Since we didn’t finish using our CityPass last time, we decided to head back to Chicago for 2 days – mostly for shopping but we’ll also be squeezing in the Field Museum and John Hancock Observatory. I like mapping out my trips to make sure the day flows well & thought this map might help you plan your trip to Chicago too. Click here for the actual map.
Here’s the plan so far:
Day 1:
- Arrive at the airport and check in at the Hilton
- Gibsons Bar & Steakhouse by the airport
- Fashion Outlets of Chicago
Driving into Chicago:
- Field Museum-Natural History
- The 900 Shops Mall
- John Hancock Observatory
- Mike Ditka’s Restaurant
Day 2:
- Dedicated to Premium Outlets out in Aurora!

What did you think of Chicago? I’ve actually never been, but I’m planning yo go visit a friend that lives there soon. What’s your favorite thing to see with limited time?
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Hey there! Chicago is a beautiful city, though not all attractions are in close proximity from one another. I usually don’t take public transit when I travel but it wasn’t too bad in Chicago.
I’m from Toronto so I found that the museum campus as well as Navy Pier was very different than what we have so they’re my favourite attractions and where I’d visit if time is limited (not sure if I’d recommend Navy Pier in the winter – I can imagine it gets really cold).
If you’d like to do some shopping, the Magnificent Mile has a lot of options too! You can also visit my favourite Chicago steakhouse, Ditka, when you’re there.
Safe travels!
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Oh it sounds like fun I have not been to Chicago since I was young with my parents! I alway think of New York and Miami for Shopping when I come home to the USA ~ Next time I might have to check out the windy city next time! Thanks for Posting I am enjoying your blog!
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Wonderful article! Very informative about Chicago 🙂 Keep up the good writing.
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