Last night, my friend Brooke brought me to a Chicago Sky game, and I have to say: what a blast. It had everything you’d want from a night out in the city: crowd energy, talented athletes, halftime snacks, but without the sticker shock that usually comes with professional sports. Bonus: it was surprisingly family-friendly. Parents, kids, friend groups, even a few grandparents in merch. Everyone was in on the fun.

It got me thinking: if you’re visiting Chicago with your family, this might be one of the best-kept secrets in town. And if you play your cards right, it can be the perfect end to a day of outdoor adventure.

Here’s what I’d do if I were planning a day with the family in the city:

Morning: Start with an easy pickup of an adventure-ready Jeep rental right at O'Hare. It’s a smooth way to begin your Chicago road trip without the hassle of public transport or rideshares. You’ll have room for gear, snacks, and squirmy kids—and the flexibility to explore at your own pace. Book your Jeep rental here. If you’re feeling up for it, head downtown and rent a kayak on the Chicago River from places like Urban Kayaks or Wateriders. Paddling past skyscrapers is one of the most unique ways to see the city, and kids love the novelty of being on the water.

Afternoon: Take that Jeep and cruise one of the many scenic drives near Chicago or stop for a picnic at Millennium Park. Let the kids run around near The Bean or cool off at Crown Fountain. Just east of Millennium Park, you’ll find Maggie Daley Park—a family favorite with climbing walls, mini golf, an ice skating ribbon (in winter), and one of the most inventive playgrounds in the Midwest. You’re recharging, exploring, and making memories—all before dinner.

Evening: Head over to Wintrust Arena for the game. Tickets are usually affordable (read: cheaper than a movie for four), and the atmosphere is both high-energy and low-stress. You won’t be fighting crowds or emptying your wallet on concessions. Just a good time, plain and simple.

Chicago has no shortage of big-ticket attractions, but sometimes the best days are the ones that don’t try too hard. A little fresh air, a little local flavor, and a whole lot of shared memories.

So if you’re coming to town with the crew, think beyond Navy Pier. Rent a Jeep that fits your family and your plans, enjoy the city at your own pace, and wrap it all up with a game where everyone can cheer. Whether you’re just starting a road trip from Chicago or exploring day trips from Chicago by car, it’s all possible with the right wheels.

Ready to hit the road? Our adventure-ready Jeeps are waiting—perfect for a Chicago camping road trip, a weekend getaway from Chicago, or just a memorable day in the city.