Chicago Travel Guide

Hello and happy Wednesday friends! Can you believe we are already two and a half months into 2019? A couple of weeks ago, I did a “Navy Girlfriend Getaway” with my BFF Jordyn whose boyfriend is also on deployment. We did a 3-day weekend in Chicago and while there, we tried to eat like a Chicago native all while hitting those cliché tourist spots. We also planned our trip to be budget friendly, so we weren’t breaking the bank. Excited to share with y’all how we spent our three days in Chicago!

Where to Eat:

When planning our trip, we looked at eating at local restaurants. We both agreed to avoid the chain places and eat like a Chicago Native. I am so glad we decided to do this because the food honestly made our entire trip.  

Meals/ Snacks:

Chicago Pizza and Oven Grinder Co. 

Y’all, I can’t even put my comments or thoughts into words on how good this pizza was. With Kyle being a Chicago native, he gave me so many recommendations, this being one of them. OH MY LANTA, this pizza is worth your entire trip to Chicago. It’s a basement of an old cobblestone house and you will more than likely wait an hour for a table, but it is totally worth it! It is first come first serve and the owner doesn’t take names, he remembers face (believe it or not he really remembers everyone). I would say this is a 12/10 recommendation, 100% authentic deep-dish pizza. 

Yolk:

Who doesn’t love a good breakfast while on vacation? We went to breakfast at Yolk our first morning in Chicago and we were both stuffed the entire day! I had the Santa Fe Frittata with an English muffin and Jordyn had the Country Skillet with pancakes. They give you such large portions and everything is made so fresh. The veggies tasted like they were cut to order, the salsa that came with was the perfect touch, and the jam for the English muffin is homemade. We both ate so much, we weren’t hungry again until dinner! 

M Burger:

You can never go wrong with a good burger and some fries. We kept it simple our second night and picked up burgers from here on our way back to our hotel. The burgers are juicy and the house sauce they put on them makes the burger. If you’re hungry I definitely recommend doing a double, the single is a decent size but not for when you’re super hungry. 

Shake Shack:

A “Chicago Must” I was told to try was a hot dog. I hate hot dogs, but I figured since I was there, I have to try a “Chicago Dog.” We went to Shake Shack, which is across the street from Cloud Gate (the bean). Jordyn and I split a dog because we weren’t sure if we were going to like them. Truth be told, I could have eaten an entire hot dog by myself! The toppings made me hesitant, but they complimented each other so well, I’d probably eat another one. Shake Shack had great milkshakes and floats as well. They do have street vendors near Navy Pier that sell hot dogs if you want a quick grab-n-go item.

Stan’s Donuts

Our last morning in Chicago, we stopped and got donuts and coffee before heading to the Skydeck. Stan’s has quite the variety and it’s not your typical flavors. We went with the Chocolate Pocket with Nutella & Banana and the Toffee Cake. The Chocolate one was good but would have preferred a different one. The Toffee cake though was very yummy and the crumbles on top give the donut that nice little crunch. I also got a Stan’s Chocolate milk… seriously tasted like a melted milkshake, so yummy!

Molly’s Cupcakes:

I am all for my desserts… especially having them before your meal! Molly’s was the first place we stopped to eat while in Chicago. We got two cupcakes, Strawberry Shortcake & S’mores… very hard to pick just two out of the entire case! I’m a cupcake fanatic so my standards are pretty high. Molly’s had great flavor from the cake to the filling to the frosting. Doesn’t compare to the cupcakes I had while in D.C., but they are good cupcakes… plus they have cute swings you can enjoy them on. 

Garrett’s Popcorn:

Popcorn is not my go-to snack, but it’s another “Chicago Must” so we decided to swing in and grab some for our hotel room. We got two different types, Buffalo-Ranch & the Garret Mix. I was genuinely impressed with Garrett’s popcorn. The buffalo-ranch wasn’t spice but had a great flavor. The Garret mix is their classic, its cheddar popcorn with caramel crisp corn, another mix that had a great flavor. The popcorn itself had a nice crunch to it and even held its crunch for a few days after picking it up. 

Things to Do:

When planning what we wanted to do, we wanted to hit the cliché tourist spots because of course, those are the places you want to see. But most of the cliché spots are free of charge or have a small fee for additional activities which is great for staying in the budget.

Magnificent Mile:

Shopping heaven! Think of any store you want to go in, and odds are there is one if not two of it on the Magnificent Mile. The Under-Armor store has the best smell, there’s a two-story American Girl doll store which is every little girl’s dream, and there’s a Sprinkles Cupcake ATM around the corner from the Gucci store.  It will easily take two days to walk the entire strip of stores. On top of all the stores, there are many fun restaurants you can stop in, the architecture on the old buildings is amazing to look at and there are cool places like Eataly (an Italian entry with a cannoli bar and can watch fresh mozzarella be made), 

The Skydeck:

The ultimate “Chicago Must” is going on the Skydeck to get your picture in the glass box that sits 103 stories above the streets of Chicago. It does cost a lot to get into, $25 per person, but once you’re up there you can spend as long as you would like and are able to get back in line as many times as you like to take pictures in the box. It is definitely a cool experience but a one-time type of activity. Next time I go back, I would like to go to the Signature room which is the 95th floor of the John Hancock building. 

Millennium Park:

Millennium Park might possibly have been my favorite part of our entire trip… mainly because of the bean (Cloud Gate). You can easily spend an hour at the bean taking photos or you can venture down to the ice-skating rink. When it’s warm out there is so much more to the park you can explore. For a quick weekend trip, Millennium Park is a great place to stop, snap a few photos and across the street from shake shack! 

Navy Pier:

If you’re going to Chicago with kids, Navy Pier is a great place to take them. There’s a museum you can walk through, an IMAX screen, when it is warm there are rides outside you can go on, and there is a small food area with unique food options. On top of the activities, the views you can get from the lake and the city are amazing! 

Where to Stay:

Picking a place to stay in Chicago is difficult because there are so many things to do in multiple different locations. We based the location of our hotel off of what we were planning on doing and where we were eating. 

DoubleTree by Hilton Hotel Chicago – Magnificent Mile:

The DoubleTree was the perfect hotel for us to stay in. It was just a block away from the Magnificent Mile, a few blocks from Navy Pier and right over the river from Millennium Park. On top of being a great location, the hotel was nicely updated, and the workers were all so sweet and helpful. They remember who is staying and always greet you when you return. AND they give you cookies when you check-in… who can say no to cookies, especially yummy ones!  

Other Options:

When we were looking for places to stay, we looked into multiple Airbnb’s and other hotels all with great reviews and great locations. We chose the DoubleTree because of its great location for what we wanted to do. When looking for places, try to stay towards the northern end, a much safer location.  

If you’re planning a trip to Chicago, I hope this helps you narrow down what your trip itinerary looks like. If you’re thinking about visiting Chicago, the places we went and ate at are a great starting point, especially if you’ve never been. I can’t wait to visit Chicago again and I must say, that the food was worth the entire trip! We are already planning our next “Navy Girlfriend Getaway,” stay tuned to see where we will be getting away too next!