25 Hilarious Chicago Puns & Inspiration for Chicago Instagram Captions

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Last Updated on: 19th June 2023, 06:41 pm

Looking for hilarious Chicago puns to share with friends before a trip to Chicago? Or perhaps you want a few clever puns to use as Chicago Instagram captions on your trip? Here are my favorite Chicago jokes and puns to help make your amazing trip even more enjoyable!

Read Next: 30 Beautiful Chicago Quotes & Chicago Instagram Caption Inspiration

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Chicago Puns and Chicago Jokes for Chicago Instagram Captions

How to Use these Chicago Puns & Jokes

Feel free to use this post to find puns and jokes about Chicago for your photo captions, Chicago Instagram captions, Chicago Whatsapp status, Viber status, or however you want!. If you do use one, I’d love if you linked or tagged me so I can enjoy your work! 

If you use one on a website, please link to this post. Otherwise, you can follow and tag me on social media so I can see you using them in action:

Instagram: @historyfangirl

Facebook: Stephanie Craig – History Fangirl

Twitter: @ahistoryfangirl

Chicago Puns & Jokes about Chicago

My favorite Chicago jokes and puns! Travel puns are great for IG captions or for having an arsenal of endless dad jokes if you are visiting Chicago with kids.

Chicago Travel Puns

Chicago: Bean there, done that.

A trip to Chicago is an L-evated experience. 

Blown away by the Windy City!

The best views in Chicago are at Navy Peer.

Finally made it to Chicago. It’s a boat time!


In Chicago, I’m in the Loop.

Having a Fields day.

Dogs love Chicago because they get to visit Wiggly Field.


I love Chicago, but I’m ready to get the L out of here.

Chicago floats my boat.

What you talkin ’bout Willis Tower?

Chicago Food Puns

Chicago food is a weiner!

Chicago stole a pizza my heart.

You’d have to be a weir-mixture not to like Chicago Deep Dish.

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A trip to Chicago takes quite a bit of dough.


Slice, Slice baby!

Taking cheesy selfies in Chicago.

Make sure to relish the good times in Chicago.


I never sausage a beautiful hot dog!

Let me be Frank, this is a tasty dog.

Lake Michigan Puns

Chicago, I lake you a lot!

Lake hair, don’t care.

Let minnow if you want to spend the day at Lake Michigan!


A day at Lake Michigan buoys my spirits!

Lake Michigan is pretty Great.

Want more Hilarious Travel Puns?

I’m a little obsessed with travel puns. If you are too, check out:

For more great travel quotes, check out my entire library of Travel Quotes, Puns, & Memes.

5 Things to Pack for Your Trip to Chicago

Canada - Toronto -Luggage

The Lonely Planet Chicago guidebook. It can be kind of a pain to find the major guidebooks once you land, or you’ll find them overpriced. I always like to pick mine up ahead of time.

An Unlocked Cell Phone so that you can use a local sim card while here to help navigate public transportation and when you’re on the road. (For people without American cell phone plans).

Backup Charging Bank for your cell phone since you’ll be using it as a camera, GPS system, and general travel genie.

A Camera since Chicago is super photogenic. I use a mix of my Nikon D810 and my  Samsung8 smartphone these days.

A Great Day Bag so you can carry what you need with you (like your camera, snacks, water, sunscreen, cash, etc). My current favorite is the Pacsafe Citysafe, which is especially great for Chicago because it has many anti-theft features designed to deter pickpockets. It also transitions to a night bag more easily and won’t embarrass you if you go to dinner directly after sightseeing all day. 

See also
The Best Quotes about Maryland

More Illinois Travel Resources


Headed to Illinois? Check out these amazing travel quotes about Chicago for your trip. Plus, don’t forget to set aside time to visit The Lost City of Cahokia at Cahokia Mounds State Historic!

Pin these Chicago Puns & Jokes About Chicago for Your Trip!

Chicago Puns and Chicago Jokes for Chicago Instagram Captions
Chicago Puns and Chicago Jokes for Chicago Instagram Captions

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