Last year Will and I took a little trip to Chicago on my birthday weekend, and I wanted to highlight some of the places we went in case you are traveling to the windy city any time soon. This was my first trip to Chicago, but I know it won’t be my last! It was a blast.

Like on most trips, we took a red-eye into the city so we could maximize our weekend there. On weekend trips like these, we don’t really get much R&R because we want to see (and eat :)) as much as we can while we’re there. These are some of the places that we went while we were there.

3 Arts Club Cafe

3 Arts Club Cafe was our first stop when we arrived in Chicago. Hungry after our redeye, we needed to fuel up to start the day! Now, there are a few locations of the 3 Arts Club Cafe (one that recently opened up in Nashville), but when I found this spot in Chicago I just had to go!

It is a restaurant that is built in the middle of a huge Restoration Hardware showroom, so it is just a breathtaking place to dine. The place is gorgeous, with the main dining area as a huge, open atrium with cozy seating areas, lush greenery, and gorgeous chandeliers. The food was really good too! We split the smoked salmon appetizer and a sandwich because we had so many other places we wanted to try while we were there.

After enjoying your meal at 3 Arts Club Cafe, walk off some of your meal by checking out the gorgeous Restoration Hardware showrooms and their rooftop lounge and gardens!

Wrigley Field

If you have a chance to watch a baseball game at Wrigley Field you just have to go! We went to Sluggers World Class Sports Bar, in Wrigleyville, for a drink before going into the game to watch the Twins play the Cubs.

Au Cheval

After the baseball game, we worked up quite the appetite and decided to go to Au Cheval at the recommendation of a friend to try one of their famous burgers. It is actually owned by the same people that own the 3 Arts Club Cafe, but I did not realize that until after our trip!

We had a short wait to get in, but lucked out snagging a spot at the bar.

The burger was melt-in-your-mouth, delicious, and was so fresh. And just check out that bacon!

The Signature Room

For a one of the best views of the city, you should go to The Signature Room, in the John Hancock Building off Michigan Ave., for a cocktail.

Navy Pier

We had to check out all the touristy areas while we were there just to say we went. It was a nice day for walking, and we seemed to have walked around the whole city!

Navy Pier had great views, and some good people watching.

Millennium Park & Cloud Gate (The Bean)

Another Chicago landmark that is a must see is Cloud Gate (a.k.a. The Bean) at Millennium Park. The park is a beautiful place to stroll, and the bean isn’t the only attraction!

Cindy’s Rooftop in the Chicago Athletic Association Hotel

While you’re at Millennium Park you should head up to Cindy’s Rooftop for an awesome view of the park and a delicious craft cocktail. You may have to wait in line to get in, but it is worth it for a view off their balcony. The drinks were delicious too… that is, if you can decide what to get because there are so many drinks to choose from!

Sapori Trattoria

I found this, hole in the wall, Italian place in Lincoln Park area off of N. Halstead Street, and it was so good, sometimes we talk about flying to Chicago just to eat at this place again! It was seriously some of the best Italian food I have ever had.

The restaurant, Sapori Trattoria,  is nestled in an unassuming building (it looked like they were getting a new sign when we were there, we almost missed it), but it is very nice once you get inside.

We were seated right away (we did make a reservation) in a cozy little corner upstairs, and had great service too. The food is traditional Italian, and so delicious (if I haven’t said that already ;).

Will had a pesto gnocchi with sun dried tomatoes, and chicken (it was so good, I have tried to re-create this dish at home). I had a lobster ravioli that was to die for! All paired with a tasty red wine…

I wish I had taken pictures of the food, but we were enjoying each other’s company and the food too much. If you want delicious food and a non-tourist trap, this place is a must!

Side Note: Sapori Trattoria also offered occasional cooking lessons, which I thought was pretty cool. And the wine (pictured above) was so delicious, I took a picture of the bottle so I could try to find it again…

The Green Mill Cocktail Lounge

Will is a big jazz fan, so after stuffing ourselves at Sappori Trattoria, we headed over to The Green Mill for a night cap. This jazz bar was really cool, and used to be an old hang out of Al Capone! They have hung on to the nostalgia of the place too with minimal updates throughout the years, including still using a land line phone and old-school cash register! Along with the old-school cash register, however, they are a cash only bar, so just be aware of that if you want to check out this cool place.

Starting a blog was just an idea when we were on this trip, so my pics aren’t the best (and a little grainy from using a phone), but I hope you all enjoyed this post! I can’t say enough… GO TO SAPORI TRATTORIA IF YOU’RE IN CHICAGO, but all these places I would go to again!

Where are your favorite hot spots in Chicago? Comment and let me know!

And subscribe to Ship’s HQ so you can get all my posts straight to your inbox!

Cheers,

Ship