Weekend Trip to Chicago: 3 Must Do's

If you find yourself heading toward Chicago for a weekend trip (business or leisure), you’re almost guaranteed a good time. Provided you’ll have the time and disposition to leave your hotel and roam around. 

The Windy City, as it’s called by its inhabitants, is a beautiful mixture of events (music, theater, shopping, you name it) and futuristic architecture. Add to this a sprinkle of sandy beaches and the gorgeous Lake Michigan, and you have the perfect recipe for fun whether you’re traveling alone or with the entire family!

So if you want to know how to maximize your stay in Chicago, here’s a quick list of must-haves when in Windy City!

You’ll most likely land at O’Hare International Airport, which is one of the busiest airports in the world. While the airport has a beautiful design and tries to create a welcoming atmosphere, you probably want to get to the city and to your hotel as fast as possible. 

Still, if you feel your batteries are running out, you can enjoy a short meal at the airport. You’ll find a selection of meals from all over the world and there’s even a meditation center where you can relax and unwind. But once you’re done here, it’s time to get out and enjoy the city! 

There are lots of options to travel to downtown Chicago, but the best way is with the Chicago O'Hare car service, where you can rent a limo to take you to the hotel. 

As we already mentioned, Chicago is a cultural hub where both solo travelers and people who travel for business can find places to rest, communicate, and recharge. Given that you probably won’t have much time for touristy stuff, our list only includes the top three attractions you must experience.

True, you’ll look like a tourist, but you don’t have to stick with the same group all day. Guided tours, like the ones offered by bus, foot, or boat are amazing because they introduce you to the city in a general way. 

You’ll also learn about the major attractions, so you can build a quick itinerary to follow once you’re done with the tours. Our recommendation is to take the boat cruise during summer - the experience is mesmerizing and you’ll get to see some of Chicago’s most beautiful buildings from a unique perspective. 

With so many theaters, world-renowned restaurants, and exotic bars and terraces it’s easy to assume that Chicago’s nightlife is glamorous. So why not dip your toes into the fun? 

For starters, you should check out the Chicago Theater District and see if you can find any interesting Broadway In Chicago performances. If theater is not your thing, the Lyric Opera is nearby - you should see it even if you don’t enjoy opera or classical music; the building is stunning!

Once you’ve had your share of culture and architecture, it’s time to start exploring the bars, restaurants, and other venues you can find downtown. It will be a night you won’t forget!

Also known as the 360 CHICAGO Observation Deck, this is a spot that lets you see the entire city from above. You can also enjoy a bit of thrill by trying the tilting windows that allow you a way better view from a bit outside the building. 

And, if you get hungry from all the excitement, one floor above, you’ll find a wonderful restaurant with amazing dishes and atmosphere. 

Even if you don’t have much time, if you are in Chicago you must do your best to see at least one of its main attractions! In this case, we recommend the Chicago Riverwalk or boat cruise - both take you on a wonderfully relaxing trip through the heart of the Windy City.