Travel Guide: A Weekend Trip To Chicago, IL

Hi loves! My next journey takes me to a long weekend trip to Chicago, IL. A city known as a transportation hub between the eastern and western United States during the 1800’s. Also known as the “Windy City” or maybe “Chi-City”? It was Labor Day weekend and my friend and I wanted to go somewhere close and explore a city.

Saving Money

Only a three-day weekend, but we used Priceline this time and bundled our flight and hotel and paid about $490 for 3 nights. We flew on Spirit which was great for us because we only needed a small bag and used a backpack as our personal bag so we wouldn’t get charged extra fees. We left Friday night and returned Monday morning. The hotel we stayed at was amazing, very modern and chic.

If you’re looking for a great hotel, I would definitely recommend the Hyatt Regency Chicago. The rooms were spacious, the beds amazing, the hotel had so many bars and restaurants, plus the room service was amazing. The hotel is also very conveniently located, it is walking distance from the Magnificent Mile, where all the food and shopping can be found, and also walking distance to Navy Pier and Millennium Park. The drive from Chicago O’Hare International to the city is long about an hour so be prepared but there are plenty of taxis and Uber’s waiting.

Willis Tower

Saturday, we decided to explore the city. We visited the iconic Willis Tower. Formally known as Sears Tower, which is the second-tallest building in the United States. It is one of Chicago’s most popular tourist destinations. It is best to get there early because there is a line unless you buy your tickets prior. (definitely recommend buying them early) Our wait wasn’t horrible but there were times where we would sit down due to how slow the line would move.

Once you’re in you take an elevator to the sky deck. FYI: your ears do pop along the way because you’re so high up! The sky deck is where you see the whole city and find those world-famous glass ledges. It is crowded at times, especially during any holiday but the people are friendly and not pushing. Everyone wants a good photo so they make sure everyone gets a chance to take one.

The Bean

Continuing to explore around town, we made our way to Millennium Park. Here you can actually take a jog around the park. Take a stroll down the Lurie Garden or just stop by the infamous Bean. Labor Day weekend wasn’t the best time to go. It was so crowded with people but you can still manage to take a good shot.

Also make sure when you’re visiting to take a look underneath the Bean. The photo doesn’t do it just, but it is so trippy how they designed it. It is actually cool to see but don’t stare at it too long because you will get a bit dizzy. With so much to see it can take a whole day from you so make sure you plan ahead.

Labor Day weekend was a bit crazy with a lot of people visiting but still amazing to see and explore. After checking out some of the sites, we decided to stop by a local pizza place to take a bite of that deep dish Chicago Pizza. With so many restaurants to try we went with Yelp and found a cute local place and the pizza was great. From someone born in New Jersey, it DOESN’T compare to New York Pizza but it was close and at the end of the day pizza is amazing anywhere. Ha-Ha

Magnificent Mile and Chicago River

We went back to the hotel and got ready for dinner and no weekend trip to Chicago is complete without visiting the Magnificent Mile. For a girl like me, I could forever get lost down this street with stores varying from Gucci to Burberry to Nike and Forever XXI. There are plenty of shops to see and probably the best Sephora store I have ever seen as well. A great place to visit during your weekend trip to Chicago. Once you’re down shopping or window-shopping, there are plenty of restaurants to try out. We ate at Labriola Chicago, a cute space inside and outside to enjoy an amazing Italian dinner and cup of wine in the beginning of September.

On our way back, we walked over the Chicago River and saw the most incredible firework show at Navy Pier. Navy Pier is one of the coolest spot to visit during your weekend trip to Chicago. It has so many shops, restaurants, attractions for the whole family and many exhibitions facilities. We got to visit quickly during the day but did not get a chance to actually go in and explore. It is right on the water too, which makes it very romantic at night as well. You can even take a boat ride at night or during the day to see the city from a different point of view. 

Catching a game:

Sunday, we went for a walk and saw the amazing building of the Chicago Tribune right before the Magnificent Mile. Had a nice breakfast at the Hyatt Regency Chicago, then made our way to Wrigleyville. It was baseball season, we had the long weekend trip to Chicago, how do you not go to a Cubs game? We bought tickets to the Giants vs. Cubs game. As a baseball fan, I was super excited to sit down and enjoy a cold one in Wrigley Field. The history that this field has and the amazing event that was going to happen soon, made this game that more magical looking back at it now.

The fans were electric and even though the game went into lots of extra innings. They stood by their Cubs. Who, by the way, ended up winning the game. And went on to win the World Series after over 100 years of not winning. So safe to say the curse was finally over. But Wrigleyville is a super cute bar town with sports store everywhere, pubs, bars, and food! Oh so much food everywhere! I can tell this is the place to be every Friday, Saturday or Sunday during baseball season and its super family friendly. If you’re visiting during baseball season or even football season, come catch the game in Wrigleyville!

Chicago is a city like no other full of young professionals, sports fanatics, and people who are warm and open to meeting other travelers. There is so much to see and do during a weekend trip to Chicago, don’t think you’ll be bored. You’ll leave thinking you forgot about somewhere, something, someplace to visit. There are so many reasons I’m inching to go back again. Chi-City, I may be coming back sooner than you think to get another taste of you, but until then the Windy City will just have to wait.

XOXO

Karen Giuliana