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What Can You Do on a Weekend Trip to Chicago?

Sailun Tires

The Windy City, as many like to call it, has a lot to offer its visitors. From delicious deep pan pizza (you have to try it!) to jaw-dropping architecture. After all, the reason why so many people call it “The Second City” is because it’s always competing with New York City – America’s most visited destination.

But how can you take in the very essence of Chicago in just a weekend trip? Well, if you want to know the city, you can’t cover everything over a few days, but you can hit its main spots. Still, if you only go for the touristy spots and activities, you may end up pretty tired at the end of your trip. So why not take it easy and enjoy your time in Chicago based on our recommendations?

Where to Stay (in style)

If you’re looking for stylish accommodation, you have to consider some of the most good-looking hotels in the city!

Check out the Chicago Athletic Association hotel (downtown business district), where you’ll feast your eyes on its rich Venetian Gothic-style architecture and interior decorations. Or, if you want something more modern, The Robey is a former skyscraper-turned hotel following the Art Deco style.

And, to make the experience even more interesting, you can hire a Chicago limo rental service to bring you from the airport. This way, you’ll feel a little like Al Capone, one of Chicago’s biggest celebrities!

Book a River Cruise

The Chicago Architecture Foundation association offers guided river cruises (between one and five hours per ride) that will take you on an educational journey around the city. Chicago is famous for its architectural attractions and you can learn all about it in one of these boat rides without getting bored at all.

Plus, this ride is a must-have even if you don’t care about architecture or history. The views you’ll get to experience and the journey in itself are definitely worth your time!

Spoil Your Senses

When in Chicago, you must try the deep dish pizza! The city is famous for it and there are several restaurants where you can try it across town. True, you’ll feel full after one pizza, but you can’t miss the experience!

Also, once you’re full and looking for entertainment, look for a jazz show. Chicago is famous for its jazz singers and there are lots of small, intimate venues where you can catch an authentic show.

Take a Walk in the Park

Lincoln Park, to be more exact! Lincoln Park is a 1,200+ acres lakefront park that includes a zoo, a conservatory, and the Chicago History Museum. Oh, and you don’t have to pay anything to roam around.

You can spend an entire day walking among green, exotic plants and feast your eyes on the beauties around. Plus, if you get tired, there’s a huge lake nearby where you can take a break and enjoy a delicious picnic. This is the perfect touristic spot when you want some peace and quiet without spending much money.

Catch a Baseball Game

There’s no better way to immerse yourself in American culture than by watching a baseball game! And Chicago has Wrigley Field (one of the most famous fields in the area) where you can see a game whenever you want.

So, buy yourself a ticket, get a hot dog, take a seat and enjoy the atmosphere. You don’t have to know anything about the game to soak up the culture – it’s definitely worth it!

Wrap Up

Chicago is a great location for a lazy weekend trip alone or with friends and family. But if you want a bit more adventure, check out these uncommon US tourist destinations! Overall, American cities and landscapes are so diverse and interesting that you could spend a lifetime trying to soak everything in.


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