Chicago Winter Travel Tips
By Viator, May 2014
Fly into Midway
When bad weather strikes Chicago, O’Hare seems to feel the effects more than Midway. As the smaller of the two airports, Midway generally does not experience the same level of delays and cancellations when a snowstorm or other inclement weather strikes. Along the same lines, pay attention to the weather forecasts in the days leading up to your trip in case you need to make a last minute change due to the weather.
You know the saying, there is no bad weather, just inappropriate clothing? Well that definitely applies to Chicago in the winter. Bring warm, waterproof boots to navigate snowy or slushy sidewalks; a long, down or wool jacket to protect you from the wind; and a hat, scarf and gloves or mittens to keep the rest of you nice and warm. Dressing in layers is recommended as well; it may be cold outside but when the heat is cranked up inside the restaurant or museum you’re visiting, you will want to shed a layer or two.
Embrace the cold
Many of the best things about Chicago in the winter involve spending some time outdoors. Visit the Christkindlmarket in Daley Plaza, check out the Zoo Lights at the Lincoln Park Zoo, lace up your skates to go ice skating in Millennium Park or watch the river being dyed green on St. Patrick’s Day (yes, March is still winter in Chicago). You will enjoy yourself the most if you decide to simply embrace the cold rather than fight it.
If all else fails, head inside
Not a fan of the cold? No problem, just head indoors. Winter is a great time to enjoy theater in Chicago, whether it’s a Broadway production at a theater downtown or a more intimate show at the Apollo Theater in Lincoln Park or the Shakespeare Theater at Navy Pier. It is also a good time to enjoy slightly shorter lines to visit the SkyDeck at the Willis Tower. Sports fans should head to the United Center to catch the Chicago Bulls or Blackhawks in action while museum buffs can linger for hours inside the Art Institute of Chicago, the Field Museum or the Museum of Science and Industry. And at the end of a long day of sightseeing, relax with a hot drink in front of a fireplace at the Grafton in Lincoln Square, Simon’s in Andersonville or the Ten Cat Tavern in Lakeview.
Stay warm while you sightsee
For those who don’t want to hassle with public transport or brave the cold while seeing the city, hop-on, hop-off tours are a great option. They offer narration that helps you learn about the city while traveling between major attraction in a toasty warm bus. Other bus tours may be geared towards a specific interest. Learn about the history of Chicago Blues, visit the locations where several movies were made in Chicago, or immerse yourself in the seedy history of Chicago’s mobsters.