What to Pack for Chicago

Follow the Chicago packing list below to make sure you have everything you need for your Windy City getaway.

Backpacks are perfect for trouncing around town with all your stuff, but you don’t have to sacrifice style for a roomy, easy-to-carry bag. This backpack-tote combo made of water-resistant fabric delivers ample interior space, multiple compartments, and secure zipper enclosures, plus both a sturdy top handle and a long, crossbody shoulder strap. For a more unisex option, this bag converts from a messenger bag, to a backpack, and into a briefcase.

While phone cameras take great photos, SLR digital cameras take even higher-quality images and offer greater creative control for serious shutterbugs. Here's a Chicago photo tip: Capture a panoramic shot of the iconic skyline rising from the lake or silhouetted against a golden sunset from the Adler Planetarium on the Museum Campus peninsula.

It’s easy to burn through your cell phone juice snapping pictures around the city and posting them on Instagram. Maintain 100 percent power with a small but mighty high-speed charger.

Despite the Windy City's rep for bad weather, the sun actually shines here quite often—so your coolest pair of polarized shades belongs at the top of your list of what to pack for Chicago. We like classic styles for sashaying down tony Michigan Avenue, reflecting glare from mounds of snow in Chicago’s parks, sipping cocktails at sunset at a rooftop lounge, or sunbathing at one of the lakefront beaches.

Chicago's prime beach season runs from Memorial Day weekend through Labor Day, but many hotels have beautiful indoor pools with stunning city views, open year-round. Whenever you visit, you'll want to pack your swimsuit.

Want a little bling during your Chicago getaway? Keep things simple with a pair of classic earrings. Choose smooth surfaced studs or hoops with secure back-of-the-ear closures because it’s easy to catch more intricate earrings when removing a scarf or hat. Always pack extra earring backs.

Because sometimes you really need silence.

Windy City weather can be just that. Whether you're sporting a ponytail, waterfall braid, or man bun, hair ties will come in handy to keep tendrils from blowing into your camera lens.

Many famous writers have Chicago connections—like Gwendolyn Brooks, Studs Terkel, Carl Sandburg, Theodore Dreiser, David Mamet, Nelson Algren, Scott Turow, Sandra Cisneros, Shel Silverstein, and Harriet Monroe, to name a few. So an anthology of work by some of the city’s storied writers and new voices should top your list of what to pack for Chicago.

Chicago inspires creativity in everyone. While digital photographs capture the scene in a second for social sharing, old-school written documentation can be just as meaningful. Record your own descriptions and sketches in this unlined journal.

A crushable, reusable water bottle should be on your Chicago packing list to keep you hydrated on the go.

Chicago is just as beautiful in winter as it is in warmer seasons. You can keep your hands warm without sacrificing photo opportunities with these fingerless gloves.

Rain happens, so be ready to fend off the drops with a compact, sturdy umbrella. Bring a gallon-sized, plastic zip-lock bag for dry storage in your bag when the sun shines again. The Repel Windproof Travel Umbrella claims to be wind-proof.

• Chicago Travel Guide
• 9 Best Hotels in Chicago
• 10 Best Cheap Hotels in Chicago
• 9 Stylish Boutique Hotels in Chicago
• 9 Must-See Chicago Attractions
• 10 Best Day Trips from Chicago
• Chicago with Kids: 9 Fun Family-Friendly Activities
• 10 Best Cheap Eats in Chicago
• 10 Best Places for Chicago Deep-Dish Pizza
• 10 Best Restaurants in Chicago
• What to Wear in Chicago
  
  —Original reporting by Kit Bernardi