10 days in Chicago & Miami Itinerary

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

Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, observe the fascinating underwater world at Shedd Aquarium, take in panoramic vistas at 360 Chicago Observation Deck, and engage your brain at Museum of Science and Industry.

To see photos, where to stay, other places to visit, and other tourist information, you can read our Chicago online trip builder.

Playa del Carmen, Mexico to Chicago is an approximately 7-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Playa del Carmen to Chicago. Expect colder temperatures when traveling from Playa del Carmen in February; daily highs in Chicago reach 2°C and lows reach -7°C. Wrap up your sightseeing on the 24th (Fri) early enough to fly to Miami.

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.

Change things up with these side-trips from Miami: Homestead Historic Town Hall Museum (in Homestead), Tavernier (Florida Keys Wild Bird Rehabilitation Center & Scooby's Popcorn) and Key Largo (Sandal Factory Outlet & Capt. Sterling's Everglades Eco-Tours). There's much more to do: walk around Lincoln Road, shop like a local with Bayside Marketplace, see the interesting displays at Vizcaya Museum and Gardens, and look for all kinds of wild species at Shark Valley Visitor Center.

For traveler tips, more things to do, and other tourist information, go to the Miami road trip website.

Getting from Chicago to Miami by flight takes about 5 hours. Other options: drive; or do a combination of bus and subway. You'll lose 1 hour traveling from Chicago to Miami due to the time zone difference. Expect warmer temperatures when traveling from Chicago in February; daily highs in Miami reach 30°C and lows reach 21°C. Wrap up your sightseeing on the 1st (Wed) early enough to travel back home.