Ahhh Chicago. The Windy City, City of Big Shoulders, ChiTown. No matter what you call it, you’re bound to have a good time – just check the forecast first. Chicago weather can be fickle, but the heart and soul of the city remain the same. Having an Avail car gives you access to some of the best under-explored gems in Chicago that aren’t easily accessed via public transit (the CTA). Be sure to download our "Avail's Guide to Chicago" PDF guide for more info on the above recommendations, as well as more ‘off the beaten path’ experiences.
Chicago serves up unique, hearty, and eclectic food and drink, from deep-dish pizza to Chicago style hot dogs. Don’t skip Pequod’s pizza in Lincoln Park. This under-the-radar pizza joint is every local’s favorite deep-dish spot. Pequod’s is as Chicago as they come, with an herbed butter-crust and heaps of sauce and cheese. Pequod’s never fails and avoids the tourist hype of Lou Malnati’s, Giordano’s, and Gino’s East. Go during the week or skip lunch for an early dinner on Friday or Saturday. You’ll definitely want an empty stomach when you come to Pequod’s.
Take a drive down Lake Shore Drive to Promontory Point, which offers a great spot to gaze and stroll away the deep-dish with stunning views of the azure waters of Lake Michigan. It’s located on the eastern edge of Hyde Park, a historic and beautiful neighborhood famous for its restaurants, The University of Chicago, and two most notable former residents, Barack and Michelle Obama.
The Hyde Park neighborhood is also home to the Robie House. Designed by iconic architect Frank Lloyd Wright, the Robie House is recognized as a masterpiece for its display of American Prairie House Architecture. Building buffs will love Chicago for its diverse styles of modern architecture on parade in both small neighborhoods and on skyscrapers like the Willis Tower and Hancock Tower downtown.
To head back north, hop on Lake Shore Drive for an iconic Chicago experience. You can cruise up and down the coastline and get a good overview of the entire city in about 30-45 minutes and take detours by some of the better known Chicago landmarks like Wrigley Field, The Shedd Aquarium, The Bean (a.k.a. ‘Cloud Gate’), The Art Institute of Chicago, and Millennium Park. Just be sure to factor in traffic if you’re pulling off Lake Shore Drive. Traveling even a mile in dense urban areas can take up to 20-30 minutes!
Chicago is a prolific city full of heart, midwestern charm, and spunk that can entertain any traveler for months. Much like a slice of deep-dish pizza, you’ll be full after a weekend in Chicago, but you’ll always come back for more!