When Gerald and I went to Chicago to celebrate my longtime friend Victoria’s birthday (and squeeze in some quality time with Rox!) I did not expect to fall in love with the city. I’d heard horror stories about the cold, so I automatically assumed it wasn’t a city I would like — I was SO wrong. Chicago officially has a piece of my heart. It has so many things to do and places to explore, plus a lake and a beach, and the people there are SO NICE. Not to mention there’s fabulous shopping and a great food scene.
We literally spent 49 1/2 hours in the city, landing around 8 am on Friday morning and leaving at 9:30 am on Sunday. The flight was super easy — I slept the whole time both ways — and about an hour and a half from Reagan airport. Chicago does have a one hour time difference, so it was really nice to get that extra hour on Friday.
Since our flights were a little pricey — $330 each — we decided to forgo a nice hotel for the cheapest we could find and stayed at The Congress Plaza Hotel. It’s definitely one of the older hotels in Chicago, but the price was right and it was in a great location in the Loop, right near Millennium and Grant Park. I can’t really brag about the amenities or the room, but considering we were really only there to sleep and shower, it was a fine stay. We took the L (Chicago’s version of the Metro) straight from the airport to our hotel on Friday morning to drop our bags off and I was shocked at how easy the transit system was to navigate. We flew into O’Hare and it was about an hour ride to downtown, but the line is mostly above ground so you didn’t feel like you were stuck on a commuter train.
After dropping our bags, we headed to the Riverwalk to take one of the famed Chicago Architecture Tours. The tour is right on the river and you get to learn so much about the city and its architectural history! It sounds a little cheesy, but it was definitely a highlight of the trip. I booked our tour a few weeks in advance through Chicago’s First Lady Cruises, which is run by the Chicago Architecture Center, so I knew it would be legit. The first floor of the boat was covered (which was perfect since it was pouring rain), and had a bar! We rather aggressively had some 10 am mimosas, but it just added to the charm of the tour. We ended up going on the top half of the boat for the majority of the tour since it offered the best views, and the rain really didn’t ruin it. (Let’s just say it was not a good hair day for me.) I 100% recommend booking one of these tours if you visit the Windy City!
After the boat tour, I was so cold that I had to go buy pants. Rox gave me the location of the closest Forever 21, but on the way there we passed by Nordstrom and I am SO glad we went it. The Nordstrom on on Michigan Avenue, aka the Magnificent Mile, is actually the flagship store and it is insane — it made Tysons look like a dump. There are full TopShop, Reformation, Free People, and Madewell sections, in addition to a bar on the men’s floor! I snagged a pair of TopShop pants and a top and was so much happier in the chilly weather.
Straight from Nordstrom, we hopped on the L again and headed to Wrigley Field to catch a Cubs game. Wrigley Field is the second oldest baseball stadium in the US and it had SO much character. We went to a 1:20 pm game and I was shocked at how many people had dipped out of work to attend it! While I’m not a Cubs fan (#GoNats), it was a really fun game and it even went into overtime. We got tickets for a pretty great deal on StubHub (around $35 each I think?) and since the stadium is on the smaller side, every seat in the house is pretty solid.
We took the L back into the city and took some quick naps before meeting up with Rox and the Husband of Glam for dinner. (I’m not a napper, but in our defense, we had gotten up at 4:30 am EST.) We met at Beatrix in the Aloft hotel in River North and it was SO good. It was a total scene and the food was super veg-friendly. I’m still thinking about the chopped Thai salad I had! (Great choice, Rox.)
From there, the birthday celebrations started and I was reunited with my biffy since 5th grade at Point and Feather. We had so much fun catching up with Vic and my college frat brother and playing darts (sorry I was a horrible teammate, Nina) and then decided to be insane people and go get bottle service across the street at Hubbard Inn. I’m not used to staying up partying till a bar closes anymore, but we had so much fun dancing the night away. Trust me, I paid for it with the hangover the next day.
Due to the night before, we had a slower start to our Saturday morning and walked over to Eataly for lunch. Eataly was SO cute and definitely worth checking out. Imagine if Union Market was 100% Italian, and that’s basically was it is. To nurse our hangovers, we each got a Neopolitan pizza and split a bottle of wine. I could have spent hours in the food hall exploring the different wines and sampling fare from each of the different mini restaurants, but we had a city to see!
To burn off the carbs, we walked to the lake and took a stroll around the Ohio Beach area. The lake is absolutely gorgeous and offers amazing views of the skyline. We both love people watching and had so much fun seeing all of the party yachts roll in. #Goals. Right next to the lake is Navy Pier, which was pretty touristy, but still a fun spot to check out! We grabbed a beer and hung out in the amphitheater area watching all of the riverboat tours sail by.
We headed back towards hotel via the Riverwalk, and I wish we’d had more time to check out all of the restaurants right on the water — definitely something to add to your list if you are visiting Chi! We had to stop into Millennium Park and see The Bean, and there was actually a dance festival going on! I convinced G to undergo five minutes of a salsa dance lesson on one of the park lawns, you can imagine how thrilled he was. We took an obligatory selfie in The Bean, then headed to the neighboring Crown Fountain to see the splash park.
Fast forward to dinner — we tried to go to the Milk Room, a speakeasy at the Chicago Athletic Association, for a pre-meal cocktail but it was fully booked for the evening so we headed to The Gage, which used to be a woman-run hat factory! We then hopped in an Uber to Bucktown to my favorite kind of restaurant, a Mexican hole-in-the-wall to meet up with the birthday girl. Estrella Negra was perfect, inexpensive and delicious!
To cap off the night, we headed to The Whistler, a dive bar with a live DJ around the corner where I got to reconnect with one of my old coworkers! I kid you not, I ordered a round that included a glass of wine, a vodka soda, and an IPA and nearly spit my drink out when I saw that it was only $15. That’s ONE cocktail in DC! The District has ruined me.
All in all, it was a fantastic trip, chock-full of adventures. I can’t wait to go back.