February 27

The Best of Chicago in Winter

21  comments

Not for nothing is Chicago called the Windy City.  In winter, this Midwestern metropolis is blasted by icy winds off Lake Michigan that send  temperatures plummeting.  So if you are going to visit Chicago in the winter months, be sure to wrap up warm!  Although many of the activities you might plan in summer – sunbathing, swimming or picnicking at one of the beaches or parks along the shoreline of Lake Michigan – are out of the question in winter, there are still plenty of things to do in the colder months, and a lot can be accomplished even if you just spend 2 days in Chicago.

chicago in winter

Chicago is known for its architecture. Its skyscrapers look just as impressive, if not more so, in a cold blue winter sky as in a sunny summer one. They range in style from the classicism of Mies van der Rohe to the modernism of more recent constructions.  One of the best ways to see them is by taking a boat trip along the Chicago River in which a trained guide will explain the fascinating architectural history of Chicago .  There are also two skyscrapers that are open to the public and whose observation decks afford stunning views across not just the city and the shoreline of Lake Michigan, but also the wide open plains extending westward across Illinois and beyond.  The most famous of these is probably the Skydeck of the 1,451-foot Willis Tower (former Sears Tower) but the 1,500 foot John Hancock Center also has an observatory  with similarly impressive views.  And here is an insider’s tip:  if you visit the Signature Room  on the 95th floor of the John Hancock Center, one floor below the observatory, you will save yourself the admission fee and get pretty much the same view – and a drink too!

chicago during winter

Although Chicago is famed for the ivy-clad confines of Wrigley Field where baseball’s Cubs swing their bats in the summer, there are still lots of activities to attract sports fans during the winter months . The Chicago Bears, members of the National Football League since 1919, play at Soldier Field on the Near South Side. Their regular season gridiron matchups take place between September and December and are normally sold out so be sure to book early. For those who prefer to watch a puck hit across the ice, the National Hockey League’s Chicago Blackhawks  play at the United Center on the Near West Side between October and April.

chicago winter
It was -15 F when this pic was taken

You can’t go to Chicago and not visit a blues club.  The Windy City has been home to blues and jazz musicians since the 1920’s, but what are known worldwide as Chicago blues were created by artists such as Muddy Waters and Howlin’ Wolf who headed north in the 1940’s and 1950’s,. They electrified their country blues when they hit the big city, and performed the vibrant and raw music that resulted for their fellow field hands turned factory workers.  Some of the blues clubs in the downtown Loop area, such as Buddy Guy’s Legends, have a rather touristy feel and are also a bit pricier than the neighbourhood bars and taverns on the rougher South Side where locals still enjoy blues in its raw form.  A good compromise between the touristy clubs in the Loop and on the North Side and the shadier hangouts on the South Side is Rosa’s Lounge, located in a mainly Hispanic neighborhood on the Near North West Side and run by the genial Italian drummer Tony Mangiullo and his octogenarian mother Rosa- who between them serve up top class blues and authentic Italian cuisine (hint, hint).

street chicago winter

chicago during winter

Finally, if you don’t mind braving the icy temperatures or are lucky enough to be there during a mild winter day, walking down Michigan Avenue is the quintessential Chicago activity you should not skip. Stop at any of the fantastic stores you’ll find during your stroll if only to enjoy great window-shopping, or walk into a café and taste your favourite freshly brewed latte and warm up before heading out again. Perhaps the best way to call the day is by making it all the way to Millenium Park and warm up again at any of the two ice rinks you’ll find there; ice skating is very popular and even if you’re a complete novice you will soon find you are not the only one.

wrigley stadium chicago winter

Not without reason many people (including myself) call Chicago the best big city in the USA for visitors, even beating top rated New York. Winters in Chicago endure the same freezing New York weather conditions, but I find it much more tourist friendly and most of its sightseeing areas are close to each other, specially at Chicago’s downtown area. Throw in all the outdoor activities Lake Michigan allows in summer and the green areas just a short walk away from downtown and you have a great recipe for fun and thrills.


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  • I absolutely can’t choose between Chicago and New York — LOVE both cities. Born and raised in Chicago and still go back as much as possible, often in winter. Just dress in layers and bundle up. I never let the cold and snow stop me from enjoying the city. Great ideas for things to do — especially the blues clubs. I really think you should have been wearing a hat (and the other guy a pair of gloves) in that -15F pic. 🙂

  • I have a lot of family in Chicago and I try to avoid visiting in winter at all costs =) It’s just so cold, especially downtown with that freezing wind blowing across the lake. I like to escape to one of the many wonderful museums if I find myself there when it’s cold.

  • I went to Chicago for work experience as a student. It was so cold there I had to go out and buy a thicker coat to get me through the 6 weeks.

  • I love Chicago but definitely try to avoid the winter. The wind is evil! I had to travel there for work a few times in the winter, and I nearly blew away walking 5 blocks between my hotel and the office. I would definitely need warmer gear to enjoy a trip there in Winter.

  • One thing we like to do in the winter is visit the Peggy Notebaert Nature Museum. It’s in Lincoln Park just north of the Zoo – on the other side of Fullerton parkway. The draw for us here is their butterfly room – hundreds of live butterflies in the dead of winter. If you’re lucky, one might land on your head/shoulder. And then after that, if the weather is nice, we walk over to the Lincoln Park conservatory. It’s nice to wander through the lush greens and water features. Also, we walk through that part of the zoo.

  • Chicago is my favourite city in North America – hands down. Love these shots – especially the panorama of Wrigley Field.

  • I live here, one of the best cities and very clean too! We Chicagoans know how to endure this weather! piece of cake!!!

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