Travel- Chicago Edition
The Windy City 

I go to Chicago every four months or so to visit my Dad. However,  this time was a little different – it was a couple’s getaway and Dane’s first time in Chi-town. We hit all this tourist hot spots then a few “hidden gems” of the city. Early fall is by far the best time to visit – cool enough to walk everywhere but warm enough to not freeze getting place to place.

Where we stayed:
Dana Hotel and Spa – Chicago 
I always use the Hotels Tonight app to book all our hotels.
– The key to getting the best deal: Check to make sure there are not any major conventions, events or sporting games going on in the city that would cause a spike in rates. Then, I usually wait the week or even the night of my stay to book the room.
Also, use the promo code below to get $25 off your next booking!

-Dana is by far my favorite hotel in Chicago. The doorman, TJ always remembers my name and the manager Tim is beyond helpful and friendly. The location and modern design are ideal for couple’s getaway.

 

What we ate:
Yolk: Visit Yolk
Great coffee, Mexican Omelette and the banana nut bread French Toast!

 

Firecakes: Visit Firecakes
We tried the coconut donut with vanilla ice cream and a chai latte, did not disappoint! Also, loved sitting outside on the bench to enjoy the weather.

 

Chicago Pizza & Oven Grinder Co.: Visit Chicago Pizza & Oven Grinder Co.
My Dad and brother raved about this place so we had to try it but must be honest: We were not impressed with this pizza nor the host/manager (not very friendly). The pizza looked amazing but way too salty for our taste. I enjoyed Lou Malnati’s pizza much more.

 

Wildberry Pancakes & Cafe: Visit Wildberry Pancakes Cafe 
This was by far my favorite breakfast/brunch we had on the trip! We tried the pumpkin frapp, pumpkin spice pancakes and the southern eggs benedict- Delish!

 

The Signature Room: Visit The Signature Room at the 95th
Warning: you will pay a lot of money here and as far as I could tell – You’re paying for the view. The food was very underwhelming. We ordered the tuna tartare appetizer: very good. For our main courses we ordered the pork chop and steak with whipped potatoes and brussel sprouts sides. The sides were much tastier than the main dishes. Desserts were a little better: keylime cheesecake and creme brulee.
TIP: Skip eating here and make reservations at the lounge to enjoy a drink or two with a great view.

 

Portillos: Visit Portillo’s
This is a true chicago style hotdog spot- it’s always busy and tasty! It’s casual dining in or to go. I was a little nervous when I saw how greasy the bag looked but oh, it was worth it!

Do-Rite Donuts:  Visit Do-Rite Donuts
Yum, Yum and more YUM! Do yourself a favor and order the Vera Cruz sandwich and any donut here. So tasty! Skip the coffee- it was a bit bitter for our taste.

 

Nutella Cafe: Visit Nutella Cafe – Chicago
I wish we’d had time to order something to eat here, everything looked so good but we tried the Mocha Latte (of course, made with NUTELLA). Definitely worth popping in for a taste or even just a smell of the nutella!

 

Small Cakes: Visit SmallCakes – Chicago
I’m glad we walked here from Wrigley Field, it was pure sugar overload! The staff was friendly and patient as you desperately try to decide what to try because everything looks so delicious! They basically put a layer of ice cream and cupcake into a cup and viola! Enjoy!

 

Lou Malnati’s: Visit Lou Malnati’s
This place always has a wait but its worth it. Make sure you go hungry!
It’s my favorite deep dish pizza in Chicago (many will debate over this). I suggest the sausage pizza, easy on the sauce. So good! My dad got to join us here.

What we saw:
Chicago Theater: We bought tickets to see comedian Jim Jefferies at the Chicago Theater. I don’t think we’ve ever laughed so hard in our lives! Best date night ever! We were cry-laughing. This theater was built in 1921, so beautiful inside and out. Apparently, there were some protesters that did not find Jim Jefferies’ skit on circumcision very funny. (Oops 🙈)

 

SkyDeck Chicago at Willis Tower: Although, it’s a bit over-priced- I highly recommend visiting if you’ve never been to Chicago. It’s an amazing view of the entire city from the 2nd tallest building in the U.S. Formerly known as Sears Tower, the building will always be photo worthy.

“ Whatchu talkin’ bout, Willis? – I still call it Sears Tower”

 

Navy Pier: Perfect for a stroll with a view, its similar to the boardwalk. You can hop on an architecture tour on the water from here too. Great for couples or families.

 

Shoreline Architecture Tour: This is one of my favorite things to do in Chicago when the weather is nice. Grab a cup of hot chocolate and enjoy the views from the water.

 

The Bean/ AKA: The Cloud Gate: The iconic landmark in Millennium Park. Shaped like a bean or to some, a cloud. You can find tons of people visiting to take pictures with reflections of the skyscrappers in the background.

 

Wrigley Field: I’m not a big baseball fan at all. However, this field is famous for wild fans and surrounding fun bars. Its definately worth walking by to experience.

The best free things to do in Chicago:
-Lincoln Park / Lincoln Park Zoo
-The Bean
-Wrigley Field
-Navy Pier
-Millennium Park

“And all that Jazz” ~ Chicago