Travel Insider Tips | Chicago Edition

6 Tips from locals experts in Chicago

Welcome back to the 5th article of the travel Insider Tips series! For this article, we travel to the most populated city in the state of Illinois, Chicago. The city is known for its museums, arts scene, and most importantly pizza! Anyone who says money can’t buy happiness is wrong because they clearly have not bought pizza. So, let’s start discovering the best of Chicago with our travel insider tips! 

6. Caramel popcorn

I love popcorn and I have a sweet tooth, so caramel popcorn sounds right up my alley. The best place in Chicago to get this deliciousness is at Garrett Popcorn shop. They have a wide range of different kinds of popcorn to choose from caramel to cheese to butter. You can indulge in popcorn to your heart’s desire. However, you might have to queue in line for a while, because who can resist popcorn after all? If you would like to travel to amazing places and experience new things, for example tasting possibly the world’s best caramel popcorn you will ever have, then check out JoinMyTrip! You can find like-minded travelers and share costs on your next adventure. 

An insider tip for Chicago is to try their caramelised popcorn on a pink cloth table.
Caramelized popcorn

5. Lincoln Square

For anyone who is looking for a German time in Chicago, then travel to Lincoln Square. Even if you aren’t looking for a German experience, then you should still travel there for a fun time! Lincoln Square is a German part of town which you will quickly come to realize with a huge piece of the Berlin Wall in the vestibule trains. You can easily get there by taking public transportation to the Western stop. You can find all kinds of things from cute little boutiques to all sorts of restaurant cuisines. Our recommendation is to spend your time at the Chicago Brauhaus. The place is often packed during the weekends with people of all ages dancing on the dance floor. The best part? You might need to ask your travel mates to help you get home because their beers come in a 1 liter to 2 liters glass at a time. 

A city view of Chicago with high skyscrapers.

4. Pequods Pizza

The people of Chicago take their pizza very seriously, even more seriously than New York. Many of the locals would even say they have the best pizza in the country. So, don’t you dare tell a Chicago local that you have tasted better pizza elsewhere. I don’t even want to know what will happen to you. There is always a discussion about where the best pizza is in the city, but we have to say it’s Pequods Pizza. Here you can find the local specialty, which is a deep-dish pizza topped with tons and tons of meat and cheese. The more cheese the better! Who in their right mind doesn’t like pizza anyway? Plan your own trip with other travelers and experience the pizza that will blow your mind together on JoinMyTrip

When in Chicago an insider tip is to eat perquods pizza.
Pequods Pizza

3. Green Mill Jazz Club

For all our fellow Jazz lovers to have a great night out, check out Green Mill Jazz Club! It’s a great venue to grab a cocktail or two and Jazz up all night long. For those who aren’t necessarily into Jazz, you should still pop a visit at the Green Mill Jazz Club. Why? It is the longest-running jazz club in the country, including the hangout place for gangsters such as Al Capone in the 1920s. What else are you going to be doing during your time in Chicago, other than entertaining your weekends away here? Maybe even pretend you’re one of the fellow gangsters back in the 1920s. 

Men playing the saxophone with bright lights.
Green Mill Jazz Club

2. Chicago Sky-deck

Do you want to see the whole city of Chicago from above? This might not sound like an insider tip but there is no better way to spectate the city views than on the Chicago Sky-deck, which is on top of the Willis Tower. Fun fact: The Willis Tower is one of the tallest buildings in the world! Admire the high sky-scrapers and its panoramic views while being able to look straight down onto the city of Chicago with an all-glass enclosure. Once you’re done spectating the views, and you would like to learn a bit about history then you can watch a movie about the 45-year old history of the Willis Tower. Want to join unique trips? Check out JoinMyTrip

An insider tip is to check out the Chicago Sky-deck.
Chicago Sky-deck

1. Tip!

Now, this is an unusual insider tip, as it’s not a place or activity but it’s something you must know when traveling to Chicago! Compared to other states in the United States, the tipping rate is a lot higher. If you are eating out at a restaurant, you are expected to tip 20 percent of your total bill. For drinks, you should tip a dollar per drink, for cocktails you may consider tipping a tiny bit more than a dollar. Let’s not piss off any waitresses and waiters during your trip to Chicago with your travel buddies

A dollar note and some coins on a marble table.
Tip!

We hope you enjoyed this edition of insider tips for Chicago that will make your trip worth it! Find like-minded travelers to join your trip to Chicago or plan your own trip with JoinMyTrip. Share costs, experiences, and come home with unforgettable memories. Stay tuned for our next edition of the Insider Tips Series!

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