Chicago Travel Blog – Best Shopping and Things To Do

So my latest travel adventure brought me stateside to Chicago. My parents and older siblings actually used to live in Chicago and most of my family are there so I’ve been going there since I was a child. I’ve spent a summer there while in college which I loved and have returned a couple of times since. Since my trips to Chicago were always during school breaks, I had only ever visited Chicago in Spring or Summer so I was very excited to be visiting in the Autumn for this trip. October is one of my favourite months and I knew the Chicago suburbs we’d be staying in would be beautiful with the fallen auburn leaves.  

There are many reason to visit Chicago in October and the mild weather, pumpkin patches, auburn trees and fallen leaves are just a few. Flights are also quite reasonable at the moment, we got ours for around €500 return each and that was without booking too far in advance. 

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Where to stay..

I absolutely love staying in the suburbs when I visit Chicago. One of the highlights from our week were our early morning walks (to Dunkin Donut’s on occasion I might add) and it’s things like that you can’t enjoy quite as much when you’re staying downtown in a city. Shopping in malls outside of the city is less expensive than downtown and of course outlet malls are even cheaper again, and Chicago has a lot to offer. Check out my shopping section below for where to go. If you are on a budget it could be worth looking into staying just a little outside the downtown area and if you don’t rent a car just make sure you book somewhere near the Blue Line train and you very easily get to the airport and downtown. 

Thing to do in Chicago..

 Have a drink in The Signature Lounge on the 96th Floor – a bar and restaurant on the 96th floor of the John Hancock building on Michigan Avenue. We finished off a day downtown with an amazing lunch in the Cheesecake Factory located in the basement of the John Hancock building and then took the lift unto the lounge for a cocktail with a view. 

Walk the Chicago Riverwalk.

Stroll through Millennium Park and visit the fountains and the iconic Cloud Gate – better known as The Bean.

Go to the beach – be prepared for blustering winds if you visit in the colder month but it’s worth a visit and the views of Navy Pier and the Chicago skyline are worth it.

Ride the Ferris Wheel at Navy Pier and grab an Ice-Cream from the Häagen-Dazs cafe to enjoy while you walk the pier.

Catch a Baseball game at Wrigley Field – or if you can’t get tickets have a beer in one of the many bars in Wrigleyville. My sister and I went to a Chicago Cubs game once and had so much fun! 


And lastly, I cannot create a list of things to do in Chicago and not include a trip to Six Flags Great America. Some of my favourite childhood and teenage memories are from here and even if you don’t love rollercoasters (I do!) there is so much to do in Six Flags and it’s well worth a visit. 


And – don’t leave without a coffee and a glazed donut from Dunkin Donuts!


Outlet Shopping

Chicago Premium Outlets in Aurora is a great spot but quite far outside the city if you were staying downtown.

Fashion Outlets Chicago also has an impressive directory and is much closer and quite easily accessible.  


If it’s high-end fashion you’re after then Michigan Avenue is the place to go. With Chanel, Louis Vuitton, Bloomingdales, Neiman Marcus, Macy’s, and many, many more, you’re pretty much guaranteed to find any designer. But – downtown shopping is more expensive than and taxes are high within the city (many malls are outside the city line meaning taxes aren’t quite as high). 


Westfield Mall in Old Orchard is a lovely outdoor mall and home to a huge Nordstrom which is a great luxury department store. 

Woodfield Mall is one of my favourites and although it is a little far out from the city, it’s well worth a visit – just make sure you set aside a day to take full advantage of the mall and it’s extensive store directory. 

TIP: If you’re visiting Macy’s or outlet shopping centres bring your passport to customer service as they’ll likely have a visitors discount you can avail of.


What I Wore..


Shop My Looks..


Until next time,





    • March 11, 2017 / 5:56 am

      Hallu Helen. : )ich würde schrecklich gerne was bestellen nur würde ich vorher gerne wissen, wie viel die Versandkosten betragen. Außerdem muss man sein Bundesland angeben und da ist nichts, wo man es angeben könnte. Wäre echt super, wenn du das mal weiterleiten bzw. Fragen kÃc#ntest.nI¶h mag deine Vids echt sau gerne : )LG

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  3. September 13, 2018 / 8:22 am

    Never even been to Chicago but after reading this article, I’m a big fan of it. I don’t know if Aurumn is a good time to visit, but that’s my only free time this year. So I hope it’ll be nice.

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