A day in Chicago, the Windy City!

Why did I choose Chicago, Illinois?
Chicago was always a city I wanted to visit when I moved to the states. It wasn’t on the top of the bucket list, but I was still intrigued to see what it was like. A good friend of mine was getting married in Arlington Heights, Illinois on a Sunday, so we made a quick weekend vacation out of it – didn’t have to use a vacation day! We spent one day in Chicago and made the most of it.


United States Dollar (USD)

My Travel Time
End of June
Chicago is so windy; it’s called the Windy City and the wind is no joke; it would literally blow me away as I was walking. Although June is summertime, at night, and sometimes even during the day, it could get chilly from the wind – I suggest bringing a light jacket.
Click here to check the weather
Click here to check when the sun rises and sets

My Flight Details
Airline: jetBlue, JFK – ORD (2-3 hour flight)
Price: ~270 USD round-trip; we didn’t have much flexibility on dates since we were going for a wedding, but I’ve seen the price closer to ~200 USD before
We took the subway to JFK. From ORD to downtown Chicago, we took the CTA’s Chicago “L” (train) – it was very convenient and both are connected to the airport. Public transportation is the cheapest way to get to/from the airport (less than $10).

My Hotel Details
Kimpton Gray Hotel

The hotel was in downtown Chicago, near “the loop”, and was close to the Millennium Park. The hotel was modern, clean, and in a great location. In general, I love Kimpton hotels and we got a pretty good deal for this one. We were excited for a more luxurious stay than per usual.

My Chicago Trip Itinerary 
Day 1
We arrived earlier in the morning, dropped our bags at the hotel, and started exploring. We walked everywhere!
~2.5 hr of walking
Skydeck Chicago: This place is so crowded, but there is a great view of the city from up here. There are a few sections of this observatory where the floor is glass so you can see right below you. However, there are long lines for those sections to take pictures. It is a very touristy spot, but the views and overall experience was still great. It’s an activity that you would only need to do once in your life. It’s always easier to book your ticket in advance; it’s around $23 per person.
Giordano’s: Nearby the Skydeck is a famous deep-dish pizza restaurant. It’s a chain restaurant and well known. A chain restaurant sometimes has the reputation of being “not authentic”, but I still enjoyed it. A deep dish pizza is around 20 USD depending on which toppings/fillings you choose; a small was enough as it’s quite cheesy and heavy. Definitely worth a try if you haven’t already, although I have to say, I’m still a New York pizza fan.
Millennium Park/Cloud Gate/The Bean: Similar to other tourist spots, there are a lot of people at the bean. For a long time, I thought, why do people visit the bean? It’s just a gigantic bean where you can see your reflection. Honestly, I must admit, it was a lot cooler seeing it in person. The reflection of the sky and city on the bean is stunning. Because we liked it so much, we made an effort to wake up at 5 in the morning the next day to capture the bean during sunrise and with way fewer people there. 100% recommend visiting this!
Ohio Street Beach & Oak Street Beach:
If it’s a nice day out, make sure to bring your swimsuit! The beaches here have decently clean water because it’s connected to Lake Michigan. Coming from NYC, it’s not common to see a beach so close by the city. At these beaches, you can see the Chicago skyline while swimming in the clear water.
Navy Pier: We walked around here to see the restaurants, stores, and games/rides. The place was vibrant and there was something happening on every corner.
Magnificent Mile:
A shopping street in downtown; lots of shops and restaurants!
Imperial Lamian
: We had a heavy pizza for lunch so we were craving for something a bit different. This restaurant was delicious; there were noodles and dumplings and it was authentic.
Firecakes: These donuts were so good! We went a bit late, so there weren’t a lot of flavor options left. Make sure to go a little bit earlier.

There is absolutely a lot more to see and a lot more food to try! If you’re only going for a day or two, this itinerary will give a quick peek into Chicago!


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