Chicago Packing List for Every Season: What to Pack for a Great Trip

Chicago days can be long, and with all the photos you’ll be taking of the Bean and skyline, you’ll need to keep your phone charged.

Staying hydrated is so important when you’re walking miles between museums and deep dish pizza spots. You’ll find plenty of refill stations around the city and at the airports to keep your bottle full.

Don’t let the ‘Windy City’ nickname fool you into thinking it’s always cool. The sun reflecting off Lake Michigan or the downtown skyscrapers can be incredibly strong, especially in the peak of summer.

I like to keep a tiny kit with bandages and pain relievers in my daypack just in case. It’s much better to have it right there than to be hunting for a pharmacy when you have a blister from walking the Loop.

A dedicated wash pouch keeps your bathroom essentials organized and ensures that a leaky shampoo bottle won’t ruin your favorite Chicago graphic tee.

Chicago is a vibrant, bustling city, but that means street noise can be a factor. If you’re a light sleeper, these are absolute lifesavers for blocking out the sound of the ‘L’ train or late-night sirens.

The weather near the lake can change in an instant and a sudden downpour is never out of the question. A compact umbrella fits easily in your bag and saves you from getting soaked while you’re out and about.

Separating your laundry from your clean clothes is a simple way to stay organized, especially if you’re moving between different hotels or Airbnbs during your trip.

I honestly can’t travel without these anymore because they make organizing layers so easy. They’re perfect for dealing with Chicago’s wide temperature swings between the windy outdoors and air-conditioned interiors.

You’ll want a bag that can handle being dragged across city sidewalks and through busy airport terminals. Make sure yours has sturdy wheels that won’t give out on you halfway through your trip.

When that biting winter wind starts whipping off the lake, you’ll be so glad you have these. Covering every bit of exposed skin is the secret to staying comfortable while you’re out sightseeing.

The secret to surviving a Chicago winter is all about the layers. A warm sweater works for cozying up in a cafe and adds crucial insulation when you’re brave enough to face the cold.

Chicago summers can get surprisingly humid, so you’ll want breathable fabrics that won’t stick to you. The lake breeze can still make things feel cool once the sun goes down, so having a layer handy is a smart move.

These are my go-to for wandering through different neighborhoods or setting up a picnic in Millennium Park. You’ll want something comfortable that lets you move freely all day long.

You might not associate Chicago with beaches, but the lakefront is beautiful in July and August. Pack your suit in case you want to take a dip at North Avenue Beach or just lounge on the sand.

There’s nothing better than switching into cozy joggers after a long flight into O’Hare or a full day of hitting the museums. They’re my favorite travel day staple.

I find leggings to be one of the most versatile things I pack because they work for city walks and can even double as an extra layer under your jeans if the temperature drops.

This is a basic summer essential that pairs with almost anything. It’s easy to layer under a light jacket or cardigan if you find yourself in a heavily air-conditioned museum.

Chicago has an incredible dining scene, and you’ll probably want at least one outfit that’s a bit more elevated. A simple dress is an easy way to go from a day of sightseeing to a nice dinner in the West Loop.