Chicago | A Fall Day in the Windy City

Fall in Chicago can be either a mild and sunny experience or it is raining cats and dogs. The city´s location at the endless shores of Lake Michigan makes it pretty much susceptible to the ever-changing climate of a typical seaside town, yet whatever weather you will find outside when traveling to the Windy City, Chicago is great in every condition.

The Giants having their heads up in the clouds. Chicago during fall.

A great way to start the day with is a decent breakfast at my favourite places spread all over downtown. Like the Tempo Café close to John Hancock Tower. This very busy spot serves All American breakfast favourites in huge portions in a lively atmosphere.


Authentic Italian cappuccino is served at Caffe Baci. I particularly like the location at 10 S Riverside Plaza close to the river. The interiors are a little cold, but you can enjoy great views outside the panoramic windows onto the hustle and bustle of rush hour in the morning. The Portobello Mushroom Sandwich is great if you are looking just for a little bit to munch on.

Breakfast hotspot: Goddess and the Baker

A breakfast hotspot close to Millennium Park is Goddess and the Baker on S Wabash Avenue. They have awesome Croissants and Danish as well as very good coffee, it is difficult to catch a seat though. This stylish breakfast café is busy during the entire day but well worth a visit!


When it is raining in Chicago and the clouds hang low, visiting the viewing platforms of Hancock Center or Willis Tower will not make a lot of sense since there won´t be that much to see (except the grey). Walking the streets and seeing the skyscraper´s tops disappear inside the clouds is a much more mystical experience.

Cindy´s, a fab place to enjoy great views and good food

Cindy´s Rooftop Bar & Restaurant located on top of the beautiful Athletic Association Hotel is a fantastic location if you would like to combine skyline views with fantastic cocktails and good eats, even when it´s wet and grey outside. You can read everything about it in my previous blog post!


Even if you are not much into  aviation, a visit to the Boeing Company´s souvenir shop is a MUST when in Chicago! The aircraft builder runs one of its headquarters in the Windy City and the little shop is stuffed with everything around commercial and military aviation from aircraft models to clothing, hats, pins, mugs, etc. Loved it!

Pedestrian rush hour at the River

Chicago is called the birthplace of modern architecture. After the Great Fire in 1871 where most parts of the city were razed, it has been one of the first cities to make use of steel frame construction allowing to introduce the first skyscrapers. These days, the city is bribing with classic as well as futuristic buildings and you will find endless locations for amazing snapshots around downtown.

Chicago Town Hall

One of the older buildings that I find absolutely worth visiting is the old Town Hall. It is not only about the beautifully appointed hallways and elevators, the roof also holds a naturally arranged rooftop garden that is a must see and that offers amazing views onto the skyline.


Speaking of impressive interiors, the main entrance and lobby to the Hilton Chicago on S Michigan Avenue will take you on a journey back in time. Sparkly chandeliers, hand painted ceilings, exquisitely decorated ballrooms. Even if you´re not staying at this Chicago classic, these jaw-dropping premises should not be missed!

Chicago Hilton lobby

And to conclude the day, why not enjoying a little art and culture inside one of Chicago´s world-class museums or art galleries? Not to miss a selfie in front of the world-famous Chicago Bean!


See you soon, Windy City!



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