Getting Ready For The Voyage: What To Wear On A Chicago River Tour

If you’re planning a journey along the heart of the Windy City, a significant question may pop into your mind, “What do you wear on a river cruise in Chicago?”

The answer to that question revolves around comfort, the season of your tour, and, of course, personal style.

Quick Answer:

  • Comfortable Clothing: The key is to choose clothes that allow ease of movement.
  • Season-Appropriate Attire: Chicago’s weather greatly varies from season to season, and your attire should reflect this.
  • Footwear: Opt for comfort over style.
  • Accessories: Don’t forget essentials like sunglasses, a hat, and perhaps a camera to capture the scenic beauty.
  • Layers: Chicago’s weather can change rapidly; layering is your best bet to handle this.

Now, let’s dive into the details of dressing appropriately for your Chicago Tour excursion.

Comfortable Clothing: The Foundation Of Your Outfit

Whether you’re embarking on an architecture river tour or a twilight cruise, one constant remains – comfort is key. Given you’ll be spending a good part of your day on this voyage, opt for clothes that provide ease of movement and aren’t restrictive.

For women, breathable fabrics like cotton or linen in dresses, shorts, or lightweight pants can be ideal. Men can opt for khakis, lightweight denim, or shorts combined with a comfortable cotton shirt.

The essence of the waterway journey is to soak in the city’s architecture and history, and being comfortable will enable you to focus on enjoying the experience without being distracted by an uncomfortable outfit.

Season-Appropriate Attire: Dressing For Chicago’s Weather

The beauty of the Chicago River tour is that it’s not confined to a single season. Whether it’s the blooming warmth of spring, the sunny vibrancy of summer, the cool crispness of autumn, or even the chilly allure of winter, the Chicago waterway is always inviting.

In spring and summer, lighter clothing is suitable. Consider wearing light-colored clothing that reflects rather than absorbs sunlight. Short-sleeved shirts, shorts, or breathable pants are good choices. Ladies might consider a summer dress.

During fall, the weather starts to cool, and dressing in layers is recommended. A light jacket or sweater can be a great addition. In winter, Chicago’s weather demands respect. Warm pants, thermals, a heavy coat, a hat, and gloves are essential.

Comfortable Footwear: Ease For Exploration

Footwear can make or break your experience on a cruise. Uncomfortable shoes might become a nuisance and divert your attention from the stunning views of Chicago’s skyline.

Choose a comfortable pair of walking shoes or sandals. If you’re visiting in winter, warm, waterproof boots are a must. Remember, the aim is to enjoy the voyage, so let your feet relax too!

Accessories: The Essentials & Beyond

When out in the open, it’s essential to protect yourself from the elements. Sunglasses are crucial on a sunny day, as is a hat or a cap. If you’re a photography enthusiast, your camera is a must-have accessory.

In cooler months, don’t forget your gloves and a cozy scarf. If rain is in the forecast, pack a small umbrella or a waterproof jacket. An eco-friendly water bottle is also a good idea, ensuring you stay hydrated during the tour.

Layers: Embracing Chicago’s Fluctuating Weather

A cardinal rule of dressing in Chicago is to embrace layering. The city’s weather can change rapidly, and what started as a sunny day might quickly become overcast and chilly.

Carry an extra layer of clothing with you during spring and fall. Even in summer, a light cardigan or jacket can be useful, particularly if the evening brings a cool breeze from the lake. Winter, of course, calls for multiple layers to keep warm.


What you wear on a Chicago River Cruise should primarily be dictated by comfort, weather, and your personal style. While this guide provides a general overview, your outfit choice should reflect what makes you feel good and enables you to enjoy this fantastic experience.

After all, as you sail past iconic structures like Marina City, the Wrigley Building, and the Tribune Tower, you want to be admiring the architectural grandeur around you, not fretting about your attire.


  1. “Chicago Riverwalk” (
  2. “Weather in Chicago” (
  3. “Chicago’s First Lady Cruises” (