Weekender in Chicago

Changing the tune since my last trip to Los Cabos, I decided to take a quick trip to the bustling city of Chicago, also known as ‘The Windy City’, in Illinois. I went with a friend who also has never been to Chicago so it was fun exploring the city.

Below was our itinerary, and hopefully it can help you get an idea of what is possible in 48 hours of being in the city.

DAY 0:

11pm – Grab a red-eye flight from Los Angeles to Chicago. I was truly hoping for an empty flight where I can just have a row all to myself and catch some zzz’s but it was a full flight! Didn’t have a great seat neighbor as well, so my three and half hours of in-flight sleep got cut substantially.

DAY 1:

5am – Land at the airport. We were both lacking in sleep so we headed over to the United Lounge and munch and relax there for a couple of hours first. Because the Chicago O’Hare airport is the hub of United, they recently renovated their lounge and it looks amazing and clean, with plenty of seats and charging outlets.

7am – Catch the local CTA blue train, and transfer to other train linesWe continued to take the Blue Line as it took us straight from the airport to downtown Chicago in just under an hour. The fare was $2.25 per person.

8:30am – Drop off your bags at the hotel. We dropped off our bags at the Hyatt Place Downtown’s front desk, only to be informed that our rooms are ready! Wow, never had this early of a check-in before!

Quick sidenote about Hyatt Place Downtown, for being one of the lower tiered Hyatt properties, I was very impressed with this one. The customer service was great, the location was amazing (so many of the attractions were within 20 minutes walking distance from us), the rooms were comfortable, and the complimentary continental breakfast was delicious (there was even dishes like quinoa, corn salad, avocado salsa, and banana compote, and someone even walked around handing out Starbucks latte samplers complete with whipped cream and caramel!).

10am – Walk over to the Art Institute of Chicago. As one of the largest art museums in the United States, they have some of the most iconic art pieces. Some that are being exhibited are ‘A Sunday on La Grande Jatte’ by Georges Seurat, ‘The Old Guitarist’ by Pablo Picasso, ‘American Gothic’ by Grant Wood, to name a few. We spent about three hours exploring their vast collection of art pieces, including my all-time favorite piece ‘Nighthawks’ by Edward Hopper.  I’ve waited such a long time to be able to see many of their pieces in person and now I can cross this museum off my bucket list and leave a happy lady.

1pm – Grab lunch nearby. With Millennium Park right next to the Art Institute of Chicago museum, there’s bound to be an abundance of restaurants within a block or so. We ended up stopping by Potbelly – a chain sandwich shop that was founded in Chicago. The place was packed with white-collared workers on their lunch break, and we could definitely taste why it was a popular lunch spot.

2pm – Walk to Millennium Park, where the famous mirrored art installation “Cloud Gate” also known as “The Bean” is located. The park is also fairly large so perhaps you might want to bring a book and relax under a tree and enjoy the nice Chicago weather.

4pm – Rest back at the hotel. We were so tired from our lack of sleep during our red-eye flight that we wanted to catch a power nap before dinner. That power nap ended up being a three hour nap (and allegedly some snoring on my part?!).

7pm – Have dinner at Lou Malnati’s, one of the local favorites for Chicago deep dish pizza. The place was packed and we had to wait 15 minutes or so for a table for two. Each of us chose personal pan pizzas and it was so filling and delicious! Be prepared to eat the pizza with a knife and fork!


8am – Enjoy some breakfast, or if you’re like us and found yesterday’s midday visit to the Cloud Gate art installation to be way too crowded, revisit The Bean and have some alone time to take some awesome touristy photos.

10am – Walk over to the SkyDeck located at the Willis Tower and experience what it’s like to see Chicago on the 103rd floor at the tallest building in Chicago (and once the tallest building in the world). The sooner you get there (as in, as soon as the SkyDeck opens), the more time you’ll have taking some amazing photos walking over the extruding glassed ledge where it’ll look like you’re walking on air over the beautiful city of Chicago. We got there at 10am and had a pretty good amount of time on the SkyDeck with not many people, but I kid you not, within 15 – 20 minutes, the place got quite crowded and lines to walk to the ledge gets long.

12pm – Reenergize with a cup of coffee and baked goods at Dollop. I had the Dirty Chai Latte (chai latte with soy milk) and it was so good!

12:30pm – Peruse the shops! Wander on to State St. (a couple of streets from Millennium Park) to find familiar stores like Zara and Nordstrom Rack. You’ll also be able to watch the ABC Newscasters filming from the street that’s right across from the Chicago Theater. We continued walking for a mile or so north and made our way to another shopping district called Magnificent Mile for the more high-end shops like Chanel and Burberry.

4pm – On your way towards Magnificent Mile, stop at the Chicago Riverwalk and enjoy the skyscraper scenery.

5pm – Take an Uber to Navy Pier and walk along Lake Michigan, a lake that touches four states – Wisconsin, Illinois, Indiana, and Michigan. The pier is family-friend and has several restaurants, a beautiful conservatory, and some carnival rides such as a ferris wheel and merry-go-round.

6:30pm – Have a Chicago deep dish pizza one last time at Giordano’s on the pier. Be prepared to wait for a table AND to wait about 45 minutes after ordering to have your pizza arrive. But trust me, their pizza is worth the wait!

8pm – Head back to the hotel and call it a day!

It was a quick two day trip and there is still so much to see and do in Chicago, like Wrigley Field, Lincoln Park Zoo, or the Chicago theater. But those two days fulfilled a sample taste of the Windy City. Until next time, Chicago!

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