A Local's Guide To A Quick Weekend Trip To Chicago

Chicago is one of the most visited cities in the U.S. with countless blogs written about it. Instead of showing you the boring generic stuff to do and see, I'm going to focus on exciting and fun suggestions for a weekend getaway in this windy city.

Whether you have or have not been to Chicago, this guide is intended to bring you insight on local hotspots and popular activities within the city.

What To Do:

Biking

Biking is one of the best way to see a city. The flexibility of biking allows you to go anywhere and anytime you want. On top of that, you are sort of "working out" don't you think?

Picnic by the lake

There is no better way to enjoy the early fall weather in Chicago than throwing a impromptu picnic. Grab a blanket and pick up some food at the nearby supermarket, it's just that easy!

(Map location here. Also another great spot here)

Park strolling

Just like in New York City, parks are everywhere and it's free! Below is the BP Pedestrian Bridge that connects Millennium Park and Maggie Daley Park. (Map location here)

Alright, this is not a park (above) but an indoor tropical garden situated inside Navy Pier. This remarkable oasis is perfect for all occasions from celebration events to a casual date.

Art hunting 

aka instagram-ing around the city. Do you really want to miss out those Instagram hotspots in Chicago? I didn't think so! There are a few famous arts in this area. Trust me, they are so big that you will not miss it! (Map location here)

credit: Dan DeLuca

What To Eat:

Weekend Brunch is a MUST! I highly recommend Maison Marcel and their eggs benedict (one of the best in Chicago). The interesting European inspired decor will make your Instagram goal comes to life!

Smoked salmon eggs benedict, London fog (drink) and matcha latte. (Menu here)

This is Pierrot Gourmet at The Peninsula Hotel, situated on the ground floor of the hotel. I went on a busy weekend and was able to get a table without any wait.

Dark chocolate tart (left), apple yuzu tart (right) and my matcha latte.

Where To Stay:

Whether you are a first time traveler or a frequent visitor, the key to a happy stress-free trip is convenience. You want to be as close to the major subway lines and bus stops as possible, unless you plan to bike through the entire trip. Bonus: This hotel provide free bike rental too! (Bike rental is first come first serve)

This is the StayPineapple Hotel in The Loop. Just like the name suggested, everything in this hotel are either in pineapple shape or in pineapple theme. Even the exterior of the hotel looks like a pineapple!

Room with a view!

A pineapple toilet tissue roll? Yes please!

Hotel hallway.

Still interested in checking the most touristy spots off your list?

The Cloud Gate - best time to go before 8:30 a.m.

Buckingham Fountain

Or if you're into architectures, Chicago is definitely a paradise!

Rookery Building

But for me, I rather be back on my bike and do a few more loops before winter comes...

How about "Summer Street" Chicago?

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 (Please note: All photos in this post are taken by me, except the one with me in it, so please be respectful and do not use them without my consent. Thank you.)