A few weeks ago, we decided to make use of one of the last truly fall weekends and check out one of our favorite cities, Chicago, before it became a snowy winter wasteland. We’ve visited Chicago before, of course, so this time was less about tourist destinations, and more about re-acquainting ourselves with the best the city has to offer.
For this trip, I took advantage of the two free weekend nights I had earned through our Hilton Aspire American Express credit card (one earned through applying, one earned through spend) and redeemed them for a stay at the London House Chicago Hotel, right in the middle of Michigan Avenue.
We received a deluxe cityview room, which was small but adequate, and had one of the more comfortable hotel mattresses I’ve come across in a while.
Of course, the London House isn’t known as much for its rooms as it is for its very popular rooftop bar and restaurant. Being that we had gotten in late on a Friday, we headed straight up to check it out.
What we found were great cocktails, mediocre food, and a lovely view of the city. (Skyline view up top on this post!)
The next day, we were up bright and early to explore the City and started with a visit to the Garfield Park Conservatory. The conservatory featured both indoor and outdoor gardens in all types of settings.
After getting a dose of the great outdoors, we headed to the nearby Fulton Galley for some lunch. Fulton Galley is a food hall and restaurant accelerator that subsidizes the food stall’s rent as they get up and running and start to build an audience, which we thought was a really cool model.
There were five stalls in the hall, and we sampled yummy dishes from three of them: a yummy torta from Taco Mucho, a pastrami reuben from Steingold’s, and fresh made pasta from Italianette.
Stuffed with yummy food, we headed back to downtown where we were not going to miss our shot….to see Hamilton. And it was absolutely amazing.
Seeing Hamilton was easily, hands down, the best part of our trip to Chicago. But I was excited about our next stop too: a trip to one of my favorite tiki bars, Three Dots and a Dash.
There, we met up with one of the hubby’s friends and proceeded to order rum drinks galore.
Finally, we finished out the evening at nearby mediterranean restaurant Ema. Here our best dish was a hummus topped with roasted lamb ragu and served with naan bread — I could have eaten nothing but that and been satisfied!
The following day, we popped up early to explore another Chicago delicacy: the donut. We joined the Underground Donut Tour and stopped at several of the cities’ best known donut bakeries including Do-Rite Donuts, Stan’s Donuts, Firecakes Donuts and the Doughnut Vault. Looking back, we wouldn’t really recommend doing the tour; just go to the Doughnut Vault for their super light and fluffy yeast doughnuts and skip the others, which were entirely average.
Coming down from our donut sugar rush, we headed next to the Art Institute of Chicago to add a bit of culture to our trip, and experienced opening day of their new Andy Warhol exhibit.
Feeling much more cultured, we then headed to brunch at Bandit, which turned out to be a fantastic choice. Not only did Bandit offer bottomless mimosas, they had a fun atmosphere and the best bathrooms I have ever seen in any establishment ever.
After brunch, we walked over to the nearby barcade, Emporium Wicker Park, to finish off our last few hours in Chicago. There I enjoyed several games on my favorite pinball machine of all time, Addams Family Values, before we ultimately packed it in and headed for the airport.
All in all, it was a fantastic weekend away, and we enjoyed our time visiting the Sister city once again. Tell me about your favorite Chicago destinations in the comments below!
