DESTINATIONS & CITY GUIDES How to Make the Most of a Layover: Road Trip to Chicago Navy Pier Posted on October 17, 2018February 26, 2026 I finally stepped outside O’Hare and spent a long layover at Chicago’s Navy Pier. We rode the Centennial Wheel, strolled the waterfront, ate deep-dish at Giordano’s, and took an architecture river cruise. It was simple, scenic, and worth it. Chicago proved it’s more than just an airport connection. Read more