What to Wear in Chicago

The Chicago Bean, in December

The Chicago Bean, in December

Downtown, in February

Downtown, in February

Winter snow, in February

Winter snow, in February

Millennium Park in April

Millennium Park in April

The Chicago Bean, in April

The Chicago Bean, in April

Chicago River boat trip in July

Chicago River boat trip in July

Lake Michigan shore, August

Lake Michigan shore, August

The Chicago Bean, in Summer

The Chicago Bean, in Summer

White Sox baseball, in August

White Sox baseball, in August

Downtown, in September

Downtown, in September

A Message From Helen



I want you to have an amazing vacation. That's why I started WhatToWearOnVacation.com,
to help you pack with confidence and stay safe, secure and comfortable.

Disclosure: We recommend products and services that we love and think you will too. If you click on a product link on this page, the provider may pay us a small commission.
 

General Style Tips

  • Smart business-orientated clothes will carry you through in Chicago for business, sightseeing and for eating out.
  • Having said that jeans are always popular and will serve as a versatile base to your wardrobe.
  • The “Windy City” has a great deal to offer the sightseeing visitor. There really is loads to see and do and most of it is best done on foot, so make sure you take comfy footwear for daytime (for total comfort you can't beat Hotter shoes, and they look great too).
  • Ladies, save your high heels for the evenings.
  • Everything's a really great buy in Chicago - shopping's brilliant, so don't take up valuable packing space with cosmetics, medicines, books or the like. Buy them there.
  • Guys should be smartly dressed for business - but make sure your suit's lightweight in the summer months.
  • Also see What to Wear in USA

Pack for the Weather

  • The summer months (June, July and August) are hot, and lightweight clothes in natural fibers will work best. A lightweight sundress or shorts would fit the bill perfectly, but be warned the air conditioning can be fierce so take a lightweight jacket or pashmina to throw on.
  • Don't forget that conditions are arctic if you're visiting in winter - November, December, Janaury, February and March - so you need to be prepared for them. You are well advised to have a very thick, warm coat, plus gloves, a warm hat, scarf and ear muffs are also a very good idea.
  • Have some versatile shoes with a soft rubber tread to provide you with enough traction not to slip on the ice. It's important that you get soft rubber soles because even medium soles get really hard in the freezing cold. Make sure too that they have large spaces between the tracks, or the snow will get stuck in them and make them very slippery.
  • We love the Weather+ app - it gives an accurate 6 day forecast for day and night, which when you're planning from home is really helpful. You can keep all the places you've been to too - a nice way to remember your trip :) Download for iPad/iPhone or Android

Last updated 16 December 2016.

Get a Full Packing List for USA

Our Members can download a suggested packing list for USA which covers ladies' and men's clothes for all seasons, plus a checklist for must-take items. Sign up or log in below.

Join us here - it's free!

*
*
 
*
 
(min. 6 characters) *
*
*
 
Wanda in USA
joined 12 minutes ago

Or Members log in here

*
*

Or

Wanda in USA
joined 12 minutes ago

Pack Light

  • Less luggage to carry
  • Save time packing and unpacking
  • Save money on baggage fees

Pack Right

  • Respect local cultures
  • Feel comfortable and confident
  • Suitable outfits for all occasions

A Message From Helen



I want you to have an amazing vacation. That's why I started WhatToWearOnVacation.com,
to help you pack with confidence and stay safe, secure and comfortable.