Wouldn’t it be nice if you could pick the PERFECT time to visit Chicago? Wondering about the weather? What kinds of events and festivals are offered in this amazing city? What is the outdoors life like? We’re going to guide you through all of this! We’re giving you a month-by-month account of what to expect. Whether you’re riding solo or bringing the family along, we will cover all the bases! We guarantee that you’ll find the perfect time that works for you.

when to visit Chicago

If you haven’t booked your hotel yet, here are the best places to stay in Chicago.

January

Chicago in Jan

Weather: Looking for your winter wonderland? Expect to see this in January! It’s not just the coldest month of the year. It’s also the month with the most snow! The average temperature of Chicago in January is 22F. Be sure to pack a good quality coat! You’ll see lots of snow in Chicago around this time. Over half of the month will have snow on the ground.

Events & Festivals: Are you a foodie? Be sure to check out Chicago Restaurant Week! You’ll find 2 weeks of great deals on many meals! There are hundreds of restaurants that participate! The event starts towards the end of January.

Do you have a strong interest in science? Well, you’re in luck! Black Creativity Family Day takes place on Martin Luther King Jr. Day every year. The Museum of Science and Industry is the host! Expect to indulge in art exhibits, professional STEM talks, and lots more!

Are you an adrenaline junkie? Check out the Chicago Polar Bear Plunge! This event takes place at the end of January. It’s hosted by the Lakeview Polar Bear Club! Want to give back to the community? All proceeds go to area families in need! You can sign up on-site or register online.

Looking to get your “drink” on? Then you have to check out Stout and Chili Night! A home-brewing club (CHAOS) hosts this event. You’ll find 30+ stouts and a bunch of chili to taste-test! You can expect comedy acts along with music. It’s an all-around good time!

Do you have a thing for puppets? If so, we have news for you! The Chicago International Puppet Theater Festival is the event for you! It lasts 11 days and features puppet masters from all over the world! Each event requires a separate ticket. The event are scattered all throughout Chicago!

February

Weather: February is also a cold one in Chicago! The average temperature will be around 30F. Not into freezing temps? Don’t worry, because it’s usually above 32F during the day in February. Expect freezing weather at night though! You’ll see snow on the ground a little less than half of the time during this month.

Events & Festivals: Looking to spice up your love-life? Check out Cupid’s Undie Run! This run is strictly for fun. It’s one mile on Valentine’s Day weekend. Have you guessed yet? You’ll be running in your underwear! The run takes place right between two parties! Be sure not to drink too much before your fun run! All proceeds are directed towards the Children’s Tumor Foundation and NF research.

Wanting some good music? The Hideout Makeout Party will give you that! It’s a concert held every year. Local musicians team up in an orchestra performance. You can find covers from popular artists such as Celine Dion and Frank Zappa. The Hideous is big on their music. Be prepared to bless your ears! It’s located on the northern end of Chicago.

Big on the theater scene? February has you covered! Chicago Theater Week is a festival that’s actually longer than a week… it’s 10 days! You’ll find discount tickets for 100+ theater events throughout Chicago. You can see operas, plays, musicals, and lots more! Big- and small-budget acts included!

Want to check out some winter Chicago wildlife? Look no further! Polar Adventure Days is 100% free! It’s held at Northerly Island. You’ll have first-hand experience with loads of animals! This includes huskies, wolves, birds, and many more! You’ll get to drink some hot cocoa and participate in other winter-type events.

Interested in Chicago’s rich, diverse culture? Check out Neighborhoods of the World! This event features the many ethnic cultures of the city. Look for all sorts of music, food and art! It takes place every Sunday starting in the middle of February. It’s held at the Navy Pier!

March

Weather: You’ll be able to handle the cold a little better in March. You’ll find temperatures above freezing most of the time. Not a fan of being wet? This is a dry month for Chicago! You should expect occasional cold rain and some snow though. Keep that coat handy! You can probably manage with a light jacket or sweater. The nights are icy!

Events & Festivals: Looking for some great beer? Be sure to look for The Chicago Beer Festival! The Field Museum hosts this event. You’ll find 70 breweries presenting their best spring brews! You’ll have access to many samples of beer! And music, of course. You won’t be able to buy a ticket on-site! So be sure to order your tickets in advance.

Want to attend a Hindu party? Then head on out to Holi-The Festival of Colors! Expect to get colorful powders thrown at you. It’s all for fun! This Hindu holiday celebrates the start of spring and end of winter. This party is hosted by The Vedic Cultural Society in Naperville. Expects lots of food and music! Are you a cheapskate? This party is 100% free! But you’ll have to pay a couple dollars for the colored powder. This festival occasionally happens in February. Be sure to check so you don’t miss out!

Do you just love St. Patty’s Day? Then March is a great time to visit Chicago! The Shamrock Greening event is just for you! Expect to see streets and buildings lit up with lots of green! As if that isn’t enough… the river is also dyed green! Also be sure to check out the holiday parade!

April

Weather: This is a wet month! Be sure to keep your raincoat handy. An umbrella wouldn’t hurt either!April is also the windiest month in Chicago. The majority of the days will be above freezing. Don’t count out the snow though! April is known for occasional flurries. This is mostly true for the first half of the month.

Events & Festivals: Do you just wanna dance it all away? If so, then April is the month for you! Be sure to check out Chicago Dance Month. This festival lasts all of April. You’ll see 50+ classes and performances! And many of these are free or at a discount. What exactly can you find? Well… there’s ballet, tap dancing, hip hop, and lots more! These events are scattered throughout Chicago.

Looking for good movies and music? Head to The Chicago International Movies and Music Festival! The event is 4 days long. Expect lots of concerts, panel discussions, and films! You’ll see movies in the morning. And listen to the music at night! It’s located in Wicker Park and Logan square.

Are you a comic geek? Well, The Chicago Comic and Entertainment Expo is just for you! You’ll witness screenings, a mix of artists, panel discussions, and lots more! It’s a 3-day event hosting celebrities, creators, comic fans, manga, video games, and so much more! You should bring some cash to this event. Look for lots of cosplay as well!

Are you a fan of the blues? If so, you have to check out bluesSHOUT! It’s a dance festival that lasts for three days. You’ll find live blues bands putting on a show! The levels of the dance classes will be assigned based on auditions. Are you a dancing beginner? That’s fine too! You can sign up for the beginner classes.

May

Weather: This is a beautiful month in Chicago! You’ll see more sunlight and warm days. Make sure you bring a light jacket or sweater though! The nights can be a bit cold. You can expect to see rain half the time during this month. Pack that umbrella or raincoat!

Events & Festivals: Looking for local and international beers? Look no further! Chicago Beer Classic is a beerfest with nearly 100 breweries present! Each brewery provides 2-4 beers to taste-test. You’ll get 48 2-oz. samples with a general-admission ticket. Feeling important? You’ll get 60 samples with the VIP ticket! And a venue tour of Soldier field (Chicago Bears stadium).

Want to fly kites for free? Check out the Chicago Kids and Kites Festival! The event is held in Lincoln Park. The free kites are first-come first-serve! Get them while they last! You’ll also witness professional kite demos. Look for the balloon animals and face painting as well! Are you traveling with family? This is a great event for families! Bringing the kids along? A special kite will be dropping candy from the sky!

Looking for even more beer? This is the month for it! Illinois Craft Beer Week hosts hundreds of events all throughout the city! You’ll find rare beers up for sampling. These are even at discounted prices. What a deal! You can download an app to get the full scoop on this event.

Looking for fun under a big tent? Well, Mayfest has just that! Expect to find local musicians at this 3-day event. And a beer garden plus some great grub! This is a great month to travel if you have kids. Mayfest features Kids Day and Pet Pageant & Expo!

June

Weather: Looking to travel to Chicago during a warm month? June is first on the list! The humidity isn’t too rough. Expect average temperatures of 80F! Are you planning to travel to Chicago towards the end of this month? Watch out for thunderstorms! This is when they’re most likely to occur. June comes in 2nd place for wetness.

Events & Festivals: What is Chicago’s biggest festival of music like? Well, you can find out! Just attend the Chicago Blues Festival! This is the largest blues festival in the WORLD! Feeling cheap? No problem, because this event is free! Expect to see around half a million people at this HUGE event! It’s a three-day event at Millenium Park.

Searching for a good summer food festival? Search no longer! The Pilsen Food Truck Social is an event with 25 food trucks. Expect live music, good brews, and plenty of family activities! It’s a free 2-day event. Are you a charitable person? Consider donating $5 to support the food trucks and soup kitchen!

Are you really into art? The 57th Street Art Fair has been ongoing since 1943. It’s one of the oldest fairs in the USA! You can find around 200 artists showing their visual-arts work. Look for jewelry, paintings, a variety of sculptures, and so much more! It’s a 2-day event in Hyde Park.

July

Weather: Are you a fan of HEAT? July is the hottest month of the year! It’s also the month with the most rain. Please pack your raincoat or an umbrella! You can expect the entire month to be rainy. Watch out for the high amount of thunderstorms too. You’ll get about 12 hours of sun on any given day this month!

Events & Festivals: You a HUGE FOODIE? Check out the Taste of Chicago event! It’s the biggest food festival on Earth. It’s also the biggest festival in Chicago. You’ll find cuisines from all sorts of cultures here. Live music is played as well! Check out the event’s games and rides. You can find more info online.

Really into tap-dancing? Well, the Rhythm World Festival features performances just for you! The styles are both contemporary and classic. It’s a 2-day event hosted by the Chicago Human Rhythm Project.

Want some good beer and great jams? The Square Roots Festival offers three days of music and craft beer. You’ll find this event in Lincoln Square. You’ll hear all sorts of genres. Check out indie rock bands, folk music, and lots more! Local and regional breweries will showcase their best beers. Lots of dancing goes on at this event as well! Admission is free. But consider donating to support local music and the farmers market.

August

Weather: August is still a hot month for Chicago! You won’t have as much wind to cool you down though. Wind speeds are at their lowest this month. August is about as hot as July. BUT the water is hotter during this month! August would be your best bet for hitting the lakes. There’s a decent chance of thunderstorms and rain.

Events & Festivals: Do you support LGBT? Northalsted Market Days is a massive 2-day festival on the streets! It’s geared towards the LGBT community, but anyone can attend! You’ll find live music, dancing, arts and crafts, and loads of good food! It’s a free event. But a donation is appreciated. This event happens in Boystown neighborhood.

Looking for some great local brews? Oak Park Microbrew Review has just what you’re looking for! This festival features live music and appetizers as well. Look for over 200 beers from around 100 local breweries. It’s hosted by Seven Generations Ahead. Grab your ticket quick! The event is known to sell out.

Need some jazz in your life? Well, the Chicago Jazz Festival features plenty of it during Labor Day weekend! You’ll find talent on the international, local, and national levels. It’s a FREE event at Jay Pritzker Pavilion (Millenium Park).

September

Weather: Are you a fan of clear skies? You’ll get that in September! Daze into the beautiful blue of Chicago skies in September! This month is one of the drier ones. You can expect light rain on occasions. The evenings will be cool. So pack something light just in case!

Events & Festivals: Want some upscale food? Chicago Gourmet will have your taste buds on edge! There’s wine, beer, demos for cooking, and (of course) plenty of great food! Some food competitions include the Tao of Tacos and Hamburger Hop. Don’t bring your kids along! You have to be 21 years old to attend this event.

Got a poetic side? Poetry River is an event just for you. It actually has music and dancing as well. Lots of different languages will be involved. Chicago’s multi-culture landscape will be showcased here.

Isn’t architecture amazing? You’ll find out all about this at the Chicago Architecture Biennial. You’ll find a handful of art installations. Design competitions take place as well! Find where the contemporary world, urban life, and architecture meet. The main events are hosted by the Chicago Cultural Center. Stony Island Arts Bank and Lakefront Kiosks host smaller events.

Looking for more good food and drinks? The Fulton Market Harvest Fest will provide all of this for you. Find top chefs from all over the world here! It takes place in the Fulton Market neighborhood. Consider a $10 donation to help kids make healthier food choices.

Want some AMAZING and FREE music? The World Music Festival of Chicago will give you that! This event has featured hundreds of bands from over 80 countries! It’s 100% FREE to attend!

October

Weather: Love the fall? You’ll see lots of it in October! This month is the peak of fall colors. The city begins to cool during October. And the days are shortening as well. You can expect regular rain. But this is still a dry month for Chicago! You won’t have a high chance of seeing snow. But it’s not unheard of to see some small flurries! Planning on night-time events? You should carry a jacket if so. Be prepared with layered clothing during the day.

Events & Festivals: Are you a movie buff? Be sure to check out the Chicago International Film Festival! It’s a 2-week long event. Many big-name directors started here, such as John Carpenter and Martin Scorsese. More than half of the screenings feature members directly involved in the film.

Wanna rock out and drink some beer? The Rocktober Beerfest is an event for you! It has a German-style Oktoberfest feel to it. This event is 3 days long. Look for good appetizers, great beer, and amazing music!

Is Halloween YOUR holiday? Look for Northalsted Halloween Parade! Want to see some amazing Halloween costumes? You’ll find many creative get-ups at this event. It takes place in Boystown. Anyone can march in this parade! Feeling competitive? Join the costume competition! There’s a trick-or-treat event for the kids as well! It’s a several-day event.

November

Weather: Following summer, this is the 1st truly cold month. You can expect freezing temperatures at night. So bundle up! Sunny days will fill around half of this month’s calendar. Overdraft can be expected for the other half. You can expect a small handful of snowy days in November. Just don’t expect the snow to stick around for long!

Events & Festivals: Want to really LIGHT up your vacation? Check out the Magnificent Mile Lights Festival! There’s a big tree-lighting parade with Disney characters. There’s plenty of activities for your family! Look for fireworks over the Chicago river! There’s great food and music as well. This event will really light up your life. It’s one of the biggest holiday events in the USA!

Looking for your Christmas spirit? Find it at the Christmas Tree Lighting Ceremony! This event has been going on for over 100 years. It takes place in Millenium Park. You’ll find live music and many Christmas characters such as Santa and Mrs. Claus! Put that wallet down! This event is FREE!

Have a taste for the German holiday spirit? Be sure to give a shot to Christkindlmarket. It’s a German-style holiday village with all sorts of food and presents. Look for nutcrackers and beer steins! You’ll be able to eat great German foods such as sausages and strudels. It takes place in Daley Plaza.

Are you a fan of zoos? Check out the ZooLights event at Lincoln Park Zoo! This is another free event! You’ll have a huge range of activities to participate in. You’ll get to see live ice carving. And a musical light show! Are you a night owl? There are night events as well! Check out the beer festival and live music.

December

Weather: Looking for a true-winter trip? December is your best bet! You’ll find freezing temperatures on most days. Snow is highly likely! The snow will probably melt into slush. So be sure to bring some waterproof shoes!

Events & Festivals: Got a thing for handmade arts and crafts? You’ll love the Renegade Craft Fair. You’ll find an arsenal of handmade goods! And great food, drinks, and music! Going on a shopping spree? Be sure to hit this event! There are many cool and quirky gifts to choose from.

Looking for a party vibe? Check out the Sauced Night Market! It has a party-type feel to it. There’s lots of craft beers and local food trucks. You’ll also find arts and crafts! Locations for events do vary. So make sure to check their calendar for the latest news!

Really want a wide selection of handmade items? This really is the month for you! Find all sorts of great gifts at the One of a Kind Show. It’s a four-day event hosted by The Mart. There are around 600 vendors showcasing their items! You’ll find many unique gifts for the holidays. Be sure to grab some great grub at this event as well! And of course there’s entertainment as well.

Best Months For Travel Deals

 good deals to grab Chicago

There are so many good deals to grab if you’re looking to save a penny or 2. You’ll get the best deals on your plane tickets, food, and entertainment during the winter months. Look for these great deals around January or February! This is when the least amount of people are visiting Chicago. You’ll find some great deals on these things during November and early December as well.

Best Months For Traveling With Family

Chicago with family

Summer is absolutely the best time to visit Chicago if you’re bringing kids and family! This is the time when the sun is out for the longest periods of time. The weather will be warm and exciting. You’ll find truckloads of family events during the summer months. The most affordable summer month is August! The deals won’t be as great as the winter months. But you’ll still save a buck or so during this month!

Best Months To Visit Museums

Museums

Be sure to search the many museums of Chicago for free admissions! Different days of the week will offer free admission to people just visiting the city. You’ll be able to satisfy your artistic side like never before! You can expect to find free admissions during any time of the year! Just be sure to check the calendar for the latest news. There are also many theaters in Chicago! February is the best time to visit Chicago if you’re really interested in the theater setting. The summer will offer loads of music festivals!

Best Months For The Great Outdoors

Chicago Beach

Chicago has around 26 miles of beachfront! This is along the shores of Lake Michigan. Summer would be the best time to really hit the waters. The water will be warm and blue! Expect lots of river cruises and kayaking in the summer as well! Check out the beautiful city of Chicago from its amazing waters.

Looking for more of the winter-wonderland type of outdoors? Your best bet is to visit in the winter! Chicago hosts loads of snow during the cold months. Look for cross-country skiing!

The fall has a lot to offer as well! Are you looking for the beautiful orange and brown leaves falling to the city grounds? If so, be sure to hit up Chicago around October and November! Millenium Park and Graceland Cemetery are great places for seeing the falling leaves.

Overall Best Weather

This really comes down to what your favorite kind of weather is. The beautiful city of Chicago is going to offer any kind of weather you can think of. The winters are extremely harsh! And you can expect heavy wind chill from the “Windy City.” The Summers are absolute heat waves! Are you an extremist in this way? Be sure to visit during the summer or the winter.

What if you’re into mild weather? That’s fine too! Chicago has you covered! Be sure to hit the city in the fall or spring if this is your ideal weather. Just make sure to pack an umbrella or a raincoat. With the mild months comes plenty of rain.

Are you looking for more specific information about the weather in certain times of the year? Just scroll up and refer to our weather sections during each month! You’re guaranteed to find something that you’ll like. This city has weather made just for YOU!

Best Months For Food Festivals

The Taste of Chicago

When exactly is the best time to visit Chicago for the best food and the best deals? We’d have to say it’s in the summer! Why is that? It’s because of the 2 HUMONGOUS food festivals that are held during this season!

The Taste of Chicago is a big one, and it takes place in July. Nothing like warm weather and amazing outdoor foods! The Taste of Chicago is located in the Loop. Please consider this event if you’re a big fan of summer weather a great grub!

What’s that other big food festival? It’s the Chicago Gourmet! You’ll be exposed to fine dining in Milennium Park. That’s fancy! Think these are the only 2 food events going on in the summer? It’s just not true! There are plenty of other smaller food events that take place during the warm season as well. The Chicago Hot Dog Fest is another well-prepared event in the summer.

Don’t get us wrong though! There are opportunities for foodies in the cold seasons as well! Are you a fan of pizza? Be sure to check out the Chicago Pizza Party in February! You’ll find any kind of pizza with any kind of toppings. Eat up!

Let’s not forget about Chicago Restaurant Week either. This takes place during the winter! The event lasts 2 weeks and is guaranteed to leave you stuffed and satisfied. You’ll find great deals on restaurants all throughout the city. Expect this event to take place during late January and into February!

Conclusion

Have you decided which time of the year is the best for you to travel to magnificent Chicago? We hope our article has made an impact on your travel decisions. Whether you’re riding solo or bringing family along, there are so many options for you!

Kids and adults alike will find plenty of fun in this amazing city. Any type of weather can be found in Chicago. Any type of event you can think of can be found in this beautiful city. The food is absolutely amazing. And that is an understatement!

So what are you waiting for?! Pull out that calendar and start marking your next vacation! Just be sure that the time you choose matches up with your interests! We hope we’ve helped you make a great decision. Happy traveling!

Read more:
Chicago Travel Guide
Things To Do in Chicago
Where To Eat in Chicago
Where To Stay in Chicago