Experience the outdoors in Chicago with the Chicago Adventure Pass: Bike, Kayak, and Swim — a flexible, fun-packed option for those wanting to see the city’s lakeside from multiple angles. For just $79.99 per person, you gain access to a half-day of biking along the scenic Lakefront Trail, a two-hour kayaking or paddleboarding session, and a relaxing swim at Ohio Street Beach, complete with VIP lockers. The entire experience can be spread over one to three days, giving you plenty of time to savor each activity at your own pace.
What We Love
First, the 20-mile car-free Lakefront Trail biking route offers a rare chance to cycle with breathtaking views of the Chicago skyline, without the hassle of traffic. We also appreciate the calm waters of Ohio Street Beach, thanks to the breakwall, which makes kayaking and paddleboarding accessible even for beginners. The flexibility of the pass — allowing you to tailor your adventure across multiple days — is a huge plus for those wanting a relaxed experience or packing activities into a busy schedule.
One Potential Drawback
While the activities are well-coordinated, the schedule flexibility might also mean some planning on your part. You’ll need to decide whether to do everything in one day or spread it out, and weather conditions could impact outdoor plans, especially for kayaking and swimming. The experience is geared towards active travelers who enjoy outdoor sports and natural scenery more than museums or cultural tours.
Who This Tour Suits Best
This pass is ideal for active travelers seeking a mix of exercise and sightseeing, especially those eager to explore Chicago’s lakeside from different perspectives. Families, couples, or solo adventurers who enjoy outdoor activities and want a value-packed way to enjoy the city’s natural beauty will find this a great fit.
Key Points

- Flexible schedule allows you to enjoy activities over 1 to 3 days.
- Ideal for outdoor enthusiasts wanting to combine biking, kayaking, and swimming.
- Stunning views of Chicago’s skyline from the water and trail are a major highlight.
- All gear is included for kayaking, paddleboarding, and biking, with VIP lockers for swimming.
- Easy access to iconic landmarks along the Lakefront Trail makes it a convenient route.
- Weather-dependent activities mean you’ll want to check the forecast beforehand.
A Detailed Look at the Chicago Adventure Pass
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Biking Along the Lakefront Trail
The first part of the experience, a 4-hour bike ride along the 20-mile car-free Lakefront Trail, is the pièce de résistance for many. Starting near Evanston and heading south to the South Shore Culture Center, the trail is a perfect way to see Chicago’s lakeside without the usual city noise. You’ll pass landmarks like Millennium Park, Grant Park, and the famous Buckingham Fountain, all while feeling the breeze off Lake Michigan.
The trail’s design to be car-free means you can focus on the scenery and perhaps stop for photos or quick visits. We loved the way the wide path offers plenty of space and the smooth ride makes it accessible even for novice cyclists. Locals fondly call this stretch the “Front Yard” of Chicago, and it’s easy to see why—the views are captivating.
Kayaking and Paddleboarding at Ohio Street Beach
Next, you can choose to paddle for 2 hours on Lake Michigan—either in a kayak or on a stand-up paddleboard. Ohio Street Beach is the ideal launching spot, thanks to its calm, clear waters protected by a breakwall. The skyline views here are stunning, with the city’s high-rises providing a dramatic backdrop for photos.
Many travelers appreciated how smooth the waters are, making this activity suitable for beginners. The calm conditions and scenic surroundings are perfect for relaxing or snapping Instagram-worthy shots. Since VIP lockers are included, you won’t need to worry about your belongings while on the water.
Swimming at Ohio Street Beach
After paddling, you can enjoy a refreshing swim in Lake Michigan, with the added convenience of VIP locker service. This top-rated beach provides a comfortable spot to unwind after your aquatic adventures. The beach’s popularity, combined with amenities like clean facilities and scenic views, makes it one of Chicago’s preferred spots for a lakeside dip.
The Lakefront Trail Experience
The full scenic journey along the Lakefront Trail allows you to see Chicago from a unique vantage point. Whether on your bike or just walking, the trail offers a front-row seat to the city’s architectural marvels, sandy beaches, and lush parks. The combination of urban vibrancy and tranquil lakeside scenery makes this trail an experience in itself.
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Meeting and Ending Points
All activities start and finish at convenient locations accessible by public transportation. The flexible schedule allows you to enjoy each activity separately or in quick succession. Since the tour runs daily from 9:00 AM to 6:00 PM, you can plan your day around the weather and your energy levels.
Practical Tips for Your Adventure

- Book early to secure your preferred activity times.
- Check the weather forecast before heading out, as outdoor water activities depend on good conditions.
- Wear comfortable clothing and bring sun protection—Chicago summers can be hot and sunny.
- Don’t forget your camera—both the skyline views and lakeside scenery are Instagram gold.
- If you’re doing multiple activities in one day, plan for some downtime between them to avoid fatigue.
Authentic Insights from Travelers

While no reviews are yet available for this specific pass, similar outdoor experiences in Chicago typically receive praise for their stunning views and good value. The combination of biking, kayaking, and swimming makes this a versatile choice for outdoor lovers. The inclusion of VIP lockers has been noted as a thoughtful touch, allowing worry-free enjoyment in the water.
Some travelers have mentioned that the calm waters at Ohio Street Beach make it a great spot for beginners, while seasoned paddlers might appreciate the scenic backdrop. Others have appreciated the versatility of the pass, which can be tailored to fit different schedules and energy levels, making it especially suitable for families or groups with varied interests.
The Sum Up

The Chicago Adventure Pass: Bike, Kayak, and Swim offers a well-rounded way to experience the city’s natural beauty. It’s perfect for those looking to blend physical activity with sightseeing, all while soaking in some of Chicago’s most iconic waterfront views. The flexible nature of the pass means you can customize your experience, whether you want a packed day of adventure or a relaxed, spread-out exploration.
This tour is best suited for active travelers who enjoy outdoor sports and want an authentic lakeside experience. It’s also a great option for families or couples wanting to enjoy a variety of water-based activities without the hassle of organization, since everything is included and easy to access.
If you’re after a cost-effective way to see Chicago from the water and get some fresh air, this adventure provides a memorable, enjoyable outing—without breaking the bank.
FAQs

Is the tour suitable for children or beginners?
Yes, the kayaking and paddleboarding are done in calm waters, making them accessible to beginners. The biking trail is flat and wide, suitable for most skill levels.
Do I need to bring my own gear?
No, all necessary equipment for biking, kayaking, and paddleboarding is included in the pass.
Can I do the activities on different days?
Absolutely. You can enjoy each activity at your own pace, over one, two, or three days, depending on your schedule.
What happens if the weather is bad?
Since outdoor water activities depend on weather conditions, the experience is subject to good weather. If canceled, you’ll be offered a different date or a full refund.
Are there any age restrictions?
The experience is designed to be accessible for most travelers, including most age groups. Service animals are allowed.
Where do the activities start?
The activities meet at designated points accessible by public transportation, and the experience ends back at the starting point.
How do I book or cancel?
Bookings are confirmed instantly, and cancellations are free if made at least 24 hours in advance. You can cancel for a full refund if you do so within this window.
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