7 Keys to a Chicago Trip You Won’t Forget


Chicago is a city that everyone should visit at least once. Or, ideally, more than once, as It’s full of more culture and beauty than you can possibly cover in a single trip. Some of the best attractions are the most obvious ones, but if you do a little digging, there’s so much more to see. 

There are a few things we recommend to ensure that you make the most of your time. Here are 7 tips to help you have the most memorable experience:


Eat as Much as Possible


Chicago has some of the best food in the nation. You won’t have nearly enough meals to consume all of the enticing food that’s available. Because the restaurant scene is always growing, it’s hard to decide whether to visit all of the old classics or check out the new up-and-comers. Just this year, two Chicago restaurants made it onto Esquire’s list of 2020’s Best New Restaurants in America.

Whether you’re looking for a peerless fine-dining experience like Alinea, interested in chasing down the best soup dumplings in Chinatown, or going classic with some Italian beef (the original Al’s on Taylor Street is a can’t-miss), you can find an excellent option in Chicago to suit any taste. 

To make the most of every meal, have a list of your must-visits figured out before you go. Leave room for spontaneity, though. You want to be able act on a hot tip from a friendly local, who are usually happy to share their favorites.


Go Beyond Downtown


There’s more to Chicago than just the downtown area. Many people visiting the city will stick to the most popular attractions, hitting museums and shopping the Magnificent Mile. And while there’s nothing wrong with these activities, Chicago’s real richness lies in its neighborhoods.

Pilsen, for instance, made it into CNN’s list of The world’s 10 coolest neighborhoods. Named for the Czech town for which Pilsner beer is named and, more recently one of the city’s hubs of Mexican-American culture, you’ll find a variety of street art and incredible food. Don’t miss the porky delights at Carnitas Uruapan.

Just a few other neighborhoods worth exploring include Logan Square, Hyde Park, and Andersonville. You may be surprised by what you find when you branch out. But exploring the neighborhoods gives you the true richness and depth of the city.


Don’t Rent a Car


Some situations require you to rent a car. But if possible, go without it! Chicago is a very walkable city. Entertainment, restaurants, and cultural hotspots tend to be clumped together so that you can easily plan to get around on foot.

Chicago also has a great public transportation system. According to CNN, there are 129 bus routes, 10,768 bus stops, eight train routes, and 145 train stations. Plus, the “L” train is such a staple for the city, it’s part of the experience to hop on it at least once. 

Public transportation is very affordable and easy to use. It connects you to all of the most popular locations so you don’t have to worry about walking everywhere if you don’t want to. This is especially helpful during those cold midwest winters.


See a Show


There’s a show for everyone in Chicago. You could see a touring Broadway show at Cadillac Palace Theatre. Enjoy a thought-provoking performance piece in the more casual setting of the Windy City Playhouse. Shout out suggestions to the top-notch improv troupe at The Second City. Or sing along with your favorite musicians at popular venues like Metro.

Some people think of seeing a show in Chicago and only think of the touring Broadway shows, but there’s so much more. With a little research ahead of time, you can find a show for any taste and any budget. Whether you’re looking to laugh, cry, sing, or dance, you’ll have plenty of options to choose from.


Get Out on the Water


With both the Chicago River and Lake Michigan, Chicago offers a lot to do out on the water. Popular activities include riverboat tours, kayak tours, and boat rentals. Of course, this applies specifically to trips in the warmer months of the year.

If you’re looking for an unobstructed view of the city, the River Boat Architecture Tour is the way to go. These tours are perfect for first-time visitors who want to learn a bit about the buildings, their names, and the history of the city. For those feeling a bit more independent and athletic, there are also tours given on kayaks.

Renting a boat to drive around Lake Michigan may be one of the most relaxing ways to enjoy the city and its miles of beaches. Pick up lunch from your favorite restaurant, rent a boat from one of the many rental facilities in the area, and spend the afternoon on the water. It’s the perfect way to spend a summer day.


Don’t Miss the Museums


There are many museums to choose from in Chicago. Check out the art at The Art Institute or the Museum of Contemporary Art. See breathtaking artifacts at the Field Museum. Expand your mind by visiting the Museum of Science and Industry.

There’s something for every interest and age group, even young kids. Places like the Museum of Science and Industry have a lot of interactive exhibits that feel more like playtime than education. Many of these museums also have free or discounted days throughout the year. So, if you’re visiting on a budget, try to plan around these days.


Take Lots of Pictures


With all of the fun experiences that you have planned for yourself, don’t forget to take a few pictures along the way. There are so many photogenic locations in the city. Whether you’re snapping a selfie or trying to get a full view of the skyline, there are picture-perfect spots all over the city.

In fact, Chicago is so attractive, it’s a popular choice for couples who are getting engaged. According to this PartySlate list, these are the best places to propose in Chicago.

With so much to see and do, Chicago is the perfect destination for your next trip. You’ll want to come back again and again to do all the things you didn’t have time for the first time around. Use our tips to do a little planning ahead of time and you’re sure to have a truly memorable trip.

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