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Best Time to Travel to Chicago

The best time of year to visit Chicago is in June or September, when you’ll find fewer crowds than in summer and better weather than in winter.Fall offers the clearest weather.

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When is the best time to go to Chicago?

  • Best time to visit Chicago for good weather: Chicago experiences all kinds of weather, with windy winters and sweltering summers. The best times to visit during warmer weather are late spring, early summer and early fall; specifically May, June, September and October. May and June can be a bit 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 to get good deals on flights, rooms, food and entertainment is in the winter, especially in January and February.Hotel room occupancy is the lowest during these months, hovering around 50 percent, so even luxury hotels offer great discounts. late November and early December also see drops in hotel prices. Chicago Restaurant Week begins in late January and Theater Week is in February, so it’s an ideal time to save in all areas.Keep in mind that Chicago’s winters are incredibly cold, averaging -6°C in January and often snowy, so bundle up if you plan to challenge the city.
  • Best time to visit Chicago for kids and families: Summer, from June to September, is the most popular time for family vacations in Chicago. The days are long, the water is perfect for swimming and there are many family events.Summer can also be stifling, crowded and expensive for family trips:If you visit in the summer, plan for August.although you won’t get the same bargains as in the winter, it’s the most affordable of the summer months and has better weather than July (a little cooler and dryer).if you can avoid the kids’ school schedule, shoot for April.the weather is more comfortable, rooms are a little less expensive and there are still many family events.
  • Best time to visit Chicago for art and museums: Chicago’s world-class museums are required to offer free admission to Illinois residents for 52 days a year.To name a few: Sundays are free at the McCormick Bridgehouse, and the Chicago Children’s Museum is free the first Sundays for visitors 15 years and younger. Tuesdays are free at the Loyola University Art Museum, the International Museum of Surgical Sciences and the DuSable Museum. Wednesdays are free at Glessner House and Clarke House, with free tours on Wednesday, Thursday and Friday.Thursday nights are free at the Chicago Children’s Museum, 5-8 p.m. Many other museums, including the Oriental Institute, the National Museum of Mexican Art, the Museum of Money and the Lincoln Park Zoo are free every day, year-round.
  • Sundays are free at the McCormick Bridgehouse, and the Chicago Children’s Museum is free the first Sunday for visitors 15 years and younger.
  • Tuesdays are free at the Loyola University Museum of Art, the International Museum of Surgical Sciences and the DuSable Museum.
  • Wednesdays are free at Glessner House and Clarke House, with free tours on Wednesday, Thursday and Friday.
  • Thursday nights are free at the Chicago Children’s Museum, 5-8 p.m.
  • Many other museums, including the Oriental Institute, the National Museum of Mexican Art, the Museum of Money and the Lincoln Park Zoo are free every day, year-round.
  • Sundays are free at the McCormick Bridgehouse, and the Chicago Children’s Museum is free the first Sunday for visitors 15 years and younger.
  • Tuesdays are free at the Loyola University Museum of Art, the International Museum of Surgical Sciences and the DuSable Museum.
  • Wednesdays are free at Glessner House and Clarke House, with free tours on Wednesday, Thursday and Friday.
  • Thursday nights are free at the Chicago Children’s Museum, 5-8 p.m.
  • Many other museums, including The Oriental Institute, The National Museum of Mexican Art, The Money Museum and Lincoln Park Zoo are free every day, year-round.
  • The best time to visit Chicago for The Performing Arts:Chicago has one of the most popular theater scenes in the nation.Music festivals begin in June with Do Division (a family event with a wide range of music, plus a fashion show, family activities and food) and end in September with Riot Fest (punk, indie rock and hip hop).Check out April’s Chicago Dance Month, with more than 50 performances, events and classes at reduced prices. From late June to early September, visit Chicago SummerDance; this free event features dance classes followed by freestyle dancing every Friday through Sunday at the Spirit of Music Garden.
  • Best time to visit Chicago for the outdoors: Chicago is home to about 26 miles of beach along the shores of Lake Michigan.The water is cool and blue, making it an ideal place to spend the summer from late May to early September. Local favorites include Oak Street Beach, Montrose Beach and Rainbow Beach. The Lakefront Trail runs for 18 miles, perfect for walking or biking while taking in the scenery.The water is comfortable from June to September, and August is the warmest. In the colder months, Chicago is a winter wonderland with many ice skating rinks scattered throughout the city, usually open from late November to early March, although December to February is the ideal time for a good freeze.Northerly Island, where you can snowshoe or cross-country ski, is a hidden gem for winter fun.
  • Best time to visit Chicago for lunch: Chicago has two great food festivals in the summer: Taste of Chicago in July (a five-day outdoor mix at the Loop) and Chicago Gourmet in September (a star-studded food festival at Millennium Park).The smaller neighborhood festivals take place throughout the summer, mainly from May to September.Chicago Restaurant Week is a two-week fixed-price meal event at various restaurants throughout the city; it runs from late January to 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 enjoy the cityscape, whether by boat, on foot or from atop an observation deck. If you go by boat (the best way!), you’ll want to visit from April to November, when the Chicago Architecture Foundation is offering its acclaimed river cruises.», «If you’re walking, you’ll want to visit between March and September, except in July when it’s swelteringly hot and very rainy. You can see the horizon all year round from inside an observation deck at Hancock Center or Willis Tower, but you’ll still want to choose a time when the sky is clear, so choose late May to early October.
  • The best time to visit Chicago for the Leaf Peeping: Chicago and its surroundings tend to see the first leaves change in September. The peak color usually comes in mid-October, although some years the brightest colors come at the end of the month.Chicago’s many parks, including Millennium Park and Graceland Cemetery, are perfect places to get up close and personal with the leaves, or you can opt to look down from the top, having a drink at one of the rooftop bars overlooking Chicago’s green spaces, such as Cindy’s or Tavern at the Park.
  • Best time to visit Chicago to avoid the crowds: Winter is the least crowded time in Chicago.Hotel occupancy is lowest in early December, January and February. Although the weather is cold and often snowy, this is a perfect time to travel if you are interested in culture.

Tourist Seasons in Chicago

  • High (June to August): Warm weather, sunny beaches, food and music festivals and school vacations are factors that make summer the most attractive season for travelers.Winter vacation creates mini travel peaks in late November and late December. If you’re traveling at either of these times, book flights and hotels well in advance.
  • Low (November to March): Chicago’s low season is during the harshest weather, from November to March, with the exception of the Thanksgiving and Christmas holidays.
  • Average (April to May and September to October): Spring and fall make up the shoulder seasons for trips to Chicago. You’ll find fewer crowds than in summer and better weather than in winter. Spring temperatures average 18°C in the day and drop to about 7°C at night. Average drop temperatures peak at 21°C and fall to 9°C. Hotel and flight rates will not be cheap, but will be a little more affordable than during the summer.spring tends to be a little rainy, so pack an umbrella.autumn offers the clearest weather.

Chicago weather month by month

  • Chicago weather in January: January is the coldest month in Chicago, with average daily temperatures of -6°C. This is also the snowiest month.», «More than half the days you will see the ground covered with snow, although the accumulation is only about 2 cm deep. About five days a month you will see about 15 cm of snow on the ground, and once or twice a month the snow will exceed 25 cm.(Average high -1 ° C, average precipitation 43 mm, average snow 27 cm.)
  • Chicago weather in February: February in Chicago is still quite cold, although daytime highs often rise above zero.The accumulation of thick snow, with more than 10 cm on the ground, only occurs about 5 days this month. (Average high 1°C, average precipitation 38 mm, average snow 23 cm.)
  • Chicago weather in March: in March, temperatures start to rise, hovering above zero most of the time.The weather is a mixture of mostly dry days, along with some cold rain and muddy snow. Most of the time, you will want to put on your coat and boots, but rarely are the afternoons warm enough to go out in a sweater or light jacket. Wrap up again at night, when the temperatures turn cold again.(Average high 8°C, average rainfall 67 mm, average snow 14 cm.)
  • Chicago weather in April: this is the first month of the year when you will reliably see temperatures in the double digits.maximum temperatures average 15°C during the day, and nights generally remain above zero.April is the windiest month of the year and tends to be rainy.a scarf and an umbrella are ideal for travelling comfortably.snow is rare but not unknown in this month, especially in the first half. (Average high 15°C, average rainfall 97 mm.)
  • Chicago weather in May: one of the most beautiful months in Chicago, May sees more hours of sunlight and more warm days.Although the afternoons are pleasant, the nights are usually cold. Dress in layers when you travel this month. Rain is still frequent, with more than half the days seeing at least some small showers.(Average high 21°C, average rainfall 88mm.)
  • Chicago weather in June: June’s dew point is at its optimum, which means the air feels perfect, neither too dry nor too humid. This is the first truly warm month of the year, with peak temperatures of around 27° and occasional heat peaks of over 30°.Carry an umbrella; This is the second rainiest month of the year, with thunderstorms towards the end of the month.(Average high 27°C, average rainfall 99 mm.)
  • Chicago weather in July: This month is the hottest, wettest and dirtiest month of the year. It is likely to have moderate to moderate thunderstorms and rain throughout this month, so plan some rainy day activities just in case.The days are long at this time of year, with about 12 hours of sunlight (high average: 29°C, average rainfall 100 mm)
  • Chicago weather in August: August remains hot and humid most of the time, while wind speeds drop to their slowest, which means there is no breeze to cool things down.Thunderstorms and rain are likely this month, although less likely than in July. The water is warmer this month, which makes August ideal for going to the beach or kayaking. (average high: 28°C, average rainfall: 97 mm)
  • Chicago Climate in September: Many consider it the best month to visit.Like June, the dew point is at the perfect level. Mild afternoons give way to cool evenings. This is one of the driest months, with clear skies most days, and only occasional light rain spells.(Average high 24° C, average rainfall 90 mm.)
  • Chicago weather in October: Autumn colors peak during this month, days shorten and cool down, and nights drop back into single digits. Rain occurs regularly this month, but only in small bursts; this is still one of the driest months of the year.Snow is rare, but not entirely unknown. Wear layers during the day and a jacket at night. (Average high 17°C, average rainfall 68 mm.)
  • Chicago weather in November: November is the first cold month after summer, with nights hovering around freezing.Days are cool and sunny about half the time, while the rest are cold and mostly cloudy. November usually has a couple of snowy days during the month. You will want to keep warm if you are planning a night on the town. (Average maximum temperature 9°C, average rainfall 67 mm, average snowfall 1.2 cm.)
  • Chicago weather in December: December is the real winter in Chicago, with most days below 0° C on average.it is likely to snow this month, although only a couple of days will see more than 2 cm.in most cases, the snow will melt into slush, so wear warm, waterproof boots when you are out.

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