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Insider Tips for Visiting Chicago

Chicago is a vibrant and bustling city filled with so much to explore. From its iconic architecture to its world-class cuisine, there’s something for every traveler in the Windy City. To make the most of your time in Chicago, here are some insider tips from locals who know the city best. 

chicago monument and buildings

Take Advantage of Public Transportation 

Chicago’s public transportation system is one of the best in the country and can easily be used to get around the city without having to worry about traffic or parking fees. The “L” train lines cover most of downtown and other popular tourist spots like Wicker Park and Lincoln Park. There are also many buses that run throughout the city, so if you plan on exploring more than one area then it might be worth getting a day pass for unlimited rides. Don’t forget about ride sharing services like Uber and Lyft as well! 

Related Read: Famous Chicago Landmarks To Visit

Sightseeing Must-Sees 

No visit to Chicago would be complete without seeing some of its iconic landmarks such as The Bean (Cloud Gate), Wrigley Field, Navy Pier, and Millennium Park. If you’re feeling adventurous, head over to one of Chicago’s many museums such as The Art Institute or Shedd Aquarium – both located near Millennium Park – or take a stroll down Michigan Avenue where you’ll find some of the world’s most famous retailers.  If you want to know more fun things to do in Chicago Explore Live Learn Venture, They have listed 12 fun things to explore in Chicago.

Explore All Four Seasons 

Chicago has four distinct seasons—spring, summer, fall, and winter—and each season has something unique to offer visitors. Springtime brings beautiful blooms and mild temperatures while summer gives you access to outdoor concerts and activities. Fall is perfect for exploring the colorful foliage while winter is great if you love snow sports like skiing and snowboarding. No matter when you visit Chicago, there will always be something fun to do! 

Eat Your Way Through The City 

No trip to Chicago would be complete without indulging in delicious food from all parts of the city. Whether you’re looking for a classic Italian beef sandwich or deep dish pizza from one of the local pizzerias, you can find it all in Chicago. Try checking out some of the lesser known restaurants too; chances are good that you can find a hidden gem just off the beaten path! 

Food & Drink Recommendations 

Chicago is known for its deep dish pizza but don’t let that overshadow all of the other amazing food options available in this great city. From classic dishes like Italian beef sandwiches to unique flavors like Polish sushi rolls (kabobs), there is something here for everyone’s taste buds. For those looking for drinks after dinner, there are plenty of options ranging from dive bars to craft breweries throughout Chicago’s various neighborhoods. 


Chicago is an amazing city with so much to explore and live in, (check out the best neighborhoods to live in Chicago)! From taking advantage of public transportation to eating your way through town and experiencing all four seasons in one trip, these insider tips will help make your visit even more memorable. So pack your bags and get ready for an unforgettable adventure in the Windy City!

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