If you can get away, I highly recommend attending Chicago’s dining week or just a fun girls trip to Chicago! I went with a girlfriend over a weekend and we had such a lovely time dining at a bunch of restaurants participating in Chicago’s dining week (where you can try a three course menu, plus dessert, for $25 for brunch/lunch and $50ish for dinner! Such a good value). We dined at so many places and so I’m listing where we stayed and all the things we did and where we ate in this recap.
For our hotel we stayed at the Hampton Inn – Chicago West Loop. I highly recommend this hotel/location. It’s close to Fulton Market district, one of my favorite locations in the city, and also where Levain cookies is. The hotel has in/out parking which also makes it a great location if you’re driving.

During our trip I took a few notes at each restaurant/place we visited. I confirmed with my friend and it was nice to hear that she always thought similar, so nowhere was I like “oh this place is an A” and she thought it was a C or something lol. Here are the places in the order we visited them.

Day/Night 1
- Wolfhound Bar & Kitchen C- the food took forever (literally an hour and 13 min for our main courses after ordering). The food was just ok, the potatoes were good and the mocktails- the berry lychee spritz-was good. The service was not that great either, they kept mixing up orders so they’d bring your food to a different table, happened twice to our neighbors, only once to us lol. I’d skip this one.
- Levain Bakery A+ smelled so good in there, the smell of freshly baked cookies hit you right when you opened the door, it was very clean, they were really quick. And the cookies, omg, so so good. There’s a reason this bakery is famous, they’re worth it. The cookies were warm when we got back to our hotel (one can walk from the hotel to this cookie place, oh, and they’re open until 11pm).
Day 2
- The Doughnut Vault A The only reason it doesn’t get an A+ plus is because they were out of all but 2 doughnuts. They sell out fast. Doughnuts were so good, wish we could have picked other flavors. I’d definitely go back, this is a small spot, we tried it before brunch.

- The Dawson A We went here for Brunch. It had a Nordic room and had blankets on chairs! $25 for 3 courses!! The chicken and egg was so good! The service was great, they knew we were splitting everything and brought up 2 plates for each course.
- Next we drove and parked by Eataly (we used Spot Hero– you use it to find cheaper parking spots)
- Starbucks Roastery The biggest Starbucks in the world! It’s very big. They have nice bathrooms
- Jaleo by Jose Andres B- This was our lunch spot. The food was good but not great, burnt bottom on sandwiches, but I will say the sangrias were good. The staff was friendly. We both really wanted to love it but just didn’t.
- The Shops at Northbridge A – We went shopping here and around downtown Chicago. I discovered and bought several Trish McEvoy products at Nordstrom.

- 3 Arts Club Cafe at Restoration Hardware A+ Cannot recommend this place enough!! It’s a cafe and then a Restoration Hardware showroom on the upper floors. It’s so pretty, I had a great latte and cheese board and then it was so nice to walk around in the beautiful showrooms above. This wasn’t part of the Chicago dining week, but wow was it worth it, it felt like a little hidden gem. I’d recommend this place to anyone.

- Siena Tavern A, This is Top Chef Fabio Viviani’s restaurant. The whole menu was delicious, including their famous homemade pasta, but the best thing we ate was the roasted chicken, it was so so good with a lemon sauce. I got The Imposter na drink (peach nectar, mint, ginger beer ), wow delicious. They sat us quickly at the time of our reservation, friendly staff, the food was really good, the tiramisu was incredible.
Day 3
- Saba A- We went here for brunch on our last day. The French toast was great, apps were a little meh, deserts were really good.

- The Last Chapter– Our final stop was a book store. We were both kind of let down by it. It was only romance books which is fine, but it was kind of sparse inventory and there wasn’t anyone greeting or helping people. We were both just like meh to this stop.
My friend was amazing with planning, I was so impressed. She shared she uses Wanderlog – a travel app- it syncs with Google, puts things like operating hours in and then you can make an itinerary. Hope you’ve enjoyed reading about our girls trip to Chicago for Chicago Restaurant Week, and a big thank you to my friend Molly whose idea this trip was and who let me borrow some amazing photos for this post!



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