The Best Time to Visit Chicago

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Updated: May 27, 2021
By Santorini Dave

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In my opinion, the best time of the year to visit Chicago is in June or September, when you’ll find fewer crowds than in summer and better weather than in winter. Rates on hotels and flights won’t be the cheapest during this time, but they’ll be a bit more affordable than during the summer rush. Fall offers the clearest weather.

Me and my wife in Chicago.

My wife and I in Chicago during a September visit.

When is the best time to go to Chicago?

  • Best Time to Visit Chicago for Good Weather:
    Chicago experiences the full range of weather, with blustery winters and sweltering summers. The best times to visit for milder weather is in late Spring, early summer, and early fall; specifically May, June, September, and October. Temperatures are usually mild during these months, with averages between 12°C and 21°C. May and June can be a little rainy, so pack an umbrella, just in case. September and October have mostly clear skies.
  • Best Time to Visit Chicago for Good Deals:
    For Chicago, the best time for getting good deals on flights, rooms, food, and entertainment is in winter, especially in January and February. Hotel room occupancy is at its lowest during these months, hovering around 50%, so even luxury hotels offer deep discounts. Late November and early December also see dips in pricing for hotels. Chicago Restaurant Week begins in late January and Theater Week is in February, making this an ideal time for savings across the board. Be advised that Chicago winters are incredibly cold, averaging -6°C in January, and often snowy, so do bundle up if you plan on braving the city.
  • Best Time to Visit Chicago for Kids and Families:
    Summer, June through September, is the most popular time for family vacations to Chicago. The days are long, the water is perfect for swimming, and there are plenty of family-friendly happenings. Summer can also be stiflingly hot, overcrowded, and expensive for family travel! If visiting in summer, plan for August. Though you won’t get the same bargains as in winter, it’s the most affordable of the summer months and has better weather than July (a little cooler and drier). If you can work around the kids’ school schedule, shoot for April. The weather is more comfortable, rooms are just a tad less pricey, and there are still plenty of family events going on.
  • Best Time to Visit Chicago for Art and Museums:
    Chicago’s world-class museums are required to offer free entry to Illinois residents for 52 days of the year. Each museum chooses different days to honor free admission, and for those living outside Illinois, free admission is also available on certain days. To name a few:

  • Best Time to Visit Chicago for The Performing Arts:
    Chicago has one of the hottest theater scenes in the nation. Anytime is good for catching a show, but the best time to visit is during Theater Week in February, with over 100 productions taking place over ten days. Music festivals begin in June with Do Division (a family-friendly event with a wide range of music, plus a fashion show, family activities, and food) and ending in September with Riot Fest (punk, indie rock, and hip hop). The summer weeks in between have music festivals for jazz, blues, Latin, and more. Chicago also has an amazing dance scene. Check it out in April for Chicago Dance Month, with over 50 performances, events, and classes at discounted rates. From late June through early September, visit for Chicago SummerDance; this free event has dance lessons followed by freestyle dancing every Friday through Sunday in the Spirit of Music Garden.
  • Best Time to Visit Chicago for Getting Outdoors:
    Chicago is home to around 26 miles of beachfront along the Lake Michigan shores. The water is here cool and blue, making this a prime summer hangout spot from late May through early September. Local favorites include Oak Street Beach, Montrose Beach, and Rainbow Beach. The Lakefront Trail runs for 18 miles, perfect for a walking or cycling while taking in the scenery. The summer months are also prime time for river cruises and kayaking. Water is comfortable from June through September, with August being the warmest. In the colder months, Chicago is a winter wonderland, with plenty of ice skating rinks scattered around the city, generally open from late November through early March, though December through February is the ideal time for a good freeze. For great sledding, visit Soldier Field Sledding Hill, which stays lit at night (they do add fake snow occasionally). Northerly Island, where you can snowshoe or cross-country ski, is a hidden gem for winter fun.
  • Best Time to Visit Chicago for Food:
    Chicago has two huge food festivals in the summer: Taste of Chicago in July (a five-day, outdoor smorgasbord in the Loop) and Chicago Gourmet in September (a star-studded, fine dining festival in Millennium Park). Smaller neighborhood festivals occur all summer long, mostly from May through September. Chicago Restaurant Week is a two-week event of prix fixe meals at various restaurants citywide; it takes place from late January through early February. For Chicago’s most beloved foods, try the Chicago Pizza Party in February and the Chicago Hot Dog Fest in August.
  • Best Time to Visit Chicago for Architecture:
    Chicago is known for its stunning architecture and skyline. There are many ways to take in the urban landscape, whether by boat, on foot, or from high up in an observation deck. If going by boat (the best way!), you’ll want to visit from April through November, when the Chicago Architecture Foundation is offering their acclaimed river cruises. If going on foot, you’ll want to visit between March and September, except for July, when it’s sweltering hot and very rainy. You can see the skyline all year long from inside an observation deck in Hancock Center or the Willis Tower, but you’ll still want to choose a time when the skies are clear, so choose late May through early October. Late August through mid-September is clearest.
  • Best Time to Visit Chicago for Leaf Peeping:
    Chicago and the surrounding areas tend to see the first leaves changing in September. Peak color usually lands around mid-October, though some years the brightest colors come at the end of the month. Colorful leaves can usually be seen through November, when the frost begins to take over. Chicago’s many parks, including Millennium Park and Graceland Cemetery, are perfect spots for getting up close to the leaves. Or you can opt to have a look from above, by grabbing a drink at one of the rooftop bars overlooking Chicago’s green spaces, like Cindy’s.
  • Best Time to Visit Chicago for Skipping the Crowds:
    Winter is the least crowded time in Chicago. Hotel occupancy is at its lowest in early December, January, and February. Though the weather is cold and often snowy, this is a perfect time to travel if you’re interested in culture. Museums and restaurants will be less congested, and theater tickets will be easy to come by.

Chicago Travel Seasons

  • High (June through August): Warm weather, sunny beaches, food and music festivals, and school holidays all factor into making summer the most attractive season for travelers. Expect to pay top dollar and deal with crowds, but the long days are filled with an abundance of things to do for any range of interests. Winter holidays create mini travel spikes in late November and late December. If traveling during any of these times, book flights and hotels well in advance. Book the Best Chicago Hotels and the best Chicago Family Hotels far in advance.
  • Low (November through March): Chicago’s low season is during the harshest weather, from November through March, with the exception of Thanksgiving and Christmas holidays. Flights and hotels are cheap, sometimes half the price of summer rates. This is a great time to travel for those interested in arts and culture, when indoor attractions outweigh the bitter winter weather.
  • Shoulder (April through May and September through October): Spring and fall make up the shoulder seasons for Chicago travel. You’ll find fewer crowds than in summer and better weather than in winter. Spring temps average 18°C in the day and fall to around 7°C at night. Fall temps average highs of 21°C and lows of 9°C. Rates on hotels and flights won’t be cheap, but they will be a little more affordable than during the summer rush. Spring tends to be a little rainy, so pack an umbrella. Fall offers the clearest weather.

Chicago Weather by Month

  • Chicago Weather in January: January is the coldest month in Chicago, with average daily temps at -6°C. This is also the snowiest month. More than half of the days will see the ground covered in snow, though the accumulation is only around 2cm deep. About five days in the month will see around 15cm of snow on the ground, and once or twice a month the snow will exceed 25cm. Pack waterproof boots, a thick parka, and a hat if traveling in January. (Average High -1°C, Average Precipitation 43mm, Average Snow 27cm.)
  • Chicago Weather in February: February in Chicago is still quite cold, though daytime highs often rise above freezing. Snow is still frequent, and just under half the days see a thin layer of snow on the ground. Thick snow accumulation, with more than 10cm on the ground, only happens around 5 days this month. (Average High 1°C, Average Precipitation 38mm, Average Snow 23cm.)
  • Chicago Weather in March: In March temperatures start rising, hovering above freezing most of the time. Weather is a mix of mostly dry days, along with some cold rain and slushy snow. Most of the time, you’ll want to keep your coat and boots on, but on rare occasions afternoons warm enough to get away with a sweater or light jacket. Bundle back up for night, when temperatures get icy again. (Average High 8°C, Average Precipitation 67mm, Average Snow 14cm.)
  • Chicago Weather in April: This is the first month of the year when you’ll reliably see temperatures in the double digits. Highs average 15°C in the day, and evenings typically remain above freezing. April is the windiest month of the year and tends to be rainy. A scarf and umbrella are ideal for traveling comfortably. Snow is rare but not unheard of this month, especially in the first half. (Average High 15°C, Average Precipitation 97mm.)
  • Chicago Weather in May: One of the most beautiful months in Chicago, May sees more sunlight hours and more warm days. Though afternoons are pleasant, nights are often chilly. Dress in layers when traveling this month. Rain is still frequent, with more than half of the days seeing at least some small showers. (Average High 21°C, Average Precipitation 88mm.)
  • Chicago Weather in June: June’s dew point is in the sweet spot, meaning that the air feels perfect, neither too dry nor too humid. This is the first truly warm month of the year, with afternoon highs around 27° and occasional heat spikes over 30°. Days are lengthening now. Do carry an umbrella; this is the second wettest month of the year, seeing thunderstorms toward the end of the month. (Average High 27°C, Average Precipitation 99mm.)
  • Chicago Weather in July: This month is the hottest, wettest, and muggiest month of the year. Thunderstorms and light-to-moderate rain are likely for all of this month, so do plan a few rainy day activities just in case. Days are long this time of year, with around 12 hours of sunlight. (average high: 29°C, average precipitation 100mm)
  • Chicago Weather in August: August remains warm and muggy most of the time, while wind speeds fall to their slowest, meaning there’s no breeze to cool things down. Thunderstorms and rain are likely this month, though less likely than in July. Water is warmest this month, making August ideal for hitting the beach or kayaking. (average high: 28°C, average precipitation: 97mm)
  • Chicago Weather in September: This is considered by many to be the best month to visit. Like June, the dew point is at the perfect level. Balmy afternoons give way to cool evenings. This is one of the drier months, with clear skies most days, and only the occasional spell of light rain. (Average High 24°C, Average Precipitation 90mm.)
  • Chicago Weather in October: Fall colors peak during this month. Days are shortening and cooling off, with nights seeing temperatures back down in the single digits. Rain happens regularly this month, but only in little bursts; this is still one of the drier months of the year. Snow is rare, but not entirely unheard of. Wear layers in the day and a jacket at night. (Average High 17°C, Average Precipitation 68mm.)
  • Chicago Weather in November: November is the first cold month after summer, with nights hovering around freezing. Days are crisp and sunny about half of the time, while the rest are cool and mostly overcast. Usually November gets a couple of snow days over the month. You’ll want to bundle up if you’re planning a night on the town. (Average High 9°C, Average Precipitation 67mm, Average Snow 1.2 cm.)
  • Chicago Weather in December: December is true winter in Chicago, with most days below 0°C on average. Snow is likely this month, though only a couple of days will see more than 2cm sticking. More often than not, the snow will melt into slush instead, so do wear warm, waterproof boots when out and about. (Average High 2°C, Average Precipitation 63mm, Average Snow 22cm.)

Chicago Events and Festivals

Chicago in January

  • Chicago Restaurant Week – Two weeks of prix fixe restaurant deals for brunch, lunch, and dinner. Over 300 restaurants participate, offering a variety of cuisines, from downtown out to the suburbs. Restaurant week begins in late January and runs through early February.
  • Black Creativity Family Day – Hosted by the Museum of Science and Industry every Martin Luther King, Jr. Day, this event features the opening of their juried art exhibit, talks with STEM-field pros, collaborative printmaking and more. Though the celebration itself only lasts one day, the art exhibit runs for one month, and their innovation studio runs for six weeks.
  • Chicago Polar Bear Plunge – At the end of January, members of the Lakeview Polar Bear Club invite all to join in on their polar plunge at Oak Street Beach. The event is a fundraiser for area families in need, and 100% of all proceeds go directly to them. Swimmers can register online at a reduced rate, or sign up on site the day of the event.
  • Stout & Chili Night – CHAOS, a homebrew club, throws this annual event, pairing over 30 home-brewed stouts and with a variety of chilis. A few pro brewers will add to the mix, along with music and comedy acts.
  • Chicago International Puppet Theater Festival – An 11-day event featuring puppeteers from around the world, with performances, workshops, and symposiums. Venues are scattered throughout the city, and tickets are sold per event.

Chicago in February

  • Cupid’s Undie Run – A one-mile fun run on Valentine’s weekend, with runners wearing only their skivvies. The party starts at noon, followed by the run (so don’t drink too much at the first party!), followed by yet another party. Proceeds go to the Children’s Tumor Foundation and toward NF research.
  • Hideout Makeout Party – Billed as “an evening of aural intercourse,” the Hideout Makeout Party is an annual concert featuring an orchestra made up of musicians from local bands playing love songs and film soundtracks, plus a few originals. Expect to hear covers of songs from various artists, ranging from Frank Zappa to Celine Dion. The Hideout venue is a Prohibition-era bar that’s a mecca for the Chicago music scene. It’s in the north end of the city in the industrial strip between Wicker Park and Lincoln Park.
  • Chicago Theater Week – A 10-day festival, featuring discounted tickets for over 100 performances throughout the city. This event showcases the range of the Chicago theater scene, delivering everything from plays to musicals to operas, from big budget to shoestring budget shows.
  • Polar Adventure Days – A free event at Northerly Island, highlighting the Chicago area’s natural environment. Get up close with wolves, huskies, birds of prey, and more, snowshoe on the island, drink hot cocoa, and make wintery crafts.
  • Neighborhoods of the World – Celebrate Chicago’s many ethnic cultures with traditional live music, dance, food, and crafts. From Chinese to Polish to Brazilian and more. This is a recurring event every Sunday beginning mid-February and continuing through March at Navy Pier.

Chicago in March

  • The Chicago Beer Festival – Hosted by the Field Museum, the Beer Festival brings together 70 breweries, all with their latest spring seasonal brews. Ticket price includes beer sampling, music, and access to museum exhibits. Buy a VIP ticket to get in early for exclusive samples poured only during this first hour. Tickets must be purchased in advance; no tickets are sold at the door.
  • Holi-The Festival of Colors – Best known in the U.S. as a big party, where people throw colorful powders at each other, Holi is a Hindu holiday that celebrates the end of winter and beginning of spring. This is traditionally a time to forgive and forget old grudges, to make friends out of your enemies. The Vedic Cultural Society in Naperville invites everyone to celebrate at their festival, featuring food and music. The event is free, but the color powder is $2 per bag; buy it online and pick it up there or have it shipped to you ahead of time. (Some years this event occurs in February, so check the date ahead of time.)
  • The ShamROCK GREENing – In honor of St. Patrick’s Day, several landmark buildings, iconic monuments, and streets are all lit up green. They even dye the river! Other events include a parade, marathon and their annual ball. Events take place citywide.

Chicago in April

  • Chicago Dance Month: A month-long festival featuring over 50 performances and classes, many of them free or discounted. Featured events vary in style, and include ballet, hip hop, tap, circus acts, and more at venues scattered all around the city.
  • CIMMfest – The Chicago International Movies and Music Festival is a four-day event full of concerts, film screenings, and panel discussions. Movies in the morning; music at night. The party takes place in Wicker Park and Logan Square at various bars, galleries, and theaters.
  • Chicago Comic and Entertainment Expo – AKA C2E2, this comic and pop culture convention has artists, exhibitors, screenings, panel discussions, and autograph sessions. Since 2010, this three-day event has hosted creators, celebs, and fans of comics, video games, manga, and more. Expect lots of cosplay, and do bring cash; not all vendors here accept plastic.
  • bluesSHOUT! – This is a three-day blues dance festival, featuring live bands, classes, performances, and competitions. Dance class levels are assigned by instructors based on auditions, or anyone can opt for beginner level classes.

Chicago in May

  • Chicago Beer Classic – This huge beerfest features almost a hundred local and international breweries, each providing two to four beers for sampling. General tickets include 48 two-ounce samples, while VIP access gets you 60 samples, plus a tour of the venue, Soldier Field, home of the Chicago Bears.
  • Chicago Kids and Kites Festival – Held on Cricket Hill in Lincoln Park, this spring festival features free kites (first come, first served, so get there early before they run out!), along with pro kite demos, balloon animals, and face painting. This popular family event also features a special kite in the afternoon that drops candy from the sky.
  • Illinois Craft Beer Week – This event coincides with American Craft Beer week and features hundreds of events at venues citywide. Sample rare beers at discounted prices in landmark spaces across the city, such as the Garfield Park Conservatory. Download their smartphone app for Android or iOS for a full calendar of events.
  • Mayfest – This three-day event features live, local music and entertainment, plus a beer garden and fantastic food, all under a big top tent. Highlights include Kids Day and the Pet Pageant & Expo.

Chicago in June

  • Chicago Blues Festival – This is not only Chicago’s largest music festival but also the largest blues festival in the world. This free event attracts big-name acts and a crowd of half a million. The festival takes place over three days with five stages going, all at Millennium Park.
  • Pilsen Food Truck Social – This summer food festival features 25 trucks serving a variety of cuisines, along with live music, family activities, and beer. This two-day event is free, though a $5 donation is suggested, benefitting the food trucks association and a food bank/soup kitchen.
  • 57th Street Art Fair – Taking place annually since 1943, this is one of the oldest art fairs in the nation. The focus is on visual arts, with around 200 artists exhibiting their works. Genres include paintings, sculptures, and glass art, along with jewelry and leatherwork. The event runs for two days in the Hyde Park neighborhood.

Chicago in July

  • Taste of Chicago – The largest food festival in the world, the Taste of Chicago has been going on in Grant Park since 1980. This is the single largest festival in Chicago, attracting millions of visitors to try out classic Chicago and multi-ethnic cuisines. The event also has a strong and varied lineup of live music; past events have seen Robert Plant, Jennifer Hudson, and Death Cab for Cutie, among many others. Rides, games, and family activities are all on site.
  • Rhythm World Festival – Presented by the Chicago Human Rhythm Project, this festival of percussive dance, especially American tap, features performances, workshops, classes, and more. Classic and contemporary styles are included over this two-day event.
  • Square Roots Festival – This three-day music and craft beer festival takes place in Lincoln Square. Musical acts include indie rock bands, world music, folk music, and more, while beer is presented by local and regional craft breweries. Expect great food, dance parties, and jam sessions, and more. The event is free, but there is a suggested donation, which supports a local music school, farmers market, and concerts.

Chicago in August

  • Northalsted Market Days – This is a huge two-day street festival with an LGBT slant but open to all. It features live music on three stages, a dance floor, food, arts, crafts, and vendors. Several big-name acts come through each year; past events have seen Joan Jett and Salt-N-Pepa, among others. The event is free, with a suggested donation of $10, and takes place in the Boystown neighborhood.
  • Oak Park Microbrew Review – A zero-waste, craft brew festival with live music and light bites. Featuring around 100 local brewers, and over 200 beers, the event is produced by Seven Generations Ahead and is committed to having not a scrap from the festival going into a landfill. Tickets are limited, and it has been known to sell out, so be sure to grab yours early; only a handful will be available at the door.
  • Chicago Jazz Festival – Taking place over Labor Day weekend, this four-day jazzfest features live performances from a wide range of jazz genres, which can be local, national, or international. This free event takes place at the Jay Pritzker Pavilion in Millennium Park.

Chicago in September

  • Chicago Gourmet – This upscale food festival offers cooking demos, wine seminars, premium spirit, beer, and wine tastings, and of course, plenty of world-class eats. Highlights include the Hamburger Hop burger competition and the Tao of Tacos competition, where gourmet chefs create wild, new taco flavors paired with beers. This event is 21 and older only.
  • Poetry River – A mixed media performance, featuring poetry, music, dance, and a light show. This experiential event features performances in several languages, showcasing Chicago’s multicultural landscape.
  • Chicago Architecture Biennial – This exhibition highlights Chicago as the home of modern architecture and a center for creativity and innovation in design. The event features several art installations, design competitions, and discussions on the intersection of architecture, urbanism, and the contemporary world. The Chicago Cultural Center hosts the main events, while smaller events take place at the Stony Island Arts Bank, Lakefront Kiosks, and elsewhere.
  • Fulton Market Harvest Fest – This food and drink festival features live music and cooking demos with chefs from top restaurants in the Fulton Market neighborhood and throughout the city. The $10 suggested donation for admission benefits Pilot Light, a program teaching healthier food choices to kids.
  • World Music Festival Chicago – Founded in 1999, this event takes place in several venues citywide and has featured several hundred bands from over 80 countries since its inception. Free admission to all concerts.

Chicago in October

  • Chicago International Film Festival – This two-week long film fest began in 1964 and has been the breakout event for several big-name directors, including Martin Scorsese and John Carpenter. Over half of all film screenings feature writers, directors, or actors from the film, who introduce the movie and stick around afterward for discussions and meetups with the audience.
  • Rocktober Beerfest – A beer festival in classic German Oktoberfest style, Rocktober Beerfest is a three-day event with live music and a stein hoisting competition. Expect plenty of brats, pretzels, and dudes wearing lederhosen.
  • Northalsted Halloween Parade – Featuring some of the best Halloween costumes in the nation! This Halloween Parade takes place in Boystown and features everyone from drag queens to costumed dogs. All are invited to march in the parade, and there will be several costume competitions, along with a kid-friendly trick or treat treasure hunt. Related events take place over several days in the neighborhood.

Chicago in November

  • Magnificent Mile Lights Festival – Featuring a tree lighting parade with Mickey and Minnie Mouse, family-friendly activities, and fireworks over the Chicago River, this is one of the largest holiday events in the nation. With food, music, Santa sightings, and Mag Mile shopping.
  • Christmas Tree Lighting Ceremony – Chicago’s Christmas Tree Lighting Ceremony has taken place in Millennium Park for over 100 years. Featuring live music, a visit from Santa and Mrs. Claus, and a range of iconic Christmas characters. Admission is free.
  • Christkindlmarket – A traditional German-style market, this open-air holiday village is filled with unique foods and gifts. Pick up traditional German gifts, like nutcrackers and beer steins, then fill up on sausages, strudel, and Glühwein. The market begins in mid-November and runs through Christmas Eve. Located in Daley Plaza, overlooked by the Chicago Picasso.
  • ZooLights – Visit the Lincoln Park Zoo (always free!) on select nights from late November through New Year’s Day to see the holiday lights and enjoy activities throughout the park. Enjoy crafts and snacks, get a photo with Santa, and watch live ice carving or a musical light show. The zoo even stays open late a few nights for special events, including a beer festival, market night, and live music.

Chicago in December

  • Renegade Craft Fair – This curated craft fair features cutting edge, contemporary, and independent makers of handmade goods, plus artisanal food and drinks, and live music. This is a perfect spot to shop for quirky, cool gifts and maybe something for yourself, while you’re at it.
  • Sauced Night Market – This boozy market has a party atmosphere, with craft beer, local food truck faves, and artsy crafts. Locations change per event, so check their calendar for the latest news.
  • One of a Kind Show – For four days in December, The Mart hosts around 600 vendors selling thousands of handmade items. From bath products to fashion to metalwork sculpture, this is a great spot to find unique holiday gifts, and enjoy food and entertainment while you shop.

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About Santorini Dave

Santorini Dave Author Bio. Santorini Dave was started in 2011 by a guy who loved Greece, travel, and great hotels. We're now a small team of writers and researchers on a mission to deliver the most helpful travel content on the internet. We specialize in Santorini, Mykonos, Athens, and Greece and recommend the best hotels, best neighborhoods, and best family hotels in top destinations around the world. We also make hotel maps and travel videos. I can be contacted at dave@santorinidave.com.