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A view of Millennium Park in Chicago in the winter
A Business Insider reporter has some regrets about her first trip to Chicago.

Joey Hadden/Business Insider

  • I visited Chicago for the first time in February 2026 and spent two days there.
  • Booking a winter trip was a mistake, and so was spending so much time outdoors.
  • I also regret booking multiple hotels and exploring too many neighborhoods.

When I decided to take the longest train ride in the US from Chicago to Emeryville, California, on Amtrak's California Zephyr, I thought I might as well spend some time in the Midwestern city I'd never been to.

So I flew from my home in NYC to Chicago two days before my train trip, stayed in a couple of hotels, and explored the sights.

I enjoyed my short time in Chicago, but I still left with four regrets.

I picked the wrong season for my first trip to Chicago.
A curved edge of a frozen lake with a pathway and buildings on the left

Joey Hadden/Business Insider

The first time I visit any city, I like to spend a lot of time walking around outside to get the lay of the land. So when I was exploring parks in downtown Chicago on a freezing day in February, with a stiff face, frigid fingertips, and cracked lips, I thought that the timing of my first trip to Chicago was a mistake.

Although the fresh snow sparkled and the icy lake was mesmerizingly beautiful, I should have picked a warmer season for my first trip to this city.

Since I visited in winter, I should have explored indoor spaces, such as museums and libraries.
A park in Chicago with snow and trees lining either side of a concrete path and buildings in the background

Joey Hadden/Business Insider

I didn't let the weather stop me from spending my days outside exploring neighborhoods and parks. I even went to the beach. This ended up being a mistake.

While I enjoyed getting to know the city on foot, I couldn't help thinking all of these places would have been more fun to see for the first time in warmer weather. And Chicago has so much to offer indoors.

Instead of sitting on a freezing bench in Millennium Park, I could have stayed warm all day at the Art Institute of Chicago next door. The museum houses over 300,000 artworks by iconic artists from Georgia O'Keeffe to Vincent van Gogh.

My room at theWit Chicago was so luxurious for the price point that I regretted staying just one night.
Inside a hotel bathroom with a vanity on the left, a shower and tub on the right, and wide windows on the back wall

Joey Hadden/Business Insider

I decided to book a different hotel each night of my trip so I could get a taste of the Chicago travel scene.

I spent my first night at theWit Chicago, a downtown Hilton hotel with a whimsical take on modern luxury. I booked a Spa King Guestroom for one night for $240. It was a corner room on the 16th floor with floor-to-ceiling windows on every exterior wall. Asymmetrical mirrors, cartoonish light fixtures, and mismatched nightstands made my stay feel unique.

While taking a bath in the large soaking tub with a view of downtown Chicago, I felt more wrapped in luxury than I have in some $1,000-a-night hotel rooms, so I was bummed I only booked one night.

For such a short trip, I should have focused on one neighborhood rather than covering more ground.
a street in downtown Chicago viewed from above

Joey Hadden/Business Insider

I explored a few Chicago neighborhoods along the coast, from the Loop to Hyde Park. I also spent a morning strolling the nearby town of Kenilworth.

Looking back, I packed too many locations into this 48-hour trip. Instead of scratching the surface in all these places, I wish I'd stuck to just one neighborhood and gotten to know it as deeply as possible. Next time, I will.

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I spent 48 hours in Chicago for the first time and left with 4 regrets