Chicago is one of those cities where you just can’t see and do everything in one trip. This was my third time to the city and I still haven’t checked everything off my list yet. However, there are few places I would consider to be “must gos” if you’re there. This past week, it was too cold to do a few of the things we enjoy, but I’ll list them out anyway. Of course, a lot of these stops are focused on food and treats because that’s an obvious desire when traveling. I had lots of positive feedback from doing a travel recap and guide to Scottsdale last summer (view that post here), so I thought I would do one for Chicago as well. Here are some of my (and Luke’s) favorite things to do/places to go while visiting The Windy City.
Food
Ditka’s: I cannot say enough good things about this restaurant. The food and service is incredible. Honestly, probably the best filet I’ve ever had (and I’m a huge Kayne Prime fan here in Nashville). Ditka’s is named after Mike Ditka, famous from his time as the head coach of the Chicago Bears. It’s a very nice steak house with a more causal ambience… a different take on things. We dined at Ditka’s twice on this past trip and were not disappointed either time. White table cloth dining, sports memorabilia for decor, and high quality meats… Very different, very unique, a true must go!
Gibson’s: Gibson’s is another steakhouse in the Gold Coast neighborhood. It’s famous and for good reason. We had the best waitress I have ever had at a restaurant anywhere. The portions here are huge, but so delicious. Go when you’re really hungry for sure. Fun fact: Gibson’s is the only restaurant in the USA to have their own classification of beef… no wonder it’s all so delicious. Everything here is a step above!
Lou Malnati’s: Chicago pizza. You have lots of options, but this one is real good. There’s going to be a wait if you go on the weekend, so plan ahead! It’s also in the Gold Coast neighborhood. You can pre-order your pizza while you wait for a table which helps speed things up a bit. Huge fan of that process.
The Purple Pig: I feel like this restaurant is always recommended by many and I can see why, it’s very good and has a cool vibe. The portions are a bit smaller and the game plan should be to get several things for the table to share. Because it’s a very popular spot, expect a wait. We went for lunch to beat some of the crowd. Especially if you’re a foodie, you need to go! It’s near the river and just off of the Magnificent Mile, so there’s plenty to do right around.
Summerhouse Santa Monica: This is another spot Luke and I have been multiple times. Each time we’ve gone, it’s been for brunch so that’s all I can speak of but, in our experience, the food is good. What I love most about this place though is the ambience and aesthetic. Even though it was freezing outside when we went last week, I instantly felt like I was in California from the moment I sat down. It’s warm, bright, and cheery. Summerhouse is a very accurate name for this eating establishment.
Treats and Coffee
Goddess and the Baker: This place is a must!! That glittery gold latte that everyone freaked out about from my insta stories was from here. Best latte I have ever had… tasty and pretty! All the treats and coffee creations that Luke and I have tried here have been delicious!
Stan’s Donuts and Coffee: This place is a Chicago staple and for good reason. Not only do I love donuts and coffee, I love pink and I can get my fill of all of these things at Stan’s. There are also several locations in Chicago, so you’re bound to be near one at some point.
Petit Margeaux: This is a great spot to grab a quick coffee and pastry. It’s a small french cafe and patisserie attached to the Waldorf Astoria in the Gold Coast neighborhood. This was right on the backside of our hotel (The Talbott, which I’ll get to later) and very convenient. Delicious lattes and the cutest purple awnings and bulb lights backdrop from the Waldorf. Yes, please!
Sprinkles Cupcake ATM: Chances are you have seen a picture of or been to a Sprinkles bakery/ATM before. We actually used to have one in Nashville and then they closed down. Sad day. I think satisfying your sweet tooth by grabbing a cupcake out of an ATM is a genius idea and absolutely adorable. Worth a visit if you’ve never been to one before. 
Things to do
Signature Room at the 95th: GO! Go here at sunset if you want a real treat. The views of the city and lake are unreal. The Signature Room is on the 95th floor of the Hancock Building. You can get drinks or appetizers with the most amazing views without having to pay to go up to the touristy view floor— Chicago 360.
Field Museum: Luke and I love going to this museum. All the history that is archived here is incredible. When you’re finished at the museum, you can exit our the back and walk along the lake all the way to Navy Pier. It’s a long walk but, during warmer months, is very enjoyable.
Millennium Park: Because you’re going to want a picture with THE BEAN. When in Chicago, right? We also went ice-skating last week because they had a rink set up for the winter. That’s obviously a seasonal activity, but so fun!
Architecture Boat Tour: We didn’t do this last week because #frigid (I actually don’t think they were even doing them to be honest. A feels like of -18 degrees is not exactly ideal boating conditions ha.), but have done it during the summer when we’ve been in town and it is delightful. The history behind all the architecture of the skyscrapers is really interesting and cruising down the river on a pretty day is just lovely.
Sporting Event: With all the major pro-sports teams that Chicago has, there are lots of options to go to some sort of game at any time of year. We’ve been to Cubs games and most recently a Bulls game. So much fun and highly recommend. It’s also a way to bargain with the boys… “If you go shopping with me on Michigan Ave, I’ll go to the __________ game with you.” I personally enjoy sports, so these type of bargains are a win-win for me.
Shop Magnificent Mile: Pretty much any store you could possibly dream of going into is on or around Michigan Avenue. Whether your on a mission to find something in particular or just want to browse through the high-end designer showrooms, you can accomplish that with a trip down the Magnificent Mile.
Where to Stay
The Talbott Hotel: Luke and I have stayed at The Talbott hotel twice now and plan on returning for all of our future trips as well. It’s a boutique hotel located in the Gold Coast neighborhood of the city and is a real gem. The location can’t be beat and we walk to just about everywhere we go. Your minutes away from incredible shopping and restaurants and a delightful walk down Michigan Ave. to get further into downtown. The hotel is located on Delaware Ave. and although it’s right in the middle of everything, it’s on a quieter street and has a quaint feel to it. The staff here is wonderful and they always go above and beyond to make you feel welcome and enjoy your stay. The hotel has also recently had a facelift and the eclectic, mid-century modern vibe they have going on is top notch. PS: they have the cutest elevators which make for fantastic elevator selfies (a personal favorite of mine haha).
Luke and I really love visiting Chicago and it’s one of those places that we continue to make plans to return to. If you’ve been, do you have any other “must go” spots we should try out next time we are there? Happy Friday. xoxo.
