Our flight to Spain left Chicago O’Hare on Monday, so we decided to position ourselves in the city on Sunday just in case of travel delays. Unfortunately, Southwest only had an early Sunday morning flight or a later evening flight to Chicago, so we grudgingly accepted the 7:15a option… which was delayed by two hours. So we arrived in the later morning and discovered that while the Shamrock Shuffle was taking place, it was complete as we arrived downtown on a windy, fairly cool (40F) morning.
After dropping our bags off at the hotel we set out in search of brunch. Wildberry’s was absolutely mobbed, but Eggy’s Diner was only a 15 minute wait (though a little tricky to find two levels down from the road along a park). Leandra ordered the March special corned beef and cabbage skillet with a latte, while I went for the classic eggs, sausage, and potatoes platter with a pancake and OJ. Service was quick and our choices were tasty.
Full, we decided to walk around town. First, we walked through Millennium Park where several flowers were in bloom, then by the Bean which was closed for renovations – boo!
From there we went down to the Riverwalk for some lovely architectural views.
By early afternoon we were able to check-in to our hotel, where we rested for a while before heading downstairs to the cozy lobby bar. The couches by the fireplace was taken, but we found seating near the windows and ordered cocktails (an Old Fashioned and a Manhattan), served with popcorn.
Next up was jazz at Andy’s Jazz Club, where we had reservations for the 6pm show. We had lovely seats at the middle high top table with good views of the band. I ordered an espresso martini, then a Laphroaig 10, while Leandra ordered an(other) Old Fashioned. The band was talented and we quite enjoyed the show.
Afterwards we headed down the street to our dinner reservations at Il Porecellino. They were quite busy, but we were seated within a few minutes. Leandra paired the gnocchi Bolognese with a Sangiovese, while I paired the pappardelle porcellino (pork shoulder and beef, definitely meatier than L’s) with a Sauvignon. Pricey but tasty!
On our walk back to the hotel we enjoyed more views of the city at night along the river.
Monday morning was leisurely, with a late breakfast at the hotel. Wanting to stretch our legs before our flight we headed out to try a few free indoor options. The famous Rookery building was our first stop with its Wright-designed lobby that feels like a web of iron and glass, quite impressive.
The Chicago Fed Money Museum was our second stop, with a small museum about money supply and printing. Smaller than expected, but free! Note that you had to show ID and go through metal detectors to get in.
Finally, some notes on our hotel, Pendry Chicago.
- Beautiful lobby space and common areas, especially the Art Deco elevator doors
- Our room was on 16th floor – comfortable, but allowed in more road noise than expected
- Sleep was OK, streets were fairly quiet after 11pm
- Gym at hotel was temporary housed in a meeting room – surprisingly nice with a variety of equipment, quiet.
- Breakfast at the attached restaurant was fine – definitely overpriced and only worth it if it’s included with booking. That said, my eggs were better than Eggy’s Diner and the potatoes were crispier. Leandra liked her latte better as well.
- As part of our booking we had a $100 food/drink credit. We used half of it for the cocktails on Sunday but we were disappointed that the hotel bar was closed until 4pm on Monday. We went to the restaurant instead around 1pm, and their bar was also closed, but instead of just seating us (like they did for breakfast), they told us to get in a long line at the cafe to order. Feeling it wasn’t worth the hassle, we gave up on using our extra funds and caught an earlier Uber to the airport instead.
