#WeekendWarrior - Chicago

I'm really working on being a more flexible person in my daily life. I'm a natural planner of things so it's hard to relax and go with the flow sometimes. When a recent trip to San Francisco was cancelled due to weather I had to switch gears literally last minute, unpack my rain boots for a much more suitable walking shoe, and find a hotel and things to do within hours. 

Willow and I had discussed a trip to Chicago last summer but the hotels were sky high and we are budget friendly travelers to say the least. After checking a few sites, we came across a great weekend deal even though it was a holiday. The other two factors were weather and seat availability. The weather decided to be great that weekend! Temps were in the 60s and even hit 70 at one point so the weather was beautiful for February. Seat availability was great too; a nonstop, early morning flight on Saturday with a nonstop return on Monday. So ladies and gents, here's my weekend in Chicago.

Day 1

Swissotel - Chicago

I love Hotel Tonight because it gives you great last minute deals between competing hotels but you have to act quick. The initial hotel I wanted was there at 3:00pm and was gone by 4:30pm. That's how we ended up at the wonderful Swissotel. The service here was great and our view was even better. It was right off of Navy Pier so we were able to see the water and the pier and it was simply gorgeous. I felt a little spoiled because Willow sprung for the uncharge for the view because I mentioned I wanted it the night before.

 Hotel view of Navy Pier (Chicago)

Hotel view of Navy Pier (Chicago)


25 Degrees

After getting up at 6:00am for a flight and getting to the hotel around 10:30am, we were hungry. I did a little digging online and came across this hip little restaurant called 25 Degrees. Mostly known for their burgers I was there for the bottles of champagne for brunch. Biggie, Tupac, and De La Soul tracks were the entertainment for the day which made the brunch even better. It can be a little cramped in there and they sat us behind the bar at a table that was up against a wall so I was little uncomfortable but it really wasn't a problem once I ordered peach juice to go in my mimosa. That's right, peach juice!

Willow ate a breakfast sandwich and I opted for a burger. His sandwich had scrambled eggs, cheddar cheese, applewood smoked bacon, arugula and a herbed aioli. It was simple but still full of flavor. It was served with breakfast potatoes and eggs on the side. I did the Number One burger. It had fontina and blue cheese, applewood smoked bacon, cartelized onions, arugula, and thousand island dressing. I did a split order of onion rings and sweet potato fries. The burger was so damn delicious. it was sweet and cheesy and just made a beautiful mess.

Navy Pier

After a great bunch we went over to Navy Pier to walk around and see what we could see. It was super packed with tons of people and the breeze was slowly getting warmer so it was a beautiful time to walk around. My parents recommended a boat tour but we couldn't find a time to make that happen so maybe when it warms up we will have more times to choose from. We thought about the ferris wheel but someone named Willow is afraid of heights so we passed it up. He might have considered it if the life wasn't so terribly long. There was a sign for a beer garden but we never actually found it so we settle for a food and drink detour at a spot called Riva's. It had great views, lots of windows and was great for a snack. I know, we just ate but the menu looked great. I had a crab cake and killed it. Willow had a soup of sorts, I can't really remember. 

Molly's Cupcakes

As we were strolling back to our hotel I saw a cupcake shop so of course I was intrigued. I've had nasty cupcakes before so I'm always looking to taste and judge accordingly. They offered a variety of cupcakes but they also offered an option to build your own. It was limited but fun nonetheless. I had a peach cobbler cupcake and Willow had hot chocolate...

Both were top notch.

The Marq

After we took a nap it was time for dinner. We found this random place that had a pretty good menu. It really was a decision based on what was the third option on the list we found. SO off to The Marq we went. It was pretty quiet for a Saturday night which was fine for us. I started off with a Smoke 'n Spice which tasted like fall in a glass. We decided to get the Fromage and Charcuterie board from the starter menu. Three cheeses, a meat and some other toppings was a great start to the night. It was light and simple and didn't make me feel heavy. For dinner, I had the Sticky Ribs with Brussel Sprouts and Fries. I tore those sprouts up! I think because I was never forced to eat them as a child I have a love for them while others would rather drink sewer water than eat them. I enjoyed my meal thoroughly. I asked for dessert but they had just sold their last one to a man who didn't eat it after they prepared it because it had nuts on it. I was thoroughly pissed at that man. I treated myself to another drink instead. The Caribbean Queen was light and tropical so it felt like dessert.

Day 2

Millennium Park

We started our Sunday a little earlier than usual. My cousin was picking us up for lunch so we got up and headed over to the beautiful Millennium Park...Home of The Bean! It was within walking distance of our hotel and the weather was perfect. The park has some great food and some shopping, an ice rink, and of course The Bean. There were so many people there since it was such a nice day. It was good to get out and get a good walk in before we went in on another day of food.


My cousin Tracy's scooped us up from our hotel and took us to Manny's. It's one of the last Jewish deli's still in existence and it's amazing. Over 70 years of history can be seen on the walls and tasted in the food. Of course we had to go because it's also one of Barack Obama's favorite places to eat in Chicago. It's a cafeteria style restaurant with so many choices. It was almost overwhelming because I wanted a little bit of everything in my belly. She got a sandwich that had so much meat it was enough for several sandwiches and it was under $14! I know it sounds like a lot for a sandwich but Jesus it was a lot of meat! 


I guess it would be a sin to visit Chicago and not sample some pizza. I had tons of suggestions from friends but by the time we made it to pizza we were slightly full and tired so we made a pit stop at Giordano's and had personal sized pizzas just to get the idea. I have had it before but it was a shipped, frozen one from their store and I didn't cook it as well as Should have so to have it in person was great. It was worth the wait and I almost wished I brought one back. I didn't think of it until the guy on the plane next to me had a large one he was bringing back. There are plenty other amazing options I have to go back and try and I'll be sure to check it out on the first day and not the last.

Bottle and Baptiste

Our last stop was a restaurant and bar I found on yelp called Bottle and Baptiste. It was in Conrad Hotel and overlooked the city. It was a beautiful view with a sex appeal. They focus on rare spirits as well on bourbon and whiskey. We were too stuffed for food but a stop in the bar was a good way to end the trip. My first drink was the Sazerac Flight. It was a three versions of the cocktail made with rum, rye, and cognac. It took me a while to get through all three but I enjoyed it. The next drink tickled me so much. It was the Southside Mule; made with koval “baptiste series” bourbon, pineapple-rosemary shrub, ginger. It was delicious and the cups were everything.

It's safe to say that we had a ball in Chicago. It was a bit more expensive than our usual weekend getaway but well worth it. Next time, we are definitely checking out a boat tour, venturing out more, and trying more pizza. Thanks for a wonderful time Chicago!