Chicago River Cruises: The Ultimate Windy City Tours

If you're heading to Chicago, one thing you have to do is take a Chicago River cruise. It's hands down one of the best things to do in Chicago! Whether you're a history nerd, an architecture buff, or just want to see the city from a fresh angle, there’s a river cruise for you. Let’s dive into the top picks—from leisurely architectural tours to high-speed adventures. And spoiler alert: we’ll also tell you about the perfect spot to stay after your river escapades—Villa D'Citta.

Wendella Chicago River Architecture Tour: A Must-Do for Architecture Lovers

The Wendella Chicago River Architecture Tour is like Chicago 101 for anyone interested in the city’s iconic skyline. It's 90 minutes of jaw-dropping views and fascinating stories about how the city grew into the architectural powerhouse it is today. You’ll float through all three branches of the river, past the Willis Tower, the Merchandise Mart, and many more of Chicago’s greatest hits.

• Why It’s Awesome: Chicago’s most famous buildings up close, plus a guide who knows everything about the city.
• Perfect For: Architecture lovers and history buffs who want to learn all the cool stories behind Chicago’s skyline.

Chicago Fireboat Tours: History on the Water

Ever cruised on a fireboat? With Chicago Fireboat Tours, you’re not just taking a tour—you’re riding on a piece of Chicago history. This 1937 fireboat used to battle blazes, and now it takes you on a scenic, info-packed ride through the river. You'll even get to experience passing through the river locks, which is pretty cool.

• Why It’s Unique: Learn more of Chicago’s history while cruising on an authentic fireboat from the city’s early days.
• Perfect For: History buffs, families, and anyone who wants a different spin on the classic river cruise.

Tall Ship Windy: Sail Like a Pirate

If you’ve ever wanted to sail the high seas (Lake Michigan counts, right?), the Tall Ship Windy has you covered. This 148-foot schooner gives you sweeping views of the Chicago skyline from the water while you cruise in vintage style. They’ve even got themed tours, like pirate adventures for the kids (or the kid in you).

• Why It’s Fun: A classic sailing atmosphere and pirate stories. Need we say more?
• Perfect For: Families, adventurers, and anyone wanting to enjoy the skyline with the wind in their hair.

Chicago Sunset River Cruise: Romance & City Lights

For the ultimate relaxing experience, nothing beats a Chicago Sunset River Cruise. Picture this: the sun setting behind Chicago’s skyline as the lights begin to twinkle on the buildings. It’s the perfect mix of relaxation and breathtaking views. Whether you’re with friends or a special someone, this is an experience you’ll want to savor.

• Why It’s Relaxing: Gorgeous sunset, city lights, and no rush—just peaceful cruising.
• Perfect For: Couples, photographers, or anyone looking for a romantic evening in Chicago.

Chicago Seadog Lakefront Speedboat Tour: For the Thrill Seekers

If you’re more about adrenaline than architecture, the Chicago Seadog Lakefront Speedboat Tour is where it’s at. This high-speed boat zips you around Lake Michigan, showing off Chicago’s famous landmarks at lightning speed—plus, the 360-degree spins are a total thrill!

• Why It’s a Blast: It’s basically a rollercoaster on water, and you get to see Chicago from a whole new angle.
• Perfect For: Thrill-seekers, families with teens, and anyone looking to kick up the excitement.