Chicago Spring Packing List

Aerial view of Chicago, Illinois, showcasing Lake Michigan’s shoreline, green parks, and the city's skyline on a sunny day.

Welcome to Chicago in the Spring!

Travel Dates: March, April, May

Spring in Chicago can be unpredictable, so layers are key! Early spring is still chilly, especially in March, so you’ll want a warm jacket, sweaters, and possibly a beanie. As April and May roll around, you can switch to lighter layers like long sleeves and a light jacket, but be prepared for rain, especially in May. Comfortable walking shoes are a must for exploring the city, and don’t forget an umbrella for those spring showers!

Dress Code

Chicago is a mix of casual and stylish, depending on what you’re doing. During the day, comfortable outfits like jeans, sweaters, and jackets are great for sightseeing and walking along the Riverwalk. If you’re heading out for dinner or a show in the evening, you might want to dress up a little more—think smart casual, like a nice dress or a stylish jacket. Chicagoans love their sports teams, so don’t be surprised to see lots of Cubs gear if you’re at Wrigley Field!

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MARCH

33 – 47F (1 – 8C)

Cold, windy, occasional snow showers

2.6 inches

APRIL

42 – 59F (6 – 15C)

Mild, breezy, rain likely

3.3 inches

MAY

52 – 70F (11 – 21C)

Warm, sunny, with occasional rain

3.7 inches

Tops & Layers

1. Long Sleeve Shirts: Perfect for the mild spring days as you explore Millennium Park or the Art Institute of Chicago. I loved having these for the variable weather!

2. Sweaters: Great for layering over your shirts on chilly mornings or evenings.

3. Light Jacket: Ideal for breezy afternoons, especially when you’re strolling along the Chicago Riverwalk.

4. Warm Jacket: Necessary for the colder days in early spring, especially in March when temperatures are still low.

Bottoms & Dresses

1. Pants: Comfortable and versatile, great for walking around the city or catching a game at Wrigley Field. I liked having these for the cooler, windy days.

2. Skirt: A good option for warmer spring days, especially if you’re heading out for dinner or drinks in the evening.

3. Dress: Perfect for a night out in Chicago’s vibrant restaurant scene or catching a show in the theater district.

4. Jumpsuit: Great for both daytime exploring and an easy transition to evening outings.

5. Leggings: Ideal for comfortable travel or casual days spent exploring museums or shops.

Shoes & Accessories

1. Comfortable Walking Shoes: Absolutely essential for exploring Chicago’s neighborhoods, museums, and Riverwalk. I found these really practical for all the walking I did!

2. Flats: A stylish yet comfortable choice for an evening out or a day spent at an outdoor festival.

3. Sunglasses: A must for sunny days in May when you’re spending time outdoors, especially by the lake.

4. Hat: Great for keeping warm in the windier days of March and April, especially if you’re walking along the lakefront.

5. Swimsuit: If you’re planning on visiting the beach by Lake Michigan later in the season, a swimsuit is a must.

6. Pajamas: Comfortable and cozy for relaxing after a day exploring the city.

Luggage & Packs

1. Carry-On: Perfect for a spring getaway to Chicago, with space for layers, rain gear, and casual outfits.

2. Daypack: Handy for carrying your umbrella, water, and camera while sightseeing or walking along the Riverwalk.

3. Purse: Ideal for evenings out or a casual day spent exploring museums or shopping.

4. Tote Bag: Useful for carrying extra layers and any items you pick up while shopping on Michigan Avenue.

Travel Essentials

  1. Reusable Water Bottle: A must-have for travel days and while exploring for the day.
  2. Packing Cubes: Helpful for staying organized rather than ending up with a heap of clothes in your luggage.
  3. Luggage Tags: Even if you’re not checking luggage, still good to have in case you misplace your bags.
  4. Luggage Locks: Can be handy even if you’re not checking luggage, making your backpack more pickpocket-proof.
  5. Sleep Mask: An eye mask is a game changer for helping you get quality sleep each night.
  6. White Noise Machine: Same as above. White noise machines have helped me get more consistent sleep.
  7. Ear Plugs: Much better than the generic foam ones that never stay in my ears.
  8. Jewelry Case: Especially nice for organizing necklaces and not getting them all tangled.
  9. Dry Bag: An item to bring if you plan to do a lot of water activities or boat trips.
  10. Water Shoes: Same as above. Great to bring if you plan to do water activities or boat trips.
  11. Travel Umbrella: Only if you’re going somewhere where it’s going to be wet and rainy (but not too windy).
  12. Deck of Cards / Fox in the Forest: I love playing card games while traveling. It’s a fun way to pass the time.
  1. Portable Charger: It’s surprising how often you don’t have an outlet when you need one, and your phone is essential for everything from directions to your mobile boarding pass.
  2. Universal Travel Adapter: This universal adapter works in 200+ countries. Great for airports too.
  3. E-sim: I’ve used Airalo in four different countries now, and it’s the best solution for using data abroad.
  4. Phone: Currently travel with an iPhone 13 Pro, which also works as my camera for most trips.
  5. Tablet: I use my iPad mainly for watching shows and movies and checking emails while traveling.
  6. Headphone Splitter: I use this one with my iPad Air so I can watch shows with my husband on long flights.
  7. GoPro: A great camera for underwater photography or adventure activities.
  8. Memory Card for GoPro: This is the one I use for my GoPro, high-quality and reliable.
  9. Waterproof Phone Case: Even with my GoPro, I end up using this all the time since phone quality photos are so good now.
  10. Kindle: I love traveling with my Kindle and being able to read multiple books on a trip without the extra weight.
  11. Noise-Canceling Headphones: These wraparound ones are a must for long plane rides if I want to get any sleep. I also bring Airpods for local bus trips or on-the-go travel when I want to carry something smaller.
  12. Air Tags: Great if you’re checking luggage in case it gets lost or stolen.
  13. Chargers: Don’t forget all the chargers you’ll need for the electronics listed above.
  1. Toiletry Bag: Great for going through security, and they make it easier to find what I want to use.
  2. Reusable Containers for Toiletries: I use reusable containers so I don’t need to buy expensive travel-sized products.
  3. Electric Toothbrush: I’ve tried those tiny travel toothbrushes, and they just don’t work for me.
  4. Toothpaste: These are the perfect travel size that lasts about a month or so for two people.
  5. Floss: Any floss will do.
  6. Natural Deodorant: I finally discovered a good natural deodorant. Plus, it’s small, so it’s perfect for travel.
  7. Shampoo: I get the large size and then just put it in my mini travel containers.
  8. Conditioner: Same as above. I don’t worry about bringing body wash since I’m okay using whatever’s provided.
  9. Panty Liners: For when you want some extra protection. Also great for sweaty travel days to keep you more dry.
  10. Tampons: I like that these are made without plastic, and they’re easy to put into small purses and travel with.
  11. Tide to Go Pen: Surprisingly handy for getting out those random stains or spills.
  12. Travel Laundry Detergent: These are useful because you can use them for hand washing or as washer detergent.
  13. Travel Clothesline: Handy when you need to wash your clothes but realize most of the world doesn’t use dryers.
  1. Hairbrush: I don’t use a travel-size version because it’s not worth it for me. I’d rather have a full-size brush.
  2. Hair Ties: Any brand works, but I also make sure to have plenty on hand in my bags.
  3. After Sun Lotion: Great to have if you’re traveling during the hotter months and expect to get a lot of sun.
  4. Face Sunscreen: I’ve tried many sunscreen brands, and this is the best face sunscreen I’ve found.
  5. Body Sunscreen: Reef-safe, easy to spread, and smells good.
  6. Face Cleanser: I usually get a regular-size bottle and then put it into my refillable travel containers.
  7. Moisturizer: I’ve tried many fancy moisturizers, and I’ve realized that the simplest ones often work best for me.
  8. Overnight Face Mask: I use this in daily life as well, but during travel it’s especially good because it’s so hydrating.
  9. Lip Balm: I’ve been a Burts Bees stan for over a decade, and I don’t think I’ll change anytime soon.
  10. Makeup: The three essentials I always bring are lip gloss/lipstick, my Clinique CC Cream + makeup brush, and mascara. Everything else is added on depending on the vibes of the trip.
  11. Travel Razor: I love this size and how easy it is to change the razor heads once a week.
  12. Razor Replacements: I usually bring enough to replace the razor head once per week while traveling.
  13. Hydrating Face Sheets: I pack a couple of these to use after long plane rides, great for hydrating your face.
  14. Travel Mirror: This is a luxury item, but it’s surprising how often I use it when there’s only one bathroom.
  15. Dry Bar Blow Dryer Brush: Another luxury item. It’s bulky to bring (and I don’t always bring it), but it’s a versatile tool for looking more put together in non-humid destinations.
  16. Heat Protectant Spray: For the Dry Bar Brush.
  1. Bug Spray: The most effective spray I’ve found that doesn’t use DEET.
  2. Tylenol: The best remedy when a headache strikes.
  3. Motion Sickness Pills: You never know when you might get motion sickness, especially if you’re prone to it like me.
  4. Tums: Handy for dealing with indigestion or heartburn when eating foods different than you’re used to.
  5. Pepto Bismol: Another thing to help soothe an upset stomach.
  6. Other Travel Medications: Make sure to research what else you might need to bring for the destination.
  7. Electrolyte Powder: Great for staying hydrated, especially after a day in the sun or a long flight.
  8. Band-Aids: Useful for minor cuts and blisters.
  9. Anti-Septic Wipes: Keeps wounds clean and prevents infection.
  10. Unisom SleepMelts: Obviously optional, but these are the only way I’m able to sleep on planes.
  11. Melatonin: Helps with sleep, especially if you’re adjusting to a new time zone.
  12. Hand Sanitizer: Essential for keeping your hands clean when soap and water aren’t available.
  1. Passport
  2. Travel Visas (if needed)
  3. Travel Documents, Tickets, Boarding Passes & Booking Confirmations
  4. Driver’s License / International Driving Permit (if needed)
  5. Photocopy of Passport (hidden in your pack)
  6. Emergency Cash – I usually bring US $200 and hide it in 1-2 packs/purses I have with me on travel days in case of an emergency. I make sure it’s separate from my wallet.
  7. Credit / Debit Cards
  8. Travel Insurance – Nice to have in case of any medical or travel emergencies.

What to Know Before You Pack

  • Layers: Chicago’s spring weather can be unpredictable, so pack layers like long sleeves, jackets, and sweaters.
  • Rain gear: It’s likely to rain, especially in May, so a light rain jacket or umbrella is essential.
  • Comfortable shoes: Chicago is a walkable city, so bring shoes that are comfortable for lots of walking.
  • Casual style: During the day, casual clothes are perfect for sightseeing, but pack a nicer outfit if you plan to go out in the evening.
The iconic Chicago Theatre sign glows red in downtown Chicago, Illinois, surrounded by historic and modern buildings at dusk.

Chicago Spring Travel FAQs

WHICH SPRING MONTH IS THE BEST TO VISIT CHICAGO?

May is the best month to visit Chicago during the spring, with warmer temperatures, blooming flowers, and fewer rainy days than earlier in the season.

WHAT SPRING FESTIVALS & EVENTS ARE THERE IN CHICAGO?

March: Chicago St. Patrick’s Day Parade – A lively parade celebrating Irish heritage, with the Chicago River dyed green.

April: Chicago Comic & Entertainment Expo (C2E2) – A pop culture convention featuring comics, movies, and television.

May: Chicago Mayfest – A neighborhood festival with live music, food, and local vendors.

March: Chicago Beer Festival – A celebration of local craft breweries at Union Station.

May: Millennium Art Festival – A juried art show featuring sculptures, paintings, and crafts.

WHERE SHOULD I GO IN CHICAGO IN THE SPRING?

Spring in Chicago is a great time to explore the city’s famous landmarks and outdoor spaces. Start with a visit to Millennium Park to see the Cloud Gate sculpture, then take a stroll along the Chicago Riverwalk for great views of the city’s architecture. Visit the Art Institute of Chicago, which houses one of the largest collections of art in the world. You can also spend a day in Lincoln Park, where you can visit the free zoo and enjoy the blooming gardens. Don’t forget to check out the views from the Skydeck at Willis Tower!

HOW MANY DAYS DO I NEED TO VISIT CHICAGO IN THE SPRING?

A 4-5 day trip is ideal for exploring Chicago’s parks, museums, and neighborhoods in the spring.

Suggested Itineraries:

2 Days: Day 1: Visit Millennium Park and the Art Institute of Chicago, then take a walk along the Chicago Riverwalk and enjoy dinner in the Loop. Day 2: Spend the morning at Lincoln Park Zoo, then visit the Skydeck at Willis Tower, and finish with a stroll along Michigan Avenue for shopping and dining.

5 Days: Copy the itinerary of the 2-day schedule. Add: Day 3: Take an architecture boat tour on the Chicago River, then visit Navy Pier for rides and attractions. Day 4: Spend the day exploring the Museum of Science and Industry, followed by a night out in the West Loop’s dining district. Day 5: Visit Wrigley Field for a Cubs game, then relax with a scenic walk along the Lakefront Trail.

1 Week: Copy the itinerary of the 5-day schedule. Add: Day 6: Visit the Field Museum and Shedd Aquarium at the Museum Campus, then take a leisurely walk through Grant Park. Day 7: Spend your last day visiting the Chicago History Museum, then revisit your favorite spots along the Riverwalk or enjoy a final meal in one of the city’s top restaurants.

10 Days: Copy the itinerary of the 1-week schedule. Add: Day 8: Explore more of the city’s neighborhoods, like Wicker Park for trendy cafes and boutiques. Day 9: Take a day trip to Oak Park to visit the Frank Lloyd Wright Home and Studio. Day 10: Spend your last day relaxing in Maggie Daley Park or taking a scenic boat cruise on Lake Michigan.

2 Weeks: Copy the itinerary of the 10-day schedule. Add: Day 11: Visit the Garfield Park Conservatory and its beautiful indoor gardens. Day 12: Spend the day at the Adler Planetarium, followed by dinner in Chinatown. Day 13: Explore Andersonville, known for its Swedish heritage and local shops. Day 14: Revisit your favorite Chicago attractions or take a leisurely day in the parks.

WHAT SHOULD I PACK 2 DAYS, 5 DAYS, 1 WEEK, 10 DAYS, AND 2 WEEKS IN CHICAGO?

2 Days

  • 2 Long Sleeve Shirts
  • 1 Sweater
  • 1 Light Jacket
  • 1 Warm Jacket
  • 1 Pair of Pants
  • 1 Skirt
  • 1 Pair of Comfortable Walking Shoes
  • 1 Pair of Flats
  • 1 Hat
  • 1 Pair of Sunglasses
  • 1 Swimsuit
  • 1 Pair of Pajamas

5 Days

  • 3 Long Sleeve Shirts
  • 2 Sweaters
  • 1 Light Jacket
  • 1 Warm Jacket
  • 1 Pair of Pants
  • 1 Skirt
  • 1 Dress
  • 1 Jumpsuit
  • 1 Pair of Comfortable Walking Shoes
  • 1 Pair of Flats
  • 1 Hat
  • 1 Pair of Sunglasses
  • 1 Swimsuit
  • 1 Pair of Pajamas

1 Week

  • 4 Long Sleeve Shirts
  • 2 Sweaters
  • 1 Light Jacket
  • 1 Warm Jacket
  • 1 Pair of Pants
  • 1 Skirt
  • 1 Dress
  • 2 Jumpsuits
  • 1 Pair of Comfortable Walking Shoes
  • 1 Pair of Flats
  • 1 Hat
  • 1 Pair of Sunglasses
  • 1 Swimsuit
  • 1 Pair of Pajamas

10 Days

  • 5 Long Sleeve Shirts
  • 3 Sweaters
  • 1 Light Jacket
  • 1 Warm Jacket
  • 1 Pair of Pants
  • 1 Skirt
  • 2 Dresses
  • 2 Jumpsuits
  • 1 Pair of Comfortable Walking Shoes
  • 1 Pair of Flats
  • 1 Hat
  • 1 Pair of Sunglasses
  • 1 Swimsuit
  • 1 Pair of Pajamas

2 Weeks

  • 6 Long Sleeve Shirts
  • 3 Sweaters
  • 1 Light Jacket
  • 1 Warm Jacket
  • 1 Pair of Pants
  • 2 Skirts
  • 2 Dresses
  • 2 Jumpsuits
  • 1 Pair of Comfortable Walking Shoes
  • 1 Pair of Flats
  • 1 Hat
  • 1 Pair of Sunglasses
  • 1 Swimsuit
  • 1 Pair of Pajamas

WHAT SHOULD I NOT PACK FOR CHICAGO IN THE SPRING?

Heavy Winter Coats: Chicago’s spring can be chilly, but a warm jacket is enough without the bulk of a heavy winter coat.

Open-Toe Shoes: It can be cold and rainy, so sandals or flip flops are impractical for most days.

Formal Wear: Unless you have a specific event planned, casual to smart-casual is enough for most Chicago activities.

WHAT SHOULD I BUDGET FOR A TRIP TO CHICAGO IN THE SPRING?

Airfare: $200 – $500, depending on your departure location and when you book.

Accommodation: $150 – $300 per night, depending on location and hotel class.

Transportation: $30 – $70 for local travel, including Ubers or public transit.

Meals: $50 – $150 per day, depending on whether you’re dining at casual spots or high-end restaurants.

Activities: $50 – $200 for museum entry, tours, and attractions like boat tours or Cubs games.

IS THERE A TIPPING CULTURE IN CHICAGO? WHAT IS APPROPRIATE TO TIP?

Yes, tipping is expected in Chicago. A 20% tip is typical in restaurants, and $1-3 per drink depending on the location.

WHAT ARE SOME LOCAL TIPS I SHOULD KNOW ABOUT CHICAGO BEFORE I VISIT?

  • Windy weather: The “Windy City” lives up to its name, so pack a jacket and be prepared for gusty days, especially near the lake.
  • Public transport: Chicago’s “L” train system is easy to use and affordable, making it a great way to get around the city.
  • Crowds: Popular attractions like Millennium Park and the Art Institute can get crowded, so plan to visit early or during off-peak times.
  • Lake Michigan: Even in spring, it can be too cold for swimming, but walking along the lakefront is still a beautiful experience.

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