Five Tips to Help You Plan Your Trip to Chicago

The Midwest’s biggest city is naturally a can’t-miss in the United States. From its fantastic dining options to summer-long festivals, use my tips to help you plan the best trip possible!

Pick the Perfect Neighborhood for Your Accommodations

When it comes to Chicago, it’s important to find the right Chicago hotel for your stay and where you want to be. You can stay in the heart of the city, but Chicago’s surrounding suburbs hold the charm in my opinion. My personal favorite is Andersonville for its cute antique and thrift shops, restaurants, and annual summer festival. Because using the train makes it easy to get downtown, I recommend staying in the outskirts to avoid those higher prices.

Indulge in Chicago’s Fabulous Dining

When one thinks of Chicago cuisine, deep-dish pizza immediately comes to mind. Chicago’s Italian heritage is highly present throughout the city, and you absolutely must make a visit to one of the city’s many famous pizza places (my personal favorite being Gino’s East on La Salle St). One tip: arrive and order your pizza as you’re starting to get hungry; deep-dish can sometimes take up to an hour to bake! Other than pizza, I highly suggest checking out India Town on Devon Ave toward the north to indulge in curries, ordering an authentic Chicago-style hotdog, and hitting up one of Chicago’s many, many brunch specialty restaurants (you HAVE to get the bread pudding bowl at M Henry Café).

Get the Best View of the City

Many people know to visit the Willis Tower, but one of Chicago’s newest attractions is at the John Hancock Center, called 360 Chicago. Situated right on the lake, I recently visited this year and had a great time! On an absolutely clear day, you can see for miles and miles from the 94th floor. Each direction has several interactive screens that give you more information about the buildings and attractions you’re seeing in that view. It really is a fantastic way to get to know the city’s rich history!

Research Local Festivals Before Booking Your Trip

Besides Andersonville’s Midsommarfest, Chicago is so packed to the brim full of festivals that it’ll be hard to visit without some kind of event already happening. So make sure to plan your festival visit ahead of time! For example, wouldn’t you hate to find out that you could have attended Rib Fest the weekend before you’re scheduled to arrive? Or that the one weekend you stop by Navy Pier they have nothing exciting going on? It’s totally worth planning your trip around these festivals to make the most of your Chicago experience.

Getting Around

If you haven’t already, download Lyft and Uber to make your life easier getting around the city. What’s better than pushing a few buttons on your phone and having your own personal driver pull up with a smile in minutes? I started using both of these services in Chicago, and they’re AMAZING. Use my promo codes (samantha278567 on Lyft and samantha6689ue on Uber) for ride credits!

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