Day Trip: 24 Hours to Explore Chicago in the Winter

Your complete photography guide on how to experience Chicago in 24 hours if you visit during cold Winter. Grace Molteni (@gemolteni)

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For most folks visiting Chicago, the idea of going during Winter sounds more like punishment than pleasure. Heralded for both historic and modern architecture, it’s easy to assume Chicago is best explored in the warmth of summer rays. But I beg to differ. A city this cool doesn’t stop for the cold. The trick is balancing indoor and outdoor exploration — knowing just how far you can wander before seeking a warmer, still beautiful indoor refuge. Remember, public transportation is your friend when the weather is less than ideal (and a good coat doesn’t hurt.)

Here’s how to experience Chicago in 24 hours if you visit during Winter:

#1 – Roam the Loop

To start, if you’re taking the trains in from the airport, make a stop or two on your way downtown. Related note: I highly recommend taking the trains in general, as parking is often more of a hassle (both in time and money, than it is worth) in these areas. Plus, you get to see more of the city from a local’s point of view.

If you’re coming from Midway:
Chinatown: Get off at the Halsted Orange line, walk up Archer to grab dimsum and hot tea in MingHin or Cai, and pop in and out of the trinket shops. Weather pending, head over to Tom Ping Parkfor a great view of the city from the south, generally unobstructed, including the river.

OR if you’re coming in from O’Hare:
Wicker Park: Get off at the Damen for a rad view of the city from the train platform – if you’re feeling hungry, grab some donuts Stan’s or Glazed & Infused (my personal preference), and coffee at La Colombe right off of the stop before continuing on to The Loop.

#2 – Downtown

Once you’re downtown, check out the murals in the South Loopnear Columbia College. After you marvel at the iconic “El” train tracks winding through the city’s gridded streets and iconic lookups (see: Chase Building and interior of The Thompson Center), make your way over to Maggie Daley Park. This wonderful park was transformed from a sunken rail yard into a magnificent example of human-centered design for the public space. With winding paths, dramatic landscape, and futuristic architecture, the park offers a whimsical escape, in any season, from the rigid structure of the city. Don’t forget to stop by the ice ribbon to watch the skaters or try out some blades for yourself.

When you need a place to warm up, check out the Cultural Center. If you’d prefer a warm place with a drink, hightail it to the Chicago Athletic Association and Cindy’s rooftop bar. (Pro tip: take advantage of the outdoor fire pits, and stop by the 2nd floor game room/library)

#3 – Over The Bridge: River North

Heading north, you’ll find some of Chicago’s most infamous sights: rows upon rows of bridges, wrapping around the river. Nothing feels more like a Midwestern port city than red iron ore and lift bridges.

The 360 Observation Deck at The John Hancock building is a pretty common spot when people are looking for a good view of the city from above, as you can see Lake Shore Drive, The Trump Tower, The Aon, The Willis (formerly, and in my heart forever known as The Sears) Tower. However, if you feel like saving a few bucks, the Signature Lounge Bar, which is also located at the John Hancock building offers the same views, and the only cost is a drink while you snap a photo or six.

On your way there, make time to stop in the MCA for interactive exhibits, installations, and plenty of photo opps. And, if you’re looking for something more luxurious without breaking the bank, stop by 3 Arts Care and Restoration Hardware. This upscale home furnishing store is Pinterest come to life. With an indoor garden cafe, chandeliers, espresso bar, and wine room, this is the perfect stop on a wintery day. However, if you feel like braving the ice, the lakefront is never far, and the views are sometimes worth the frozen fingers.

#4 – Find a Tropical Escape:

If the cold and gloom of winter in the city are getting you down, observatories and atriums are surely the cure. If you’re pressed for time, continue north to the Lincoln Park Zoo. It’s free, houses a decent resume of animals (like a snow leopard, appropriately), and has a lovely conservatory full of tropical plants and plenty of greenery. The park is walkable from both train and bus lines.
If you’ve got more wiggle room in your schedule, catch the Green Line West out of downtown to the Garfield Conservatory. This is one of the best places in Chicago, and because it is out of the way, it’s not swamped with visitors. Their newly finished Palm Room is an ideal escape from winter’s chill – lush and steamy, complete with a reflecting pool and scattered seating to take it all in. On the ride there, you’ll also be able to get a classic shot of the “El” tracks above Lake Street for a few miles – the vanishing points on the horizon are too good to pass up.

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