Two and a Half Days in Chicago

August 3, 2018

While it's slightly embarrassing to admit this (honesty is the best policy, right?), I've wanted to visit Chicago since I was a kid ... because Frank Sinatra sang two songs about it. My mom regularly played Sinatra when I was growing up and, well, put it this way: if he sang about a trash chute, I'd probably hang out by trash chutes. Case in point: I love Frank Sinatra, so I always knew I'd love Chicago because he loved it himself. 

Even more embarrassing to admit is the fact that I also always wanted to visit Chicago because it's the backdrop to two of my all-time favorite '90s rom coms: While You Were Sleeping and My Best Friend's Wedding. That you are free to judge me for.  

To no surprise, the legendary Sinatra was right about Chicago. When I visited, I loved it and it definitely felt like "my kind of town." The city, the people, the food (!), the architecture and surrounding neighborhoods all filled me with the kind of exciting joy only a beautiful, bustling and multicultural city can deliver. And this trip was just two and a half days in length, so I know my experience was just a very small taste of what the city has to offer. Still, a taste is better than nothing. I'd say we made the most of our short time in the city (not to mention the fact that we squeezed a concert in - more on that below!). 

Planning on visiting Chicago soon and only have a couple days to spend in the city? Read on to see what we did - and ate (food is one of the best parts of traveling, no?).

Day 1

Image via Conde Nast Traveler

After my friend Ro and I met up with my friends Jess and Sam at the airport, we headed straight to our hotel. We stayed at the Virgin Hotel in Downtown Chicago, which sits in a convenient spot in the Chicago Loop just steps away from the river and Millennium Park. It felt cool and trendy, yet cozy and friendly (nothing ruins a hot spot like pretentious people, amiright?), and has a coffee shop, restaurant and rooftop bar. They also offer complimentary cocktails during a guest social hour, which is a nice bonus. The only downside we experienced staying here was that we planned to go to the rooftop bar, Cerise, Sunday night, only to discover they were closed early despite it being a holiday weekend (Monday was Labor Day). Lesson #1: if you want to visit a specific destination on a trip - whether it's a restaurant, club/bar, museum or monument, call to verify their hours of operation. Don't rely on the web to tell you. We were so disappointed that we didn't get to make it up, as we heard several positive reviews about it. 

Our first authentic Chicago deep dish at Lou Malnati's. Not the best photo, but this pizza was seriously delicious. For some pics that better showcase their pizza, check out Lou Malnati's Instagram.

Never say no to cheesy garlic bread. Never.

We were so exhausted after our early morning flight from Orlando that we immediately took a two hour break/nap in the hotel after checking in. We woke up feeling ravenous, so naturally, we proceeded to Lou Malnati's for some Chicago deep dish pizza to kick off our stay in the city. And here comes Lesson #2 of the trip: when embarking on your first authentic Chicago deep dish pizza journey, avoid ordering a pizza that isn't just a traditional damn pizza. I ordered something with veggies and turkey sausage in an attempt to get some nutrition in and instantly wished I had ordered what Ro decided on: a simple pepperoni pie. Hers was incredible. I didn't make the same mistake when we grabbed our second deep dish (more on that later). Also, this place had a typical wait of over two hours, so I suggest putting your name in and then exploring the nearby streets while you wait. It helps the time go by faster while allowing you the opportunity to stumble upon a hidden gem (we wandered into a mysterious antique shop).  

After stuffing our faces, Ro and I walked around the river and nearby streets, eventually making our way to Millennium Park to see the Bean, in typical Chicago first-timer fashion. We spent a couple hours exploring and people watching. Few things bring me as much peace and joy as simply walking around a new place, taking in all the sights and sounds. It's the little things, people. Also, was anyone else surprised by how difficult it is to get a solid photo of your reflection in the Bean? I was not prepared for that struggle and eventually I gave up. I was much happier with the photos below.  


After exploring and taking a few pictures, we made our way back to the hotel to get ready for the aforementioned concert. Who did we see, you ask? Another legend in my book: John Mayer. It was my second time seeing him live, but the experience was just as magical as the first. I teared up when he sang In the Blood and Stop This Train. 

Unexpectedly yet unsurprisingly packed and wore the same exact Amish-inspired hat as Jess.  
Day 2

We kicked off the next morning with yet another walk through the city and picked up some coffee and doughnuts from Glazed and Infused, which is now permanently closed. The buttermilk doughnut was delicious, but I wouldn't say the others were memorable. Still, #doughnuts. R.I.P. G&I. 

Since stomachs magically double in size on vacation, we made our way directly from Glazed and Infused to Summer House Santa Monica for brunch. Nestled near the beautiful Lincoln Park neighborhood, it has an airy, fun and chic SoCal-inspired interior. The drinks were great, as was the food. The star of the show for me was surprisingly the Butternut Squash soup. So. Damn. Good. 

Summer House Santa Monica

After brunch, we walked through Lincoln Park, admiring the dreamy homes (another hobby of mine: walking by pretty houses and daydreaming about what my future home will look like while also trying to figure out how to afford the multimillion dollar homes I'm walking by). Ro and I ended up stumbling upon Hotel Lincoln and decided to head up to the rooftop bar, The J. Parker, for some cocktails with a beautiful view of Lake Michigan. 

Hotel Lincoln, standing tall behind the coolest moss/plant covered apartment building

View of Lake Michigan from Hotel Lincoln's 13th floor rooftop bar, The J. Parker 

Image via The J. Parker

To close our second and final night, we made our way back to the hotel to get ready for a river cruise. Jess planned this after hearing it was a must-do and I'm so happy she did. It was a perfect night spent on the water, sipping on cocktails, mingling with friendly visitors and locals alike, and admiring the skyscrapers (we even got to see Lady Gaga's Chicago penthouse!). 

Photo taken and edited by Jess 

After the cruise, Ro and I had dinner at a restaurant close to our hotel and went for a short post-dinner walk around the city while Sam and Jess had a date night elsewhere. We all met up at Cindy's Rooftop for cocktails with a view over Millennium Park, and then walked over to Three Dots and a Dash, a tropical island-themed bar in River North, for a night cap. Remember how I mentioned earlier that we couldn't make it up to our hotel's rooftop bar? This was that night. Every bar closed slightly earlier than we expected for a holiday weekend, and since we got such a late start, we were bummed to not have much free time for bar hopping. So, to repeat what I stated earlier: always, always, always call a location to verify their hours of operation on holiday weekends.  

Cindy's Rooftop. Image via Chicago Athletic Hotel

Three Dots and a Dash. Image via Chicago Eater

Day 3

We couldn't get a reservation for Girl and the Goat, which was recommended to us by just about everyone we know who has visited or lives in Chicago, so instead, Ro and I went to Little Goat, the former's diner-style sister restaurant in the West Loop. For me, the breakfast at Little Goat made up for not getting dinner reservations. I had the Bull's Eye French Toast: sweet onion brioche french toast with fried eggs IN THE DOUGH, meaning the yolk poured out once I cut into the french toast *drools profusely.* It was topped with crispy fried chicken, seasonal berries and bbq maple syrup. I could have died of pure bliss right then and there.

After breakfast, Ro and I made our way to the The Skydeck, located on the 103rd (!!!) floor of the Willis Tower. Lesson #3 (this one we got right): pay for the "fast pass" that they offer in the security line area. The line to get to the Skydeck was originally over two hours long, and getting these passes cut our wait time to less than half of that for a very reasonable cost. It was 100% worth it. As far as the experience goes, I was nervous as hell on the elevator ride up (you can start to feel the elevator shake from the wind at a certain altitude), but it felt incredible being up so high and taking pictures on the glass. My stomach definitely felt a little uneasy when I looked down, but the overall experience was thrilling nonetheless. 

Chicago-style hot dogs at The Wiener's Circle. During late weekend hours, the employees are known for having foul-mouthed fun with the customers. I intend to go back on a Saturday night when I'm back in the city for a hot dog with a side of verbal abuse.  

To wrap up our time in Chi-Town, Ro and I visited Wrigley Field and then made our way to get more - you guessed it - food. We stopped at The Wiener's Circle for Chicago-style hot dogs and then immediately made our way to Giordano's for our last meal: deep dish pizza. I was smart enough to order a simple pizza this time around: nothing but good ole' extra cheese. We made our way to Millennium Park to devour our pizza while people watching in the park. It was the perfect way to end our short stay in the city.


Stay beautiful and delicious, Chicago. 


A few other recs I plan on taking advantage of when I return:

Feel free to share any of your own personal recommendations in the comment section below!