Chicago could be the city that never sleeps, just as much as it is the windy city. No last call for alcohol, and you can always find a place that’s open and happening, even if you are visiting the city on a Sunday and Monday like we were. Having been to Chicago before, we skipped the major tourist attractions and headed straight for the food and music scene. If it’s your first time in Chicago, I recommend taking in a 90 minute Chicago Architecture Foundation boat tour (well worth $50), heading to Randolph Street for a nice dinner, shopping on the Magnificent Mile, and exploring the many attractions in the enormous Grant Park. For a great review and photos highlighting many of Chicago’s key attractions, check out this recent post on Travelux blog.
Arriving around 10pm after a long day of driving from Nashville, through Kentucky and Indiana, and passing back and forth between time zones multiple times, we still managed to get ourselves out to explore some of Chicago’s Sunday nightlife. The River North area, particularly around Hubbard Street, offers lots of options for restless tourists and is just a stone’s throw from many hotels. After bar hopping a bit, we finally settled in at Howl at the Moon, a dueling piano bar that also features a live band. Once it shuts down, everyone seems to move to O’Callaghan’s across the street, which is open until 4am. As I said, no need for sleep!
On Monday we turned our sights to eating, starting with lunch at The Hopleaf Bar. It’s uptown location makes it less accessible for tourists without access to a car, but as a result there’s a distinctly local watering hole vibe. The food here is very unique and experimentation is the name of the game – our Charcuterie Trio ($14) included head cheese, fat back and duck liver mousse. The organic grass-fed brisket on light rye ($13) was also delicious, but I’ve been a bit spoiled by Schwartz’s in Montreal, which still can’t be beaten. As the name implies, Hopleaf has an excellent selection of beers.
Dinner was a no-brainer – in Chicago, deep dish pizza is an absolute must try! Yes it’s rich and heavy and filling, but that sauce…that cheese…that crust. Yes please, and can I have some more! Actually we took half of it home to eat for breakfast the next day. Lou Malnati’s was our pizza of choice, although it seems to be having a spirited competition with Giordano’s for “best in Chicago”. I’ll let you decide which you like best.
If you ever happen to be in Chicago on a Monday night, I highly recommend checking out Robbie Fulks at the Hideout where he brings his own special brand of folk storytelling to an intimate crowd most weeks. He’s an incredible singer-songwriter and usually brings up a special guest, who is inevitably very talented. Keep in mind that the Hideout is a hole in the wall surrounded by industrial buildings, so best to grab a taxi or Uber back rather than trying to find another bar in the area. Don’t let that dissuade you though! For drinks we headed to Hopsmith in the East Division Street area, which had a great Monday night special – $5 Fat Pours (large pints) and $5 Burgers! It too is open until 4 AM, just in case you have no interest in sleeping on a Monday night.
Do you have a favourite Chicago neighbourhood or hole in the wall?