Minahil Odyssey

Travel

Chicago

Winter Travel Guide

Chicago

Dec-2023

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Christmas in Chicago

Winter in the Midwest mean shorter days and chilly nights, ​which may sound intimidating, but it also provides an ​opportunity to walk in the late afternoon to see festive ​Christmas lights, and Chicago is especially magical during this ​time!

What to do in Chicago ​In Winter?

Chicago, IL

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Navy Pier

As an iconic Chicago landmark, the Naby Pier dosnt ​disappoint in the holiday season. With light displays, an ​array of restaurants to chose from, and the iconic Ferris ​wheel, this iconic spot shouldn’t be missed

tips on visiting Navy Pier with a family:

  • Strollers are easy to navigate, there are a few stairs, but an ​elevator nearby
  • Although buying tickets to the Ferris wheel in advance on ​the website is convenient, keep in mind there are no ​refunds if you decide not to go. Unfortunatly, it was foggy ​when we went, if I hadn’t pre-purchased the tickets we ​would have skipped it
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Navy Pier, Chocago

Maggie Daley Ice Skating, Chocago

Maggie Daley ice skating

Another favorite not just for tourists, but locals as well is ​skating at Maggie Delay

tips on Ice Skating at Maggie Delay with the ​family:

  • Pre-booking your tickets is the best way to ensure you ​have a spot, even when it’s busy
  • There are designated areas to put your shoes and you ​can leave a stroller in the same area, but you won’t see ​them while skating, so it’s a good idea to bring a small ​purse or bag to wear while skating
  • They only have some of the larger size toddler skates ​to rent, we were able to get a size 10, but they didn’t ​have size 6 toddler skate
  • There are handy penguins (and polar bears for adults) ​to hold onto if you’d like help while skating
  • You can save quite a bit if you bring your own skates, ​but renting was easy and worth it!

Chicago lights

Chicago is a magical place in the winter, with lots of lights ​and decorations. During the Christmas season, there’s a large ​tree in millennium park, and may buildings are lit up in red ​and green.

tips on seeing the lights in Chicago as a family:

  • The main tourist area in Chicago is known as “the loop” ​and well lit even after dark. Thanks to a close attention to ​security, the area is safe to walk at night
  • The main places to walk in Chicago for lights include:
    • Millenium park Christmas Tree
    • Maggie Daley Park
    • Lakeshore Park
    • Navy Peir
    • Along Michigan Avenue
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The Blackstone Hotel, Chicago

hotel downtown

One way to enhance your Chicago experience is to stay ​in the downtown area. The South Loop is a great choice ​due to its close proximity to the lake and Museum ​Campus, which includes the Shedd Aquarium, Field ​Museum, and Planetarium. During my recent trip, I ​opted to stay in this neighborhood and found it to be ​both fun and iconic.


The Blackstone Hotel, located near Grant Park, is a ​historic gem and icon of Chicago since 1910. Its signature ​red brick and mansard roof make it stand out from other ​buildings in the area. The hotel's blend of history and ​elegance is truly unique and made our stay all the more ​enjoyable. Even if you don't plan on staying there, I ​highly recommend checking out this beautiful building ​and learning about its fascinating history (read about it ​here)

The Blackstone Hotel, Chicago

tips on Staying at Blackstone with the Family:

  • Read all about the history of this amazing place on ​their website to fully appreciate it.
  • Check out the Art Gallery in the hotel! It’s a small ​gallery, but a fun little place to look at fun art
  • You can get breakfast at the restaurant in the hotel, or ​upgrade to a room with lounge access. The lounge is ​only open on week days, but they will give you a ​voucher for the restaurant if you stay over the ​weekend.
  • There are plenty of restaurants and coffee shops ​around the hotel, so if you go out for meals you’ll have ​no shortage of options

Abraham Lincoln, Head of State Statue in North President’s Court

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Chicago Skyline from Maggie Daley Park

Chicago Skyline from North Predident’s Court

The Lions at The Art Institute, Chicago

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The Blackstone Hotel, Chicago

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The Blackstone Hotel, Chicago

The Blackstone Hotel, Chicago

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