3 days in chicago

3 Days in Chicago: The Ultimate Itinerary From A Local

3 Days in Chicago: The Ultimate Itinerary From A Local

Chicago is one of the United States’ most famous cities. It’s architecturally beautiful, a center of art and culture, it’s full of history and one of the best places for deep-dish pizzas in the world. The Midwestern charm that Chicago has is real, and you’ll love it! There is so much to do in Chicago that you can spend weeks on end trying to do everything there is to do in Chicago. But a long weekend in Chicago is enough to see the highlights of this beautiful city. So I put together this 3 days in Chicago ultimate itinerary from nonother than yours truly- a native straight from the Chicago streets.

Day 1 in Chicago

Check into Swissotel Kids Suite at Swissotel Chicago

Designed by renowned Chicago architect Harry Weese, Swissotel Chicago is an award-winning luxury hotel facing the Chicago River and Lake Michigan. It is just a short distance from the Magnificent Mile. This breathtaking hotel will truly make you smile when you step into the Swissotel Chicago.  

From sunrise views of Lake Michigan to views of the Windy City’s skyline, the Swissotel has a range of classic, king rooms and suites for any occasion. This hotel has 662 guest rooms and suites, five premier ballrooms, state-of-the-art penthouse fitness centre, and the best service a guest can ask for. 

Since I brought my family downtown Chicago for a little staycation, we stayed in the Kids Suite. This kid-friendly themed suite offers kids their very own sperate but adjoining room. Talk about a Mom’s dream come true! This suite came stocked with kids toys galore, coloring books, stuffed animals, kid-sized table and chairs, their own bathroom, and two twin-sized beds complete with matching comforters and pillows. 

And is if that wasn’t enough, when you walk around the corner of this suite, there is a beautiful living room complete with spectacular wrap-around views of Navy Pier to Millennium Park. 

This suite also features a total of three bathrooms, including an oval tub in the Master Room. It has an executive work area, a spacious parlor, a pull out couch, a King Bed, and a skyline for days. 

In-Room Dining is available for those that don’t want to leave their room. The Amuse Bar and Lounge is also open for a Grab and Go breakfast from 8:00 AM – 11:00 AM. And last but not least, The Swissotel has an adjacent restaurant, an Italian Seafood Steakhouse, The Palm that offers take out only for lunch and dinner daily from 11:00 AM – 9:00 PM. 

After we checked into this beautiful hotel, we decided to head out to dinner. And since this hotel sits in the heart of the hustle and bustle of Chicago, we had many food choices. We decided on Pizza, a food that Chicago is very well known for. 

Dinner at Lou Malnati’s Chicago - Gold Coast

Considered the oldest family name in Chicago pizza, Lou Malnati’s is as rich in history as its pizza is in flavor. They have many locations, but the one we visited and is close to the Swissotel is the one in the Gold Coast. Lou Malnati’s has so much to offer from their very famous flaky, buttery crust of their deep dish pizza to their savory Penne Ala Malnati Pasta this restaurant will leave you wanting to come back for more. There is a variety of food on the menu, including Salads, Pasta, Pizza, Sandwiches, and mouth-watering desserts like the Tiramisu that is soaked in espresso, layered with mascarpone cheese and topped with cocoa powder.

Day 2 in Chicago

Grab and Go Breakfast from Amuse, lobby bar at hotel

Amuse, located right in the lobby of Swissotel, is currently only open for Grab n’ Go Breakfast. It is convenient, fast, and perfect for those that want to take full advantage of their time in Chicago. Their menu includes an array of breakfast items, including breakfast sandwiches, pastries, muffins, bagels, and fruit.

Photo Credit: Swissotel Chicago

Explore on your own Chicago Lakefront Trail by bike from Bobby’s Bike Hike

Since 2002, Bobby’s Bike Hike has proudly called Chicago home and has provided locals and tourists one of the most unforgettable and unique experiences in the city, bike tours. Inspired by their passion for Travel, Community, Health, and Service, they have been offering tours on many themes, including history, food, innovation, and the culture of Chicago. 

Their selection of rental bikes ranges from tandem bikes to junior bikes and even bike wagons and kid’s seats for those with little ones. Their selection of bikes is of top quality, as is their customer service. They provide you with an experience you will never forget from start to finish. 

Whether you’re a local looking for a unique experience or a first-time visitor in Chicago, you are guaranteed to have an amazing, up-close, and personal experience along Chicago’s lakefront. 

The fantastic team at Bobby’s Bikes will help you get fitted for a helmet; make sure you have the tools that you need just in case you get a flat tire or have low air and will give you plenty of advice on the must-sees if you take a self-tour of the city. 

Lunch for family at Ramen-San In River North

Ramen-San has quickly become one of my favorite places to dine. Before trying out Ramen-San, I had never had Ramen, and neither have my kids. So I was interested in trying out this neighborhood noodle joint in River North to see what all of the hype was about. Well, let me tell you, there was definitely hype. 

Ramen-San serves hot broths, ice-cold beer, and plays some of the best 90’s hip-hop in town. They have locations throughout Chicago, but the one in River North was close and convenient for a lunch break. Ramen-San, of course, has some of the tastiest Ramen, but it also serves delicious appetizers such as the spicy Szechuan chicken wings and xoxo shrimp and pork dumplings, to name a few.

Date night dinner for 2 at Hubbard Inn

For a beautiful night out with friends or a date night with your partner, the Hubbard Inn has the perfect ambiance to let you relax, unwind, and have a drink or two, along with some excellent cuisine. This beautiful, multi-story restaurant and cocktail bar offers delicious food with a high-end experience that will surely be unforgettable. 

Due to the pandemic, the Hubbard Inn has a limited menu; however, the unique dining experience with delicious food options will make it a wonderful place to wind down after a busy day in Chicago. You can try dishes such as the Duck and Truffle Risotto plate, the Prosciutto Flatbread, or the tasty Hubbard Inn Burger. You also have your choice of some of the best tasting cocktails in Chicago, like the Serious Flirt and the Lucky Rebound. 

Explore on your own Chicago Architecture Center

If you want to learn about Chicago’s famous architecture, engineering, and design, you have to visit the Chicago Architecture Center. The Chicago Architecture Center is dedicated to celebrating and promoting Chicago as a center of architectural innovation.

This nearly 10,000 square feet of exhibition space is filled with models and views of Chicago’s iconic skyscrapers. It is also your gateway to more than 50 CAC walking tours and river cruises such as the Chicago Architecture Foundation Center River Cruises aboard Chicago’s First Lady.

The Center exhibit focuses on Chicago’s very well known diverse neighborhoods, housing types, architects, and future projects. The Center is also home to the largest scale model of the city, with more than 4,250 miniature buildings, interactive touchscreens, and cinematic backdrops.

However, due to the pandemic, although the Center is open for visitors, the Center’s galleries, the CAC Design Store, the ArcelorMittal Design Studio, and Gand Lecture Hall remain temporarily closed. 

Photo Credit: Choose Chicago

Day 3 in Chicago

Brunch at Sweetwater Tavern + Grille

A must visit restaurant located right off The Magnificent Mile in Chicago is the Sweetwater Tavern and Grille. It is a vibrant bar and restaurant all in one. The Sweetwater Tavern and Grille offers both indoor seating and outdoor patio seating. We decided to have brunch here, and the food menu did not disappoint. From yummy cinnamon rolls to steak and eggs and even Beignets and breakfast tacos, the food is delicious and will certainly satisfy your taste buds. 

The Sweetwater also has a full liquor bar, smart wine list, and excellent beer selection. However, I opted for a mimosa because, on Sundays, we drink mimosas! On top of the Sweetwater’s great menu, the service was impeccable. This restaurant takes a fine-dining approach in a relaxed, upbeat atmosphere. The staff was courteous, welcoming, professional, and accomodating. 

Enjoy views at 360 CHICAGO and experience TILT

Last, but certainly not least, you must visit 360 CHICAGO, your experience starts from the ground floor with a museum-style exhibition showcasing Chicago’s history and nine of its very well known culturally rich neighborhoods. 

It ends with the 17,000 square food observation deck on the 94th floor of the former John Hancock Center, where you will experience the beautiful 360 view of Chicago’s skyline and grand lakefront. On our visit, the kids noticed that the 360 CHICAGO’s elevators were very fast. It turns out they actually travel at 20 miles an hour. Wow! And because we came to visit on a clear, beautiful day, we were able to see four states from the 94th floor. It was quite the view, to say the least. 

When at 360 CHICAGO, you have to try out the exciting new attraction, the TILT, at the top of the observation deck. The TILT tilts outward over 1,000 feet above The Magnificent Mile. It holds eight visitors at a time, and you will see an up-close and personal view of the Chicago skyline on this breathtaking attraction. 360 CHICAGO is a fun and exhilarating spot to experience with your family and friends. It will give you a new way to experience and take in the beauty of Chicago’s skyline.  

There are so many ways to spend 3 days in Chicago. What kind of things would you like to do in Chicago?

*This trip was sponsored by Choose Chicago however the opinions on this post are my own. 

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