What Is a Good Road Trip to Chicago?

By Michael Ferguson

Are you planning a road trip to Chicago? If so, get ready for an unforgettable adventure filled with stunning architecture, delicious food, and exciting attractions.

But with so many things to do and see in the Windy City, it can be overwhelming to plan your itinerary. That’s why we’ve put together a guide to help you plan the ultimate road trip to Chicago.

Getting There

Before embarking on your road trip, it’s essential to have a good plan in place. If you’re coming from out of state, consider flying into Chicago O’Hare International Airport or Midway International Airport and renting a car from there. Alternatively, if you live within driving distance of Chicago, pack up your car and hit the road.

Where to Stay

Chicago has plenty of accommodation options for every budget. If you’re looking for luxury accommodations, check out The Langham or The Peninsula Chicago.

For mid-range options, consider The Godfrey Hotel or the Radisson Blu Aqua Hotel. Budget-friendly options include Freehand Chicago or HI Chicago Hostel.

What to Do

Chicago is known for its stunning architecture, so make sure to take an architectural boat tour along the Chicago River. You’ll get a unique perspective on the city’s iconic buildings like the Willis Tower (formerly known as Sears Tower) and Marina City.

For foodies, don’t miss out on trying deep-dish pizza at Lou Malnati’s or Giordano’s. Another must-visit is Portillo’s for their famous hot dogs and Italian beef sandwiches.

If you’re interested in museums, check out the Art Institute of Chicago or the Museum of Science and Industry. For sports fans, catch a game at Wrigley Field (home of the Cubs) or Guaranteed Rate Field (home of the White Sox).

Day 1

Start your first day by visiting Millennium Park and taking a picture with “The Bean,” a.k.a. Cloud Gate. Then, head over to the Willis Tower for stunning views of the city from the Skydeck.

In the afternoon, take an architectural boat tour along the Chicago River and learn about the city’s history and architecture.

Finish off your day by enjoying deep-dish pizza at Lou Malnati’s or Giordano’s.

Day 2

Begin your second day by visiting Navy Pier for fun attractions like the Ferris wheel, carousel, and IMAX theater. Don’t forget to grab a classic Chicago-style hot dog at Portillo’s.

In the afternoon, head over to Wrigley Field for a Cubs game (if there’s one scheduled) or take a stroll through Lincoln Park Zoo.

End your day with a delicious Italian beef sandwich at Portillo’s.

Final Thoughts

Chicago is an incredible city full of history, culture, and delicious food. With this guide, you should have no problem planning an unforgettable road trip to this amazing destination.

Just remember to pack comfortable walking shoes and dress in layers as Chicago weather can be unpredictable. Safe travels!