Are you searching for what to wear in Chicago this summer? This ultimate packing list has got you covered!
I spend tons of time in the city during all seasons of the year, and I completely have your back.
This list is based on personal experience and created with a carry-on-friendly mindset.
Summer in Chicago can be hot, so it’s important to pack accordingly.
Chicago summers can be hot and humid, so it’s important to pack versatile pieces that keep you comfortable.
You’ll also want to consider packing for activities like beach days, walking tours, Cubs games, or evenings out in the city.
Some of the best things to pack for your Chicago summer trip are comfortable walking shoes and sandals, t-shirts, shorts, a flowy dress or skirt, a swimsuit, jeans, and a baseball hat.
Let’s start packing!
What to Wear in Summer in Chicago
Essentials
1. Comfortable walking shoes
I would argue that the best way to explore Chicago is by foot! There is so much to see and do all around you. But your comfort should never be compromised.
There are tons of stylish walking shoes for every type of foot. Find one that works best for you.
2. Comfortable walking sandals
Definitely throw a pair of sandals in your bag for going to the beach, or just a breathable alternative.
I highly recommend my Tevas because they are so comfortable and waterproof, so I can wear them to the beach and walk around the city afterward.
Clothing
3. T-shirts
Breathable shirts are ideal in Chicago summers because of the hot temperatures.
However, I also recommend throwing a long-sleeved shirt or cardigan in your bag for exploring museums or going out for a night on the town.
The air conditioning is strong!
4. Shorts
Shorts are essential for summer in Chicago. Whether you are exploring the city or hanging out at the beach, summer temperatures can get super hot.
5. Flowy Skirt or Dress
Chicago summer is perfect weather for flowy skirts and dresses!
These transition easily from day to night and are ideal for rooftop drinks, brunch, or a Broadway in Chicago performance.
⭐Popular Chicago Hotels
6. Swimsuit
Yes — you’ll want a swimsuit in Chicago this summer!
There are 24 public beaches along Lake Michigan, and North Avenue Beach is a local favorite.
North Avenue Beach is one of the most popular beaches and has some of my favorite city views.
7. Jeans
I usually pack just one pair for cooler nights or museum days (Think strong AC!) They pair great with a nicer top for dinners or rooftop bars.
Jeans really are honestly debatable on a Chicago summer packing list, but I usually like to have just one pair on hand.
Bonus Packing Essentials
8. Hat
The sun can be intense, especially during mid-day walks or bike rides on the lakefront trail. Or spending time at the beach!
I recommend throwing a baseball cap or a wide-brimmed hat in your bag before heading out for the day
9. Sunscreen
Chicago summers are full of sunshine.
Don’t forget sunscreen for walking tours, Cubs games, or kayaking on the Chicago River!
10. Sunglasses
Of course, you need a pair of sunglasses in the windy city this summer!
A stylish pair that feels right to you will add something to your look and is, of course, essential to protect you against those UV rays.
11. Microfiber Towel
I recommend a microfiber towel because you’re probably going to want to swing by the beach, and you typically cannot take your hotel towels into the sand.
A cheap towel can cost as little as $10 and is totally worth the price- I have used mine again and again.
Microfiber towels are so lightweight and take up almost no room in your luggage.
Bonus: Consider packing it in a vacuum seal bag to save even more space
12. Foldable Backpack
A foldable travel backpack is one of my favorite travel essentials for almost any trip.
I love this for city exploring because I can throw in a water bottle, a change of clothing, or anything else I might need for the day. It’s light and compact and takes up almost no room in my luggage.
Popular Chicago Tours
13. Hiking Boots
While not necessary, consider throwing a pair of hiking boots in your bag if you are hoping to take day trips to Starved Rock State Park or Indiana Dunes National Park.
What to Wear in Chicago at Night
Nights can be breezy, especially near the lake.
I recommend layering a light cardigan or denim jacket over your daytime outfit.
Dresses or jeans with a cute top work well for evening plans like cocktails at Cindy’s Rooftop or a night filled with comedy at Second City.
- Light cardigan or denim jacket – Even hot days can turn breezy at night, especially near Lake Michigan. A lightweight layer keeps you comfortable without overheating.
- Cute tank or bodysuit – Perfect base layer for evenings out and easy to pair with jeans, skirts, or linen pants.
- Flowy maxi dress – A go-to for rooftop bars, dinners, or sunset walks along the riverwalk. Breathable and comfortable in warm weather.
- Black or dark-wash jeans – Great for cooler nights, comedy shows, or casual dinners. Easy to dress up or down.
- Midi skirt or casual summer skirt – Stylish but comfortable for walking around the city at night.
- Comfortable dressy sandals or flats – Ideal for cobblestone areas, patios, and walking between neighborhoods without hurting your feet.
- Simple jewelry or statement earrings – Instantly elevates a casual daytime outfit for evening plans.
Conclusion
There is a reason most people say their favorite time of year in Chicago is summer! The city truly comes to life, and there are limitless things to do.
From catching a film at an outdoor movie theater to watching a live Chicago Cubs game at Wrigley Field, Chicago summers are truly one of a kind.
I really hope this packing list helps you begin planning your trip.
Check out some of my other Chicago planning guides for more help on your trip!
Safe and happy travels to Chicago this summer!
