You’d be crazy to plan a trip to Chicago in winter, right?! Well, maybe, but we’d like to make a case for it. With Chicago being our favourite city we’ve visited so far we’re probably biased, but we think the Windy City still has plenty to offer in the winter months to make for a unique and fun-filled bite-sized break.
If the weather is kind and you’re not put off by sliding on frozen water, the Millennium Park ice rink is an excellent way to spend an hour or two. Situated just in front of the Bean, this rink is perfect for beginners, and fellow skaters generally give you lots of room if you’re a bit wobbly. Skates can be rented opposite the rink for $15 on weekends for adults. Soak up the crisp air and the stunning skyline as you gracefully (or not so gracefully) glide around the rink. If you’re looking for more of a challenge, the Maggie Daley Park skating ribbon, just east of Millennium Park, is the way to go. This ribbon of ice has some gentle inclines and curves so some basic skating skill is advised. More advanced skaters will fly past you as well. Just be warned that both the rink and the ribbon are popular and the lines for skate rental can be long, but if you bring your own skates admission is free and you can skip the line.
If ice skating is not your jam, we’d recommend jumping on a tour by Free Tours by Foot. This company offers a range of amazing pay-what-you-want tours that are run by locals. So far we’ve tried four of their tours and loved every single one, plus we’ve learnt a lot about the city. As a bonus, the tour guides are usually happy to offer advice on activities and good food places. Even if the weather turns nasty, in the winter months FTBT also offer a Pedway Tour, which takes groups through the underground pedway system that connects many of the buildings in the Loop (downtown) and has some fascinating history to boot. Just be sure to book into their tours in advance via their website.
If the weather is really howling outside, take advantage of Chicago’s glut of amazing museums to shelter indoors and get some culture. Our hot tip is to check out the little-known gem of the Chicago Cultural Center, which is directly across the road from the Bean. In addition to hosting a range of cool exhibits, admission is free! Be sure to check out the Tiffany glass dome which alone makes the centre worth a visit. If art is more your thing, don’t miss the Art Institute just south of Millennium Park for one of the world’s best collections of impressionist art. Be sure to bring your student ID or Illinois ID for discounted entry because tickets are exxy. Our favourite museum, though, is the Museum of Science and Industry. Unfortunately it’s south of downtown Chicago and is therefore harder to get to, but it has some amazing exhibits and really interesting short-term exhibitions. A highlight for us was the space capsule from Apollo 8, the mission that first took humans around the moon. If you don’t have a car we’d recommend jumping in an uber to get there from the Loop because the public transport options are annoying and will take you through some of Chicago’s sketchier areas. If you do drive and you visit on the weekend, save yourself the museum parking fee and park on S Stony Island Avenue to the west of the museum, where you can find plenty of free street parking. Thank us later. 😉
If you’re lucky enough to visit Chicago before Christmas, we’d recommend checking out Chicago’s answer to a German Christmas market. It’s called Christkindlmarket and runs from mid November on Daley Plaza in the Loop. Entry is free but be prepared to wade through large crowds at peak times. There’s a number of stalls selling beautiful hand-made Christmas ornaments which are cool, but there are also a few stores selling tacky “German” gifts. If you’ve visited Christmas markets in Germany, close your eyes and be transported straight back there by the smell of warm glühwein, then be jolted back to reality when you discover the line to buy glühwein is painfully long. All that aside, if you are in town it’s worth checking out. We recommend having dinner somewhere nearby (pizza perhaps?) and then calling in to grab a traditional German dessert. A hot chocolate or glühwein and some strudel will cap off the evening nicely.
Finally, a trip to Chicago wouldn’t be complete without a lot of food. No matter what the weather is doing, you need to eat, and Chicago has some regional food specialties that you need to try. For a uniquely Chicago food experience you can’t go past Chicago style pizza. Pizza is one of the best foods in the world, and it tastes great fresh, cold, microwaved and even a few days old. The versatility of toppings and bases means many places have a signature pizza style and Chicago is no different, with its pizza made in a deeper pan giving the dough a characteristic high edge. The space in the middle is then filled like a regular pizza but in reverse order, culminating in a chunky tomato sauce on top. This is called deep dish. Some places will go even further and add another layer of dough before the final tomato layer, making a stuffed pizza. Every local has their own opinion on who makes the best pizza and we’re certainly not going to enter the debate. Our motto is just try all the pizza! We’ve tried Lou Malnatis, Pizano’s, and Giordano’s and they are all worth trying, just don’t arrive too hungry as the pizzas take around 45 minutes to cook. On our next visit we’re going to hit up Gino’s East, we’ll let you know how that goes. If you have any recommendations of great Chicago pizza let us know in the comments!
If the humble cheeseburger is more your thing, head down to Billy Goats Tavern. Made famous by a Saturday Night Live sketch featuring John Belushi, Dan Akroyd, and Bill Murray, the cafe is an iconic establishment hiding under North Michigan Avenue… yes under. Look out for a set of stairs on the western side of the road opposite the Tribune Tower. If you’ve seen the SNL sketch you’ll know to order a cheezborger (make it a double) with chips (no fries) and a coke. We loved how unpretentious this place is, offering simple food, simple service and just good food. Just don’t forget the condiments section.