This was my first time visiting the Windy City! What a fantastic city it is! My husband had a work conference so we decided to go early and check out the city.
We flew into Midway, and Ubered into town – a super easy experience. Our Uber driver recommended the CityPass – and so we checked it out when we got to our hotel and decided it would be a great way to save some money during our trip. It covers 5 attractions in 9 or 10 days and if you are visiting two you will get your money’s worth out of it. We visited 3 of the 5 — the Willis Tower (formerly known as the Sears Tower), The Art Institute and the Aquarium.
Packing for the Trip
This was a couple’s trip to Chicago, so I wanted to dress nicely. I also knew that we would do alot of walking (and it turned out we did alot of biking). We had reservations at 4 fancy restaurants, and plans to see Hamilton, AND although most of our trip the forecast was sunny and 75 degrees, there were a couple of rainy days in the forecast as well.
For bumming around and sightseeing: I packed two pairs of jeans, jean shorts, a workout garb (for sleeping and if I got motivated to hit the gym), a black cami, mustard yellow short sleeve, black birks, prana travel hat, and of course an umbrella and rain coat.
For nightlife and the theatre: I packed a midi striped skirt (went w black cami too), two long dresses, a black romper and these super comfortable wedge sandals by Clarks.
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