Chicago Trip Report:
Living in NY - I need creative reasons to burn my Southwest miles while I still have a companion pass. I have more points to burn than I have days to take off work, so I’m really looking for weekend quick trips. When this deal came out:
http://www.dansdeals.com/archives/71220, I decided it’s time for a one day trip to Chicago to finally see what all the fuss is about.
I booked myself a roundtrip between LGA and MDW for 9,429 Rapid Rewards points. Not the cheapest available, but flights that worked for my schedule. My wife was booked using companion pass, total cost: $11.20.
The plan was to leave Saturday after Shabbos, hopefully grab a bite somewhere and then head to the hotel. Spend the day Sunday, and go back home early Monday morning.
The outbound flight boarded early and left the gate early, with a plan of early departure. However – ATC had a radio outage affecting LGA, JFK, EWR and TEB with no flights leaving for two hours. At that point we had to go to back to the gate to allow people to choose to get off the plane due to the two hour rule.
During that time, a customer service manager came on the plane to explain options, and apparently many people were asking about compensation, so he announced to the plane that he made a case for all of us and that he was going to fight to get compensation. We pulled out from the gate and took off about three hours behind schedule.
By the time we landed it was too late to go anywhere to eat that night, so we went straight to the Sheraton Chicago Hotel and Towers. The hotel is on the Chicago River and has views of Lake Michigan. I had a free night award specific to Sheraton that had to be used within a month or so, and I used 12,000 points for the second night. As a Platinum I was hoping for a suite, but the hotel was “fully committed” and it was too late for me to care enough to try and push harder for it. I was blocked in a deluxe room with views overlooking the river and lake. The views were great, and the room serviceable. My peeves with it were that the minibar had a sign on it that they charge $25 to empty it and $25 for a mini fridge. We kosher travelers really need that room fridge. Since I planned to eat out all meals though didn’t push back on this either.
Sunday:
We started the day by walking across the river to Millennium Park. We walked around that area, saw the bean, and the surrounding area which is quite nice. We had perfect weather, 65 degrees and sunny, so the day was just conducive to ambling around the neighborhood in this manner. There were people ice skating in the park, which looked fun.
After a couple of hours we went back to the hotel, picked up the car from the valet ($63! w/ in and out) and headed out to Milt’s Barbecue for the Perplexed. It’s located in a cute neighborhood with fun shopping so we walked around there for a bit. We actually walked past Milt’s without noticing, so we turned around and went back.
At Milt’s we asked to speak to the mashgiach and asked if anything was Yoshon. I was expecting to have to stick to the GF menu, which is admittedly substantial. However, it turns out the regular buns were Yoshon, just not the pretzel buns. We went with the Milt’s Burger and the Brisket Sandwich, along with the Brisket Chili Nachos and fries on the side of one, and cole slaw on the other. They bring out a trio of Barbecue Sauces, a Kansas City molasses based sauce, a Mustard based sauce and a tomato and vinegar sauce. Adding the sauces to various bites of the sandwiches gave a different spin to each bite, all in all the experience was very good, and the food was also very good. I think fries say a lot about a place, and their fries are very good – skin on, thick cut, crispy, with real potato flavor. If I had eaten here two years ago, I’d probably be blown away. However, in NYC we’ve recently had a couple of great BBQ places open, notably Izzy’s Smokehouse – so the brisket wasn’t so impressive. I’d probably grade it an A-, which is a very high rating from me. We left the place stuffed so we knew we’d need a late reservation at Shallots for dinner.
After that went back to the hotel to rest a bit. Then we walked to the Chicago Navy Pier, and took in an Imax there. There are some interesting touristy shops there, including a candy store (expensive) that carries some hard to find items, including real bugs, and lollipops with scorpions inside. The guy said the bugs taste like sunflower seeds. We picked up some candy for the kids (not the bugs!) and started the walk back. We had noticed some upscale looking bowling places, so we decided to stop in at Pinstripes on the way back. They have bowling, bocce and food there. It’s a modern, clean place that has leather couches and arm chairs at every lane, and touchscreen interfaces for the bowling lanes. They give out sweat socks for those who aren’t wearing socks, and even have blankets there with a sign: take a blanket, get cozy. We bowled there, I scored 180, not bad. I ordered a craft beer on tap for $8. All in all – a great place.
After that we went back to the hotel to get the car and headed up to Shallot’s, a 20 minute drive from our hotel. Shallot’s steakhouse is in a commercial strip mall, but once inside the décor and ambiance are really nice. The server was really professional and knowledgeable. We ended up ordering some sushi – the Spicy Escolar was great. We also had the Hush Puppies – not what I was expecting – and not as good as we thought. Then we had the Patron Steak, marinated in Tequila. We ordered sides – fries and onion rings - thinking that they were part of the dish, turns out they were additional. For a $72 steak – this was a small piece of meat. They serve it really charred on the outside but tender in the inside. I’m good with that, but my wife doesn’t like that style. We also ordered a cocktail, the “Kickin Rita” which was kinda like adult lemonade. We were too full to order dessert. Even sharing a main, the bill is high, we clocked in at $143 before tip after we had the sides removed. I would definitely go back to Shallot’s, although I certainly wouldn’t fly out special again – unless it was a super DDF DO.
If I wasn’t flying Southwest, I would have probably taken a late flight out of ORD with Avios rather than staying that second night – there are costs to getting a good deal sometimes! Overall, we had a really nice day in Chicago.
