Chicago is a vibrant and diverse city with a lot to do. Make sure to hit the must-sees, but branch out to explore the city’s other aspects, like hole-in-the-wall restaurants and boat tours. And if you’re not able to get it all done in one trip, that means you’ll just have to visit again some other time!

Must-Visit Spots

Chicago is loaded with history and rich in culture. Museum fans will want to spend a day at the Chicago Art Institute, and kids of all ages will enjoy their time at the Shedd Aquarium. The Field Museum of Natural History is also a must-see. If you’d like to get off the beaten path, plan to spend some time at the Driehaus Museum, which offers a gorgeous view into Chicago’s gilded age. 

Take a Historical Tour

To get a detailed glimpse of Chicago’s remarkable architectural history, be sure to take a river cruise. In addition to studying the details of construction in some of the most iconic buildings of the city, you can also learn about the history of Chicago. The great fire of 1871 wreaked destruction on both sides of the river, but how? On the tour, you can begin to understand what was going on in Chicago at the time, why the fire was so destructive and how the city rebuilt. If possible, try to schedule your trip to Chicago around March 17th. Your tour can include a look at the river after it’s been dyed green for the huge St. Patrick’s Day celebration in the city.

Car or Boat?

Renting a car to get around in a big city like Chicago isn’t very practical. Not only may you be struggling to figure out where to go and how to get there, but your rental car may not handle as easily as your regular car at home. Sudden panic stops or quick lane changes in heavy traffic can get dangerous in an unfamiliar vehicle, and the traffic ticket will not be cheap if you get pulled over. Rideshare apps are an option, as is the L train, but these can cost you a fortune over the course of your trip. 

Alternatively, you can see Chicago from the comfort of a pontoon boat and avoid the stress of traffic altogether. Renting a pontoon can be a breathtaking way to experience Chicago while saving time and money. Most importantly, some of the most beautiful views of the city of Chicago can be seen from the water. If you’re ready to view the city lights, don’t look for a tall building where you can look down on the city. Get out on Lake Michigan and look up at this remarkable metropolis. When you return your pontoon rental, you might be ready for dinner. There are several dinner cruise options, both on the shore of Lake Michigan and on the Chicago River. In fact, the dining options available in Chicago will satisfy any palate.

Eat a Little Something

Of course, a stop for some deep dish pizza is critical. However, if you have some cash in your pocket, you can also find great food in less obvious spots around Chicago. Spend some time in the Loop and save space for Cajun food at Heaven on Seven. There are no signs, and you’ll have to talk to the doorman for dinner. The walls are lined with different hot sauce options, and the sweet potato polenta can’t be beat. Chicago is a great place for food of all cultures. Oasis Café on Jeweler’s Row is an excellent spot for falafel and other Mediterranean treats. If you’re fond of farm-to-table local food exploration, the Stock Café is a wonderful stop for the sandwich special. Be ready to do some hunting when you’re looking to dine at a hidden gem in Chicago, as not all addresses are easy to locate. Also, be aware that many places don’t take credit cards, so you will need cash to cover your bill. 

Your Chicago trip can include all of the popular attractions, and they deserve your attention. But don’t forget about the lesser-known but still fun alternative options, like boat cruises and historical landmarks. This city is a wonderful place to explore and has something fun for every member of the family.

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