About This Trip
These are combined notes from two trips to Chicago, both in the May/June timeframe in different years. One trip was with my husband while I was pregnant, the other a girl's trip. I did a few repeat activities and found the city experience pretty consistent. Lucked out with the weather both times. I think Chicago is the prettiest downtown in America and one of my favorite places to be in the summer.
Architecture Boat Tour, Cloud Gate (Bean), Millenium Park
One of my favorite things to do in Chicago is the architecture boat tour. This is a fun "first" activity because it helps you get the lay of the land; the tour guides are really knowledgable too. Millenium Park, "the Bean," and Navy Pier are all fun first time (and repeat!) stops too. Eric and I enjoyed the Agora art installation as well; it is comprised of 106 nine-foot tall headless torsos made of cast iron, the artwork derives it name from the Greek word for meeting place.
Shows
On the girl's trip, we saw Hamilton at the CIBC Theater and it was one of my all time favorite theater experiences. We paid for a VIP ticket that included an area that you could visit before the show and at intermission where you could get drinks, eat snacks, take photos, and have access to a bathroom with no line - worth it! The musical itself was a lot of fun too. Another highlight was visiting Second City, a well-known comedy club in Chicago where some of the greats like Eugene Levy and Catherine O'hara got their start. We booked the two shows in advance and planned other activities around them.
Beaches
Being on a beach with a whole city behind me was new to me had a really had a fun vibe about it. I wished we had allowed more time here.
Food
On our first trip to Chicago, our visit coincided with Taste of Chicago, so we got to try a lot of fun culinary surprises. My favorite deep dish pizza is Lou Malnati's. We also really enjoyed Soho House, and Somerset.
Rooftops and Views
The Willis Tower Observation deck is a cool experience; pay to skip the line if you can - well worth whatever that costs. There a lot of cool rooftop restaurants and bars to choose from too to take in pretty city views.
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