Auston Matta a RoamRight Blog Author

How To Make The Most Of A Visit To Chicago

Chicago is the third most populous city in the United States

Chicago is a historic American city whose fame and fortune grew from its strategic location fostering the transport of goods across the US via boat and train. While much of the city burned to the ground in the Great Chicago Fire of 1871, the city was rebuilt and now stands as a symbol of perseverance and architectural wonder. Chicago is a perfect place for a long weekend visit but doing a bit of planning in advance can help you make the most out of your trip.

Time of Year to Visit

Chicago is internationally known for being cold and windy. Frequent winter snow and wind chills down to -20F are common and are best avoided. Plan your trip between May and October to take advantage of the best weather. Summer is typically warm and humid but is the most enjoyable times of year to visit because the city comes alive after the long winter's hibernation. During the peak of summer, Chicago hosts music, culture and food festivals every weekend all across the city so you'll always find events to occupy your time.

Transit Passes

Chicago is one of the few cities in the US where you don't need a car to get around. In fact, driving a car in Chicago can be stressful given all the narrow roads, traffic and lack of public parking. Public transit is the best way for a tourist to get around the city. As a visitor, you'll be able to reach most places on the elevated train (called the L) or city bus. If you plan on using the system at least 3 times daily as most tourists do, you're better off buying a visitor pass which gives you unlimited use of the trains and buses during your stay.


Chicago is most famous for their deep-dish pizza and unique style of hot dogs. Any visitor to Chicago should take the opportunity to try both, but finding a restaurant with a good ambience that focuses on quality can sometimes be a challenge. Gino's East or the original Uno Pizzeria are both famous restaurants for deep-dish pizza but you'll find large crowds of tourists at both places. Consider making a visit to Giordano's or Lou Malnati's for a more local atmosphere and equally great pizza. Hot Dougs or Gold Coast Dogs are great places to find a good quality hot dog, perfectly made Chicago style always without ketchup and heaped with onions and relish. For more information on food in Chicago, read Classic Food Spots in Chicago or A Foodie Tour of Chicago in Five Meals.

Seeing the Skyline

There are a few tricks worth noting when experiencing Chicago's famous skyline. Visiting the observation decks at the Willis Tower or the Hancock Building is on most people's list and is definitely a great experience. If you go to the Willis Tower, you can plan on spending one to two hours waiting in line on weekends, especially during the summer months. Try visiting first thing in the morning, late in the day or on weekdays to avoid the lines. You can also visit the bar at the top of the Hancock building to get the same view as the observation deck for free or at least for the price of the cheapest drink on the menu. There are two locations within Chicago where you'll find stunning views of the skyline from the ground. Go either north of downtown on the lakefront near North Avenue Beach or south to the Adler Planetarium for the best photos.

Have you been to Chicago? What did you think?

Note: Available plans and coverages may have changed since this blog was published.


About the Author

Auston Matta

Auston Matta, a RoamRight Blog Author Auston grew up in Phoenix before escaping to Chicago in 2008. After 4 years working as an engineer, he sold his belongings and embarked on a round-the-world trip. After traveling non-stop for a year, he finally settled in Spain with his husband where he now calls home. When he's not traveling or writing guides about events, festivals or the best LGBT destinations, he enjoys the long sunny days and nightlife of Madrid. Read Auston's blog at Two Bad Tourists, or follow him on Google Plus, Twitter, Facebook, YouTube, or Instagram.

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