Chicago Skyline View Ultimate Chicago Guide
By Destination

The Ultimate Chicago Packing List

With a white-hot culinary scene, swanky boutique hotels, and trendy neighborhoods aplenty, Chicago warms our hearts, even in those infamously brutal winters. From an MLB ballpark and Frank Gehry architecture to world-class art museums and—come on, we weren’t going to forget it—cheesy, saucy, deep-dish pizza, the Second City truly has something for everyone. When it comes to packing for a Windy City trip, your main considerations will be the length of your stay and the month’s forecasted weather. Below, we dive into both so you’ll land prepared. Read on to discover what to wear in Chicago, what not to wear in Chicago, the best walking shoes for exploring, and more.

YOUR SUITCASE PACKING CHECKLIST

*Keep these items in your carry-on

Clothes to Pack

Shoes to Pack

Accessories to Pack

Toiletries to Pack

  • Toothbrush
  • Toothpaste
  • Deodorant
  • Face wash/makeup remover
  • Makeup
  • Lip balm*
  • Sunscreen*
  • Contact lenses/solution
  • Razor/shaving cream
  • Brush/comb
  • Hair elastics/hair accessories
  • Tampons/pads*
  • Birth control/condoms*
  • Hand sanitizer*
  • Medications/vitamins*

Tech to Pack

  • Phone/charger*
  • Portable battery charger
  • Earbuds/headphones*
  • Laptop/tablet/e-reader*
  • Device chargers*
  • Camera/video camera*
  • Memory card/film*

Other Essentials

Helpful Printouts

  • Emergency contacts*
  • Boarding pass/hotel and car rental reservations*
  • Maps/directions*
  • Bank/credit card contact info*
  • Copies of passport/ID*

 

ADD/SUBTRACT FOR LONGER/SHORTER TRIPS TO CHICAGO

Long Weekend

  • Underwear: 4 pairs
  • Bras/camis/undershirts: 2 pairs
  • Socks/tights: 4 pairs
  • T-shirts: 2
  • Jeans/pants: 2 pairs

Two-Week Trip

  • Underwear: 8 pairs (more if you won’t have laundry access)
  • Bras/camis/undershirts: 5 pairs
  • Socks/tights: 8 pairs (more if you won’t have laundry access)
  • T-shirts: 8 pairs
  • Jeans/pants: 4 pairs

THE PERFECT LUGGAGE

Successfully packing for a trip to Chicago first requires finding the right luggage. Are you swinging into town for a quick weekend or dropping your bags for an extended stay? Once you know the answer, you can easily decide between a weekender, carry-on, or checked bag. Below, we’ve picked out one of each, starting with Sole Society’s ultra-cute and reasonably priced Mason Weekend Bag. The faux-leather tote’s sophisticated design belies its price tag, and a separate zippered compartment on the bottom makes it easy to keep dirty shoes away from white tees. Next up, we’ve got Rebecca Minkoff’s So Connected 22-Inch Spinner. The sleek, black matte suitcase can easily be tucked in an overhead bin, and an integrated 10,500 mAH battery means you can juice up your electronics on the go. If your trip calls for more space, Away’s The Large checked bag is an exceedingly popular pick—and for good reason. The polycarbonate hardshell—marketed as unbreakable—features all the regular bells and whistles, plus an interior compression system (overpackers, rejoice!) and a hidden laundry bag.

THE 3 PAIRS OF SHOES YOU’LL NEED FOR EXPLORING CHICAGO

Women’s Shoes

Men’s Shoes

Sorry to break it to you, but a trip to Chicago really doesn’t merit more than three pairs of shoes. Hear us out: Ladies and gents alike need to cover two major bases—something for casual sightseeing and something for going out, be it to hearing jazz at The Green Mill, sampling whiskey at Delilah’s, or going to an opening night at Goodman Theater. Now, the third pair can be whatever you want it to be—within reason, of course. If you’re touching down during winter, your best bet is a heavy-duty pair of cold-weather boots; likewise, during summer, you’ll want comfy walking sandals that won’t cause blisters. Whatever your style and budget, the most important thing to consider is the distinct purpose each pair will serve, and as a trio, do they fit every event on your itinerary? Below, we’ve picked out our favorite options, from classic low-top sneakers for long days on the Magnificent Mile to traditional derbys for dinner at one of Chicago’s legendary steakhouses or at three-Michelin-star Alinea.

CHICAGO FASHION

Women and Men's Style for Chicago

Chicago style strikes a fine balance between practical and fashionable. While residents certainly buy into the same trends that take New York City and Los Angeles by storm, at the end of the day, their Midwestern sensibilities have them valuing comfort and common sense the most. That means when winter’s winds zip through skyscraper-lined streets, trenches are traded for puffers and suede heels are replaced by weatherproof boots. If you want to dress like a local, go casual—think tees, jeans, and sneakers. You’d really have to try to stick out as a tourist here. That said, learn to embrace layers and you’ll look like a true Chicagoan in no time.

FIVE FOOLPROOF OUTFITS FOR CHICAGO

1. WHAT TO WEAR FOR AN ARCHITECTURAL BOAT TOUR IN CHICAGO (assuming it’s a little chilly)

There’s no need to dress up for an architecture river cruise—Chicago’s casual dress code applies here as well. Just be sure to pack a light sweater or cute coat as chilly winds commonly come off the river. That said, most boats offer indoor and outdoor seating, so you can step inside if you need to warm up.

A light bomber and some sunglasses will do you well on a Chicago architecture tour. Should the wind off the river feel too chilly, you can always step inside for a little respite.

2. WHAT TO WEAR IN MILLENNIUM PARK (assuming it’s warm)

Whether you’re picnicking on the grass, taking selfies at Cloud Gate (or The Bean, as it’s better known), or parked on a bench in Lurie Garden, keep things cool with a breezy minidress and some shades. Should it really cool down later in the day—Chicago is known for its dips in nighttime temperature—a denim jacket will also come in handy.

If it’s warm outside, opt for breathable cotton tees, a hat, sunglasses, and comfy sneakers. Millennium Park doesn’t offer much in the way of shade, so it’s also smart to keep a water bottle and sunscreen at hand.

3. WHAT TO WEAR AT A CHICAGO CUBS GAME

Jeans, tees, and caps are the way to go at a Cubs game. But if you’d like to support the team via color coordination, you can’t go wrong with a red, white, and blue outfit; we suggest starting from the bottom up with Chuck Taylor All-Stars—the classic sneaks feature all three shades.

Wrigley Field is a jeans-and-tee type of venue, just be sure to pack a windbreaker or sweatshirt in case of rain or wind. If you’re really looking to fit in, throw on a Cubs cap, but rest assured no one will heckle you even if you’re in support of a rival team (AKA the Cardinals).

4. WHAT TO WEAR AT A JAZZ CLUB IN CHICAGO

If you’ve been jonesing to dress up, now’s your chance. Always be sure to check the club’s website specifics regarding a dress code, but generally, pairing a nice dress, jumpsuit, or blouse with a pair of heels or booties will suit the night well.

Now is the time to look dapper, gentlemen. Leave your New Balances back in the hotel room and go for a sharper look. Pair some oxfords or derbys with a smart pair of chinos and a button-up, and your date will be proud.

5. WHAT TO WEAR FOR SIGHTSEEING IN THE WINTER IN CHICAGO

A long, faux-fur-trimmed parka is the way to go in winter. Block out frosty winds and keep in warmth by adding a scarf, beanie, and mitten.

Protect yourself from the Windy City’s bitter elements with a hooded coat, wool cap, and water-resistant boots. If you’re visiting in peak winter, throw some hand-warmers into the mix, just to be safe.

WHAT NOT TO PACK FOR CHICAGO

Chicago is a vast metropolis where you can pick up just about anything. For this reason, it’s not necessary to pack everything but the kitchen sink (though if you’re anything like us, you’ll be tempted). While first aid kits and protein bars are smart for island hopping in Thailand, Chicago is a whole different ballpark. Plan to leave behind your essential toiletries and hairdryer (your hotel with have them), impractical shoes (Midwesterners care about comfort, not stilettos), and the five extra just-in-case outfits you laid out. Putting together a suitcase for the Windy City is an excellent opportunity to practice packing light. Chicagoans have mastered the art of layering, so you don’t need to pack an outfit for every day—just embrace a mix-and-match approach to dressing.

THE *ONE THING* WTP EDITORS ALWAYS BRING TO CHICAGO

Wet Ones Sensitive Wipes for Face and HandsWet wipes really pull their weight in a place like Chicago. In the summer, they’re helpful for staying fresh in the insane heat and humidity, and year round, they’re super-handy for cleaning up messy fingers and sticky lips after devouring a two-pound wedge of deep-dish pizza loaded with toppings, a famous Chicago hot dog (with the works, of course!), and roughly two dozen mini doughnuts at the Chicago French Market. —WTP Editors

$15.90 at Amazon

CHICAGO’S WEATHER AND SEASONS

Snow Falling in Chicago

With four clear-cut seasons, Chicago really goes through the meteorological motions, from red-hot humid summers to bone-chilling winters, and everything in between. Any Chicagoan worth their weight in deep-dish pizza knows that the key to comfort is a closet full of layers. Temperatures are known to swing no matter the season (snow in late April is not totally unheard-of), so it’s smart to plan for mornings and nights that are up 20 degrees cooler than the rest of the day. And while annual rainfall clocks in at around the U.S. average, it’s never a bad idea to carry a travel-friendly umbrella in your bag come spring. Below, we lay out what weather to expect each month and how best to dress for the elements.

Note: Below is a packing forecast, not a traditional forecast. A packing forecast focuses on how cold it’s likely to be in the early mornings and evenings based on historical data. We recommend using this together with a traditional forecast as you get closer to your departure date. This data comes from our friends at Weather Underground.

JANUARY

  • Plan for day temps between -4° F and 25° F
  • Temps will drop near -9° F at night and into the early mornings
  • Expect 0.06 inches of precipitation in January

What to Wear in Chicago in January: Chicago winters are notoriously freezing and January sees the lowest temperatures of the year. To make the most of your time outdoors (though let’s be real—you’ll be darting between the Art Institute, Shedd Aquarium, and other indoor attractions), be sure to pack plenty of toasty accessories like hats, mittens, scarves, and boots.

Recommendations: Women’s long puffer coat, women’s shearling lace-up boots, knit hat.

FEBRUARY

  • Plan for day temps between 5°F and 29° F
  • Temps will drop near -3° F at night and into the early mornings
  • Expect 0.18 inches of precipitation in February

What to Wear in Chicago in February: Much like January, February’s freezing temps and biting winds call for an assortment of warm layers and weather-resistant outerwear, so be sure to leave room in your bag for gloves, scarves, sweaters, and thick socks.

Recommendations: Women’s thick pullover sweater, women’s merino-wool infinity scarfwomen’s cable-knit mittens.

MARCH

  • Plan for day temps between 27° F and 37° F
  • Temps will drop near 19° F at night and into the early mornings
  • Expect 0.06 inches of precipitation in March

What to Wear in Chicago in March: The last month of winter may see temps start to rise, but it’s a slow go. If you plan on walking the Magnificent Mile, checking out Millennium Park, or hitting Navy Pier, you’re going to want your warmest pieces.

Recommendations: Men’s short parka, sturdy men’s boots, men’s lambswool beanie.

APRIL

  • Plan for day temps between 30° F and 42° F
  • Temps will drop near 20° F at night and into the early mornings
  • Expect 0.10 inches of precipitation in April

What to Wear in Chicago in April: April is when Chicago truly sees the light at the end of the tunnel. While the start of the month hovers in the mid-30s, the last days can see highs in the upper 60s. To pack accordingly, go for a mix of layers than can easily be added and subtracted.

Recommendations: Women’s hooded anorak, women’s fringy scarf, women’s canvas sneakers.

MAY

  • Plan for day temps between 47° F and 66° F
  • Temps will drop near 44° F at night and into the early mornings
  • Expect 0.28 inches of precipitation in May

What to Wear in Chicago in May: With sustained temps in the 60s, it’s time to pull out your spring clothes, guys. That means T-shirts, cropped pants, and breathable fabrics. May is more susceptible to rain, though, so throw a small umbrella in your bag.

Recommendations: Women’s cropped jeans, women’s short-sleeve tee, compact umbrella.

JUNE

  • Plan for day temps between 61° F and 72° F
  • Temps will drop near 48° F at night and into the early mornings
  • Expect 0.31 inches of precipitation in June

What to Wear in Chicago in June: This month is a sweet spot for Chicago, one where the weather is warm but not blistering and the wind is refreshing, not polar. Wear tees, midi dresses, and cropped pants, but still stow a thin sweater in your bag should nighttime temperatures dip.

Recommendations: Women’s sleeveless jumpsuit, women’s jean jacketwomen’s classic white Birkenstocks.

JULY

  • Plan for day temps between 70° F and 77° F
  • Temps will drop near 59° F at night and into the early mornings
  • Expect 0.04 inches of precipitation in July

What to Wear in Chicago in July: Shorts, sundresses, and a whole lot of sunscreen are the way to go during Chicago’s hottest and typically most humid month. Breezy clothes, a hat, and a water bottle are musts. This is also the time to whip out your swimsuit and go for a dip in one of the city’s numerous public pools and beaches.

Recommendations: Off-shoulder midi dress, one-piece swimsuit, women’s aviators.

AUGUST

  • Plan for day temps between 67° F and 76° F
  • Temps will drop near 58° F at night and into the early mornings
  • Expect 0.24 inches of precipitation in August

What to Wear in Chicago in August: Though the stifling heat of July starts to slow in August, you can still expect high humidity and lots of sun. Be sure to pack comfortable sandals and accessories—like baseball caps and sunglasses—to avoid harmful rays while outdoor sightseeing.

Recommendations: Men’s chino shorts, men’s cork walking sandals, baseball hat.

SEPTEMBER

  • Plan for day temps between 52° F and 69° F
  • Temps will drop near 42° F at night and into the early mornings
  • Expect 0.13 inches of precipitation in September

What to Wear in Chicago in September: September weather can be unpredictable in Chicago, but as the city saunters back into fall you can begin to expect crisper days and cooler nights. Travel with a light jacket, short-sleeved shirts, and breathable cotton layers.

Recommendations: Women’s denim jacket, women’s black jeanswomen’s slide-on loafer mules.

OCTOBER

  • Plan for day temps between 39° F and 53° F
  • Temps will drop near 28° F at night and into the early mornings
  • Expect 0.18 inches of precipitation in October

What to Wear in Chicago in October: Temperatures certainly start to slip in October, but it’s not quite time to whip out your winter-weight coat. Instead, opt for something like a wool overcoat or shearling jacket that can be slipped on over sweaters, sweatshirts, and long-sleeve tees.

Recommendations: Men’s long-sleeve tee, men’s crewneck sweater, men’s shearling jacket.

NOVEMBER

  • Plan for day temps between 22° F and 35° F
  • Temps will drop near 17° F at night and into the early mornings
  • Expect 0.14 inches of precipitation in November

What to Wear in Chicago in November: Chicago sees its weather take a sharp turn in November, so prep for chilly temps and the possibility of snow with ample winter accessories.

Recommendations: Women’s cocoon coat, women’s cashmere scarfmerino-wool beanie.

DECEMBER

  • Plan for day temps between 21° F and 33° F
  • Temps will drop near 16° F at night and into the early mornings
  • Expect 0.12 inches of precipitation in December

What to Wear in Chicago in December: Without question, plan on packing winter-weather essentials: a heavy coat, hat, gloves, thick socks, and snow boots. Bonus points for thermal long johns.

Recommendations: Men’s down parka, men’s waterproof boots, thick socks.

 

FREQUENTLY ASKED QUESTIONS ABOUT PACKING FOR CHICAGO

Chicago aerial city view

What should I wear to a Chicago Cubs game?

As we’ve noted above, Chicago style is pretty casual, so you can expect to see a whole lot of jeans, tees, sweatshirts, and sneakers at a game. That said, throwing on a Cubs cap will certainly help you blend in (and drum up team pride). Depending on the season, it’s also smart to pack a sweater, wind breaker, or light coat, as Wrigley Field is famously windy thanks to gusts off nearby Lake Michigan.

What should I pack for winter?

Chicago undergoes notoriously brutal winters. While it’s still a magical time to visit—there’s ice skating in Millennium Park, sledding in Soldier Field, holiday light shows in Lincoln Park Zoo!—you’ll need to come prepared. Pack a heavy winter coat; waterproof boots; thermal long underwear; accessories like hats, gloves, scarves, and hand warmers; and a whole lot of layers.

What is the dress code for going out in Chicago?

You’ve probably picked up on the fact that Chicago is a pretty casual destination. Jeans, tees, and sneakers are largely accepted, but if you’re heading out to an avant-garde cocktail bar or a show at Steppenwolf, you may want to elevate your look. Try throwing on a pair of booties (or leather sneakers, for the gents) and topping off your outfit with a nice jacket or blazer. If you’re headed to a jazz club or a white-tablecloth restaurant, check their website to see if they have a dress code. 

What are the best winter boots for a trip to Chicago?

Whether your trip features fresh snow, icy sidewalks, below-freezing temps, or all the above, you’ll want a reliable pair of winter boots in your travel wardrobe. Key boot considerations should be warmth, traction, and water repellency. Opt for something like L.L.Bean’s shearling-lined waterproof duck boots, and you should be good to go. 

Related Stories