Chicago Vacay Weekend Highlights

Surprise! I was in Chicago over the weekend! Some of you who follow me on social media probably realized that MG and I had taken a little long weekend trip to Chi-town :)
We left early Thursday morning and got to Chicago and our hotel around 11am. We immediately dropped off our bags and went to explore. Lucky for us, the weather was perfection the entire weekend.

Here are my Chicago weekend highlights (prepare for photo overload!)

-obligatory selfie in the Bean
-delicious lunch at The Gage (get the smoked salmon BLT if you go!)

-walking around Millennium park, and then all the way up to Oak Street Beach (so cool to see beach and lake in one direction, and behind you see huge city buildings)
-shopping along magnificent mile

-room with a view

-happy hour at City Winery on the river and meeting two local girls who we ended up chatting it up and exchanged info with after asking them to take our photo
-Took in the beautiful views on our walk to dinner
-Dinner at Joe's seafood: had the best crab bisque of my life, crab stuffed shrimp and this amazing corn they had on special
-Made friends with our waiter who gave us his info to hook us up if we ever came back to the city again (seriously, people were SO nice!!). He also hooked us up with a free key lime pie for dessert that we couldn't finish because we were so full!

-Architecture Boat cruise (highly recommend if you guys have never been to Chicago!)
(we saw a ton of buildings and neat architecture, but these are just some highlight photos)
-partook in Chicago dogs (luckily we had walked 7+ miles the day before)
-rented a two person coupe/bike and rode out to the planetarium and got a fun view of the city from the lake

-got a pre-dinner drink at The Wit rooftop (my drink was called Liquid Lunch and it was SO tasty)
(the building on the right is the one they use in The Good Wife)
-dinner at The Purple Pig--waited an hour for a table but it was SO worth the wait because the food was insanely good (and the sangria was almost the size of my head!)
-a yummy early breakfast at Wildberry, then explored Millennium park before all of the tourists came out. 

(this was actually two screens that would change faces, and you could walk in the middle of the water between the two screens)

-did a walking food tour in the Gold Coast/Old Town area where we got to try Chicago deep dish pizza, a sushi place, tea, sample different spices, tried out oils and vinegars, a fudge/chocolate shop, and a bakery with some perogees and macaroons, all while learning about the history of the area
(that building photo on the right is the old Playboy Mansion)
-met a really awesome couple from Detroit who were celebrating their one year anniversary, and were staying at our hotel, too

-got a beer with them after the tour and realized how much we all had in common; exchanged information and made plans to meet up later that night after dinner

-spent some time along the river people and boat-watching (ended up chatting it up with the captain of a small, insanely gorgeous boat, who gave us some of the boat swag)
-went to dinner and then met up with the Detroit couple to go up to Signature Lounge of the Hancock building for a city-wide view and a round of drinks

-got to take in the view once the clouds cleared
-up early Sunday morning for our flight back, and got reunited with our little love, who was exhausted from his time with our friends while we were gone

There was seriously not a bad moment of the trip. We did so much walking (which was good because of all of the insanely delicious food we were eating), got to see so many cool spots, and meet some really awesome people, and getting to do it all with MG was the best part. Honestly, the worst part of it all was leaving.
Chicago definitely has a place in my heart as one of my favorite cities!


  1. Ahhh you little sneaky lady you!! Gary is headed there soon and I keep telling him that the architecture tour is a must! You guys were able to pack so much amazing stuff in and literally made me realize that Chicago is perfect for a little weekend getaway!! I'm taking notes!! xo, Biana -BlovedBoston

  2. I was seriously LOVING all of your pics on IG. I've never been to Chicago but would love to someday! And i'm so thankful you had great weather!!

  3. Ahh so jealous of your trip to Chicago! It's definitely on my bucket list. Your weather looked amazing for sure! That hotdog has me drooling this morning. Glad you guys had an amazing trip!

    <3, Pamela
    Sequins & Sea Breezes

  4. Spontaneous trips are just the best! Especially when they're to awesome destination cities like Chicago! Ive never been but everyone I know who's been only has great things to say about it. Y'all obviously had the best time ever! Looks like I'm gonna have to add Chicago to my "travel to" list! :)

  5. Love Chicago. You all packed a lot into that little trip.

  6. omg it looks like an amazing trip! I wish I was there. you and MG had a great time and it shows! Weather looks gorgeous.

    Trish - tales from trish

  7. I have always wanted to visit Chicago, it's definitely on my list!

  8. How FUN! What a perfect getaway!! I'm so glad the weather was amazing and that the whole trip was just GOOD! You guys totally deserved this! I'm dying to go to Chicago someday (especially for the food, ha ha!) Definitely at the top of my vacation destination list! Ah! I have so much I want to see... I hope we are able to fit it all in during our life time, ha!

  9. My husband and I live right outside Detroit and go to Chicago every chance we get! It is definitely my most favorite place to visit, it never gets old :) Looks like you had a great trip!

  10. Ahh looks like so much fun! I've only been to Chicago once, but I loved it. It's such a fun city with SO MUCH to do!

  11. I'm glad that you had such a nice trip! You really lucked out with the weather this weekend. And, look at you guys making new friends everywhere! That's the Midwest for ya. :)

  12. So fun! I've only been to Chicago once, on a short trip. This makes me want to go back and explore more!

  13. Wow you have me dying to go to Chicago now! All your food pictures look AMAZING! I will be re-visiting this post in the future after I convince my hubs to take me there ;)

  14. I LOVE Chicago! LOVE it. Looks like you had a great time! It was seriously some of the best food I've eaten and I didn't feel guilty because I walked 14 miles in one day! :) Glad you had such a great time! xo

  15. Yeah!!!!! So glad you had such a wonderful trip! You are making me totally miss our annual Summer trip! Isn't that the best meeting random couples and then getting to hang with them? Mark and I always seem to do that!

  16. You guys did Chicago right!! So glad you had a great time with perfect weather! Was that a Portillo's hotdog?!

  17. So glad you had a good vacation, you so needed it after summer school!
    Looking at all these pictures are making me super jealous and hungry. Can't wait to head to Chicago, everyone always raves about it when they go so I am definitely going to head there next summer.
    Food tours are the best, I always end up booking one on vacations.

  18. Hooray for The Purple Pig!! I'm glad you loved it. I have a conference in the city in December and am already plotting how to fit in a trip to The Pig!!

  19. Love love loved following along with all of your updates, snaps and instas!! Looks like so much fun!!

  20. Sounds like you had an amazing weekend!! Those hot dogs are making my mouth water...were they Portillos?!? They have my all time favorite hot dogs!

  21. Wow what a fun trip! This makes me miss Chicago. We went last year and did a lot of similar things. Had dinner at Purple Pig too and waited forever but the food is excellent! The view from your room is perfect. Loved also going for lunch/brunch along the river and drinks at different rooftop bars.

  22. Oh how I LOVE Chicago! Such an amazingly beautiful city with the best food ever! I was living vicariously through you on Instagram and Snapchat all weekend <3

  23. Hi Jen! I'm glad that you enjoyed your trip here. The Gage and the Purple Pig are both great restaurants. I have never been on that food tour, I will have to check it out some time. I just go to Old Town when I go to the gym haha. Anyway, glad that you had a fun time and met some nice people. :-)

  24. I don't usually care for big cities, but I would love to eat pizza in Chicago!

  25. Chicago is one of my favorite cities, it looks like you had an amazing weekend! Xo, Stephanie

  26. Chicago is great!!! I live about 3 hrs from there. I've only been once since moving to Michigan and I really need to go again. You gave me so great ideas! Thanks for linking up this week.

    ~Ashley @ A Cute Angle

  27. OKay, I just devoured your Chicago post over lunch and pinned a million things to remember for our August trip! SO SO excited - thanks so much!! - Meg, Life of Meg


I LOVE hearing your thoughts and comments--so, make my day and leave me some lovin'!