The Best Chicago 4 Day Itinerary

If there’s one thing I love as much as eating it’s traveling. I love to research a place before I visit. Find out all of it’s must do’s and see’s but also discover the little hidden gems. As expected by my hubby, I did the same for our first visit to Chicago. Here is our 4 day itinerary to help you plan your own vacation to the windy city.

Day 1:
We stayed at the London House hotel. It’s riverfront and within walking distance to many of the places you’ll more than likely be visiting. The hotel is gorgeous, from it’s lobby to our room which was a corner suite with amazing views of the river and Michigan Avenue. It has a great rooftop lounge which you can enjoy in the warmer months.

We checked in, relaxed a little and then started our first day exploring Chicago. Our first stop involved breakfast. We walked to Wildberry Cafe where I had some of the yummiest cinnamon roll pancakes ever. There is usually a big line because it’s a pretty popular spot so try to make it over either close to opening or during non-peak hours.

After breakfast we walked over to “the bean” for pictures of course. It was right before lunch so there weren’t that many people walking around.

From the bean we walked to the Cultural Center where I wanted to take pictures of the world’s largest stained glass Tiffany dome.

We then walked to the Art Institute of Chicago. How much time you’ll spend there depends on how much of an art lover you are. My husband and I aren’t that big on art so we were there for about an hour just looking at the pretty paintings and sculptures etc..,

After the art institute we walked to the Chicago Athletic Association and made it up to their rooftop restaurant Cindy’s for some afternoon drinks and a snack. I definitely recommend a visit to Cindy’s, the drinks and atmosphere are great and you get one of the best views of Millenium park.

We then made our way back to the hotel to recharge our batteries before dinner at Girl and the Goat . I was fortunate to get a reservation. It is one of those must do’s as far as restaurants go in Chicago so you will want to score a reservation early on. The meal and service were exceptional. I recommend ordering at least five different dishes to share.

After dinner we decided to walk across the street to Bombobar for their s’mores hotter chocolate. This was a dream in a cup, delicious creamy and rich hot chocolate topped with torched marshmallows, Hershey chocolate, graham crumbles, a small donut and chocolate biscotti. It was the perfect way to end our first day in Chicago.

Day 2:
On our second day we chose another Stephanie Izard restaurant for breakfast called Little Goat Diner. I loved the diners retro feel, from the decorations to the servers uniforms. The food was delicious and unique. I ordered the bull’s eye french toast which is made with crispy chicken, fried eggs in brioche french toast, topped with bbq maple syrup and strawberries.

After breakfast we Uber’d to the Skydeck. Definitely take the “ledge” picture, it’s worth conquering your fear of heights for the views and an awesome picture.

For lunch we went to the gorgeous 3 Arts Cafe at Restoration Hardware. Expect to wait a while for a table. On the plus side, because it’s located in a store, there are plenty of nice comfy couches you can lounge in while waiting.

After going back to the hotel and resting a little, we walked to dinner at Lou Malnati’s Pizzeria for authentic deep dish pizza of course.

It was really cold on most nights during our visit so a lot of hot chocolate was involved. On this night, after having the delicious pizza we chose to walk to Xoco by Rick Bayless for Churros and hot chocolate.

To end our second night, we went up to our hotels rooftop for some beautiful views of the city.

Day 3:
For breakfast on our third day we made reservations at Mindy’s Hot Chocolate. Mindy Segal is a James Beard award winning pastry chef, her restaurant reflects her dedication to the craft. As you’d expect, on the menu she has some excellent hot chocolate options that come topped with a house-made marshmallow (YUM.)  The restaurant also has a great brunch menu. There was a lamb hash special on the day we stopped in and it was perfection.

After brunch we visited the Lincoln Park Zoo. It isn’t as big as other zoo’s we’ve visited but we enjoyed it. On our visit we saw polar bears, tigers, monkeys, a Lion, sea otters and even a kangaroo.

After the zoo we went to Navy Pier and rode the Centennial Wheel. I recommend a visit to the pier, the views are great and the views of Chicago from the wheel are even better!

A visit to Chicago isn’t complete without a stop at Portillo’s for a Chicago style dog. A Chicago style dog is topped with mustard, relish, celery salt, freshly chopped onions, sliced red ripe tomatoes, a kosher pickle and sport peppers inside of a poppy seed bun. This is definitely the place to go for one.

I made reservations months in advance for The Aviary by the Alinea Group. They require a $20 deposit per person to hold your booking and is applied to your final bill. The experience is excellent, from service to presentation. Attention to detail is in every single thing brought out to your table. The picture to the left is of the “chicharron” and I don’t know about you but that’s the biggest one I’ve ever seen.

I think something else that you must do while in Chicago is listen to live Jazz. We ended our night with just that at Untitled Supper Club. We loved the venues speakeasy vibe. The performer that evening was wonderful, as were the cocktails. You’ll want to check their calendar as there are different performers almost every night.

Day 4:
Sundays mean brunch, for me anyway, so we headed to Blue Door Kitchen by Chef Art Smith for some chicken and waffles. The restaurant is absolutely adorable with little Victorian details throughout. The menu is farm to table, with plates made from fresh, seasonal ingredients. The cocktails are garden to glass with herb elements like in the Pear with me which is made with pear infused tequila, rosemary, lemon, cranberry bitters, and bubbles.

After brunch we were fortunate that the day was warm enough for there to be architecture river cruises running. These tours take you all around Chicago, sharing with you interesting facts about the many beautiful buildings that you’ll see from the river.

We then walked around Michigan Avenue where I did a little shopping and then we headed back to the hotel to rest before our last dinner in Chicago. For that meal we chose Bavette’s Steakhouse and let me just say it is one of the most memorable dinner experiences we’ve had. The restaurant is very romantic, dim lighting and red leather booths, it’s perfect for a date night. Everything we ordered was exceptional. I recommend getting the baked goat cheese as your starter ::drool::

Day 5:
On our final morning in Chicago we decided to start off with coffee and a donut. We first got a donut at Do-Rite and then walked to coffee at Two Zero Three inside Virgin’s hotel. I love cheese danishes so I was thrilled when I saw that Do-rite had a cheese danish donut. It went perfect with the mocha latte I ordered at Two Zero Three. After our little morning break we stopped in at Garrett’s Popcorn to bring some back for the family. My favorite popcorn there is the Garrett Mix which is their cheddar and caramel popcorn.

We walked a little around downtown and then made our way back to the hotel to get our Uber to the airport.

This pretty much sums up what we did in our visit to Chicago. Hope it helps you explore this incredible foodie city in all its glory.

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