Chicago’s weather can be quite variable, so dressing appropriately is key. Winters (December to February) are cold and often snowy, so bundle up with heavy coats, hats, scarves, gloves, and insulated boots. Spring (March to May) and fall (September to November) can fluctuate between warm and cool, so layered clothing is recommended to adjust to changing temperatures.
Summers (June to August) are warm and occasionally humid, so lightweight clothing like shorts, t-shirts, and sundresses are suitable. No matter the season, comfortable shoes are important for exploring the city, as you’ll likely do a fair amount of walking.
What To Wear in Chicago: A Month-Wise Guide from January To December
Planning your wardrobe for a trip to Chicago involves understanding the city’s distinct seasons and the corresponding weather conditions. Chicago experiences hot summers, frigid winters, and everything in between. Knowing what to wear each month ensures you stay comfortable and stylish while exploring this vibrant city.
During my visits to Chicago, dressing appropriately for the weather not only kept me comfortable but also allowed me to enjoy the city’s attractions fully. Here’s a comprehensive month-by-month guide on what to wear in Chicago.
January
January in Chicago is very cold, with temperatures often dropping below freezing and frequent snowfall.
- Heavy coat or down jacket
- Thermal layers (long underwear, sweaters)
- Scarves, gloves, and hats
- Waterproof boots with good traction
February
February continues the frigid winter conditions.
- Thick coat or parka
- Warm layers (thermal tops, wool sweaters)
- Insulated gloves, scarves, and hats
- Sturdy, waterproof boots
March
March marks the transition from winter to spring, with gradually warming temperatures but still a chill in the air.
- Light to medium-weight jackets
- Long-sleeved shirts and sweaters
- Jeans or trousers
- Comfortable walking shoes
April
April brings milder weather and occasional rain showers.
- Light jackets or trench coats
- Long-sleeved tops or blouses
- Jeans or casual pants
- Waterproof shoes or boots
May
May is warmer and perfect for outdoor activities.
- Light sweaters or cardigans
- T-shirts or blouses
- Skirts or lightweight pants
- Comfortable sneakers
June
June ushers in the summer heat with clear, sunny days.
- Short-sleeved shirts or blouses
- Shorts or skirts
- Sandals or lightweight shoes
- Sunglasses and hats
July
July is hot and humid, perfect for beach outings and outdoor events.
- Cool, airy outfits
- Swimwear for beach visits
- Sun protection (hats, sunglasses, sunscreen)
August
August remains hot and humid, with occasional thunderstorms.
- Lightweight, moisture-wicking clothing
- Sandals or open-toed shoes
- Light rain jacket or umbrella
September
September sees a transition to fall with cooler temperatures.
- Light sweaters or jackets
- Long pants or jeans
- Comfortable sneakers
October
October is cool and crisp, ideal for enjoying fall activities.
- Medium-weight jackets
- Long-sleeved tops or sweaters
- Boots or sturdy walking shoes
November
November is chilly, with temperatures dropping further as winter approaches.
- Warm coat or jacket
- Sweaters and cardigans
- Scarves, gloves, and hats
December
December is cold, often festive with holiday decorations.
- Heavy coat or down jacket
- Thermal underwear
- Winter accessories (hats, gloves, scarves)
Easy To Understand Month Wise Table Guide On What To Wear in Chicago
| Month | Essential Clothing | Features |
|---|---|---|
| January | Heavy coat, thermal layers, scarves, gloves, waterproof boots | Layering, warmth, snow protection |
| February | Thick coat, warm layers, insulated gloves, waterproof boots | Versatility, warmth, fashion |
| March | Light jackets, long-sleeved shirts, jeans, walking shoes | Transitional, layering |
| April | Light jackets, long-sleeved tops, jeans, waterproof shoes | Unpredictable weather, rain protection |
| May | Light sweaters, t-shirts, skirts, sneakers | Breathable fabrics, lighter layers |
| June | Short-sleeved shirts, shorts, sandals, sunglasses | Breathable, sun protection |
| July | Airy outfits, swimwear, sun protection | Lightweight, hydration |
| August | Moisture-wicking clothing, sandals, rain jacket | Airy, rain preparedness |
| September | Light sweaters, long pants, sneakers | Layering, fall colors |
| October | Medium-weight jackets, long-sleeved tops, boots | Autumnal colors, warmth |
| November | Warm coat, sweaters, scarves, gloves | Layering, winter preparation |
| December | Heavy coat, thermal underwear, winter accessories | Festive touches, warmth |
What To Wear in Chicago in Summer?
Chicago summers are known for their warmth and humidity, making it essential to choose clothing that keeps you cool and comfortable while exploring the city’s numerous attractions. From lakefront activities to outdoor festivals and rooftop dining, your summer wardrobe should be versatile, breathable, and stylish.
During my summer visits to Chicago, I found that lightweight fabrics and practical accessories made all the difference in staying comfortable. Here’s a guide to help you decide what to wear in Chicago during the summer months.
1. Essential Summer Tops
- Cotton or linen t-shirts
- Tank tops
- Breathable blouses
Features to Look For:
- Lightweight and breathable fabrics
- Loose-fitting designs
- Light colors to reflect the sun
2. Essential Summer Bottoms
- Shorts
- Light skirts
- Loose-fitting pants or capris
Features to Look For:
- Breathable materials like cotton or linen
- Comfortable fits that allow for air circulation
3. Essential Summer Footwear
- Sandals
- Lightweight sneakers
- Breathable flats
Features to Look For:
- Comfortable insoles for walking
- Breathable materials
- Non-slip soles
4. Must-Have Summer Accessories
- Sunglasses
- Wide-brimmed hats
- Lightweight scarves
Additional Tips:
- Opt for UV-protection sunglasses
- Choose hats with ventilation
- Lightweight scarves can protect against sunburn and add style
Easy To Understand Table for What to Wear in Chicago in Summer
| Category | Essential Items | Features |
|---|---|---|
| Tops | Cotton t-shirts, tank tops, breathable blouses | Lightweight, breathable, loose-fitting |
| Bottoms | Shorts, light skirts, loose-fitting pants | Breathable materials, comfortable fits |
| Footwear | Sandals, lightweight sneakers, breathable flats | Comfortable insoles, breathable, non-slip |
| Accessories | Sunglasses, wide-brimmed hats, lightweight scarves | UV-protection, ventilation, sun protection |
Tips for Staying Cool in Summer in Chicago
- Choose Breathable Fabrics: Fabrics like cotton and linen are excellent choices for hot weather as they allow your skin to breathe and help you stay cool.
- Light Colors and Patterns: Opt for light colors and floral patterns to reflect the summer vibe and stay cool.
- Comfortable Footwear: Select shoes that are comfortable for walking, as you’ll likely be exploring the city’s many attractions. Sandals and lightweight sneakers are great options.
- Protective Accessories: Use sun hats and UV-protection sunglasses to shield yourself from the sun while adding a stylish touch to your outfit.
FAQs On What To Wear in Chicago
During the day in Chicago, you should dress according to the season. In summer, lightweight, breathable clothing like shorts, sundresses, and T-shirts are ideal. In winter, you’ll need warm layers, including a heavy coat, sweaters, and thermal wear. Spring and fall can be unpredictable, so layering with a light jacket or sweater is recommended. Comfortable walking shoes are essential for exploring the city.
Evenings in Chicago can vary depending on your plans. For casual dining or outings, jeans or stylish pants with a nice top are suitable. For more upscale restaurants or events, consider a chic dress or smart separates for women, and a dress shirt with slacks or dark jeans for men. Pair your outfit with dress shoes or heels.
Yes, casual clothing is appropriate for most of Chicago’s attractions. Wear comfortable, casual outfits like jeans, T-shirts, and sneakers. If you plan to visit more upscale venues or theaters, consider bringing a slightly dressier outfit.
Comfortable footwear is crucial in Chicago due to the amount of walking and the city’s varying weather. In summer, wear comfortable sandals or sneakers. In winter, opt for insulated, waterproof boots to keep your feet warm and dry. For spring and fall, comfortable walking shoes or ankle boots are ideal.
Some of Chicago’s upscale restaurants and venues have specific dress codes. For fine dining, men should wear a collared shirt and slacks, while women can wear a dress or smart separates. Always check the venue’s dress code in advance to ensure compliance. For most casual dining and attractions, casual attire is acceptable.
