Well, sneak peak to the rest of this post: Chi-town did not disappoint! Both Josh and I ultimately agreed that Chicago was our all-time favorite city we have ever visited. We can not wait to go back and maybe even bring the boys along to experience all there is to offer.
In the months leading up to our trip, we both did a lot of research, but as I do whenever I visit somewhere new, I had a hard time figuring out the lay of the land. When trying to decide what we should/could do each day, it was hard to figure out what was near what and therefore feasible/logical to do together. But through a combination of that research and some dumb luck (probably more the latter than the former), we maximized our time in Chicago and saw everything we wanted to see (and then some). I kept commenting that it ended up being the perfect Chicago itinerary, so I figured I should share it in case someone else is feeling equally as stooped as I was before going.
As for accommodations, we stayed at the Hotel Palomar in River North. We are a big fan of the Kimpton hotels as they usually cater to our style/needs. Plus, I have noticed they are typically located pretty centrally, and this one certainly followed suit.
We found the hotel to be very convenient. We could walk pretty much everywhere. In fact, we only took the subway once, and Ubered it a few more times!
That one subway trip, though, was basically minutes after our arrival day 1. We had tickets to a Cubs game at Wrigley Field for 1:20 the day we got to town. So we basically arrived, dropped our bags, and headed over to Wrigleyville. Considering neither of us are Cubs fans per se, we were really aiming to take in the atmosphere that is Wrigley. We walked around for awhile (just long enough for Josh to purchase a hat anyway!) and then stopped in to have a drink at Casey Moran's, one of Wrigleyville's famed bars.
And then, of course, we headed into the game.
It was a great day to spend the afternoon, but by the time we got back, we were ready for some grub. And what could be more satisfying than a big ole Chicago deep dish. From our hotel, we walked over to Giardinos. Don't let our couple leftover slices fool you...it was awesome!
On the way back to the hotel, we stopped in at the Rock Bottom Brewery mainly because of their rooftop bar...our first of many rooftops over our four days! This was super chill and easy, which was nice after a long day. And with that our first day in Chicago came to a happy close!
Day 2 was sightseeing day for us! We started out pretty early as I had read it was best to get to the Willis Tower (or Sears tower or Skydeck...all three names were used!) right when they opened at 9. We Ubered over to it and didn't get there until a little after 9 but still had virtually no wait. The line was considerably longer when we left, though, so I guess it was good advice.
I should also mention that Josh had purchased the CityPass for each of us, getting us admission into 5 of our choice of Chicago attractions. The pass was well worth it! Anything that we would have wanted to see or do (Field Museum, River architecture tour, Navy Pier ferris wheel, etc( was included and we got quicker admission to each of the things too with our pass.
So anyway, we used our pass to soar up the 1451 feet to the Skydeck of the Willis Tower and caught some pretty amazing views...
stood where Ferris Bueller had stood...
and then braved the glass platforms to get some amazing pics standing/sitting on top of the city! I must admit those first steps were really disorienting, but luckily you don't get to stand there very long because there's a whole line of people waiting for their few seconds on the platform!
After we got back down on the ground, we took another Uber trip over to the opposite end of the city to check out the Field Museum. This really wasn't my thing, but Josh wanted to go, so along I went. It was cool if you're into animals and all (which I'm not really!), but we did see Sue, the famous T-Rex.
After taking in the highlights of the museum, we decided we were hungry and started off along the lakefront to Grant Park. I had wanted to see the park (and mainly the Buckingham Fountain) anyways, but the Chicago Food Fest was also happening there while we were in town. We had been told it could not be missed, so we figured it was the perfect lunch stop. Without being locals, it was hard to figure out what were our best options though. We pretty much struck out with some just ok food, although I did have some pretty amazing gouda ice cream from Pastoral!
From Grant Park, we walked the couple more blocks to Millennium Park, home of arguably the most iconic Chicago figure...the Bean! Of course, we did the typical tourist thing and took a ton of pics and selfies in front of/under the giant mirror!
At this point, we needed a proper break, so we took the opportunity to check out another rooftop bar...Cyndi's which is on top of the Chicago Athletic Association (which is actually a hotel). It was really cool up there with the Fixer Upper/farmhouse look that I'm currently loving, and the view of Millennium Park was pretty awesome. Plus, I had a mojito...in the middle of the day...with no children to go home to! So it was a major win!
From there, we decided to head back and rest up for dinner. We had negotiated between trying a few different places, but on our walk back, we decided on the Purple Pig, and oh my goodness am I glad we did! It was a completely unique, but so, so yummy dining experience, They don't take reservations, so we got there around 5 PM. There was about a 30 minute wait, but we managed to find two seats at the bar immediately and just decided to do that (which ended up being pretty cool as we watched the owner/staff hustle out dinner after dinner!). I didn't take any pictures of our meal because we were seated too close to the staff for it not to be embarrassing, but honestly, it was one of my favorite meals ever...the manchego cheese balls, chicken thighs in tzatziki sauce, and the cauliflower were all perfection! I can't wait to go back.
After dinner, Josh had made us reservations at the Aviary, an exclusive, high-end cocktail lounge. I can't decide what I think of this place! Honestly it was like entering an alternative universe. You show up at a door on a quiet side street where the guy has to radio in to get approval to let you in. And then when you walk in they usher you to a dark table among 10 or so other groups drinking super expensive, super fancy cocktails. Josh ordered a whiskey in an ice rock that he had to use a sling shot to break open, and I had some concoction with frozen peach slices strung over it that I had to release in. We also shared an infused drink that seemed to be really popular. It was definitely an experience...and certainly something we can not do here in VB...but then again, I think I just prefer a simple vodka tonic!
The drinks put an end to night 2, but day 3 began with quite the recovery: some doughnuts from Glazed and Infused. We tried the vanilla bean glazed, red velvet, and strawberry frosted and they were all so good!
Afterwards, we headed to the river for an architecture river cruise. Again this was something I repeatedly read was a must do, and again, people were so right. It was an awesome way to see Chicago's riverfront, learn a little something about the city, and just spend some time riding and relaxing in the midst of a few days of lots of walking.
When we got off the boat, we walked along the Magnificent Mile for some browsing and then noticing we had plenty of time decided to take a trip to Wicker Park. Our boat guide had recommended Big Star for tacos and guac which was as good as it sounded...and maybe even better. We got a fish taco, an al pastor (roasted pork and grilled pineapple), and a walking taco (basically beans and cheese inside a fritos bag). I didn't try the fish one (and honestly Josh didn't love it), but the other two were amazing!
We had planned to explore Wicker Park a little, but we were really hot and over it at that point, so we headed back to our part of town! I had wanted to check out the City Winery (a wine bar on the Chicago riverfront that was the perfect, relaxing place for people/boat watching) and Josh had wanted to check out the rooftop of Trump Tower (which, despite my personal feelings about the man, probably offered some of our prettiest views).
That night was actually Josh's birthday, and my meat-and-potatoes husband had long ago selected the iconic Chicago steakhouse, Gibson's, for his birthday meal. The food was good, the portions huge, the service left something to be desired (our first and only issue in Chicago with service at probably our most expensive meal...), but the birthday boy was happy and called it the best steak of his life.
After dinner, we walked off all that meat and headed to the Signature Lounge at the Hancock Tower. By this time, we had obviously seen the city of Chicago from several different rooftop vantage points, but seeing it at night was pretty spectacular too. Plus, the lounge just makes a really cool setting for a drink or two.
By our last day in Chicago, we had pretty much checked off everything from our wish list, so we decided to take time to get an actual breakfast. We walked over to Yolk. We both had basic scrambled eggs with bacon, but Josh had a side of french toast and I couldn't resist trying the red velvet french toast...OMG! I'm no food photographer, but I hope I did them justice...
We were a short walk to the Navy Pier at this point, so we decided to walk down there and ride the ferris wheel. Honestly this was kind of womp womp. Sure it gave incredible views of the city, but at this point, we had pretty much seen them all! And the ride itself was a lot more anti-climatic than I was expecting, but we had time to kill anyway so it worked!
From there, we walked about 2 minutes along the lakefront and found the Ohio Street Beach. Truthfully, we didn't "find" it...I was very much headed there! Ever since I had read about the beaches in Chicago, I knew I, at least, wanted to see one. As kind of a running joke in our relationship, Josh protested (he ***hates*** the beach; I love it...been dealing with it for almost 15 years). But once we wandered on to the sand, even he had to admit that he was so glad we had found it. Not only was it amazing to see a beach with a sprawling skyline as its backdrop (at least to a beach lover like me), but there was also a really cool, beachy bar in the sand that we stopped at too. I think we both could have stayed there all day...
If you are visiting Chicago in the summer, I can not recommend the beach enough. Or for that matter, I would also make sure to walk or rent a bike and ride along the lakefront. We walked that path back, and it was just a perfect ending to our Chicago vacation.
Til next time Chicago...