Convertible car rental in Chicago

For a true city center convertible experience, start your journey downtown near Millennium Park. Then cruise along Michigan Avenue, past Chicago icons like The Art Institute, The Bean, and the historic Chicago Theatre.

The Loop’s grid layout makes it ideal for leisurely weekend driving. From the driver’s seat, you’ll get to enjoy a wide array of towering architecture, bustling streets, and easy detours into neighborhoods like River North and West Loop. It’s a short and satisfying drive that puts you right in the heart of Chicago. And your convertible makes it feel like a moving postcard.

About 25 miles west of downtown, the Morton Arboretum in Lisle is a dream day trip for nature lovers. Enjoy the drive down I-88 in your convertible rental and take in all the gorgeous scenery, which is especially vivid and lush in spring and fall.

The arboretum features 1,700 acres of trees, meadows, and trails, plus 16 miles of scenic roads you can drive through. From lush groves to curated gardens, it’s peaceful, spacious, and a perfect counterbalance to the curated chaos of the city. Don’t forget your camera, though. You’ll want to capture all the colors and open skies for posterity.

Roughly 35 minutes north of downtown, the Bahá’í House of Worship in Wilmette, Illinois, is one of the state’s most serene architectural sites. The drive itself - up Lake Shore Drive and Sheridan Road - is full of lake views and leafy neighborhoods, making it quite perfect for a little top-down cruising.

Once there, you can explore peaceful gardens and admire the intricate latticework of the temple’s dome, one of only a few of its kind in the world. It’s a short trip that feels like a genuine reset, with equal parts beauty, calm, and jaw-dropping curb appeal.