Exploring the Windy City | Chicago Travel Guide
What to see in a 2-3 Day Trip

The Windy City…it brings back so many wonderful memories and experiences. Growing up in Wisconsin, trips to Chicago were a real treat. These trips were special events to spend time with family in the big city! I remember walking in downtown Chicago bundled up with snow blowing in my face, in awe of the holiday lights perfectly wrapped around the tree-lined streets and holiday decorations all around. Those were some great times as a kid and I was so inspired to visit again now many years later as an adult.

I planned a trip to Chicago to attend a medical conference with my boyfriend near the end of 2017. I was also excited to explore the city before heading up to Wisconsin to visit family. After living in Los Angeles for 10+ years, I’m definitely more used to the city-life Chicago offers and was excited to walk the city to see all the sights. I will say that I’m not a cold weather fan and was glad when the city had a slight “heat-wave” during our trip up to 45-55 degree temperatures! Despite this, I still bundled up every day and felt the cold more with all the wind from Lake Michigan!

Best Deal for Chicago Travel – CityPass

Outfit Details: Blanket Scarf; Bloomingdale’s Beret; Burberry Haddingfield Coat (similar or less expensive here); Paige Denim (my blog post); Tory Burch Polarized Sunglasses; Tory Burch Wallet (my blog post); Winter Socks (my blog post with discount code); 2 pairs of gloves! (thin layer + thick wool layer)

Where we Stayed: Hyatt Centric Magnificent Mile

The location near Magnificent Mile was perfect. I highly recommend finding an area of the city that you are interested in exploring and staying near there. I was able to walk to all of the tourist places I went during this trip and only had to take public transit to get to the conference at McCormick Place (~4 miles south of this area).

We were one block from high-end stores on Michigan Avenue like Burberry, Salvatore Ferragamo and Crate and Barrel. I enjoyed walking over here to see the tree-lined street lit up with holiday lights each evening.

This area also felt very safe and walkable alone as a young female (my boyfriend attended the conference while I explored during the day). This is very important to note because many areas of large cities can be difficult to navigate and feel safe while visiting.

Getting the Most out of Chicago Travel (in a 2-3 day trip):

What I love most about traveling is learning to live like a local, see the history of the city and do my own exploring. Yes, there are many museums in Chicago but my goal was not to visit all of them this trip – honestly, I had seen so many museums in Washington DC (4 months earlier) that I just focused on seeing the city in this 2-day trip.

My recommendations for fitting it all in within 2 or 3 days? Here was my schedule:

Day 1: SkyDeck with photos in glass boxes (formerly known as the Sears Tower) + afternoon Architectural Boat Tour and Dinner in downtown

Day 2: Walk Michigan Avenue, Head north to the John Hancock Center, Enjoy lunch at The Signature Room at the 95th floor (you can replace this with 360 Chicago tour if you prefer); Walk to Navy Pier, Take the Navy Pier Ferris Wheel, Walk to Millennium Park and The Bean, Photos at the Bean and Christmas Tree, Walk back through Michigan Avenue to Hotel, Dinner nearby or in Little Italy area

Best Deal for Chicago Travel – CityPass

You can easily fit all of these activities into 2 days. My favorite experience from this Chicago trip? The architectural boat tour was my favorite. I highly recommend it and if possible, do it early in your trip. It was so informative and gave me an opportunity to see a large portion of the city within an hour. Remember to bundle up for it because it gets chilly (maybe pack hand warmers) and get in line early to pick your best seat.

I will say that I preferred the SkyDeck over the 360 Observatory building but they do give you different views of the city. Navy Pier was amazing with their updated Ferris Wheel cars completely enclosed in glass. I did not pay to upgrade my seat and did not notice any difference – there were amazing 360 degree views of the city from the lake side that were unmatched. For families, the Children’s Museum is located here for easily fitting in activities for the kids.

Our favorite meal? I highly recommend Pierrot Gourmet at the Peninsula for dessert and macarons. We didn’t plan out our dining ahead of time but enjoyed Copper Fox Gastropub for a Midwestern meal (the bread was amazing according to my boyfriend- I primarily eat gluten-free and did not indulge). We also considered RPM Italian and RPM Steakhouse but didn’t make reservations ahead of time.

I didn’t do any shopping on Michigan Avenue (I know, can you believe it!) but that was because many of those stores are also in Los Angeles and the purpose of this travel was to get to know the city and what it has to offer.

Items I brought along while exploring:

• Selfie Stick (I did most sightseeing alone so this came in handy for some of the photos above)
• Portable External Battery Charger – I needed this because the cold temperatures drained my phone battery + I was using my phone often to look at the map and take photos
• Hand Warmers – For winter months, I highly recommend these. The wind definitely makes it cold to walk around!
• 4-in-1 Chain Wallet – great for carrying when going out for dinner or exploring
• I wore sneakers to explore. If I could pack again, I would wear fleece-lined boots to keep my feet warm in the winter!

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Have you been to Chicago? What are your favorite memories from travels and adventures here? Please comment below.

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Jessica Louie, PharmD, APh, BCCCP is the CEO of Clarify, Simplify, Align and Host of The Burnout Doctor Podcast. Dr. Louie uses her signature Burnout Doctor Method to coach burned out pharmacists & professionals to simplify because work-life balance is a LIE. Align work into your life & break free from people pleasing, perfectionism and thrive in life on YOUR TERMS.