Start your trip with a stroll down the Magnificent Mile, a famous shopping district with high-end boutiques, department stores, and popular restaurants. Admire the beautiful architecture of the historic buildings that line Michigan Avenue.
Head to Navy Pier for a day of entertainment and fun activities. There are various attractions, including the Ferris wheel, an IMAX theater, a beer garden, a children's museum, and numerous restaurants. Enjoy the panoramic views of Lake Michigan.
Explore the world-renowned Art Institute of Chicago where you can see an impressive collection of artworks from around the globe. It's the second-largest museum in the US, and the collection includes everything from contemporary art to impressionist paintings.
End your trip at Millennium Park, an iconic public park in the heart of Chicago. Marvel at the magnificent Cloud Gate sculpture, also known as the Bean, and take a walk through the serene Lurie Garden. Meet your friends for one last Chicago-style hotdog before taking off.
Chicago has an extensive public transportation network that consists of elevated trains, buses, and several taxi services such as Uber and Lyft. Visitors can obtain a Ventra Card to access the train and bus networks. The city also has ample bike rental services, including the popular Divvy Bike sharing program. All the major attractions in Chicago are easily accessible on foot, so be sure to bring comfortable shoes.
To get from one place to another, expect a 10-20 minute drive, or 20-45 minute public transit ride for most cities. Taxis from the airport to downtown Chicago are roughly $60 or you can take the Blue Line "L" train for $5 and it will take approximately 45 minutes to one hour.
If you have more time, consider exploring the neighborhoods of Chicago such as Wicker Park, Lakeview, or Logan Square. For foodies, make sure to indulge in deep-dish pizza, Chicago-style hotdogs, or Italian beef sandwiches. You can also take a boat tour from Navy Pier to get a scenic view of the skyscrapers and architecture. In case you have fewer days, you can skip any spot so that you can focus on the best of Chicago daily.
Chicago has two international airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). O'Hare is approximately 16 miles northwest of downtown Chicago, and there are several ground transportation options, including the Blue Line train, taxis, and airport shuttles. Midway is approximately 10 miles southwest of downtown Chicago and has several trains, taxis, and buses available for transport.