20 days in Chicago & Rome Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Get out of town with these interesting Chicago side-trips: South Bend (Grotto of Our Lady Lourdes & Basilica of the Sacred Heart). There's much more to do: explore the world behind art at The Art Institute of Chicago, get curious at Field Museum, take in panoramic vistas at 360 Chicago Observation Deck, and stroll around Millennium Park.

To see more things to do, maps, photos, and more tourist information, you can read our Chicago driving holiday planner.

New York City to Chicago is an approximately 4-hour flight. You can also drive; or take a bus. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. Plan for little chillier nights when traveling from New York City in March since evenings lows in Chicago dip to 30°F. Finish your sightseeing early on the 18th (Fri) so you can fly to Rome.

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.

Explore Rome's surroundings by going to Tivoli (Casa Gotica, Villa d'Este, &more). There's still lots to do: steep yourself in history at Palatine Hill, admire the masterpieces at Galleria Borghese, don't miss a visit to Trevi Fountain, and contemplate in the serene atmosphere at Vatican Museums.

To see other places to visit, where to stay, traveler tips, and tourist information, use the Rome trip builder.

Traveling by flight from Chicago to Rome takes 12.5 hours. Traveling from Chicago to Rome, you'll lose 7 hours due to the time zone difference. Plan for a bit warmer temperatures traveling from Chicago in March, with highs in Rome at 61°F and lows at 45°F. Cap off your sightseeing on the 31st (Thu) early enough to catch the flight back home.