CHICAGO My Kind of Town (How to do The Windy City on the Cheap)

I visited Chicago once when I was fourteen. My brother was going to a gymnastics camp at the University of Illinois in Champagne, so my mom and sister and I, and our friends drove into the city for a day. The trip consisted of getting some deep dish pizza for lunch visiting the American Girl Doll museum, the Hershey's Chocolate museum, and driving by Harpo studios. So, lets just say that I was overdue for a visit.

Turns out that experiencing Chicago as an adult and experiencing Chicago as a fourteen-year-old girl is much different. Who knew?

JD had to go to Chi Town for work, so I decided to tag along, and I'm so glad I did. We wanted to experience Chicago like the locals, so we asked some friends who have been Chicago residents for some advice on the must-see places and the best eateries. We went simple and cheap on this trip and even though we skipped the fancy dinners and expensive tours, we had an absolute blast. 

Here's a travel guide for doing Chicago on the cheap...


If you can, stay somewhere in Mag Mile near Rush street, especially if you want to get a feel for the city. The public transportation in Chicago is pretty reliable, and the train made it really easy to get around. The system is easy to navigate and is color coded for people like me who still get lost with Google Maps in front of their face.

TRANSPORTATION

Here's a tip for doing Chicago on the cheap: make use of the CTA. My suggestion is to buy day passes if you are planning to make your way around the city and don't want to pay for taxis or Uber. You can buy 1, 3, or 7 day passes on the website by buying a Ventra card. Or you can just buy it at the stations (just make sure to factor that into your travel time). 

We used the train, walked, and rode the bus and had no problem getting everywhere we wanted to go from downtown. For longer distances at night you may want to consider calling a cab, just for the sake of safety, but we honestly had no problems or strange encounters during our time on trains and busses. 

SITES

If you are staying in the city center you can walk most places or take a quick train ride to some beautiful spots. On our first day we took the train to Grant Park, stopped for some Cuban sandwiches at a restaurant called Cafecito and walked through Grant Park and Millennium Park where we saw the bean! (Cloud Gate)

Here are a few shots of the parks as we walked our way through the fun weekend, city scenes...

As if the architecture wasn't enough to take your breath away, the weather was FRIGID, and even with coats, hats, and scarves we were a little on the cold side. If you visit Chicago in the winter or spring keep in mind that 28 actually means it feels like below zero because of the WIND. We stopped at Oak Street Beach, which was in walking distance from our hotel, but did not linger because we couldn't walk another mile with numb hands and faces. 

Next time I'll be sure to bring gloves. It was mostly having cold hands all of the time that was bothersome. Especially when you're being all touristy and carrying around shopping bags and coffee cups.

A cute little hipster red beanie couple in front of the bean

For some great Jazz we visited the Green Mill Cocktail Lounge and it definitely did not disappoint. The drinks were so-so, but it was a packed house as Steve Wilson & Wilsonian's Grain serenaded with their smooth sounds. The overall experience was just fun. We arrived around 8 PM and stood for most of the time even though people were circulating in and out until 2 AM. So, just expect to sip your cocktail while standing if you go on a weekend night.

FOOD

I have to be honest and say that living in Seattle for nearly six years has ruined me forever. The food here is just so incredibly good and I measure all of my food experiences based on my best Seattle food memories, which if I'm honest haven't really been outdone in my recent travels. So while the food was good, I can't say that I was blow away at any point, with a few exceptions...

Our first night we embraced the tourist stereotype and grabbed some deep dish pizza. The popular place to do that is Lou Malnati's. It was a fun spot and the crust really was all you'd hope for in a deep dish: buttery and dense, but I wouldn't say that it was anything but a good slice of pizza.

Per our friend's suggestion who was a Chicago-ite for many years, we grabbed lunch the next day at D'amato's Bakery on Grand Ave. We got a little bit mixed up and got sandwiches there, instead of next door at Bari's, like everyone says to do. Apparently D'amato's is where you should go for pizza, but since we had already had pizza the night before we went for the sandwiches. 

I can say with confidence that the meatball sub there was the best I've ever had. The fresh baked bread really put that sandwich over the top. The Italian sub was delicious too, though I can't say that sub sandwiches are my favorite things in the world. But if you're trying to do Chicago on the cheap or you love sandwiches, this is your spot. If we go back I want to grab a pizza at D'amato's (they looked AMAZING and I am so bummed we didn't go for it anyway) and try the subs at Bari's instead. The cool Chicago-y thing to do is to get giardiniera on your subs. It's essentially a condiment with pickled peppers, cauliflower, carrots, celery, and gherkins. It did amp up the sandwiches, but again, not my favorite flavors. There's a spicy and non-spicy version. Go for spicy if you can handle it.

If you're doing some shopping in the downtown area grab a coffee at Intelligentsia. Another former resident recommendation, I was thoroughly impressed with their roast and the the service was really great. I tried a Salvadorian blend in an Americano and it had some really complex notes like Marzapan, which I enjoyed. Carrying a cup of coffee around also helped with the cold hands problem. They have locations in NYC and L.A as well.

Our last full-meal was at a thin crust pizza place in Lincoln Park called Pat's Pizza. It has good reviews, but again I think we can chalk the experience up to just a good piece of pizza. I did love the Lincoln Park area, though. It's a place I'd love to explore a little more when we go back.

Last, but definitely not least was probably our favorite stop during our trip: The Violet Hour. This little gem in Wicker Park is a speakeasy that you'd miss if you weren't looking for it. When we walked up to the door that is cleverly disguised by a wall of graffiti, we were approached by a young guy asking if we were wanting a table. We told him it was just the two of us and he lead us into a dark entryway with a curtain and checked our IDs. After checking with the hostess for seating availability, he led us through the curtain and to the bar. I would recommend sitting at the bar if you can, because it's so fun to watch the bartenders work their magic. 

I ordered their signature drink the Romeo + Juliet (gin, rosewater, lemon, and cucumber) and it was one of the best cocktails I've ever tasted - expert balance and just the thing I was craving. It was so refreshing. JD ordered something with tequila. We got a few small bites, but they were nothing special. The ambiance is really what impresses. The lighting is really dim, with mostly candles providing the light, and the expansive space has small tables with chairs that have incredibly high backs and velvet seat covers. A fun part of the experience are observing teir "house rules" which includes not using your cell phone and keeping your voice down to keep with the mood. The bartenders were incredibly nice and helpful and I even had one of them whip up something on the fly for me at the end with Rum and it was heavenly. Put this place on your list when you visit! You won't be disappointed. 

Can you spot the door handle?

Another thing worth mentioning about this fun city is the people. Everyone is SO friendly. At least that was our experience. Chicago breaks the big city stereotype. You wouldn't expect such a warm and inviting feeling, but we were pleasantly surprised by how welcoming everyone made us feel. In fact, locals went out of their way to ask us if we needed help navigating the city, and that just made us enjoy our time there even more.

We packed quite a bit into our weekend stay in Chicago, but there's so much we didn't get to do and see, what are your travel tips for the Windy City?