A recap of our week in Chicago – what we did while we were there, all the good food we ate, and what I wore.

Last week, Philip and I spent the week in Chicago celebrating his birthday. We had the best time exploring and eating our way through the city.

After our trip, tons of you asked for recommendations on where to stay, what to do, and what to wear while traveling there.

So today I’m sharing all about the hotel we stayed in, the activities we did each day, and links to everything I wore during the week.

Where we stayed in Chicago

We stayed at the Trump International Hotel. It was a perfect central location that was super easy to get to everything, and it’s the third tallest building in the city, which Philip loved. We stayed on the 24th floor on the city side (not the river side) and had great views.

Anywhere in that area by the river and the bridges is a great choice.

What we ate in Chicago

Deep dish pizza:

Lou Malnati’s
Giordano’s
- There are several famous deep dish pizza places in downtown Chicago. We were there for four days and didn’t feel like we could try all of them (ha!) so we chose these two. So many people said Giordano’s was best, but it was definitely more of a chain restaurant feel (they actually are a chain) and we thought Lou Malnati’s was significantly better. I wish we’d had time (and stomach room) to try all of them!

Gold Coast Dogs

Our plan was to go to the Cubs baseball game on Friday and get a Chicago dog, but the game was cancelled because of the rain. So instead I had to resort to getting one at the airport before our flight (a hot dog before a flight…I like to live on the edge..). Chicago dogs are different than any other kind of hot dog. They are served on a poppy seed bun and topped with yellow mustard, sweet relish, onions, a pickle spear, tomato slices, and sport peppers. I was honestly a little nervous about it, but it was unexpectedly delicious!! I don’t even like sweet relish, but it all mixed together so well and was super good. I’m glad I tried it!

Italian Sandwich

Portillo’s
Al’s
- Italian beef sandwiches are also famous in Chicago, and there are several famous places that sell them. The most famous is Portillo’s, but we also heard amazing things about Al’s, so we did a back to back taste test to see which we liked better. You have to get them with peppers and dipped in gravy, and although both were excellent, the meat at Al’s was definitely better. The Chicagoans who follow me were outraged by this judgment on their beloved Portillo’s…if that’s you, relax, we still liked Portillo’s. Just thought the meat was better at Al’s.

Gibson’s Steak House

This is a famous steak house in a really nice little neighborhood in downtown Chicago. We loved walking around through the shops and then had dinner at the steak house. It was packed, so definitely get a reservation. The steak was incredible, but it’s famous for their Macadamia Turtle Pie. We got one slice, and when it came out it was absolutely humongous. Like bigger than my head (it’s $21 for one slice, so at least you get your money’s worth). We definitely couldn’t finish it, but we took it home and put it in our hotel room freezer and had the rest of it a few days later. It was delicious, but take a group of more than two if you want to try it, ha!

Wildberry

Several of my readers on instagram shared Wildberry as a good brunch spot, so we decided to go on Friday afternoon. They closed at 2pm, and we got there at 1:20. It was pouring rain, and since they were close to closing, there wasn’t any wait and they said we could come in as long as we ordered by 1:30 and paid our bill by 1:45, and then we could stay after that as long as we’d like. It worked out perfectly and it was DIVINE. We had the Barbacoa Chilaquiles and the Berry Mascarpone Waffle. They were both incredible. We ran by the restaurant the next morning (Saturday) when the sun was out and there were probably 80 people waiting in line outside, so we felt really lucky that we got right in the day before. If you have a chance to go, you should!!

Parlor Pizza for Tacolatos

After dinner one night, we stopped by Parlor Pizza and got a Tacolato from the Dessert Dealer inside. It’s a waffle cone taco shell with gelato in it and topped with lots of different topping. We got the caramel one with caramel gelato, caramel sauce, chocolate covered pretzels, and rolos. It was sooo good.

Donuts:

Stan’s
Do-Rite’s
- We stopped in Stan’s donuts for a donut one morning and it was good, but we went in Do-Rite’s when we went out to Wrigley Field and it was even better.

Chicago Mix Popcorn from Garrett Popcorn

Another Chicago food item people told us we had to try was the Chicago Mix popcorn. It’s a mix between cheese popcorn and caramel popcorn. I was dubious of the weird combination, but as we stood in line wondering aloud if we should try the “Mix,” the lady in front of us said we had to try it. So we did, and it was surprisingly tasty!!

Molly’s Cupcakes

This is a cupcake shop and the owner won the Cupcake Wars TV show a few years ago. It was a cute shop with plenty of seating, and lots of flavors of cupcake. We tried a few and the Nutella Peanut Butter one was by far the best!!

What we did in Chicago

Art Institute of Chicago

My husband and I love to go to art museums in different cities and this museum was fantastic. It had several very famous paintings and so much other gorgeous art.

Observation decks:

Willis Tower
Chicago 360
- We did the Chicago 360 deck in the day, and the Willis (formerly Sears) Tower at night. Both were spectacular. Both have upgrade options to do the Ledge and the Tilt. We didn’t do either and still had a great experience. The Willis Tower had a fun museum to walk through with photo ops and informative videos and signs, so that definitely added to the experience!

Big Bus Tour

We went on the Big Bus Tour in New York and it was a little cheesy with the audio tour, so I was a little hesitant to go on this one. But it’s a great way to see the city quickly, so that’s why we chose to do it again. And then our bus driver ended up being the tour guide and he was fantastic!

Navy Pier

We went down to Navy Pier one evening and walked all the way down it. I didn’t realize it was so huge and mostly indoors until we got there, but it was nice to walk all the way down inside where it was warm (it was unusually cold while we visited). We went outside and took a ride on the ferris wheel, which was totally worth it for the great views of the city.

Architecture Boat Tour

So many people recommended this, and when the sun came out on Saturday morning, we booked tickets so we could go before we flew home. The tour was 90 minutes and was so informative and gorgeous. The tickets said to arrive 15 minutes before, and we arrived about 25 minutes early and were almost the last people on the boat, so arrive EARLY so you get a good seat! There are seats on the bottom of the boat, but you definitely want a seat on the top where you can see everything much better without roof obstruction!

The Bean (Cloud Gate)

Of course we had to stop by The Bean while we were in Chicago! Definitely a landmark worth checking out and grabbing a picture.

Cubs Game

We planned to go to the Cubs game, not because we’re fans necessarily, but because it’s just a fun experience (and I wanted a hot dog!). But it was rainy all week and the game was cancelled. Next time!

L Train to Wrigley Field

Philip still wanted to go out to Wrigley Field, but it’s a little way outside of the city, and when we looked at Uber rates, it was $35 one way to get there. We decided to take a ride on the L train just to check out the Loop, and realized that the train would take us straight to the Stadium, and a one-day ticket for two people was only $10, so we went there and back for WAY cheaper than if we’d done an Uber. It was perfect and we got the train experience!

Magnificent Mile

We didn’t really do any shopping (Philip bought a coat for himself since it was so cold), but we did walk down Magnificent Mile a few times because it’s fun to window shop and walk into pretty shops. I was surprised at how clean and nice the area was, with gorgeous tulips planted literally everywhere!

What I wore during our trip

Honestly, it was a weird week during our trip there…it was in the low 40s and was windy and rainy most of the time, so my outfits basically all looked the same…long black coat, jeans, a sweater, and boots. Here are links to the things I wore over and over during the week.

BLACK WOOL COAT
GREEN PUFFER COAT (I layered these coats together since I was so cold!)
WOOL SOCKS
BLACK BOOTS

I also brought my WHITE ROTHY’S SNEAKERS (code MERRICK20 works still!) but only wore those on the last day when the sun came out.

This CROSSBODY BAG was also a great bag for the trip cause it was small enough to go under my coat and held a room key and my phone and some chapstick.

Our 24 hour trip through Milwaukee

At the beginning of our trip, we rented a car for 24 hours and drove up to Milwaukee. My dad went to Marquette Dental School, and although they had moved away from Milwaukee by the time I was born, I was born not too far away and we lived about an hour away. I’ve heard about Milwaukee my whole life, and since we were so close, decided to go up and stay for the day.

We stayed in Historic Third Ward, which was darling, and then drove around downtown and through neighborhoods and along the water. Everything was just so beautiful. It was for sure worth the stop! And of course we ate Wisconsin cheese curds!

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