For most, the thought of visiting Chicago between November and April is enough to send a shiver down the spine, both figuratively and literally. And it’s true, Chicago in the winter can be bone-chillingly cold, especially when you factor in the infamous wind chill.
Naturally, that cold weather is going to rule out a few activities. For example, kayaking on Lake Michigan probably won’t be high on your activity list – unless you have fondness for hypothermia. But equally, there are several reasons that make visiting the Windy City over the winter an idea that shouldn’t entirely be poo-pooed.
So, on a December visit to Chicago my wife and I decided to put those reasons to the test and ultimately answer the question ‘would we recommend Chicago in the winter?’. Read on to find out.
5 Great Reasons to Visit Chicago in the Winter
Cut Price Hotels and Airfare
Living on the US east coast, we typically like to take the short trip up from Washington D.C. to New York in the weeks preceding the Christmas holiday. There’s something particularly magical about New York in the run up to the holidays. So magical that I’m usually more than willing to part with my hard-earned cash to pay for an unreasonably priced New York hotel. But, having searched for New York hotels for longer than seemed reasonable, all I’d concluded was that it would take a Christmas miracle to justify paying what New York hotels were charging.
It was this precise reason that I started looking at other weekend getaway destinations.
To my surprise a weekend in Chicago in the winter was a fraction of the cost – despite having to fly instead of taking the bus or train. The main reason was the hotel price differential. We only paid a total of $150 for three nights in a 4.5* hotel on Magnificent Mile in Chicago. A similarly central 4.5* hotel in New York over the same long weekend was running at $850 for three nights.
And it’s not just the ‘New York Factor’ affecting the price. That same hotel we booked in Chicago was three times the price in September. So, it clearly pays to visit Chicago in the winter rather than the summer!
And the bargains extended beyond the hotel. Flights were also incredibly reasonable and availability on mileage flights was high (not so to New York). This combination meant that I managed to snag two non-stop return tickets from D.C to Chicago for a measly total of 40,000 United Miles at peak travel time (i.e. not that god-awful bargain flight that leaves at 6am).
Chicago In The Winter: Fewer Crowds
Chicago is summer city. Crowds flock to the city’s beaches and riverside restaurants and bars. Major tourist attractions (most notably the city’s museums) have queues you’d typically expect to see only at Disney.
Chicago in the winter is, by contrast, quiet. Major tourist attractions, such as the Adler Planetarium and Skydeck, can be visited mostly unimpeded by the masses. It makes for a much more enjoyable experience – and seeing as many of these major attractions are based inside, the bitter weather outside is of little consequence!
In addition to smaller crowds at the city’s major attractions, winter also brings a whole host of additional attractions to town that’ll fill you with the holiday spirit:
Christkindl Market: Taking its inspiration from the Christkindlesmarkt in Nuremberg, Germany, Chicago’s main Christmas market offers up a dose of wintery cheer and an even larger offering of mulled wine. A regular fixture since 1996, it’s the city’s largest open-air Christmas festival (Winterfest at Navy Pier being located indoors) and is typically open from the middle of November until Christmas Eve.
Ice Skating: There are a whole bunch of outdoor rinks in the Chicago area over the winter. However, there are two that, in my opinion, deserve a special mention. The first is the Millennium Park McCormick Tribune Ice Rink. Situated right underneath Cloudgate (the bean) in Millennium Park, it’s the perfect place to get your skate on with a great cityscape backdrop. Admission is free, but you’ll have to pay for skate hire. The second option is the Skating Ribbon at Maggie Daley Park. This rink offers up something completely different because the rink is not your standard oval. Instead you follow the ribbon around the landscape in a big loop (the total length is twice the length of a lap around a traditional skating rink). Again, admission is free, but you’ll have to pay for skate hire.
Zoo Lights: Over the winter period (from late November until early January), Chicago’s Lincoln Park Zoo (which itself is a wonderful, and free, place to visit) turns into a winter wonderland adorned with 2.5 million twinkling lights. It may be cold outside, but you won’t feel a thing once you have a cup of hot, spiced, wine in your hand and wander around the zoo listening to festive tunes, watching ice-sculpting displays, and riding the Ferris wheel. Entry into Zoo Lights is free, but there are several ticketed attractions once inside. For this year’s offering check out the zoo’s website.
Winter Wonderfest: One for the families, the Navy Pier’s Winter Wonderfest is 170,000 square feet of indoor rides, an ice-skating rink, winter playground and festive themed fun (so long as you enjoy screaming children). It typically runs from the end of November until the start of January.
Holiday Shows: Chicago’s theaters are full of festive offerings in the run-up to the holidays. Make sure to check out the Chicago Theater website for listings (including Chicago’s Ballet’s Nutcracker).
Chicago In The Winter: Photography Opportunities
Smaller crowds at some the city’s photography hotspots, in addition to the occasional sprinkling of snow, provides a whole new set of photography opportunities.
Nowhere is this more abundantly clear than Millennium Park, where hordes of tourists often make it difficult to get a decent photo (unless you don’t mind your photos being filled with selfie-stick wielding tourists). By contrast, a winter visit to Chicago provides an opportunity to try honing your skills at some of Chicago’s winning locations when you have the chance to set up a tri-pod and take your time without feeling like your impeding others trying to go about their business. If I had to recommend four spots that are worth visiting at this time of year for photos then I’d recommend Cloudgate, The Chicago Theater, the Adams/Wabash Station and Calder’s Flamingo.
Finally, it’d be tough to write a full article about Chicago without making any mention of the city’s famous food scene. Firstly, visiting Chicago in the winter makes getting reservations to some of the city’s hotspots easier. That doesn’t necessarily mean you won’t need to book a fair while in advance, but at least your chances are better if you’re trying to secure that coveted table. The second thing worth noting is that Chicago’s restaurant week is from February 1-10 each year. Restaurant week offers the opportunity to sample some of the city’s most famous restaurants at decent discounts, with over 250 restaurants offering fixed price meals for both lunch and dinner.
We’d undoubtedly recommend Chicago in the Winter. What about you? What other great reasons have you found to visit Chicago in the Winter? Make sure to comment below!