Chicago Travel Guide

Chicago is one of the United States’ most exciting cities. Known for its deep-dish pizza, its love for jazz and blues, its looming Sears Tower and historic Wrigley Field, Chicago is a favorite hot spot among many tourists. Drawing in large crowds of business travelers each year, Chicago isn’t without attractions that are purely fun like the famed Navy Pier and its very own theatre district that provides a generous selection of both Broadway and off Broadway shows. Chicago is definitely a city where the worlds of work and play collide.

Airports and Ground Transportation

Chicago is home to two major airports. O’Hare International Airport is located 20 miles outside of the city and is widely known as a popular connecting hub. An estimated 70 million travelers pass through O’Hare International Airport each year making it constantly full of activity. O’Hare conveniently offers travelers the ability to connect into Chicago’s public transportation systems directly from the airport. 

Chicago Midway Airport is not an international airport and serves just 17 million travelers per year. Only 10 miles outside of the city, this airport is often a popular choice among domestic travelers who want to spend less time getting into the city. Midway, too, provides immediate connections into Chicago’s public transportation system.

In Chicago the methods of ground transportation are plentiful, and it truly is up to you to find the method of travel that is best for you. Some travelers opt for rental cars, while others choose to rely on taxis (which can be pricey, although Chicago cab fare is known to be far more reasonable than certain other cities). Others still choose to rely on public buses or the elevated “L” trains which are the equivalent of above ground subways.

Discount airfare to Chicago is easier to find when you fly into O’Hare since it is a hub for many airlines and there are many direct flight options. Cheap flights to Chicago can be found for as low as $380 from LAX, $300 from JFK, or $367 from SFO. Other discount airfare to Chicago can be found by flying into Midway, but you will more than likely have to connect as direct flights are limited. Cheap flights, with at least one connection, can be found for as low as $318 from LAX, $300 from JFK and $350 from SFO.

Peak Travel Seasons and Ideal Times to Travel

Summer is peak travel season in Chicago, so you if you are planning to visit then you will need to make sure you book your travel arrangements well in advance. If you want to actually walk around the city, make sure you avoid the winter season as everything is typically covered in ice and snow. Fall and spring tend to be the best times of year to visit because the weather is typically mild with temperatures in the 60s and 70s.

However, Chicago is known as a rainy city and it does tend to rain there throughout the year. So make sure you check the forecast before visiting, and pack a poncho or umbrella if needed. Air travel to and from Chicago can be difficult in the winter months as many flights tend to get grounded due to inclement weather.

Main Attractions

Both those who are into baseball and those who are into history will appreciate Wrigley Field, home of the Chicago Cubs. The second oldest ballpark in existence, Wrigley Field is where Babe Ruth hit his famous “called shot” in the 1932 World Series. Fans must take public transportation to the stadium or park in a designated lot where they can catch a shuttle to the stadium for a small fee. Those visiting Wrigley Field will want to come early so they can enjoy the festive atmosphere around the ballpark.

Families and the young at heart will both enjoy the countless attractions at the famed Navy Pier. Fireworks, rides, an IMAX theatre and live stage performances can keep you and your family entertained for hours. Navy Pier is also a connecting hub for several Chicago sightseeing cruises.

Or, if your time is limited, you may prefer to simply spend an afternoon shopping along Chicago’s Magnificent Mile. Hailed a “Shopper’s Paradise” the Magnificent Mile provides shoppers with local boutiques, high-end designer stores and several other offerings.

Hotels and Lodging

Most Chicago travelers stay in larger chain hotels, especially if they are traveling on the company tab. Hotels range in price, and Chicago isn’t much different than any other city in its range of options. Chicago offers everything from budget hotels to luxury suites. But a unique alternative to your typical hotel is one of Chicago’s bed and breakfasts. Mostly housed in older brick buildings, these bed and breakfasts offer a homier feel while still keeping you within close proximity of everything the city has to offer.