What To Wear in Chicago This Spring: Chicago Outfit Ideas

Are you looking for suggestions on what to wear in Chicago in the spring? If yes, then you have come to the right place!

As someone who has visited Chicago multiple times, I can suggest the best Chicago outfits to pack for your trip.

Chicago is the third-largest city in the United States. Everyone knows that Chicago is famous for its deep-dish pizza, stunning skyline, vibrant cultural scene, and deep-dish pizza.

Trust me, this city has something for all kinds of travelers and spring is the best time to visit Chicago.

The city begins to emerge out of the icy winters slowly and the trees start blooming, making it the perfect place to be outdoors.

Spring in Chicago is a beautiful time to explore the city, and with the right wardrobe, you’ll be ready for anything the weather throws your way.

So, if you are wondering how to dress for Chicago spring, read my blog below on What to Wear in Chicago in the Spring!

What To Wear in Chicago This Spring

Chicago Weather in Spring

Now, before I start sharing ideas on Chicago outfits for spring, let me share a little about how the weather is in the spring here.

The spring season begins from March and stays till May leading to a wide range of temperatures and weather conditions. Here’s what to expect:

• March: Since the city has just started thawing from the snow, the weather is still chilly and unpredictable. You can expect the temperature averaging between 47°F (8°C) and the 30s (1-4°C). There are still chances of snow in early March and the winds can make it feel even colder.
• April: This is the transition month, with highs in the mid-50s to low 60s (13-17°C). Since it frequently rains this month, make sure you carry an umbrella at all times.
• May: Finally, the weather becomes a bit more mild with highs reaching the 70s (21-24°C), especially by the end of the month. There are more sunny days so you can enjoy the outdoor spaces more with lighter outfits.

Tips for Choosing the Right Spring Outfit

Here are a few tips to keep in mind when deciding on outfits for your spring vacation to Chicago:

1. Layering is Essential: As I said before, spring weather in Chicago can change rapidly, so make sure to layer your outfits to be ready for everything.
2. Mix and Match An important advice is to pack outfit pieces that can be mixed and matched. This includes neutral-colored tops, bottoms, skirts, and so on.
3. Prepare for Rain: Since it does rain in Chicago in spring, do carry a compact umbrella and pack water-resistant outerwear for your vacation.
4. Be Comfortable: You will be walking a lot in the windy city so, wear comfortable footwear.

What to Wear in Chicago in March

If you are wondering on what to wear in Chicago in March, then this section will cover it for you.

First and foremost, March is less spring and more winter because it is still snowed out in most places.

The weather ranges between 28°F-35°F (-2°C-1°C) and 40°F-47°F (4°C-8°C). Plus, with the Chicago winds, it feels much more colder than it is.

Moreover, there is still chances of rain and snow, so your Chicago outfit should keep you warm and comfortable.

That’s not all, if you time your visit well, you could even attend the St. Patrick’s Day parade here. You can wear green to join the festive spirit and watch the vibrant floats around the city.

Read my post about the best things to do during Spring in Chicago to get some fun tips.

Clothing Recommendations

• Coat or Parka: One thing that I would highly recommend it a warm, insulated coat or parka. Go for windproof ones with hoods to protect you from the cold city winds.
• Sweaters: Since it will be cold, make sure to pack a mix of heavy and lightweight sweaters for layering. Generally, wool or cashmere is ideal for warmth and comfort.
• Jeans or Slacks: To protect your legs, dark jeans or slacks would be great. Pair them with thermal leggings for extra warmth.
• Boots: Waterproof walking shoes or insulated ankle boots are a no-brainer, especially if you wish to keep your feet dry and cozy. Make sure they have good traction so that you don’t slip on the icy sidewalks.
• Accessories: Don’t forget a warm scarf, gloves, and beanie/ear muffs to protect yourself from the chill.

What to Wear in Chicago in April

Now, what to wear in Chicago in April?

Thankfully, April is the transition month so the Chicago weather slowly leans towards a warmer temperature.

The temperature ranges between 38°F-46°F (3°C-8°C) and 52°F-60°F (11°C-15°C) with occasional rainfall.

Since the weather is still a bit unpredictable while transitioning to the warmer season, it is important to layer your outfits.

If you only have a weekend in Chicago, read my 3-Day Chicago Itinerary.

Clothing Recommendations

• Lightweight Coat: With higher temperatures, you can swap your parka for a trench coat or a waterproof jacket to stay dry during the rain.
• Cardigans and Blouses: You can also wear light layers like cardigans and blouses. Choose breathable fabrics like cotton or linen for higher temperatures.
• Jeans or Cropped Pants: Jeans are still a good choice or you can experiment with cropped pants.
• Waterproof Shoes: Stylish waterproof sneakers or loafers are perfect for wet streets.
• Accessories: Due to the high rainfall, you must bring an umbrella. But, don’t forget to get sunglasses for sunnier days too! You can also keep a silk scarf to keep your neck warm while adding a pop of color to your outfit.

What to Wear in Chicago in May

May is probably the best time to visit Chicago in the spring as the weather becomes more milder and consistent.

The spring is in full swing by now and most of the city parks are buzzing with people and flowers. You can expect temperatures between 50°F-55°F (10°C-13°C) and 65°F-75°F (18°C-24°C) with occasional rainfall.

Most importantly, you can enjoy longer and sunnier days in this month.

Plus, there is the famous Chicago Mayfest to attend where you will find live music, plenty of food vendors, and a vibrant beer garden.

Chicago In Spring Clothing Recommendations

• Light Jackets: For cool mornings and evenings, a denim jacket or lightweight blazer is an ideal choice.
• Tops and Dresses: Great news, you can finally pack your cute dresses, short-sleeved blouses, and more for daytime exploration.
• Skirts and Shorts: As temperatures increase, it is time to bring out the skirts and shorts for a trendy yet comfortable look. If you still feel cold, then you can simply pair it with lightweight tights.
• Comfortable Flats or Sneakers: Since the weather is warm now, you can swap your boots for comfortable flats or sneakers.
• Accessories: As the days are sunny, do keep a sun hat, sunglasses, and a mini daypack to keep your essentials like water, sunscreen, and more.

Fun Things to Do in Chicago In Spring

Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago: Gangsters and Ghosts Guided Walking Tour

Chicago: 360 Chicago Observation Deck General Admission

Chicago: Secret Interiors Architecture Walking Tour

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Places to Stay in Chicago in the Spring

If you are planning to visit Chicago in the spring, then make sure to choose the right stay to make the most out of your vacation.

Don’t worry because Chicago has a wide range of options available from luxury to budget-friendly. Here are a few of my recommendations:

Luxury Stays

• The Langham, Chicago: If you want the best services with stunning city views, then the Langham is a great choice. It is perfect for young professionals or couples looking to splurge a little.
• Four Seasons Hotel Chicago: Another great luxury hotel that offers you both convenience and elegance is Four Seasons Hotel. If you want a high-end experience while being close to shopping and dining scenes, then this is the ideal choice for you.

Boutique Hotels

• The Robey: This trendy hotel is located in Wicker Park and offers both modern and vintage vibes. You can enjoy the amazing views of the city from its rooftop bar and meet with other fellow travelers here.
• Hotel Lincoln: For families or solo travelers, Hotel Lincoln near Lincoln Park is a good option. It is a cozy stay with easy access to outdoor spaces.

Budget-Friendly Options

• HI Chicago Hostel: If you are a budget traveler, then HI Chicago Hostel is perfect for you. It is centrally located and offers clean, comfortable dorm rooms for your stay in the windy city.
• Club Quarters Hotel Central Loop: Another good choice is Club Quarters Hotel Central Loop which offers easy access to top attractions like Millennium Park, the Art Institute of Chicago, and Willis Tower.

What To Wear In Chicago In Summer Packing List

If you will be traveling, either by plane or by car to Chicago, here are some tips on how to pack lightly.

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and so easy to use.

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect for when exploring.

And the replacement carbon filter ensures fresh clean water whenever you fill the Bobble.

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great.

Not all beaches are created equally and these quick dry slip-on Aqua shoes will come in handy for pebbly Chicago beaches.

These men’s quick dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in a lot of lens colors and frame designs and are extremely affordable too.

If you are fond of aviator-style sunglasses these polarized aviators may interest you.