Chicago You Were Beautiful

Psssst... can you keep a secret? I have been a lifetime lover of NYC, but everyone has always told me that if I love "the city" then I'll love Chicago even more. I never understood how that could be true until this past weekend. I'm absolutely in love with Chicago, and can't stop raving about all the amazing food and incredible site seeing.

We arrived Friday morning and packed as much as we could until our flight back home Monday morning. I'll leave you all with a photo dump and my recommendations from what we enjoyed during our short time in this beautiful city.

We took the train into the city from Midway (only $3 each way and the train connects directly from the airport to downtown Chicago), and when we arrived at our hotel our room was already ready for us. So, we dumped our stuff as I took a quick "ready to hit the ground running" selfie and a pic of the city view from our room. We stayed at the Hard Rock Hotel which was in a great location and we even had a view of the river from our room.

First thing we did was head over to the Sears (Willis) Tower, then we just explored the city before stumbling upon the Plymouth Restaurant & Roof Top Bar for some happy hour drinks and to meet up with Emily and K to officially start our vacay. Next stop was Millennium Park to see the infamous Bean.

That night it was time to celebrate K's birthday. We started off the evening with some pre-dinner drinks at The Signature Lounge on the 96th floor of the Hancock Building (absolute MUST DO when in Chicago). Drinks are a bit pricey, so go for a drink and enjoy the views before heading elsewhere for the evening. 

Then it was time for dinner at Ditka's where the birthday boy was sang to, and some roof top drinks at Vertigo Sky Lounge to cap off the evening.

Saturday morning, H and I walked around a bit before grabbing the best donuts we've ever had and a gingerbread latte at Glazed & Infused.

Then it was time for my first deep dish pizza experience at Giordano's, and it was absolutely delish! Emily and I met up with Nikki and enjoyed a round of cocktails while chatting over pizza while the guys had lunch at a rooftop bar. 

Saturday afternoon consisted of an architectural tour (we booked through Shoreline Siteseeing), a spin on the ferris wheel on the Navy Pier, and some drinks at the hidden tiki bar Three Dots & a Dash.

We had heard from several people that Cantina Laredo was the best Mexican place, so we checked it out for dinner and they couldn't have been more right. Amazing fresh table side guacamole, margaritas, and entrees.

Sunday morning, H and I grabbed brunch at Wildberry Pancakes before taking the red line train to Wrigley Field to meet up with Emily and K for our first Cubs game. Afterwards, we hung out in Wrigleyville and grabbed some more drinks before heading back into the city. We knew we needed to grab a real Chicago dog so we headed over to Portillo's, and of course the dogs were delish! This is coming from a girl who hates raw onions and relish, but all the ingredients together was amazing!

My Chicago Must-Do's:

~ Drinks at the Signature Lounge in the Hancock Building
~ Roof top bar hopping
~ The Bean at Millennium Park
~ Catch a Cubs game at Wrigley Field
~ Architectural River Cruise
~ A drink at Three Dots & a Dash
~ Deep dish pizza at Giordano's
~ Donuts at Glazed & Infused
~ Ride the ferris wheel at the Navy Pier
~ Eat a Chicago style hot dog
~ Sunday brunch

What are your must-do's in Chicago?


  1. Chicago is such a fun city! Glazed & Infused is on my list of places to try!

  2. Love the Signature Lounge pictures! Was that one of the oreo donuts you had?! Most amazing things ever!! Wish we could of had the chance to get together but so glad you had a great trip!!

  3. OMG what a fun trip!!! That pizza looks unbelievable! And the rooftop bars... omg jealous of those views!

    <3, Pamela

  4. Such awesome photos! What a fabulous trip with great food, company and scenery!

  5. I love the Chicago reviews! I am glad you had such a fun time! xo

  6. I LOVED following you along on IG because I love Chicago so much. I've only been once, but would move there in a heartbeat. I'm a city girl, and this city captured my heart for sure! So glad you had a fun trip :) Those donuts!! YUM

  7. Fabulous photos! I'm so glad you guys had a great trip!

  8. Looked amazing! ;)

    When I went to the Signature Lounge, we were blown away by the view as well. We also got the black bean dip with our drinks and it was delicious! But when I walked into the bathroom I pretty much had an "are you kidding me" look on my face and then proceeded to take a billion pictures. lol

    Next time you go, you MUST go eat at Hub 51 and the Donut Vault - both were recommended by Tess and they were amazing. I'm still obsessed with Hub 51. lol

    Last time I went we got a City Pass to do the Sky Deck, Field Museum, Shedd, Planetarium, etc. It's a great price to do all those things though I recommend the Sky Deck and Shedd the most. Field third but the planetarium was sort of meh for us.

    I'm glad you had such a great trip though! Whenever you go, it's definitely not long enough. haha

  9. This looks amazing!! I've only been to Chicago once, but it was for the Ryder Cup, so I didn't get to see the city at all. We didn't even get to try Chicago deep dish! This looks like an amazing trip, and to be honest, I can't stop looking at those donuts haha!

  10. I really need to make a trip there now. Looks like so much fun and the Mexican place would be on my list for sure!

  11. I haven't been to chicago in forever! I love it!! I want to go back!

  12. It looks absolutely beautiful! I want to go now more then ever haha

  13. All that food looks delicious! I've never been to Chicago but it is on my bucket list- everyone says it is amazing and I believe them, I just need to get there!

  14. Glad you had fun girlie love the recap!

  15. We went to Chicago for our anniversary this past year--it was pretty awesome, there's plenty to do, I know I could stay longer than a weekend, that's for sure!

  16. I have always wanted to go to Chicago! I've have hear as well that I will enjoy much more the NYC. My husband and I went to NYC for our honeymoon last December, and I had a blast but a lot of the sites left me a little disappointed with how much you build them up in your mind. I hear Chicago is wonderful and I really want to travel there very soon!

    Found your blog through the Let's Be Friends blog hop, and would love for you to check out my blog, a beauty and lifestyle blog. I love getting the opportunity to connect with bloggers and read new content!

    Thank You,

  17. Hi Kate! Just found you through the blog hop on The Dwelling Tree! When picking which bloggers to add, I immediately veered for your Chicago themed post because I'm a biiiit partial towards Chicago myself (now that I've been living here for two years and feel like an official Chicagoan! haha) Looks like you had an amazing time and definitely hit up a lot of the must-sees!