How to Spend 3 Days in Chicago!

Chicago is one of the most culturally rich cities in the United States! Back in November, we met up with some of our closest friends and had a blast. There were so many places to eat and see, so I thought I would pull together a list of our favorite stops so you can explore these to during your next visit to the windy city. Enjoy!

Where to Eat in Chicago:

Lou Malnati’s Pizzeria

A trip to Chicago would not be complete without grabbing a slice of their traditional deep dish pizza. There are dozens of pizzerias to choose from, but many locals recommended Lou Malnati’s pizzeria since they are the oldest family name in the city for this style of deep dish pizza.

After visiting, we quickly learned why Lou Malnati’s is one of Chicago’s favorite pizzas! The crust was buttery and crispy, the sauce was absolute perfection, and the toppings were fresh as well. We ordered the traditional Chicago style pizza, and added pepperoni. I have 3 recommendations when visiting here: 1) Ask the waiter to go light on the sausage. Our pie was full of sausage, and it honestly overpowered some parts of the pizza, 2) the pizza is heavy, so don’t over order and 3) the dish takes around 45 minutes to cook. So be sure to order an appetizer like a salad to hold you until the pizza is ready.

Starbucks Reserve

If you’re a coffee lover, then I recommend visiting the famous Starbucks Reserve in Chicago, which is actually the largest Starbucks in the world! The lines can get a bit crazy, so I recommend visiting early in the morning. This Starbucks has 4 levels, with a cocktail bar, dining area, two levels for ordering coffee drinks and a shopping section on the ground floor.

Teatro ZinZanni

Teatro ZinZanni was hands down one of the most entertaining and immersive dinner experiences we’ve ever had. The show is located on the 14th floor of the Cambria Hotel. When we arrived, we immediately felt as if we stepped into another world. I recommend spending a bit extra to be as close to the center stage as possible, as their performers do engage with the audience throughout the show and between meal courses. I do not recommend this show for children, but it is certainly a fun and exhilarating show for a fun / unique nigh out, date night or celebration.

Maple & Ash

If you’re willing to splurge a little on dinner, then Maple and Ash should be on the top of your list. We went here for our friend’s anniversary dinner and were not disappointed with all of the surprises and service. Our dinner started off with a complimentary welcome cocktail. For an appetizer our table shared the seafood tower. Being someone who grew up on the coast and knows great seafood, this was hands down the best and freshest seafood tower I’ve ever enjoyed. The seafood tower was a collection of crabs, lobster, clams, and shrimp, smoked in a garlic butter sauce! For dinner we shared a bone-in ribeye, branzino, lobster truffle mac and cheese, asparagus, and brussels sprouts. Each dish was absolute perfection and one of my favorite restaurants in Chicago. If you decide to come here for a special occasion, be on the lookout for a special surprise on your menu ;).

The Violet Hour

The Violet Hour is a great little speakeasy to visit with nice music and wonderful seasonal cocktails. Since we were visiting in November, warm drinks such as a Hot Toddy were part of the menu. The speakeasy is hidden when you initially arrive at the location behind some street art. Be sure to make reservations in advance. No password was required when we visited.

Holu

If you’re a steak lover, then you should absolutely pay Holu a visit. This restaurant specializes in 90 day age steak, A5 wagu, fresh seafood, which includes enormous tiger shrimps! Everything about this restaurant was sublime. The service and food was 10/10. We absolutely loved our waiter @antithesis5603, who made our evening so special and cooked our steaks perfectly. Some of our favorite dishes for the night were the house pickles, lobster fried rice and definitely order the Meat Paradise to try a variety of 8 different steak cuts. We can’t wait to visit here again during our next stay in Chicago.

Devereaux

If you’re looking for a great location to have a nice rooftop cocktail, then I recommend visiting the Devereaux at the Viceroy Hotel. Since we visited in November, we were given beautiful fire pits, blankets, and heaters to feel comfortable outside while taking in the beautiful Chicago skyline in at dusk. There were even a few igloos available for booking if you choose to stay longer and make an evening of their rooftop service. All of their cocktails were of high quality and the service was great as well.

Adalina

For all of my Italian lovers, I recommend taking time to visit Adalina for a nice upscale Italian dinner. The decor of this restaurant was stunning and the food and service were even better. Each dish was perfectly seasoned and all of their pastas were made fresh daily. Some of our favorite dishes of the night were the truffle caesar salad to start, smoked meatballs, pecan crusted salmon and lumache seafood pasta. They served their salmon with gnocchi, but I recommend asking for a substitute or a different side. For dessert, our group shared apple cider donuts with poached apples and fresh chai tea gelato that was made in house as well (amazing seasonal dish!).

Harold’s Chicken

You cannot travel to Chicago and talk about their food scene without stopping in to visit Harold’s Chicken. Harold’s is a historically black owned chicken chain in Chicago that was established by Harold Pierce in 1950 on 47th street. When visiting here, I recommend ordering the wing meal with mild sauce. We tried a few other sides such as mac and cheese and greens. I wasn’t a huge fan of these sides, but the real star of the show was truly Harold’s chicken wing recipe.

Nobu

There are only a handful of Nobu restaurants in the US, and Chicago happens to be one of these cities. If you’re ever in the mood for fresh sushi, Nobu and their share style restaurant should be on your list. For the Chicago location, they have 2 serving styles – 1) You can review their al la carte menu and order as you please or 2) you can describe your food wishes to the server and allow the chef to create special plates for you! Some of our favorite dishes from the night were the: Yellowtail Jalapeño, Wagyu Dumplings, and the House Special Sushi Roll. If you also have time, be sure to visit their rooftop to enjoy a drink and take in the views of the West-Loop neighborhood.

Quick TikTok Video on Where to Eat in Chicago:

@elicitfolio

Checkout some of these great eats next time you’re in #chicago #chicagoeats #nobu #teatrozinzanni #adalina #mapleandash #loumalnatis #haroldschicken

♬ Kanye Went West-JP – D Sirrom / David Morris

What To Do When Visiting Chicago

Visit the Ledge at Sky Deck

The Ledge at the Sky Deck is a thrilling yet fun activity to do while you’re in the city. Upon visiting, you’re taken to the 103 floor of the Sky Deck at Willis Tower. You have to purchase your tickets in advance and you have a choice to pay for general admission or expedited. I recommend paying for general admission if you’re visiting on the week when it is not busy. If you’re visiting during the weekend, the expedited route may be worth the extra few dollars since lines are longer. Prior to traveling some 1,353 feet (412m) in the air! … Willis Tower also engages you in an immersive self-guided tour about Chicago. This tour was probably one of the best I’ve seen in a long time, sharing interesting facts on architecture, the city history, culture, and celebrities.

Visit “The Bean” AKA Cloud Gated

While you’re in Chicago, you have to take a trip to Millennium Park, in Chicago’s downtown loop and take a photo in front of “The Bean“, which is formally known as Cloud Gate.

Crown Fountain

If you’re looking to visit the “Bean” you can also swing around the corner and see Chicago’s interactive video sculpture called “Crown Fountain“. This 50 foot tower projects various faces from citizens throughout Chicago to showcase the city’s diverse culture.

Navy Pier

Depending on the time of year you visit, spending some time at Navy Pier and taking a ride on the Ferris Wheel is relaxing way to spend the afternoon and capture great sights of the city and Lake Michigan. There are also a good amount of food stalls at the pier, so you can grab a bite to eat as well.

AIRE Ancient Baths

If you enjoy spa retreats when you vacation, then you should definitely add AIRE Ancient Baths to your spa visit list! I wish I had more photos to share from this experience, but the facility did not allow cameras inside. The atmosphere here is absolutely amazing. You feel as if you are transported back into ancient times with low dim hallways, only to be brightened by candles, soothing sounds of multiple public baths (each with their own health benefits), lavender infused sauna rooms, salt exfoliation showers, and the treat of the day for my best friend and I was enjoying a red wine bath! That’s right … you read that correctly, a red wine bath. This was probably one of the most thrilling and intriguing spa experiences I’ve ever had. If you decide to book this service, you are escorted to a private room surrounded by candles and wine bottles, served wine and cheese as you relax in a marble basin that is filled with red wine. This is a must try experience!

The Tilt

If you love heights and thrills, I recommend visiting the John Hancock Center and purchasing tickets to the Tilt. The Tilt takes you up to the 94th floor, tilts you in the air, and allows you to view Chicago’s famous Magnificent Mile some 1,030 feet in the air. If you decide to visit here at night, why not visit Bar 94 before dinner and grab a drink? This is the highest rooftop bar in Chicago, and allows you to have some fun before heading off to dinner that evening.

Catch a Chicago Bulls Game at United Center

If you love basketball, why not find a game while you’re in town? This iconic city was once home to Michael Jordan who led the Bulls to their fame during the 1990’s. If you’re visiting during COVID, be sure to bring proof of vaccination in order to attend a game.

Go Shopping at Magnificent Mile

Before visiting, I only heard about Chicago’s shopping scene. However, when we actually visited, I was so impressed! There are so many blocks full of shops and famous boutiques. If you enjoy shopping while on vacation, I recommend starting early and making it a full day as there is so much to see!

There were so many other places we wanted to see and visit, but ran out of time. So I guess we will have to come back soon so I can continue to add to this list! If you’ve been to Chicago before, what are some of your must see recommendations?