Quick overview:
- Best time to visit Chicago
June and September is arguably the best time to visit Chicago. You’ll not only experience smaller crowds but nicer weather as well. Hotels and flights won’t necessarily be cheaper, but they will be more affordable than in the summer. - Best time to visit Chicago for good weather
Chicago has very hot summers and blustery winters. Because of the various weather patterns, most people prefer to visit Chicago during early summer, late spring, or early fall. The temperatures during these seasons range between 76-94°F. - Best time to visit Chicago for good deals
If you want to get good deals on hotels, flights, and entertainment, then the best time to visit Chicago is during January and February. Hotel occupancy is low during the winter, with many hotels and restaurants offering deep discounts. However, the average temperature will be around 23°F, and it snows…a lot. - Best time to visit Chicago with family
According to travelers, the best time for family vacations to Chicago is during the summer. This is because the days are long, Lake Michigan is perfect for swimming, and there are tons of family-friendly festivals. However, this period is usually hot, humid, overcrowded, and relatively expensive. - Best time to visit Chicago for art and museums
Chicago’s world-class museums offer free entry to residents with a limit of 52 days a year. The museums choose their favorite days for free admission to both residents and non-residents of Illinois. For instance, on Sundays, the Chicago Children’s Museum as well as the McCormick Bridgehouse offer free access to those who are 15 years old and under. On Wednesdays, free guided tours are available at Clarke House and Glessner House. - Best time to visit Chicago for the performing arts
Chicago is also a popular destination for theater. Any time of the year would be good to catch a show. February is a great time to go since there are hundreds of productions that take place in the span of two weeks.
If you’re like me, you probably prefer visiting places in the summer for obvious reasons: sunny weather and tons of fun outdoor activities.
- Related: 54 Best things to do in Chicago
Chicago hosts many outdoor festivals in the summer, as the weather is much nicer than the freezing temperatures of winter.
However, this time of the year can be very expensive as hotels and restaurants bump up their prices to meet demand. But there are those who actually don’t mind the cold and ended up enjoying the city more.
I’m going to share with you what the weather is like each month of the year. I’ll also include some of the most popular events happening in Chicago throughout the year.
So let’s get started!
1. January: Lots of snow
Weather
January is the coldest month for Chicago, with average daily temperatures of 22° F. There’s also a lot of snow blanketing the city, up to 9 inches in a single day at times.
Festivals and Events
Chicago Polar Bear Plunge in January | Photo by @chicagopolarbearclub via Instagram
- Chicago Restaurant Week – Despite its name, this is usually a two-week deal with more than 300 restaurant participants who offer a range of cuisines. It starts in late January and goes through early February.
- Black Creativity Family Day – The Museum of Science and Industry hosts this month-long event that features collaborative printmaking, art exhibits, and talks with STEM field experts.
- Chicago Polar Bear Plunge – The Lakeview Polar Bear Club usually invites all willing people to join them for a fundraiser to help needy families.
- Stout and Chili Night – CHAOS Club usually throws this event every year, pairing more than 30 varieties of stouts and chilis. Some comedy acts and music also accompany this event.
2. February: Cold month with lots of snow
Weather
Chicago’s weather in February is also quite cold. It snows a lot, with the snow four inches thick and covering the ground for the entire month.
Festivals and Events
Cupid Undie Run Event in Chicago | Photo by @cupidundierun via Instagram
- Cupid’s Undie Run – This is a one-mile fun run that happens on Valentine’s Day weekend. There’s usually a party at noon before the run starts and another one right after.
- Hideout Makeout Party – An annual concert that features an orchestra composed of local artists who play a variety of songs, you’ll have a ton of fun.
- Chicago Theater Week – This is a 10-day festival featuring discounted tickets to more than 100 performances throughout the city. You’ll witness tons of plays, music, operas, and other budget shows.
- Neighborhoods of the World – This event involves celebrating ethnic cultures in Chicago with a variety of traditional live music, crafts, food, and dance.
3. March: Drier days
Weather
The temperatures begin to rise during this month when there are some dry days. The average temperature is 46°F, with an average snowfall of about 5 inches.
Festivals and Events
- The Chicago Beer Festival – The Field Museum hosts this event, where at least 70 breweries are invited to showcase their latest brews. The ticket price includes music, beer sampling, and even a museum exhibit. If you want to get early samples, consider buying the VIP ticket.
- Holi-the Festival of Colors – This is typically a big and popular party in the US where people smash powders on each other. It’s a Hindu holiday celebrating the end of winter and the beginning of spring. It’s a free event, although you’ll have to pay $2 for a bag of colored powder.
4. April: Average 59°F
Weather
April is the first month where you see temperatures rise to almost comfortable digits. During the day, the average temperature is 59° F, whereas it remains slightly above freezing in the evening. The average precipitation in April is 3.8 inches.
Festivals and Events
People dancing to jazz at the BluesShout! | Photo courtesy of BluesSHOUT!
- Chicago Dance Month – This is a festival that features more than 50 free and discounted classes and performances. The events vary in style and include hip hop, circus, ballet, and more.
- Chicago International Movies and Music Festival – This is an event that involves film screenings, concerts, and panel discussions. During the morning hours, you’ll see movies and music at night. The event is hosted by Wicker Park and Logan Square in various galleries, bars, and theaters.
- BluesSHOUT! – This is a three-day blues dance festival that features various performances, live bands, classes, and competitions.
5. May: Warmer days
Weather
May is a beautiful month to be in Chicago, when you’ll experience warm days with more hours of sunlight. Most afternoons are pleasant, although the nights are chilly. There are some rainy days. The average high temperature is 69° F, and the average precipitation is 3.5 inches.
Festivals and Events
Chicago Beer Classic Event at Soldier Field in May | Photo by @chicagobeerclassic via Instagram
- Chicago Beer Classic – This beerfest touts more than 100 local and international breweries where each provider is allowed to give 2-4 beer samples. The fest sells both general and VIP tickets.
- Chicago Kids and Kites Festival – This is hosted by Cricket Hill in Lincoln Park and features face painting, balloon animals, free kites, and pro kite demos.
- Mayfest – This is a three-day event that features local music, live bands, and entertainment. You’ll also get a beer and fantastic food.
6. June: Best time to visit Chicago
Weather
This month has perfect weather—not too dry, not too humid. It is one of the best months to visit Chicago. Temperatures around this time are around 80°F to 86°F. In June, there are a lot of thunderstorms and rain. It is known as the second wettest month of the year with an average precipitation of 3.9 inches.
Festivals and Events
Pilsen Food Truck Social Event in Chicago | Photo by @truckfoodsocial via Instagram
- Chicago Blues Festival – This is the largest music and blues festival in the world. It’s a free event that attracts a huge crowd hosted at Millennium Park. There are five stages, and it goes on for three days.
- Pilsen Food Truck Social – This is a food festival that serves various cuisines along with family activities, live music, and plenty of beer. It’s a two-day event that has a $5 charge.
- 57th Street Art Fair – This is the oldest art fair in the US, featuring visual arts and genres, including sculptures, leatherwork, painting, glass art, and jewelry. It’s hosted in Hyde Park.
7. July: Hot and rainy
Weather
July is the wettest and hottest month. There are a lot of thunderstorms as well as moderate rains. July also has long days. The average high temperature is 84°F, and the average precipitation is 3.9 inches.
Festivals and Events
Taste of Chicago Festival | Photo by @tasteofchi via Instagram
- Taste of Chicago – This has been around since 1980 and is the largest food festival in the world. It attracts millions of people every year and features a wide variety of live music from popular singers.
- Rhythm World Festival – This event features performances, classes, workshops, and dances.
- Square Roots Festival – This three-day music and craft beer event is hosted by Lincoln Square. You’ll get to enjoy musical acts, jam sessions, great food, and local brews.
8. August: Warm days
Weather
The weather in August is usually warm, and the winds are calmer. There are also thunderstorms and rain, although they’re relatively low compared to July. The waters are warm and ideal for swimming and kayaking. The average high temperature is 82°F, and the average precipitation is 3.8 inches.
Festivals and Events
Performers at Chicago Jazz Festival | Photo by @chicagofestival via Instagram
- Northalsted Market Days – This festival runs for two days and features live music, arts, crafts, foods, and many vendors.
- Oak Park Microbrew Review – This is a craft brew festival that features live music as well as light bites. Buy your ticket early enough before they’re sold out.
- Chicago Jazz Festival – Usually takes place during Labor Day weekend and features live performances from a variety of jazz music from the local, national, and international artists. Jay Pritzker Pavilion at Millennium Park hosts the event.
9. September: Comfortable weather, great events
Weather
September is the best month to visit Chicago. There are balmy afternoons that ensure the evenings are comfortably cool. It’s also a drier month with very clear skies. The average high temperature is 75°F, and the average precipitation is 3.5 inches.
Festivals and Events
Wine tasting at Chicago Gourmet Week | Photo by @chicago_gourmet via Instagram
- Chicago Gourmet – This upscale food festival features cooking demos, world-class eats, premium beer, spirits, wine tastings and seminars, among others.
- Poetry River – Offers mixed-media performances that feature music, dance, poetry, and a light show. The performances come in several languages.
- Chicago Architecture Biennial – This event features design competitions, art installations, as well as discussions involving urbanism, architecture, etc.
10. October: Getting cooler again
Weather
The days are typically shorter, and the nights start becoming cooler. There are regular rains during this month, but snow is rare. The average high temperature is 62° F, and the average precipitation is 2.7 inches.
Festivals and Events
Northalsted Halloween Parade | Photo by @northalsted via Instagram
- Chicago International Film Festival – This two-week event started in 1964 and features directors, writers, and actors in the film industry.
- Rocktober Beerfest – This beerfest runs for three days and features a stein-hoisting competition and live music.
- Northalsted Halloween Parade – This event features the best Halloween costumes, ranging from costumed dogs to drag queens.
11. November: Back to cold
Weather
This is the first cold month immediately after summer. The days are sunny, while the evenings and nights are cold. There are some snow days, and the average high temperature is 48°F. The average snowfall is 0.5 inches, and the average precipitation is over 2 inches.
Festivals and Events
Santa at the Magnificent Mile Lights Festival | Photo by @themagmile via Instagram
- Magnificent Mile Lights Festival – This event features family-friendly activities, a tree lighting parade, fireworks together with music, food, Santa sightings, etc.
- Christkindlmarket – This is a traditional German-style market that features unique foods and gifts such as strudel, nutcrackers, and beer steins. The market starts in mid-November and runs all the way to Christmas Eve.
- ZooLights – You’ll enjoy free visits to the Lincoln Park Zoo and have fun throughout. Some of the fun activities here include watching live ice carvings, enjoying crafts and snacks, and watching musical light shows.
12. December: True winter
Weather
This is the true winter, with a majority of the days seeing temperatures well below 30°F. There are a lot of snowy and cold days. The average high temperature is 36°F, with an average snowfall over 8 inches.
Festivals and Events
People visiting Sauced Night Market | Photo by @saucedmarket via Instagram
- Renegade Craft Fair – This craft fair features live music, independent and contemporary handmade good makers, and artisanal foods and drinks.
- Sauced Night Market – This market has a party-like atmosphere filled with various kinds of foods, craft beer, and artsy crafts. The market’s location changes with the event.
- One of the Kind Show – This show runs for four days, host to more than 600 vendors who sell many kinds of handmade items ranging from fashion to metalwork sculptures.
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