chicago is often called the birthplace of the skyscraper, and its buildings are one of the main reasons people visit. There are two classic ways to see them: from a boat on the Chicago River, or on foot through the Loop. Both can be done with a guide or on your own. This guide compares the two, explains what each one shows you and suggests how to choose.
Key takeaways
- A river cruise shows dozens of buildings in about 90 minutes from a comfortable seat.
- A walking tour lets you go inside lobbies and see details you cannot see from the water.
- Open House Chicago, a free festival each October, opens the doors of more than 200 buildings.
The river cruise
The Chicago River runs through the heart of downtown, and many of the city’s most important buildings line its banks. From a boat you see them from below, with the full height of the towers above you, and you pass through the canyon of buildings where the river splits into its branches. The best-known cruise is run by the Chicago Architecture Center, a nonprofit, with volunteer docents who explain the buildings and the history behind them. Tours usually last about 90 minutes.
River cruises are seasonal, generally running from spring through fall. They are a good choice on a warm day, for visitors with limited mobility and for anyone who wants a large overview in a short time. The main drawback is that you only see buildings from the outside.
The walking tour
On foot, you can step into the lobbies and public spaces of historic buildings, notice ornament and materials up close, and understand how the streets and the elevated tracks shape the city. Guided walking tours focus on themes such as early skyscrapers, Art Deco or modern towers. You can also build your own route through the Loop with a map, using the Chicago Riverwalk, which runs for about 1.25 miles along the south bank of the main branch, as a starting point.
The Chicago Cultural Center, free and open to the public, is a good stop on any walking route for its stained-glass domes. Walking tours run year-round, though winter tours can be cold and windy.
River vs. walking compared
| River cruise | Walking tour | |
|---|---|---|
| Duration | About 90 minutes | 1.5 to 3 hours |
| What you see | Many buildings from the water | Fewer buildings, more detail, some interiors |
| Physical effort | Low | Moderate walking |
| Season | Spring to fall | Year-round |
| Best for | First-time visitors, big overview | Architecture fans, repeat visitors |
Tip: If you are doing both, take the cruise first. It gives you the overall picture, and the walking tour then fills in the details.
Open House Chicago
Every October, the Chicago Architecture Center runs Open House Chicago, a free festival that gives the public access to more than 200 buildings across the city, including many that are normally closed. It covers downtown towers, churches, theaters, private clubs and neighborhood landmarks. It is one of the best free events of the year for anyone interested in buildings. Check the official site for this year’s dates and list of sites.
Which one fits your day
Choose the river cruise if
- It is your first serious look at Chicago architecture.
- Someone in your group cannot walk long distances.
- The weather is warm and clear.
Choose a walking tour if
- You want to go inside historic buildings.
- It is the off-season for cruises.
- You like to stop, look and take your time.
Before you go
- Book cruises in advance on summer weekends; popular times sell out.
- Bring a jacket on the river even in summer; it is cooler on the water.
- Wear comfortable shoes for walking tours; some routes cover several miles.
- Check the Chicago Architecture Center’s website for tours and events.
Common mistakes
Many people book a river cruise with a general sightseeing company expecting an architecture tour, and get jokes and trivia instead. If architecture is what you want, choose a tour that says so. Another mistake is skipping the lobbies on a walk: some of the most beautiful interiors in the Loop are open to the public during business hours.
Frequently asked questions
How long is the architecture river cruise?
The Chicago Architecture Center’s docent-led cruise lasts about 90 minutes.
Can I see Chicago architecture for free?
Yes. Walk the Riverwalk, visit the Chicago Cultural Center, and plan around Open House Chicago in October.
When do river cruises run?
Generally from spring through fall. Check the operator’s official schedule for exact dates.
Architecture fans should also plan a trip to Oak Park: A Frank Lloyd Wright Day Trip by Train and to Robie House in Hyde Park and Jackson Park: A Day on the South Side Lakefront.