The BEST Time to Visit Chicago! [August 2019]

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No city gives the USA’s Midwest more fame and recognition than Chicago. Perhaps it’s their world-famous sports teams – like the Chicago Bears. Or the fact that they play at legendary Wrigley Field that still uses its original 1937 manually-operated scoreboard. Or maybe it’s their unique architecture, museums, thriving art and social scene. It could also definitely be their own Chicago-style hot dogs and Chicago-style deep dish pizza!

No matter what your reason is for planning a trip to Chi-town, you undoubtedly want to go when it’s the best time to visit Chicago. Maybe your priority is for going when the weather is the most pleasant, or perhaps when there are better travel deals and fewer tourists.

When finalizing your travel plans for the best time to visit Chicago for you, you want to consider all of these factors- weather, tourist season, and cost. And don’t forget that the city has tons of amazing year-round events, so you’ll want to consider those too! 

When is the best time of year to visit Chicago?

Generally, the best time of year to visit Chicago is in the late spring to early summer and in the fall. These seasons are when everything is the most balanced – the weather is not too hot or too cold, tourist crowds aren’t at their peak, and travel and accommodations prices aren’t at their highest either. Plus, there are plenty of outdoor activities and events happening!

Chicago

This is our INSIDER GUIDE for the best times to visit Chicago! (Photo credit – 10best.com)

Summer has the most events to offer – over 400 – but the weather is very hot and often uncomfortably muggy. If attending one of these events is your reason for going, just be prepared for the heat, peak prices and tourist crowds! Winter is very cold – yes, it snows! Whether or not you can handle Chicago winters depends on how prepared (and willing) you are to endure below freezing conditions!

 

Interested in history? Read up on the history of Chicago!

Is Chicago safe?

While nowhere in the world is 100% safe, as long as you use your common sense, you’ll likely be fine in Chicago

Having said that, you should NEVER travel without proper travel insurance. We’ve tested all of the best travel insurance providers, and World Nomads is our favorite! Fill out the form below to get a quote for your trip to Chicago so you can keep yourself (and your belongings!) covered and safe 🙂

 

Want to go deeper? These great museums in Chicago are perfect for learning a little more.

What months are the best time to visit Chicago?

As mentioned previously, the most ideal conditions in terms of weather, tourist levels and travel costs are in late spring and early fall. This is especially true in May, early June, September and into October – making these the best months to visit Chicago.

The average temperatures stay in the mild 70s℉ (20s℃) range, representing the months when it’s not too cold (like in the winter) and not too hot (like in the summer). These months fall outside of the prime tourist season summer months and make them even more appealing!

Besides just weather and tourist factors, it’s worth being aware of the events and activities happening throughout Chicagoland. There are options available year-round, and there may be something you simply don’t want to miss!

chicago in winter

Read below for information about Chicago weather in January (Photo credit – yourusacityguide.com)

Chicago Weather in January

The Windy City lives up to its name in January – it’s the city’s windiest and coldest month of the year! Chances are you’ll see snow as Chicago gets an average of almost 11 inches of snowfall this month. Average temperatures are an outright-cold 15℉ (-1℃) to 30℉ (-9℃) – and with that high wind factor – brrrrr!

Chicago Events in January

  • Cubs Convention (mid-January)
    • A real treat for Chicago Cubs fans! The Sheraton Grand Chicago hosts an annual event that includes autograph signings, meet-and-greets with the players and some cool exhibits. Be sure to get tickets!
  • SoxFest Chicago (late January)
    • The sports buzz continues with this special opportunity to go to the Chicago Hilton for an up-close experience with the Chicago White Sox. If you’ve been dying to get an autograph from a current or former Sox player, this is your chance! 
  • Chicago Restaurant Week (late January)
    • One of the best ways to stay indoors and sheltered from the cold is by enjoying some world-class dining. These 2 weeks allow you to try some of the Chicago area’s best restaurants at special prixe-fixe lunch and dinner menus. Over 350 establishments participate, so take advantage and try out as many as you can pack in!

Have some time in Chicago? These are our favorite day trips from Chicago!

 

chicago in feb

Read below for information about Chicago weather in Februray (Photo credit – jdvhotels.com)

Chicago Weather in February

The cold weather conditions from January continue through February. Average temperatures are from 17℉ (-8℃) to 33℉ (0℃) and with anywhere from 5 to 21 miles per hour winds, it will feel even colder! There’s an average of 8 inches of snow and only about 3 hours of daily sunshine.

Chicago Events in February

  • Chicago Theater Week (early to mid-February)
    • If you’re in Chicago this month, you must take advantage of this deal! For 10 days, you have the opportunity to see over 100 extraordinary shows in the Chicago area – from musicals to comedies – at discounted prices. Another bonus – all performances are indoors!
  • Chinese New Year Parade (mid-February)
    • Chicago prides itself on its multicultural energy, and one of the best ways to experience its Chinese community is with the annual Chinese New Year Parade in Chinatown.
  • Chicago Auto Show (mid-February)
    • This isn’t just any ordinary car show. Chicago’s auto show is known to be the largest and biggest and oldest in the country. It started back in 1901 and continues to go strong with over 1,000 cars on display – from passenger cars to concept cars. With 2.7 million square feet dedicated to exhibit halls, you can be sure you’ll have plenty to see!

If you’re going to Chicago, take a look at some amazing things to do in Chicago while you’re there!

 

chicago skyline

Read below for information about Chicago weather in March (Photo credit – feelthebreezeoftuscany.com)

Chicago Weather in March

March conditions warm up a bit from January and February, but it’s not the time to leave the coat and scarf off your packing list quite yet! Average temperatures remain chilly with a low of 28℉ (-2℃) and high of 45℉ (7℃) with around 7” of snow.

Chicago Events in March

  • Dyeing of the Chicago River (early March)
    • You’ll want your cameras ready for this! Get some shots of the all-green waters of the grand Chicago River that are dyed annually around St. Patrick’s Day. Boats dump orange powder into the water – and voilà – the entire river turns into a green St. Patrick’s Day phenomenon!
  • St. Patrick’s Day Festival and Parade (weekend closest to March 17)
    • Chicago loves St. Patrick’s Day and pulls out all the stops for this Irish celebration! The St. Patty’s Day parade is one of the largest in the entire country and showcases thousands of marching bands, floats, and plenty of marching leprechauns.
  • Good Food Expo (end of March)
    • Since 2004, this nationally recognized Good Food Movement event has grown into one of the largest expos of its kind. The event features speakers, farmers, chefs, investors and other members of the good food community that come together to celebrate organic, sustainable, local food. 

Not yet booked? Take a look at our favorite hotels in Chicago!

 

cloud stock footage

Read below for information about Chicago weather in April (Photo credit – shutterstock)

Chicago Weather in April

April brings a welcome break to the extreme cold, and you can see the beginning of new blooms and a gradual return to outdoor life. It can be a rainy month with variable weather, so be prepared for anything if you plan on visiting Chicago in April! Average temperatures range from 39℉ (4℃) to 57℉ (14℃). 

Chicago Events in April

  • Buckingham Fountain (starting mid-April)
    • Considered by many to be Chicago’s most notable landmark, the Windy City’s beloved Buckingham Fountain gets turned back on after being off since mid-October. Locals and visitors alike make it a point to witness the 20-minute water show that takes place every hour on the hour. After dusk, enjoy the show with some multi-colored lights and music!
  • Chicago Chef Week (mid-late April)
    • Get a taste of some of Chicago’s best culinary offerings during Chef Week when popular downtown and neighborhood eateries offer set multi-course prixe-fixe menus at a special discount. New and different restaurants participate every year, so be sure to check out as many as you can!
  • C2E2 – Chicago Comic and Entertainment Expo (end of April)
    • Known as the only pop culture and comic expo in downtown Chicago –  and the largest in the Midwest – this event is a hit its many activities from exhibitors to the industry’s top comic artists and authors. For anyone who loves comic books, anime, video games and anything of the sort, this one’s for you!

Ready to book? Here are our favorite areas to stay in Chicago!

 

Chicago in may

Read below for information about Chicago weather in May (Photo credit – timeout.com)

Chicago Weather in May

As spring’s cold and rainy weather passes and summertime vibes enter the scene, May might be the best time to visit Chicago! There’s a chance of rain with about 8 rainy days in the month, but overall, you can enjoy pleasant temperatures of 51℉ (11℃) to 70℉ (21℃). 

Chicago Events in May

  • Chicago Kids and Kites Festival (early May)
    • A family-fun favorite, this free event gives away free kite kits for kids to build and fly their own uniquely-decorated kite. Bring the kids to Cricket Hill in Lincoln Park and have some good old-fashioned kite flying fun!
  • Memorial Day Parade (end of May)
    • If you’re in Chi-town over Memorial Day weekend, be sure to take part in the local tradition to celebrate those who serve the country. Events start with a wreath-laying ceremony to honor the heroes who have fallen in combat and is followed by a grand parade through the heart of the city.
  • Maifest (end of May)
    • This fun, free event celebrates German heritage in Chicago’s Lincoln Square, known as the heart of the city’s German community. Enjoy a traditional German keg tapping to kick off the event and all the German food, drinks, live music and the popular maypole dance!
Chicago Ale Fest

Read below for information about Chicago weather in June (Photo credit – solsticepr.com)

Chicago Weather in June

Tourists begin flocking to the Windy City in June as summer conditions take over the city. There are outdoor activities aplenty going on as temperatures reach a pleasant 57℉ (14℃) to 79℉ (26℃). Rain is still possible, but is slight for Chicago, with an average of around 3 inches for the month.

Chicago Events in June

  • Chicago Blues Festival (early June)
    • If you enjoy some amazing music in a welcoming outdoor setting, be sure to check out this free 3-day festival at Millennium Park. The lineup features top talent that represents the blues and the genre’s influence on hip hop, soul and R & B.
  • Pivot Arts Festival (early June)
    • This annual celebration includes 10 days of multi-genre performances to highlight contemporary, innovative arts in Chicago in dance, theater, music and comedy. The festival also includes talks, workshops and more. 
  • Ribfest (mid-June)
    • Ribs and rock & roll – enough said, right? You can’t beat this 3-day event that features live music, family entertainment, and – of course – ribs! Over 14 of Chicagoland’s restaurants compete for the “People’s Choice” award, so don’t miss out on tasting all the goodies and casting your vote.
Chicago in July

Read below for information about Chicago weather in July (Photo credit – thechicagolifestyle.com)

Chicago Weather in July

July is Chicago’s hottest – and most crowded – month. Tourists and locals alike are out enjoying the long days with 15 hours of sunshine. If visiting in July, be prepared for average temperatures of 63℉ (17℃) to 84℉ (29℃) that often feels hotter with the high humidity.

Chicago Events in July

  • Fourth of July Celebrations (July 4)
    • Celebrate the country’s independence day by enjoying one of the many fireworks displays taking place throughout Chi-town. If you’re looking for the biggest show and spectacle, head down to the famous Navy Pier.
  • Pitchfork Music Festival (mid-July)
    • One of the most popular events for the Chicago area’s music lovers, this 3-day fest entertains the crowds with top acts representing all musical genres. If you like to stay on the cutting edge of the music scene and discovering emerging artists, this is a good one! 
  • Taste of Chicago (mid-July)
    • Not only is the Taste of Chicago known as the biggest festival in Chicago, but it’s also said to be the largest food festival in the entire world! For 5 days in Grant Park – with free admission – experience and sample the diversity of the Windy City’s culinary scene. Non-food highlights include live music and performances on multiple stages.
cHICAGO IN AUGUST

Read below for information about Chicago weather in August (Photo credit – timeout.com)

Chicago Weather in August

  • There are plenty of outdoor activities to enjoy as August provides a break from July’s highest temperatures, but less wind and higher humidity levels up to 88% keep conditions feeling steamy. On average, temperatures range from 63℉ (17℃) to 81℉ (27℃).

Chicago Events in August

  • Millennium Park Summer Film Series (through late August)
    • August is the last month to spread out a blanket and take advantage of Chicago’s free outdoor movie screenings on the large 40-foot LED screen set up in Millennium Park. Once a week, enjoy the featured film that ranges from contemporary to popular classics.
  • Lollapalooza (early August)
    • This 4-day music festival based in Chi-Town’s Grant Park has been drawing crowds from near and far since its start in 1991. You’ll find the music industry’s top acts along with plenty of food, drinks and party options!
family in chicago in september

Read below for information about Chicago weather in September (Photo credit – urbanmatter.com)

Chicago Weather in September

With thinning crowds as summer comes to an end – and unpredictable but overall warm weather conditions – September can also be the best time to visit Chicago. There’s an average of 10 days of rainfall, so some rain is highly possible, but you can expect a pleasant and comfortable temperature range of 55℉ (13℃) to 74℉ (23℃).

Chicago Events in September

  • Oktoberfest by the Bay (mid-late September)
    • Who says you need to be in Munich for an epic Oktoberfest experience? You’ll have a blast at this German-themed fest South Bay style – with nonstop music, a live Bavarian band, dancing, bratwurst and, of course, beer!
  • Chicago Jazz Festival (early September)
    • If you plan on spending Labor Day weekend in Chicago, be sure to bring a lawn chair and check out this popular music festival held annually in Grant Park. The event is free and features performances from jazz greats along with rising talent.
  • Chicago Gourmet (late September)
    • Sponsored by Bon Appetit, this multi-day food festival delights guests with tastings of delicious food, beer, spirits and wine. Celebrity chefs entertain with live cooking demonstrations of their favorite dishes.
October in Chicago

Read below for information about Chicago weather in October (Photo credit – tripsavvy.com)

Chicago Weather in October

Especially in the first part of the month, October is another good month to visit Chicago. Daytime temperatures are cool and comfortable and nights get cold – requiring adequate layers – with an average low of 44℉ (7℃) and high of 63℉ (17℃). The weather can get stormy and windy, so be prepared for variable conditions.

Chicago Events in October

  • Chicago Marathon (mid-October)
    • Hotels get booked up for this important marathon, so be sure to plan ahead if you’re planning on being in the Windy City during this time. Thousands of visitors from neighboring areas around the world – runners and spectators alike – come into the city and make it a busy weekend in Chicago. But it’s fun to watch, so take advantage of the high energy and help cheer on the athletes!
  • Chicago International Film Festival (mid through late October)
    • This important film festival was started in Chicago in 1964 as an alternative to the Hollywood-dominated movies shown at local theaters; it’s now known as the oldest competitive film festival in North America. The festival has introduced international movie greats like director Martin Scorcese and is known globally as a reputable annual event that discovers and highlights the best in the industry – from A-listers to up-and-comers.
iceskatingribbon

Read below for information about Chicago weather in November (Photo credit – chicagonow.com)

Chicago Weather in November

If your Chicago plans involve visiting in November, be sure to pack for cold, wet and possibly snowy weather. Average temperatures typically don’t go above 47℉ (8℃) and nights reach freezing levels at or below 32℉ (0℃). The Windy City offers lots to do, but you’ll need to bundle up!

Chicago Events in November

  • Thanksgiving Day Parade (Thanksgiving Thursday)
    • Since 1934, Chicago delights spectators on Thanksgiving morning with a grand parade with the top marching bands from all over the country, performances and crowd-pleasing gigantic inflatable balloons!
  • The Magnificent Mile Lights Festival (end of November)
    • One of Chicago’s most-anticipated annual holiday season kick-off traditions includes a weekend full of festive family-friendly events – like photos with Santa Clause and live music – that lead up to the spectacular Tree Lighting Parade down North Michigan Avenue. A fireworks show over the Chicago River tops off the schedule of events!
  • Millennium Park Ice Skating (starts in November)
    • Have a go with a few laps around the famous ice skating rink set up on Michigan Avenue every holiday season- it’s free! If this doesn’t get you in the holiday spirit, we’re not sure what will!
Chicago in december

Read below for information about Chicago weather in December (Photo credit – 10best.com)

Chicago Weather in December

If you’re looking for a cold, magical white Christmas season, you’ll find it in Chicago! Winter coats, scarves, hats and gloves are required as average temperatures linger around 35℉ (1.5℃) with below-freezing nights.

Chicago Events in December

  • Christkindlmarket (through December)
    • Chicago loves this annual German-inspired outdoor holiday market! Light-covered stalls and huts offer delicious European delicacies and sweet treats, warm drinks, crafts, gifts and more. 
  • Winter Wonderfest (through December)
    • If you need a break from the cold outdoors, bring the fun indoors at this family-friendly winter wonderland. Attractions include an indoor ice skating rink, rides, giant slides and holiday decor as far as the eye can see!
  • New Year’s Eve Celebrations (December 31)
    • As you may expect, you’ll find plenty of amazing options for ringing in the new year in Chicago! From fancy luxury hotel parties to award-winning restaurant sit-down dinner offerings, there’s something for everyone. Or, really celebrate Chicago-style by joining the crowds at the Navy Pier for the magnificent fireworks extravaganza over Lake Michigan. 

 

What is the best time to visit Chicago weather-wise? 

Chicago offers countless things to do and see year-round, which is why it’s one of the most visited cities in the US. But extreme cold and dealing with snow are not the ideal travel conditions for everyone.

For the most temperate and pleasant conditions, the best time to visit Chicago weather-wise is late spring to early summer – particularly May and June. In these months the freezing and bitter-cold weather have passed and the stifling summer heat and humidity haven’t peaked. 

The second best time to visit Chicago weather-wise is early fall – in September and October. By September, the worst of the trapped city heat has lifted and rainfall is low. October is cooler with variable weather, but still, a good time to visit before the average temperatures plummet.

Final thoughts on the best time of year to visit Chicago

Lucky for you, during any time of year, Chi-Town will show you a great time! Usually, warm weather is associated with the ideal trip, but that doesn’t mean that times of cold and snow can’t also be the best time of year to visit Chicago. The city is magical and vibrant in a different way, and you may find that it makes for the perfect way to experience the Windy City. Rain, sun, snow or wind – Chicago will win you over with its Midwestern charm!

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About the Author Nicola Smart

Gin lover. Coffee addict. Nicola has traveled the world for 7 years and is a staff writer for Hotel Jules. Born in London, Nicola first got the taste of travel studying abroad in Barcelona. Since then she's been hooked - traveling the world non-stop. Passionate about green travel and vegan lifestyle, Nicola spends more of her free time staring at maps wondering where she will head to next!