Before I even get into the Windy City all the wonderful things we love to do there and share some pictures from a recent weekend there, I have to ask you to bear with me. Today is the day I leave my oldest at college. Today we will be busy doing last minute things and getting his dorm room all set so if I'm not able to comment or email you back, know I'll be reading blogs in full force tomorrow to keep my mind off of this mixed emotion milestone.

Mr. Nine did a great job of erasing my worries for one weekend in our favorite city before these little birdies fly off on their own. 

We are so blessed to live just two hours away from Chicago and have been there many times. However, it never ceases to amaze us how many new things we stumble upon during each visit. I thought it would be fun to compile "Nine" of our favorite things in case you ever get the chance to explore this great city.

1. Riverwalk
All our trips to the city and we've never walked along the Riverwalk. What an amazing stroll on a sunshiny day. With its gorgeous scenery, pop up bars, boat watching and architecture admiring, it's a great way to see a fun part if the city. They are currently in construction to expand it so you can walk even further. Tiny Hat was a new, fun bistro. Had a delicious frozen rum concoction.

2. Michigan Avenue
I never really buy much on Michigan Ave, it's a little touristy but so fun to stroll for a bit on every trip. I always like to see what is new. There is a cool new Under Amour store and I just love how they dress the giant mannequin.

Also loved that they dedicated a display to our beloved Notre Dame Fighting Irish and of course using the number "9"!! Less than a month to kick off!!!

3. Marina/Lake Michigan Shore
After we were done along the Riverwalk, we turned around and walked the opposite way to Lake Michigan and admired the view with all the boats in the marina. Such a lovely day!

4. Rooftop Terrace
I am a sucker for a rooftop terrance and this one was right at our hotel. We went for a drink in the afternoon where we enjoyed sitting in comfy oversized chairs, watching corn hole and admiring the view. We went back that evening after dinner where we got to see fireworks over the lake and met some couples who told us that actually rooftop terraces made public are a rarity in Chicago. Lucky us, this one was an elevator ride away. It's called Steeterville Social.

5. Eataly
I told you about this place after my Mom's Birthday Trip so of course had to take Mr. Nine. He loved it, especially the brewery and found a new brew he loved. Just look at this meat and cheese plate we indulged in and I had my favorite moscato...Brandini

6. Food
You know when you go to Chicago, you can literally have anything you want to eat!! Pure bliss, if you find the right spots.
Here are some of our favs...
Yolk for breakfast, great "get in line" app..hour wait but we literally walked right up and our table was ready thanks to my husband and the app.....fabulous Eggs Benedict! 
Love West Egg for breakfast as well.

From my trip with Mom last November for her birthday...RPM Steak!

From our April trip for my Birthday...Our other favorite Steak place...The Capitol Grille

Our Favorite Italian: Carmine's, RPM Italian and Maggianos

Such a great caprese salad at Carmines.

7. Deep Dish Pizza
There is nothing like pizza in Chicago and because the wait is usually a couple hours and the pizza itself another 45-60 min, we don't always have the time to indulge but oh when we do....so worth it! The spots we know and love are Pizzeria Uno, Giordano's and where we devoured it recently: Gino's East

8. The Hotels
I think we found our new Favorite! We have stayed at the James, the Trump, the Hard Rock (back in its Heyday when it was great) among many others but The Loews is our new favorite and we WILL be returning. The smell in the lobby is intoxicating and probably enough to bring me back, lol, not to mention this is were the rooftop terrace is!!

The Trump is indeed amazing but pricey so cannot stay there every visit.

The Hard Rock was our thing and you can get great deals there but its getting older and just doesn't have the same punch.
Last time we stayed there for our Luke Bryan concert weekend

9. Christkindlmartket
If you find your self in Chicago around Christmas, this is a Must. For many years , we went to Chicago the weekend after Thanksgiving and this market was a tradition as we both have ties to Germany and love the culture.
Inspired by the Christkindlmarket in Nuremberg, Germany, which began in 1545, the Christkindlmarket Chicago brings cherished German and European tradition with international flair and local charm to Chicago. It's the city's largest open-air Christmas festival an is held every year in Daley Plaza from Thanksgiving to Christmas Eve.
Warm Gl├╝hwein mulled wine is a treat on a crisp, cool night.
Have you been to Chicago? What are your favorite things to do and eat there? 

I am so excited for Wednesday as I mentioned on Friday that Wednesday is National Smore's Day so get ready for food and fashion to celebrate this campfire holiday!

Happy Monday sweet friends....I can do this, right?



  1. Keeping all of this in mind for when we head out there next!! We are getting an eataly here in the next few months and I can't wait!! xo, biana -BlovedBoston

  2. I'm saving this for when we visit Chicago someday! You have me wanting to go before Christmas to hit up that outdoor market! I love anything Christmas related! And pizza is my favorite food ever so I've always heard how amazing the pizza is. Great post!
    Sarah at MeetTheShaneyfelts

  3. Be strong, lady!! I would be a mess. I've never been to Chicago and now you're making me want to go even more!

  4. Loving seeing your Chicago favorites! I'm sharing my Chicago staycation tomorrow! Eataly is the best!

    Doused In Pink

  5. Oh my goodness Gino's is my favorite pizza place in Chicago ! I love love Michigan Ave. many wonderful places to shop :) I miss Chicago and hope to go back soon. Happy Monday !

  6. Good luck moving him in today love! I hope everything goes super smoothly!! Loved reading this post--I have actually never been to Chicago but it's pretty high on my list! I'll have to bookmark this for when we take a trip there!


  7. Good luck with drop off! It's going to be an exciting new chapter. Love all these suggestions and the food...oh my! You look gorgeous on your "river walk". I have always wanted to visit Chicago but have not make it yet.

    Shelly||The Queen in Between

  8. Chicago has been on my list FOREVER! What a gorgeous city, and such an equally gorgeous couple! Looks like the best kind of trip, and hello that pizza looks divine! That's the first place I'm stopping if I ever get to Chicago! Have a beautiful week!



  9. Chicago is a great town but I've only ever been for the day! I love seeing everyone else's favorite things and places about a city . . . glad you had a good weekend! My heart goes out to you today mama . . . smile and kiss that boy goodbye and cry in the car. He's embarking on a grand new adventure and it's going to be fabulous!!! xoxo

  10. Such a great list, Andrea! Chicago is one of my favorite places, so much to do and SO much good food! I'm definitely with you on Michigan Avenue and the pizza! Happy Monday!

    xo, Rachel
    A Blonde's Moment

  11. Thinking of your today as you drop off your "baby" (they always stay our babies, don't they?) at college!!! He'll be fine and you'll be fine. I promise! Our oldest recently turned 25, and it seems a bit surreal to me. Where did the time go????

    I love your list of things to do in Chicago. Chicago is definitely on my "list," and I'll dig up your list if we ever make it there!

    Andrea’s Wellness Notes

  12. Chicago totally won me over as my favorite U.S. city, and I can't wait to return! It's just so pretty with so much to do and see, and the food.... oh the food! We stayed at the Hard Rock too, and loved it. Such a great location right by the river <3
    Green Fashionista

  13. Yum, the food pictures look amazing. I've only been to Chicago once, and we ate at Gino's. It was so good! My husband has never been, so I'd love to go back with him & take him to Wrigley.
    Praying for you today, and in the next few days, as you adjust to your new normal. :)

  14. I love places that have rooftop terraces like that. I'm such an outside person anyways so any place that brings the classy look of indoors out? I'm all about it

  15. Oh my goodness, all the food!!! Food and rooftops are my favorite things to check out in different cities!!! And I have stayed at a Loews in Atlanta before and loved it! I totally need to get to Chicago!

  16. Yes, you've got this! I've only driven through Chicago, but never got to stay and visit. Going on my list for sure!

  17. This made me hungry! Haha! I would love to visit Chicago one day and try all of these things! I hope you have an amazing Monday!
    xo, Lily
    Beauty With Lily

  18. I love that you did the top 9 things!! We love Chicago too. It's a bit of a longer drive for us, so we only make it a couple of times a year. I usually end up in the area a time or two for work as well. We used to make it out to some really cool restaurants when we visited my in-laws that live in the city. Now they've got two little ones and we have ours, so we are a whole lot more likely to order Giordano's in. I'm sure we'll be more adventurous again soon!

  19. I'm definitely saving this for future reference! We went to Chicago when my husband graduated from Navy training, but didn't get to do much sightseeing/enjoyment while there. I'd love to go back! I'm also definitely hungry now-haha Have a great week!

  20. I'm thinking that we need to make another trip to Chicago sometime soon! The river was definitely my favorite part of our last trip, and oh my goodness, the Chicago food is out of this world! I think that I need to make it back at Christmas this year!

  21. Chicago is my favorite! The architecture boat tour is a must sometime - I went a few visits ago and loved it! You get to see so much of the city. The Capital Grille is amazing, too. I love Portillo's - anytime we are near the city I always try to go and get a hot dog and chocolate shake. Thinking of you today!

  22. I love love love Chicago!

  23. Next time you come to Chicago we have to meet up! Totally agree the Riverwalk is a must! We love it too even tho we live here! It never gets old! Anyhow, so glad you had a such a great time in Chi city! Love ya! Happy Monday, love!
    xoxo, Vanessa

  24. Ooh, fun post and I'll be pinning it! We are going to Chicago in October when I run in the marathon and I want to plan a few things to do while we are there! That caprese salad does look good and just all the food you shared here! Yum! Hope your boys enjoy going to college in the city!


  25. Great post, Andrea. I went to college in the Chicago suburbs and it remains my favorite city. I will definitely have to go back soon before it gets too cold. Hope you are having a great summer.

  26. Yes to Carmines! When we went there, we went there twice for dinner, delicious!!! We love Chicago, Baby Fox always asks when we can go back. I think 2018 we need a trip to Chicago :) Good luck today!

  27. Ah! I love Chi-town! The last time we were there it was December so we definitely got to enjoy the Christkindlmartket! :) And I SO love all the deep dish pizza in Chicago. I haven't had it from Gino's East yet, but I've heard good things. It's on my list for the next time we're there! :)

  28. What a big day for you, friend! You are in my thoughts! And I love the Christmas market in Chicago! Can we meet there this year??

  29. Chicago is such a fun city! Now, I want to check out Eataly :)

  30. I would take the architectural tour from Navy Pier any chance I could. A trip to Licoln Park Zoo is fun especial good for kids. I love walking in Pilsen looking at all the murals.

  31. I'm saving this for when I get a real trip to Chicago. Going for my first time next month for literally 20 hours, and a few of those hours are for sleep. I will have to tackle at least one of these! Great guide!

  32. Chicago is such a beautiful city and that Marina area on the water is hard not to love! You're so lucky it's a quick trip to experience it in all the seasons. Christkindlmartket sounds so fun around the holidays and definitely would be a new experience for me. (which I love of course).

  33. Alas, I have never been to Chicago. Actually, I haven't been anywhere past Kentucky, Maryland, Tennessee, or the Caribbean. Darn it! BUT if I ever go to Chicago then I'm calling you STAT. That rum drink - well hello! The hotel, beautiful! The food, the scenery, and that blue dress! Love it all. But most of all I'm in love with the fact your baby is at college and though it is hard you are rocking it even with a few tears here and there! Be proud :) xoxoxoxoxox

  34. So fun seeing this after having gone to Chicago back in June with some friends! We totally went to that Gino's while there and the rooftop bar on top of Loews was on our list but we never made it unfortunately.


  35. Great post, Girlie! I hope I get to the Windy City one day! S and I were talking about it last night, actually! Her dad is flying there this week! Hope you've had a great Monday!

  36. We were just in Chicago this summer for a wedding! Only spent one day in the city and we walked Michigan Ave (bought a few things at H&M) and ate at Carmine's! Love you chica! You can do this!!

  37. I love that crocheted or lace dress, I wore a similar one last week. Lovely pictures, great food, and the gluhwein! Hmmmm, I like that.

  38. I have never been to Chicago and now these suggestions and photos are making want to go more than ever!! Looks so beautiful!

    xx, Elise

  39. You're making me want to visit Chicago!


  40. Love, love, love Chicago! I've only been once, but I cannot wait to go back! Thanks for the great list of things to do for next time! :)

  41. We are just over an hour from Chicago (Milwaukee) and love to make it down to Chicago once in a while. West Egg is delicious! We love going to Greek town for dinner too!

  42. I am dying to go to Chicago, it sounds like such an amazing city. A good friend of mine was born and raised there and it sounds fantastic, and now your pictures just add to that. Glad you got to have some fun, thinking about your son embarking on a new adventure and sending you love and hugs! XO -Kim

  43. I've never been to Chicago (I've actually only been to the US twice. Once to visit Vegas and New York and the other time to visit Washington DC and then we hired a car and headed down to Florida), but it's on my must-visit list! It looks gorgeous there! I must say I loved your outfit the last time you stayed at Hard Rock Hotel. Those boots and dress combo is GORGEOUS!!
    Suzy xx

  44. My children live in a Chicago suburb, so we visit often. I love Chicago! But I've hardly done any of the things you mentioned. I need to!

  45. Lovely walk through the nine favorites! Great places!

  46. Ugh, I'm a bit behind on my blog reading, so sorry for the late comment...but I LOVE Chicago. We have only been there once, a few years ago for my birthday. Our friends lived there at the time and gave us such great places to go, and we even went to a Cubs game which was SO awesome. I LOVED the Riverwalk. Eataly and Yolk look sooo yummy, and oh my the views and fun on that rooftop terrace...that sounds like the hotel jackpot! Loving all these beautiful pictures and the great places told by you...thanks for sharing!

  47. I will have to add Chicago to the top of my ballpark tour when the Jays come to town!

  48. Such lovely pictures and all your outfits are just adorable! I'm getting ready to make dinner and those food pictures look so yummy!

  49. I have never visited Chicago, but your activity list looks like a lot of fun. Thanks for sharing your travel photos and advice at the #HomeMattersParty this week.

  50. You hit the nail right on the head with the sky terrace and Gino's. I admit we try and hit Gino's at least 3 times a year and being about 40 miles south of chicago we have one in our neighborhood and they never disappoint! I am going to have to drive up and try Yolk's and Eataly. I am curious now! Thanks so much for sharing this with us at the DI & DI Link party. Have a great week. If you ever need dessert and haven't tried it for a lunch/dessert place (it's a bit touristy too but very yummy) you'll need to hit the cheesecake factory.

  51. I love Chicago. My husband and I have been together like 5-6 times. The first three things you mentioned are our top 3 destinations. I also love Pizzeria Uno and Capital Grille - we have one in MI too. We need to try Eately. Their prosciutto and cheese plate looks yummy. And OMG the Lewos hotel looks and sounds gorgeous!


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