Are you wondering what to wear in Chicago in Spring?

Do you live in Chicago and want to zhuzh up your looks for Spring? Do you want to know what to wear in Chicago in April?

A collage of three photos from Chicago in the spring.

Or are you considering going to Chicago for a visit and want to know what to bring?

Well lovely readers, I just returned from a ten-day visit to Chicago and thought it might be helpful to show you what I wore.

I attended many special occasions and casual visits with friends and family. I had lunches, dinners, teas, a bridal shower, Easter egg hunts, and more! Read along and see how I created many looks from relatively few pieces.

I know you might think that since I live for seven months of the year in Chicago, I already have many appropriate clothes there. The truth is my favorite, cutest pieces are with me in California. Thus, I needed to bring home a suitcase full of clothes and accessories to prepare for my schedule.

In this post...

How to Determine What to Wear in Chicago in Spring

(How do people dress in Chicago in April?)

Whenever I go on a trip, the first thing I do is determine what events are on my itinerary. The second thing I do is look at the likely weather and temperature ranges. Of course, the weather could be unseasonably warm or cool, but I use the predicted weather as a starting point.

For instance, in trying to determine what to wear in Chicago in Spring I learned the average temperature ranges are as follows:

March 26 (low) to 42 (high)

April 36 (low) to 51 (high)

May 46 (low) to 64 (high).

My trip was from April 10-20. The weather in Chicago in April During that time the temperature actually ranged from 39 to 80! Oh my! Yes, Spring weather in Chicago can be surprisingly varied! But, I was able to dress around all these weather patterns with a bit of strategic planning. As you can see from the temperatures above, what to wear in Chicago in March can be even more challenging.

Is April a good time to visit Chicago?

April is a month with very variable weather. As noted above, it can be very cold, and it can be quite warm. Overall, April isn’t at all predictable from a weather perspective. That said, Chicago is a lovely city and has many wonderful restaurants, shows, a phenomenal Botanic garden, and two terrific zoos. All these venues can be visited year-round.

The best way to determine what to wear in chicago right now is to look at a weather app for the week before and during your trip. Use that as your guide. And maybe leave a little room in your suitcase in case you need to pick something up at the multitude of wonderful Chicago shops and shopping malls.

Travel Looks (What to Wear in Chicago in Spring)

Pro-tip: When determining my Spring Chicago outfits, I first figure out what I’ll wear on my way there. For travel looks, I try to wear my bulkiest pieces on the plane so I don’t have to use up suitcase real estate. I also make sure to wear very comfortable shoes to walk through airports.

Here is a great outfit to wear on a cold Spring day in Chicago. I paired a turquoise wool coat with a turquoise v-neck cashmere sweater. I wore jeans, off-black gym shoes and a turqoise foulard bandana at my neck.

First Travel Look (Outfit Number One) for What to Wear in Chicago in Spring

I wore this turquoise wool coat and recommend you bring a wool or lined trench coat as the weather changes dramatically in Chicago springtime. I chose this brightly colored coat to look spring-like despite the cold temperature. Pro-tip: Wearing bright colors, in your accessories and even some clothing pieces will go a long way toward making you feel pretty and confident in your spring travel wardrobe. My coat is sold out, but here, here, and here are similar options.

I paired the wool coat with the underlying cashmere sweater (similar here, here, here, and here) and scarf. Pro-tip: Outfits look more expensive when you coordinate the color of your top with your third piece (sweater, blazer, coat, etc.). My Taos sneakers are wonderful and so comfy. They allowed me to walk all over town and through the airports. My pink bag is sold out but here is a similar one.

Here is a close-up of my turquoise v-neck sweater and my bandana.

I wore vintage wash J-Crew jeans as they are very comfortable for traveling and I knew I would wear them with other outfits on my trip. The bandana (similar, here, here, and here) helps accessorize the look and fills in the neckline.

This is my second travel day look. I paired a pink boyfriend cardigan with a J McLaughlin floral scarf, medium-wash straight leg jeans and tan suede booties

Second Travel Look (Outfit Number Two)

This second look was my travel outfit on the plane back to California. I frequently find planes to be cold and prefer to wear warm pieces. This J McLaughlin boyfriend (similar here, and here) sweater works well with these straight-leg medium-wash jeans, I accessorized it with a pretty spring-colored J McLaughlin scarf (last year’s but similar, here). Pro-tip: I love the scarves, belts, and purses at J McLaughlin as they are always high quality, classic in their styling, and frequently colorful.

I am wearing a v-neck white tee (GREAT BUY!) under this cardigan so that if I got hot upon arrival in Palm Springs, I could remove the cardigan and still look cute! Pro-tip: I am a big fan of v-neck tops as they elongate my neck and make it look less wrinkled. Also showing a bit of my neck and upper chest is slimming compared to crew neck tops which tend to emphasize my bust.

What to Wear in Chicago in Spring? This cute pink cashmere boyfriend sweater with a pretty floral scarf and medium wash straight leg jeans.

Chicago Spring Outfit (Outfit Number Three)

I wore this look to lunch with my friend, Julie. As I mentioned above, how to dress in Chicago in April involves creative layering of items. It was a bitterly cold, windy, but very sunny day! The turquoise coat (similar here, here, and here) worked great with the cashmere sweater (similar here, here, here, and here), and tan wide-legged pants made for a warm, stylish look.

this is a turquoise wool coat over a similarly-hued cashmere sweater. My trousers are wide-leg tan ones and my booties are tan suede. My bag is tan and quilted.

I added comfy tan suede booties (similar, here, and here) and the same bandana as in outfit number one. The booties worked because it was so cold. But the April weather in Chicago might be warmer, espcially later in the month. My tan purse is such a great value ($15.99!)! It looks like a much more expensive bag and the neutral color will make it a great piece to have in your closet.

this is a turquoise wool coat over a similarly-hued cashmere sweater. My trousers are wide-leg tan ones and my booties are tan suede. This is a close-up.

Travel Pajamas (Outfit Number Four)

Terrific Soma pajama top and shortie bottoms with a darling champagne glass print all over. the top has a notched collar.

| Pajamas |

I’m not sure that pajamas truly count as an outfit, but when you travel, it’s nice to have cute pajamas that are decent enough to wear with guests. For four nights in Chicago, I hosted my son’s soon-to-be family as I was having a bridal shower for Jake and his lovely fiancee, Rachel.

Terrific Soma pajama top and shortie bottoms with a darling champagne glass print all over. the top has a notched collar. The bottoms have a curved hem.

| Pajamas |

These darling Soma champagne glass print pajamas (similar, here) are very comfy and easy to wear. I usually wear a Soma nightshirt, but this notched collar top doesn’t need a robe to look appropriate. By the way, Soma sleepwear washes well and I hang them up right out of the dryer without any problem. The pajamas (similar, here) are 93% rayon and a bit of spandex so they hold their shape well.

| Pajamas |

Special Occasion Outfits (for What to Wear in Chicago in Spring)

Bridal Shower Look (Outfit Number Five)

This pink cashmere boyfriend sweater is worn over white pointe knit pants and nude pumps. I added a pearl necklace, bracelet and a gold watch.

I wore this outfit to the bridal shower I gave (along with my sister-in-law Sheila) at Exmoor Country Club in Highland Park, Illinois. This pink cashmere boyfriend sweater (medium) (similar here, here, here, and here) was perfect with my nude quilted bag (terrific buy!) and nude pumps. The white pointe pants fit so comfortably (similar, here).

This pink cashmere boyfriend sweater is worn over white pointe knit pants and nude pumps. I added a pearl necklace, bracelet and a gold watch. On my neck I also layered a gold chain necklace.

I wore a gold watch, a pearl bracelet, and diamond stud earrings. I added a long strand of pearls and a gold chain with a central pearl.

Here is my soon-to-be-daughter-in-law at her bridal shower wearing a sweet white ruffled dress and fabulous white pumps that have white chiffon bows at their backs.

Here’s a photo of my terrific daughter-in-law-to-be, Rachel. Don’t you love her sweet white dress and gorgeous white pumps with beautiful chiffon bows on the heels?

Here is my son looking toward the camera and my Rachel looking at Jake.

Here is the lovely bridal couple with my son Jake facing the camera while Rachel is looking at him.

Here the couple is trying on matching his and her aprons!

Here they are trying on matching his and her aprons! I found these on-line and had to get them.

Here is my son flanked by me and his former babysitter, now very close friend, Irena.

Here Jake is flanked by me and his former babysitter, Irena. She’s been a member of our family for 29 years!

This is a photo of one of the shower flower arrangements as well as one of the teapot-shaped sugar cookie favors.

These delicious cookies were made by Alliance Bakery in Wicker Park and were in the shape of teapots. The shower was a high tea party. Aren’t the flowers lovely? They were done by Eileen at Lake Forest Flowers.

A darling tote for Rachel with the words "Bride vibes" on the front!

I found this bag several months ago and had to get it for Rachel! Mr. G.Q. and I are so excited to have her join our family this July 8th!

Easter Dress (Outfit Number Six) of What to Wear in Chicago in Spring

Me in my royal blue floral Maggy London knee-length dress and white linen blazer. My sandals are light cream ankle straps and my bag is a wicker and leather one from J McLaughlin.

Wow! When you’re wondering how to dress for Chicago in April, it’s best to be prepared with pieces that can be mixed and matched depending on the temperture. For Easter (it was 75 degrees!) I wore this floral Maggie London dress. Mine is sold out, but here. here, and here are three others.

I added a J-Crew linen blazer (see how I wore it, here). My cream sandals will work all spring and summer. My bag is a classic J. McLaughlin wicker one with brown leather trim (similar here, and here). J McLaughlin has such cute bags!

Dinner Look (Outfit Number Seven) of What to Wear in Chicago in Spring

I'm wearing a black ruffled strapless top from Anthropologie over black cropped pants and black pumps with a black clutch.

I wore this outfit to dinner when I took much of my family and Jake’s new family out to dinner at Tocco restaurant in Winnetka, Illinois. This black Anthropologie top is sold out, but here is a similar one. I paired it with black cropped pants, a black clutch (similar here), and black pumps (similar, here.)

Here is a photo of both much of Jake's family and Rachel's all out together for dinner.

Above is a photo taken at Tocco restaurant. We had such a fun time. The weather was perfect! I didn’t even need a wrap at 10:00 P.M.!

Conclusion to What to Wear in Chicago in Spring

I hope you enjoyed seeing what I wore in Chicago during my Spring extravaganza stay! It was a trip filled with events and the outfits I brought worked well together. The weather is always fluctuant in Chicago springtime so you should bring layers such as cashmere sweaters, scarves, a fun wool coat, etc. Try to pack the brighter colors of springtime even if the items are made of more wintery fabrics. Let me know if you have any questions or suggestions about things you would bring to wear in Chicago in Spring.

Happy April!

XO,

Dr. Julie

Here are a few more posts for you to enjoy:

The Best Lotion for Crepey Skin on Arms and Legs

How to Wear a White Blazer Six Ways

A Pink Gingham Shirt Five Different Ways!

Bridal Shower Outfits

How to Refresh Your Patio (Five Easy, Fun Ways!)

Delicious Roasted Red Pepper and Cherry Tomato Salad

Dermatologist Advice for Anti-Aging Products

10 Comments

Jerry Kane on April 26, 2023 at 5:10 pm

your readers got their Money’s worth on this post.

JK
- drjulie on April 28, 2023 at 7:13 pm
  
  Thanks Jerry!
Eileen Weber on April 27, 2023 at 1:36 am

Dr. Julie, You are so fashionable! Love all the tips and links to these trendy accessories and closet must haves. I agree the flowers were beautiful! Perfect for a spring shower 🙂
- drjulie on April 28, 2023 at 7:13 pm
  
  Thanks Eileen! Happy Friday!
Jerry Kane on April 28, 2023 at 5:37 am

A lot of beautiful outfits
- drjulie on April 28, 2023 at 7:14 pm
  
  Thanks JK!
Elianne on May 1, 2023 at 10:11 pm

Dear Dr Julie, thank you for sharing your fun life, family and outfits with us! And congratulations on your beautiful and growing family! My fav outfit is the one with the black top from Anthro.
- drjulie on May 4, 2023 at 5:09 am
  
  Thanks for commenting Elianne. I love that top too!
Joanie on March 31, 2024 at 1:47 pm

Those wide leg pants are stunning!
- drjulie on March 31, 2024 at 11:53 pm
  
  Thanks, Joanie! I’m so glad different pant looks are all “in” these days!