We’ve been to Chicago together before, and I’ve been a couple times with family and a girls weekend so we hadn’t planned on spending time at the more touristy spots, like The Bean, Willis Tower, or Navy Pier since we’ve done all that before. More checking out cool bars and interesting spots to eat.
That was until we got the news about a month ago that Mike will be heading up a project on a federal building in downtown Chicago for the next 8-9 months.
I’ve tried writing this post a couple times, but it’s weird to put into words all the emotions we’re feeling. Mike is generally our in-house pessimist, where I see the good first and then become the cheerleader to keep everyone happy. But even I’ve had my moments of depression.Mike’s moving to Chicago
Mike and I basically starting living together 2 weeks into our relationship. I had my own apartment (albeit a tiny, tiny apartment) and he lived with his parents. It was convenient, then we realized we liked living together, and have been inseparable ever since! We’ve never before had to travel for work, and we’ve never taken more than a long weekend vacation away from each other. So, to say that this will be the biggest change in our marriage/relationship isn’t exaggerating.
We’ve gone through the roller coaster of emotions, and now we’re both into the excitement-of-the-future phase. We’re still waiting to hear when he’ll need to report for his first day on-site, (this is a federal job after all, so everything has to go through a dozen committees before a decision can be made), but he’s got all his clearance and badges, a TSA PreCheck number, and an apartment. From the conference meetings he’s been a part of, it looks like we’ll be moving him in in 2 weeks or so.
As you can imagine this very quickly changed our purely recreational trip to the city, into a apartment/neighborhood scouting trip, as well as a crash course in living in a big city, but we did get to visit some cool places that I thought I’d share.
DAY 1It’s a 6 hour drive (+ $30 tolls ouch!), so we left on Friday morning and arrived just in time for Mike to get his badges and credentials he’ll need. We then checked into our hotel. We stayed at the Hyatt Regency in the Loop, right on the river. I had waited awhile to book anything after getting the news and literally just found the cheapest/best location on Hotwire. It was clean, and close enough to walk to a lot of places, or at least grab a bus so it worked!
QUICK TIP: We parked here and it was less than 10 minutes from our hotel. It was also one of the cheaper rates, at $35/day.That night we hit up Wicker Park, (North-west neighborhood known for “local hipster culture, art community, nightlife, and food scene” according to Wikipedia – which is pretty accurate). We started at Big Star for tacos and margaritas.
QUICK TIP: We were told it would be hours for a table, and quickly found seats at the bar. We waited about 2 hours, but kept busy with drinks and nachos and could have ordered tacos, but thought it was a limited menu. It was not! I was drunk by the time we got our table and ate one small taco and we were finished within 20 minutes! ORDER TACOS AT THE BAR IF POSSIBLE!The patio is pretty awesome though, so even through my margarita haze it was still worth it.
Across the street is The Violet Hour, a speakeasy cocktail lounge which is only noticeable by the changing mural. There was a line of a handful of couples by the time we finished our tacos around 9pm, so it wasn’t that hard to find, plus the current mural has a door painted into it.
QUICK TIP: If you like fancy cocktails and a little mystery, you’ll love it here. Kind of pricey, but worth grabbing a drink or two.The couple behind us started up a conversation with us and we ended up sitting with them inside as well. They were from Texas and in town for a weekend away from their kids. It would have been just fine sitting with just Mike, but it was even more fun meeting new people as well!
We next walked a couple blocks to Saved by the Max a pop-up restaurant modeled after The Max from Saved by the Bell. When I first heard about it it was only scheduled for the month of June, so I was excited that our trip would coincide, but now it’s been extended until the end of the year!
We waited about an hour to get in, and it was around 11pm, so it was their late night offerings, which was just drinks and 2 sandwich choices, (and after all my margaritas and the cocktail at Violet Hour I wasn’t really feeling another drink). It was super kitschy and our server greeted us with “What’s up preppy?”. Any kid of the 90’s who was a fan of the show will love the nostalgia. Drinks and food weren't amazing or anything, but it was worth it to hang out!
QUICK TIP: They allowed those who only wanted to stand at the bar for a drink to go ahead of the line. If we knew they had a limited menu at time, we would have probably just done this and saved us an hour standing in line. You’re really only their for the photos, lets be honest!We started a conversation with the couple in front of us (hey, it worked out last time!), and they were locals who invited us to sit with them when they were finally sat. It was too loud to really converse inside, but it was nice to chat in line to pass the time.
It was around 2am so we took the L train back to our hotel and crashed.
DAY 2We woke up and had a couple apartment showings first thing in the morning (which was a little rough due to our late night before), and saw one in South Loop which was quiet, but a little too close to the central business district which we knew from staying in the Loop, closes down pretty early (like ghost town after 9pm). Also, the apartment was a little pricey for what it was.
We then had a showing at a small studio in Streeterville, which spoiler alert we ended up signing a lease with, near Navy Pier. The touristy proximity wasn’t ideal, but it was on a little pocket street, so it didn’t seem to busy, and it came with a patio, which what sold Mike. I’ll share a little more detail once he moves in, but the space saving custom details are really nice for such as small footprint.
We grabbed our car from parking and headed out to supposedly the “best hotdog in Chicago” at Gene & Jude’s. It was about 30 minutes outside the city, but when we rolled up, there was a line almost out the door, so we knew it was worth it.
They only serve a couple items: hot dogs, fries, and tamales, and the fries are served on the hotdog. Toppings are mustard, onions, peppers, and sweet relish.
QUICK TIP: Don’t even bother asking for ketchup, they don’t have any!
I’m not a huge hotdog fan, so I wasn’t that impressed, but Mike liked it! Also, there’s not seating so we opened the back of my SUV and sat in the trunk. A lot of people did the same, or sat on the curb, so we didn’t look weird.
We tried going to the beach, but we had trouble parking since we still had the car, and it was about 90 degrees so everyone else in the city had the same idea. Instead we headed over to Half Acre Beer Company for some beers and a small bite (meat and cheese tray followed by some blueberry french toast Black Dog Gelato – whatever flavor they have get it!)
We went back to the hotel and got ready for our night out. Before we left I bought tickets to The Comedy Bar’s The Big Sexy show, a vaudeville (variety show) with comedy, burlesque, musicians, and other acts. I have to say it was really good! I had bought it more for just something to do, but it was really well done and a nice date night with Mike!
We then walked over to Three Dots and a Dash, another speakeasy - this one a tiki bar. Rum being my favorite liquor of choice, this was probably my favorite all weekend. It was super kitschy and the bartenders were so fun and ridiculous.
QUICK TIP: Make reservations (we waited an hour to get in and I got lucky getting seats at the bar because it was pretty packed). If you don't make reservations, sit at the bar – the drinks are elaborate and half the fun (next to actually drinking them) was watching them make it!
We both started with Banana Daiquiri complete with cinnamon-stick-smoking banana dolphins. We were loving it even before the bartender gave us another drink (an Aloha Felicia) for free because he accidentally made an extra. I thought both were amazing (Mike said they were too sweet for him) and would recommend both, but I think the Aloha Felicia would be my first choice next time.
We walked back to the hotel and crashed around 3 am!
Day 3We started Sunday morning with some more apartment showings (why did we schedule them so early!) this time over in the Old Town/Gold Coast neighborhoods. We really liked the neighborhoods. They were a little less downtown, with a more residential feel, but the prices for the amount of space just weren’t worth it. We’re talking 1 window for a small studio or 1 bedroom space and with Mike coming from a house in the suburbs, I knew a little more access to the outside would make the transition easier.
We met up with our friend from my high school in Lakeview where he lives (even better area, but higher price tag) at one of his favorite coffee shops, Bow Truss. We caught up and chatted about the city and then headed to what he described as the best pizza in town (everyone has their favorite, but even our Uber driver said this place was the best too), Pequod’s Pizza.
QUICK TIP: Order the pan pizza (deep dish) and ask for extra sauce – you’ll thank me!We parted ways and went back to the hotel to relax before the concert. We were only a 10 minute walk from the hotel, but opted for an Uber because I was dressed nicely and wore heals. Like I said, the concert was at the Chicago Theater and even through our excitement we appreciated the gorgeousness of the theater.
The concert actually was at the same time as the NBA Finals and two rows back was another couple from NE Ohio, so our little section was keeping each other updated on the game between sets. We were live streaming before The Lumineers came out, and updating the score during the first couple songs.
We’re not even that big of basketball fans, but have obviously always rooted for NE Ohio sports (even through years of losses), so it was pretty exciting to win! We’re also glad that the game didn’t go into overtime, because the concert was honestly one of the best I’ve ever been to!
I splurged and got tickets in the front row of the balcony, and they were the best! We could see everything, and had extra space in front of us.
Day 4The next morning we took our time and slept in, had brunch at Bongo Room (get the hotcakes!), and drove by Mike’s future job site one last time as we headed home. It was a weekend that turned into having a lot more significance than I had originally thought when I bought the tickets, but it was invaluable in getting a chance to see and walk around the areas where Mike will be living and it was an awesome sneak peak into this crazy adventure we’re about to start!
As for the blog, I’ll keep posting! Luckily we’ve completed all the large renovations and now it’s just finalizing rooms (or sometimes redecorating them completely!). I’ve got some rooms that I’ve never found the time to photograph (basement family room) and some that I’d like to switch up (guest room) so keep checking back for updates. And, after a couple more trips to the city I’m definitely going to have more places to check out in Chicago!