What Should You Pack for Chicago?
Chicago’s weather can be unpredictable, so you’ll want to pack for a variety of conditions. In spring and fall, layering is key—start with long sleeves and sweaters, and add a light jacket. Summers are warm and often humid, so short sleeve shirts and comfortable sandals are perfect for walking around the city. If you’re visiting in winter, prepare for freezing temperatures with a heavy coat, gloves, and a scarf. And always have comfortable walking shoes for all the exploring!
Make sure you’re prepared for: Visiting Millennium Park, exploring the Art Institute of Chicago, walking along the Chicago Riverwalk, enjoying Navy Pier, and taking an architectural boat tour.
Dress Code
Chicago is a city that mixes casual and sophisticated styles, so pack accordingly! For days spent exploring museums or walking along the lake, casual attire like jeans and short sleeve shirts will work well. However, if you plan to enjoy some of Chicago’s fine dining or live theater, you’ll want to pack something dressier, like a stylish dress or jumpsuit. For outdoor events like summer festivals or the famous St. Patrick’s Day Parade, pack casual but comfortable clothes.
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Spring
40 – 65°F
(4 – 18°C
)
Summer
65 – 85°F
(18 – 29°C
)
Fall
45 – 65°F
(7 – 18°C
)
Winter
20 – 35°F
(-6 – 2°C
)
Spring: Cool and rainy, with warming temperatures
Summer: Warm and humid, with occasional thunderstorms
Fall: Cool, breezy, with chilly evenings and some rain
Winter: Cold, snowy, windy
Spring
3.6 inches of rain
Summer
4.3 inches of rain
Fall
2.8 inches of rain
Winter
1.6 inches of rain (with snowfall)
Tops & Layers
1. Short Sleeve Shirts: Great for staying cool during summer sightseeing.
2. Long Sleeve Shirts: Ideal for layering in spring and fall.
3. Sweaters: Perfect for cooler mornings and evenings—I loved having mine for crisp fall days.
4. Tank Tops: Great for summer visits, especially while walking along the lakefront.
5. Casual Jacket: Essential for spring and fall, especially in the windy city!
Bottoms & Dresses
1. Pants: Versatile for both casual exploring and dining out—I really liked these for chilly evenings!
2. Shorts: A must for summer days when exploring outdoor attractions like Millennium Park.
3. Skirt: A great option for stylish city outings or evenings out.
4. Dresses: Perfect for both daytime outings and dressier evenings, especially if you’re planning a dinner out.
5. Jumpsuit: Stylish yet comfortable for day or night in the city.
Shoes & Accessories
1. Shoes: Comfortable walking shoes are a must for navigating the city—I loved having these for the museum tours and city walks.
2. Sandals: Great for warm days spent outside.
3. Sunglasses: Don’t forget these for the bright summer days along the lake.
4. Hat: A sun hat is ideal for warm days, and a knit hat is perfect for the colder months.
5. Swimsuit: If you’re visiting during summer, Chicago’s beaches along Lake Michigan are a must.
6. Scarf: For chilly evenings or adding a layer of style during the fall.
7. Gloves: Essential for winter visits to stay warm while sightseeing.
Luggage & Packs
1. Carry-On: Perfect for a short weekend trip to the city.
2. Daypack: Great for carrying your essentials while walking around museums or along the Riverwalk.
3. Purse: A practical yet stylish purse for city outings and dining out.
Travel Essentials
- Reusable Water Bottle: A must-have for travel days and while exploring for the day.
- Packing Cubes: Helpful for staying organized rather than ending up with a heap of clothes in your luggage.
- Luggage Tags: Even if you’re not checking luggage, still good to have in case you misplace your bags.
- Luggage Locks: Can be handy even if you’re not checking luggage, making your backpack more pickpocket-proof.
- Sleep Mask: An eye mask is a game changer for helping you get quality sleep each night.
- White Noise Machine: Same as above. White noise machines have helped me get more consistent sleep.
- Ear Plugs: Much better than the generic foam ones that never stay in my ears.
- Jewelry Case: Especially nice for organizing necklaces and not getting them all tangled.
- Dry Bag: An item to bring if you plan to do a lot of water activities or boat trips.
- Water Shoes: Same as above. Great to bring if you plan to do water activities or boat trips.
- Travel Umbrella: Only if you’re going somewhere where it’s going to be wet and rainy (but not too windy).
- Deck of Cards / Fox in the Forest: I love playing card games while traveling. It’s a fun way to pass the time.
- 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.
- Universal Travel Adapter: This universal adapter works in 200+ countries. Great for airports too.
- E-sim: I’ve used Airalo in four different countries now, and it’s the best solution for using data abroad.
- Phone: Currently travel with an iPhone 13 Pro, which also works as my camera for most trips.
- Tablet: I use my iPad mainly for watching shows and movies and checking emails while traveling.
- Headphone Splitter: I use this one with my iPad Air so I can watch shows with my husband on long flights.
- GoPro: A great camera for underwater photography or adventure activities.
- Memory Card for GoPro: This is the one I use for my GoPro, high-quality and reliable.
- Waterproof Phone Case: Even with my GoPro, I end up using this all the time since phone quality photos are so good now.
- Kindle: I love traveling with my Kindle and being able to read multiple books on a trip without the extra weight.
- 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.
- Air Tags: Great if you’re checking luggage in case it gets lost or stolen.
- Chargers: Don’t forget all the chargers you’ll need for the electronics listed above.
- Toiletry Bag: Great for going through security, and they make it easier to find what I want to use.
- Reusable Containers for Toiletries: I use reusable containers so I don’t need to buy expensive travel-sized products.
- Electric Toothbrush: I’ve tried those tiny travel toothbrushes, and they just don’t work for me.
- Toothpaste: These are the perfect travel size that lasts about a month or so for two people.
- Floss: Any floss will do.
- Natural Deodorant: I finally discovered a good natural deodorant. Plus, it’s small, so it’s perfect for travel.
- Shampoo: I get the large size and then just put it in my mini travel containers.
- Conditioner: Same as above. I don’t worry about bringing body wash since I’m okay using whatever’s provided.
- Panty Liners: For when you want some extra protection. Also great for sweaty travel days to keep you more dry.
- Tampons: I like that these are made without plastic, and they’re easy to put into small purses and travel with.
- Tide to Go Pen: Surprisingly handy for getting out those random stains or spills.
- Travel Laundry Detergent: These are useful because you can use them for hand washing or as washer detergent.
- Travel Clothesline: Handy when you need to wash your clothes but realize most of the world doesn’t use dryers.
- 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.
- Hair Ties: Any brand works, but I also make sure to have plenty on hand in my bags.
- After Sun Lotion: Great to have if you’re traveling during the hotter months and expect to get a lot of sun.
- Face Sunscreen: I’ve tried many sunscreen brands, and this is the best face sunscreen I’ve found.
- Body Sunscreen: Reef-safe, easy to spread, and smells good.
- Face Cleanser: I usually get a regular-size bottle and then put it into my refillable travel containers.
- Moisturizer: I’ve tried many fancy moisturizers, and I’ve realized that the simplest ones often work best for me.
- Overnight Face Mask: I use this in daily life as well, but during travel it’s especially good because it’s so hydrating.
- Lip Balm: I’ve been a Burts Bees stan for over a decade, and I don’t think I’ll change anytime soon.
- 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.
- Travel Razor: I love this size and how easy it is to change the razor heads once a week.
- Razor Replacements: I usually bring enough to replace the razor head once per week while traveling.
- Hydrating Face Sheets: I pack a couple of these to use after long plane rides, great for hydrating your face.
- Travel Mirror: This is a luxury item, but it’s surprising how often I use it when there’s only one bathroom.
- 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.
- Heat Protectant Spray: For the Dry Bar Brush.
- Bug Spray: The most effective spray I’ve found that doesn’t use DEET.
- Tylenol: The best remedy when a headache strikes.
- Motion Sickness Pills: You never know when you might get motion sickness, especially if you’re prone to it like me.
- Tums: Handy for dealing with indigestion or heartburn when eating foods different than you’re used to.
- Pepto Bismol: Another thing to help soothe an upset stomach.
- Other Travel Medications: Make sure to research what else you might need to bring for the destination.
- Electrolyte Powder: Great for staying hydrated, especially after a day in the sun or a long flight.
- Band-Aids: Useful for minor cuts and blisters.
- Anti-Septic Wipes: Keeps wounds clean and prevents infection.
- Unisom SleepMelts: Obviously optional, but these are the only way I’m able to sleep on planes.
- Melatonin: Helps with sleep, especially if you’re adjusting to a new time zone.
- Hand Sanitizer: Essential for keeping your hands clean when soap and water aren’t available.
- Passport
- Travel Visas (if needed)
- Travel Documents, Tickets, Boarding Passes & Booking Confirmations
- Driver’s License / International Driving Permit (if needed)
- Photocopy of Passport (hidden in your pack)
- 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.
- Credit / Debit Cards
- Travel Insurance – Nice to have in case of any medical or travel emergencies.
What to Know Before You Pack
- Layers: Chicago’s weather can change quickly, so packing layers helps you adjust easily.
- Comfortable walking shoes: The city is perfect for walking tours, so bring comfortable shoes for all-day exploring.
- Swimsuit: If you’re visiting in summer, there are beaches along Lake Michigan that are perfect for a dip.
- Warm accessories: In winter, gloves, a scarf, and a hat are a must to stay warm while exploring the city.
Chicago Travel FAQs
WHEN IS THE BEST TIME TO VISIT CHICAGO?
September is the best month to visit Chicago. The weather is still warm, but the summer crowds have diminished. September’s also great because outdoor events like neighborhood festivals and walking along Lake Michigan are still in full swing without the intense heat of summer.
WHAT FESTIVALS & EVENTS ARE THERE IN CHICAGO?
Lollapalooza (August): A massive music festival in Grant Park, perfect for groups of friends and music lovers.
Chicago Air and Water Show (August): A family-friendly event along Lake Michigan with incredible air stunts and water shows.
Chicago Marathon (October): One of the city’s largest events, ideal for spectators and participants alike.
St. Patrick’s Day Parade (March): A lively parade through downtown Chicago with the river dyed green, perfect for families and groups.
WHERE SHOULD I GO IN CHICAGO?
Chicago is known for its stunning architecture, world-class museums, and vibrant neighborhoods. One of my favorite places is Millennium Park, where you can see the famous Cloud Gate (The Bean). Don’t miss a walk along the Chicago Riverwalk or a visit to Navy Pier for fun attractions and lake views. The Art Institute of Chicago is a must for art lovers, and for a local feel, head to Wicker Park or Lincoln Park to explore unique shops and cafes.
HOW MANY DAYS DO I NEED TO VISIT CHICAGO?
A 4-5 day trip is perfect for exploring the major sights, museums, and neighborhoods.
Suggested Itineraries:
2 Days: On day one, visit Millennium Park and the Art Institute of Chicago, then stroll along the Riverwalk. On day two, explore Navy Pier and enjoy a boat tour, followed by a walk through Wicker Park.
5 Days: Copy the 2-day itinerary and add: On day three, visit Lincoln Park Zoo and enjoy a walk through the gardens. On day four, explore the Field Museum and Shedd Aquarium. On day five, relax at Oak Street Beach or shop along Michigan Avenue.
1 Week: Copy the 5-day itinerary and add: On day six, take an architecture river cruise to learn about Chicago’s famous buildings. On day seven, visit the Museum of Science and Industry and enjoy dinner in Chinatown.
10 Days: Copy the 1-week itinerary and add: On day eight, take a day trip to the Chicago Botanic Garden. On day nine, visit the Chicago History Museum. On day ten, spend time shopping and dining in the West Loop neighborhood.
2 Weeks: Copy the 10-day itinerary and add: On day eleven, explore Pilsen’s vibrant murals and Mexican art scene. Spend day twelve at the Adler Planetarium, and on day thirteen, take a trip to Andersonville for unique shopping. On day fourteen, take a relaxing walk through Garfield Park Conservatory.
WHAT SHOULD I PACK FOR 2 DAYS, 5 DAYS, 1 WEEK, 10 DAYS, AND 2 WEEKS IN CHICAGO?
2 Days
- 2 Short Sleeve Shirts
- 1 Long Sleeve Shirt
- 1 Sweater
- 1 Dress
- 1 Pair of Pants
- 2 Pairs of Socks
- 2 Pairs of Underwear
- 1 Comfortable Shoes
- 1 Casual Jacket
- 1 Daypack
5 Days
- 4 Short Sleeve Shirts
- 2 Long Sleeve Shirts
- 2 Sweaters
- 2 Dresses
- 2 Pairs of Pants
- 5 Pairs of Socks
- 5 Pairs of Underwear
- 1 Comfortable Shoes
- 1 Casual Jacket
- 1 Daypack
1 Week
- 5 Short Sleeve Shirts
- 3 Long Sleeve Shirts
- 2 Sweaters
- 2 Dresses
- 2 Pairs of Pants
- 6 Pairs of Socks
- 6 Pairs of Underwear
- 1 Comfortable Shoes
- 1 Casual Jacket
- 1 Daypack
10 Days
- 6 Short Sleeve Shirts
- 3 Long Sleeve Shirts
- 3 Sweaters
- 3 Dresses
- 3 Pairs of Pants
- 7 Pairs of Socks
- 7 Pairs of Underwear
- 1 Comfortable Shoes
- 1 Casual Jacket
- 1 Daypack
2 Weeks
- 7 Short Sleeve Shirts
- 4 Long Sleeve Shirts
- 3 Sweaters
- 4 Dresses
- 4 Pairs of Pants
- 9 Pairs of Socks
- 9 Pairs of Underwear
- 1 Comfortable Shoes
- 1 Casual Jacket
- 1 Daypack
WHAT SHOULD I NOT PACK FOR CHICAGO?
High heels: Not practical for walking the city’s streets and museums.
Heavy coats in summer: Chicago can be hot and humid during the summer months, so lightweight clothing is better.
WHAT SHOULD I BUDGET FOR A TRIP TO CHICAGO ?
Airfare: $200-$500 depending on your starting location and season.
Accommodation: $150-$400 per night depending on the time of year and location.
Transportation: $20-$50 per day using public transportation or rideshare services.
Meals: $30-$80 per day depending on where you eat, with plenty of casual and upscale options.
Activities: $50-$100 per day for attractions like museums and boat tours.
IS THERE A TIPPING CULTURE IN CHICAGO? WHAT IS APPROPRIATE TO TIP?
Yes, tipping is common in Chicago. Tip 20% at restaurants and $1-3 per drink. Hotel services like housekeeping and bellhops typically receive $1-2 per bag and $2-5 per night for housekeeping.
WHAT ARE SOME LOCAL TIPS I SHOULD KNOW ABOUT CHICAGO BEFORE I VISIT?
- Bring layers: Chicago’s weather can change quickly, so be prepared for temperature swings.
- Use public transportation: The “L” trains and buses make it easy to get around the city without a car.
- Avoid rush hour: Chicago’s traffic can be intense, especially on weekdays.
- Visit early: Popular attractions like Millennium Park and the Art Institute can get crowded, so visit in the morning.