Kimmy’s Joyful Travels: Chicago

I have some exciting news! As you all know, I love trying out new recipes and making food for others. Nothing brings me more joy than bringing someone else joy through food! But, a new love of mine is traveling. My fiancé travels a lot for work and because of that we both have the travel bug! The distance can be hard when he is away for work, but we take full advantage of his hotel and airline points to enjoy awesome weekends in new cities together!

Anyways, we leave for a two-week long Europe trip in less than 2 months. We booked our flights 10 months and now we are only 6 weeks away! *CUE EXCITED SQUEAL* It will be my first time traveling to Europe!! *EEK* To build up the excitement, I have decided to start a new travel series on my blog leading up to the trip, called

Kimmy’s Joyful Travels

Jake and I have travelled a bit over the years and I wanted to share our adventures with you all!

First up, is Chicago!

We went on a 4 day trip to Chicago in July. The weather was perfect and we ate lots of GOOD Food!! I figured this would be the perfect city to kick off my travel series with because its a good mix of Food and Travel. We ate so much food on this trip! But, don’t worry we ended the trip with a workout at Barry’s Bootcamp 😉 #balance.

What we Ate/Drink:

Londonhouse Rooftop

  • We stopped here to grab a drink around 2:00 pm on a Thursday. It was the perfect summer day for a rooftop drink.
  • I recommend going for a drink after lunch or before dinner. There will be a line and if you’re going at a popular time, so be ready to wait. Thankfully, we only had about a 5-10 minute wait.
  • Once you’re in, order your favorite drink, enjoy the views, and maybe talk to a local! We actually met a man who gave us ideas of some other places to visit.
  • Keep in mind, you’re paying for the views, so the drinks are a little pricey here!

Big Star Taco

  • A popular taco and whisky joint in Wicker Park with a huge patio (This place was actually recommend to us by the local we met at London House).
  • You can’t make reservations and they are pretty busy. If you don’t feel like waiting 45-60 minutes, grab a seat at the bar or you can order from their To-Go window! They have a separate patio for on the go eaters.
  • We each ordered 3 tacos each, which was plenty. My favorite taco was the Al Pastor (slow roasted pork with pineapple). Jake ordered their whisky shot of the day, which is only $3, and we each got a cocktail!
  • Highly Recommend grabbing an uber up to Wicker Park to try some yummy/unique restaurants away from the touristy spots.

Quartino Ristorante

  • We stopped by this cute Italian Restaurant, in River North, for lunch, after coming back from a morning tour at Northwestern’s MBA school (for Jake, not me).
  • This place was my second favorite place of all the places we ate at while in Chicago. Jake said it was his favorite!
  • We got Orecchiette, veal meatballs, a bottle of wine, and prosciutto pizza for under $100 (after tip)! Now you can’t beat that price!!
  • Everything we ate was so amazingly delicious and makes us EXCITED for when we will actually be in Italy in less than 2 months!!


  • Stephanie Izard’s newest Restaurant!
  • A chic rooftop spot with pool. We met up with one of my best friends on a Friday night.
  • Unfortunately, we did not get to eat here because I didn’t make reservations soon enough and they had a 4 hour wait (no joke). If you want to eat here, I recommend making your reservations at least 2 weeks in advance.
  • I am obsessed with Goats, so I thought her restaurants WERE the cutest. She has a couple all within walking distance to each other in the West Loop area.
  • I am bummed I didn’t get to try their food, but for now I’ll just stick to using their Little Goat seasoning at home.


  • My FAVORITE place of the whole trip!!
  • They have two locations, we went to the one in West Town. We took the blue line from downtown, and walked 10 minutes to get there.
  • A Boho styled restaurant with a very unique and delicious menu! (I wouldn’t recommend it to picky eaters).
  • My favorite thing they do: they recommend most of their items as shareables. They give each person their own plate and serve the food as its ready (rather than serving all at once) and place it in the middle to share. If you go with a small group of friends, its a great way to try a lot of different items on their menu!
  • We went for brunch and each got a cocktail too. Both were very unique and oh so tasty.
  • Food was all plated beautifully and tasted even better than it looks!
  • Pictured below: Carmelized banana cinnamon roll and chicken and waffles.

The Purple Pig

  • I know I keep saying this, but I promise this was another amazing restaurant!
  • We heard they sometimes had long waits (~2 hours), so we put our name in early around 5-5:30 pm. To our surprise we only had to wait 45-50 minutes for a table for 2.
  • This is another restaurant that serves their food in shareables AND I am freaking loving this idea and now think all restaurants should do this!
  • We ordered a bottle of wine, Orecchiette, and milk braised pork shoulder. They also have a “build your own board” style menu full of cheeses and cured meats. You know you’re about to have great pork when it comes out with a SPOON.
  • This restaurant was the most expensive of all the ones we went to, so be prepared to spend over $40 a person.

What we Did:

  • My uncle was in town for the Race to Mackinac, so we met up with him at the Chicago yacht club and sailed on his boat for a bit.

  • Second City – HIGHLY RECOMMEND. 10/10 A lot of of big SNL names performed here before SNL! You’ll laugh your socks off!
  • Navy Pier (Fun fact: Did you know Chicago invented the Ferris Wheel?)
  • Shopped on Michigan Avenue
  • Rooftop Bars
  • Walked along the River Walk
  • Drank a carafe of wine at City Winery (located on the River Walk).

We’ve been to Chicago before, so we didn’t hit up a lot of the main museums/attractions. But, some other places to check out if its your first time:

  • Visit Sue the T-Rex at The Field Museum
  • See all of Chicago from the Top of Willis (Sears) Tower
  • See the fishies at Shedd’s Aquarium
  • Take a super touristy photo at the Bean

Where We Stayed:

  • JW Marriot
  • We flew into Midway and landed around 9:20 pm, so we decided to uber straight to our hotel since it was a little later. Sunday when we left, we took the Orange line straight to the airport. One ride is $2.50 and the station is right around the corner from the hotel we stayed at.
  • I liked that this hotel wasn’t in the most touristy spot, but close enough to walk to many attractions/restaurants (or take a short uber/train).
  • They have one of the best gyms I have ever seen in a hotel! They also have a spa if you feel like treating yourself!

Anyways, I hope you enjoyed the first post of my new blog series! Some other cities to look forward to in coming weeks are Niagara Falls, Franconia, NH, NYC, Dallas, and Colorado! Stay tuned!

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