Chicago is a fascinating city, and you may need months to take it all in. But if you want to see and try the main attractions, three days and a well-planned itinerary should be enough. Plus, you can throw in a few things to make the experience truly unforgettable.
Without further ado, here are some of the objectives, activities, and experiences you must add to your 3-day Chicago itinerary:
The Windy City is well-known for its skyscrapers and impressive skyline, so you shouldn’t miss the chance of seeing it for yourself. For the best view of the city and its entanglement with lake Michigan, pay a visit to the former John Hancock Observatory, now known as 360 Chicago observation deck.
Here, you can admire the city from above (also known as the 94th floor of the 875 North Michigan Avenue building) and have quite a unique experience. Plus, if you want to enjoy the view and have a meal or drink, you can go up one floor where you’ll find The Signature Room restaurant. On top of that, on the 96th floor, there’s The Signature Lounge bar.
Did you know you can rent a limo to take you from and to the airport? The limo airport service Chicago is a great way to spruce up your visit and enjoy your trip from the moment you step out of your terminal.
Plus, you can continue adding style to your trip by selecting one of the many luxury hotels available in the city. Hotels like The Peninsula Chicago await their guests with a variety of menus, wellness treatments, and fun activities to make their stay more pleasant.
You can’t design a Chicago itinerary without including a river cruise on one of the days! Chicago’s buildings and the overall landscape they create is unique, and the only way to fully admire it is while enjoying a cruise.
You can also do the Chicago Riverwalk if you’re not that fond of boats and water, but you have to prepare for a long walk (there are rest spots along the way). Also, you won’t have a witty Chicagoan telling you the story of each interesting building.
Quick tip: if you want to take the cruise, make sure to visit in the summer. In the winter, the water can freeze over so there are no boats to take you.
If you’re a foodie, you have to try an authentic deep dish! The experience of trying this cheesy goodness for the first time doesn’t compare to anything you’ve ever tried before (or will try after)!
The pizza is just as good as you’d imagined and a bit more, plus you can share it with your friends or take leftovers for later since you’ll probably have a tough time eating it in one sitting.
Also, if you are lucky enough to be here in July, put food festivals on your Chicago itinerary. The largest one is called The Taste of Chicago and it’s a five-day festival that takes place in July in Grant Park. Here, you have the chance to try a variety of local foods, connect with the locals, and enjoy some cooking demonstrations.
Your Chicago itinerary will vary depending on the time of the year you visit, but it’s easy to find something to see or do regardless of the weather. Still, if you want to see the city at its best, visit in summer.
Find accommodations in Chicago, this way, you’ll spend three amazing days immersed in Chicago’s culture and locals, which is the best way to experience this great city.
