Chicago offers visitors a unique blend of urban sophistication and Midwestern charm with its iconic skyline, world-renowned architecture, and diverse neighborhoods. From its museums and art galleries to its music scene and culinary delights, there is something for everyone in the country’s third-largest city. With so much to see and do, you might wonder, when is the best time to visit Chicago?
I’ve lived here for over 12 years and have seen the city through different seasons. The best time to visit Chicago weather-wise is late May to early October. But depending on your interests and preferences, the best time to visit Chicago may be different for you.
Plus, there are seasonal activities and events that can only be enjoyed in certain months of the year. If Christmas markets are your thing, you’d be remiss skipping the Christkindlemarket – one of the top three authentic German-style Christmas markets in the world. Similarly, food lovers will truly appreciate the world’s largest food festival – Taste of Chicago.
Read this monthly guide of events along with weather details to find the perfect month for your visit!
Visit Chicago in January
Begin the year by indulging in Chicago’s award-winning culinary scene at the Chicago Restaurant Week. This annual tradition includes discounted prix fixe menus in hundreds of restaurants around the city spanning world cuisines. The best part, it even has award-winning, Michelin-star places like Boka and Moody Tongue.
This is a great opportunity for foodies to sample the city’s diverse culinary scene and indulge in delicious meals at great value. Be sure to snag a reservation here in advance. Some of the choicest and most cost-effective places can get sold out in no time.
The year 2023 started with a dynamic Lunar New Year parade in Chicago’s Chinatown neighborhood. One of my favorite local tips for visitors is to venture out of downtown and explore Chicago’s myriad neighborhoods. And attending an event like this offers you the perfect way to do so. Next year’s parade will fall on February 18, 2024, so keep that in mind if you’re planning a late winter trip.
Winter is also a great time to attend a candlelight concert. While these concerts run year-round, there’s a special joy to attending one under the soft glow of candles in January when night falls early and the air is chilly outside.
Chicago weather in January
Visit Chicago in February
Chicago Restaurant Week continues into early February so there’s still time to visit a city restaurant that you’d love to try. But don’t let your love for food and culture stop there.
One of the best ways to honor Black History Month is to celebrate African American food at the Chicago Black Restaurant Week. This annual tradition was founded in 2015 in honor of Dr. Carter G Woodson and always falls on the second week of February.
February also ushers in Chicago Theatre Week where you get value-priced tickets at more than 100 performances across the city. Sit back and enjoy a period drama, laugh at a comedy show, or tap your feet to a musical at this celebration of storytelling.
Chicago weather in February
Visit Chicago in March
March is the month of color in Chicago. But before we get there, we start with a Polar Plunge in Lake Michigan. Join the locals as they partake in this iconic winter tradition and dive into the freezing lake at North Avenue Beach. It is all for a good cause as the funds support Special Olympics Chicago and Special Children’s Charities programs. Even if you’re not convinced about jumping into the water, it’s a fun event to watch from the sidelines and cheer the Bravehearts!
The colorful festivities begin with the Hindu festival of Holi. You may not be able to travel to India but you can throw colors at the Holi celebrations at Navy Pier organized as part of the Global Connections series. This free event allows you to celebrate the festival of colors while dancing to Bollywood music in the outdoor Beer Garden. Indoors, the Aon Grand Ballroom features live music, dance, and programs that give you a memorable slice of Indian culture.
The colors continue during St. Patrick’s Day when the Chicago River turns a bright emerald green. This is thanks to a special dye poured by the Plumbers Union that has been made environmentally friendly in recent years. It is quite a sight to see boats zigzag through the waters pouring bright orange and yellow color streams into the water which instantly turns green.
The river dyeing usually happens in the morning at 10 am followed by a downtown parade. The St. Patrick’s Day Parade downtown unfolds on Columbus Dr. between Balbo and Monroe at 12:30 pm. Always check the website for the latest parade details.
If you want to venture deeper, try the South Side Irish St. Patrick’s Day Parade and Northwest Side Irish Parade on the next day. There are bar crawls all over the city or you could get creative and make your own bar crawl through the city.
Then of course there’s the Shamrock Shuffle in late March at Grant Park where runners in green take off on an 8K run, two-mile walk, or one-mile race through the Loop.
Chicago weather in March
Visit Chicago in April
April starts with Expo Chicago – an annual contemporary art fair held that features leading international galleries and artists. The fair includes a range of exhibitions, installations, and special programs for visitors to explore and discover new art trends from 90 cities around the world. Grab your 2023 Expo Chicago tickets here.
There’s no better place to watch the growth and renewal of spring than Jackson Park. Delicate white and pink cherry blossoms spread across 160+ trees are an ethereal sight. Hanami or cherry blossom viewing is one of the best ways to enjoy spring and experience Japanese culture in Chicago.
Keeping with the theme of flowers, this is also a time to start checking out the Spring Flower Shows in the city’s conservatories. Lincoln Park’s 2023 show titled “Cooler By The Lake” and Garfield Park’s “Bee’s Knees” run from mid-Feb to mid-May.
Top off the month by catching a Cubs game in their home stadium Wrigley Field. The spring training ends in late March and the regular season is in full swing in April.
Chicago weather in April
Visit Chicago in May
May is a month of festivals and farmers’ markets in Windy City. Farmers’ markets in Lincoln Park and Logan Square really come alive as the weather warms. There’s fresh produce, flowers, baked goods, preserves, and even accessories like jewelry.
May brings grooving music at the Mayfest from May 12th through 14th in Lincoln Park. Local musicians entertain alongside summer food and chilled drinks. Add to that the Armitage Art Show that runs alongside showcasing Chicago’s local talent, and you have the recipe for the perfect summer day.
The following weekend, the festivities move to neighbor Lakeview where the Belmont-Sheffield Music Festival unfolds. The neighborhood festival, now in its 38th year, brings local bands to the main stage while everyone enjoys food and drinks. Kids and dogs are all invited to the party in this pet-friendly neighborhood.
The month ends with the newest festival on the block – Sueños in Grant Park. This festival was such a huge success last year and is returning with the biggest Latin Music lineup in Chicago. Tickets are selling fast, so make sure you book them before they are gone.
Chicago weather in May
Visit Chicago in June
June is a time to really embrace the outdoors. Chicagoans understand the beauty of seasons and no warm day is wasted. Take an architectural boat tour, head onto the river in a kayak, or bike along its 18-mile lakefront trail.
Kickstart the June festivals with Andersonville Midsommarfest on June 9th. This festival, born out of Andersonville’s Swedish heritage, brings Swedish culture to Chicago with dances, food, and family activities.
June is Pride Month and Chicago sure knows how to celebrate it in style! Celebrations start with the Chicago Pride Fest on the weekend of June 17-18 followed by the Pride Parade on June 25. The Pride Fest features live music, drag shows, pet parades, and more that celebrate our strong LGBTQ+ community and culture.
The Chicago Pride Parade is one of the largest pride parades in the world featuring colorful floats, marching bands, dance groups, and other performers representing an array of LGBTQ+ organizations and businesses.
Mid-June also fills the air of Chicago with strains of classical music. The Grant Park Music Festival arrives at the Jay Pritzker Pavilion and runs for 10 weeks until mid-August. This festival plays a big role in making classical music free and accessible to everyone. Just bring your own picnic blanket and spread it out on the lawn for free. Or you can grab a free seat in the back half of the seating bowl. If you’d like to support this cause, you can buy a one-night pass or become a member and get access to the reserved seating out front.
Chicago weather in June
Visit Chicago in July
A special event is coming this year to Chicago in July – NASCAR Street Race. 75-year-old NASCAR will bring several high-speed cars with skilled drivers from around the world to the Windy City. The race track near Grant Park features several ticket options
But the NASCAR race has meant that our beloved annual food festival, Taste of Chicago, has been pushed out to later in the year for 2023.
Don’t be disappointed on missing the Taste of Chicago in July. The end of the month brings the largest Latino Festival of its kind Fiesta del Sol to Chicago’s Pilsen neighborhood. The festive Ferris wheel, and more than 100 booths of authentic food and art, against the background of foot-thumping music bring out all the carnival vibes.
Chicago weather in July
Visit Chicago in August
It’s hard to pick the biggest highlight of August given the scale of both events this month.
Early August (3rd to 6th) is Lollapalooza time. This festival was first established in 1991 and has since grown to become one of the largest and most popular music events in the United States. Lolla (as it is fondly called) features a diverse lineup of musical acts spanning a wide range of genres, including rock, pop, hip-hop, electronic, and more.
The Chicago Air and Water Show features high-flying aerial displays from a variety of military and civilian aircraft as well as thrilling performances by teams of expert pilots. The water portion of the show includes exciting watercraft demonstrations by the U.S. Navy and Coast Guard. The free event draws huge crowds who come to watch the skilled pilots perform daring maneuvers and stunts in the skies above the city and the waters of Lake Michigan. Whether you find a good spot along the beach or head to the rooftop of a high-rise building on August 19 & 20, the magic in the skies and water will leave you impressed.
Chicago weather in August
Visit Chicago in September
The month of September is bookended by music festivals. ARC, one of the most popular house and techno festivals, kickstarts the month. This is followed by local neighborhood festivals like the Lakeview East Festival of Arts along Broadway St from Belmont to Hawthorne. Here more than 150 artists showcase their paintings, sculpture, photography, furniture, jewelry, and more. The festival will run on the 9th and 10th of this year.
If you’re looking for a delightful weekend filled with the aroma of freshly printed pages and the charm of literary conversations, the Printers Row Lit Fest is your ticket to bookish paradise on September 9 and 10. Strolling through the historic Printer’s Row neighborhood, you’ll find yourself surrounded by rows upon rows of book stalls. But it’s not just about buying books; this festival is about celebrating the magic of words. Authors from various genres grace the festival with their presence, offering readings, signings, and thought-provoking panel discussions. Whether you’re into mysteries, romance, science fiction, or non-fiction, you’re sure to find an author or two who’ll spark your interest and inspire your next reading adventure.
Late September is the time to witness the fall Chicagohenge, a spectacular astronomical event that occurs twice a year. During Chicagohenge, the sun rises and sets directly in line with the city’s east-west streets, creating a stunning visual effect of the sun appearing to rise and set between the buildings. This phenomenon occurs because Chicago’s grid system is aligned with true east and west, unlike other cities where the streets are angled or curved. The dates vary slightly every year and 2023 saw the spring henge on March 20, while the fall henge is set to happen on September 23. Join the crowds on Washington St or Randolph St in downtown to watch the bright orange blob.
The month draws to a close with the free, multi-day, multi-venue World Music Festival. This festival was first held in 1999 and has since grown to become one of the largest and most diverse world music festivals in the United States. It features a variety of performances by international and local artists, showcasing a range of genres, including traditional and contemporary music from around the world. The festival’s mission is to promote cross-cultural understanding and celebrate the diversity of Chicago’s communities through music. I recently attended this festival’s Indian classical music program Raagmala and the ancient strains of Carnatic music still linger in my ears.
If you can’t be in Germany for Oktoberfest, you can celebrate right here in Chicago. Gather in Chicago’s West Lakeview area on the last weekend of September for an evening of beers and brats.
Chicago weather in September
Visit Chicago in October
October is the season of Fall colors, Harvest Maze, and Pumpkin carving. Watch the leaves turn crimson, orange, and rust near the famous Bean in Millenium Park or one of the neighboring forest preserves. Kids are guaranteed to have a great time attending the free Fall Fest at Lincoln Park Zoo replete with a Harvest Maze and Pumpkin Walk.
I headed over to Jack’s Pumpkin Pop-Up last week with my friend and we had a blast. It has everything from axe throwing, carnival games, fabulous photo ops, a corn maze, countless pumpkins, and apple cider donuts to give you all the Fall Vibes without leaving the city! The trick is to arrive right when they open (4 p.m. on weekdays and 11 a.m. on weekends) so you don’t have to worry about long lines and large crowds.
The Chicago Marathon is one of the most prestigious and popular long-distance races in the world. Held annually in October, the race attracts over 40,000 runners from all over the globe. The course covers 26.2 miles, starting and finishing in Grant Park, and takes runners through 29 diverse neighborhoods of Chicago. The event also features wheelchair racing, elite runners, and charity runners raising funds for various causes. If you’re interested in running a marathon, the Chicago Marathon should definitely be on your list. But if not, you’re probably better off staying away from Chicago for the weekend of 8th October when there are traffic and road closures.
Architecture is one of the USPs of Chicago and perhaps the best way to appreciate the city’s architecture is through Open House Chicago. This event, organized by the Chicago Architecture Center, opens the doors of some of the city’s most iconic buildings, including private homes, churches, and offices, to the public. The event allows visitors to go behind the scenes and experience the architectural heritage of Chicago firsthand.
Halloween is celebrated in style with local parties and spooky parades. The most popular event is the Haunted Halsted parade which takes place in Chicago’s Boystown neighborhood. The parade celebrates the LGBTQ+ community’s unique and vibrant spirit. Participants dress up in spooky and creative costumes, there are prizes to be won and the parade is led by drag queens and performers.
The Chicago International Film Festival also takes place in October and showcases a wide variety of films from around the world. It’s a great opportunity to see some of the best new movies before they’re released to the general public.
Chicago weather in October
Visit Chicago in November
Held in mid-November, Magnificent Mile Lights Festival marks the beginning of the holiday season in Chicago. It features a tree-lighting ceremony, fireworks, live music, and a parade along Michigan Avenue.
Chicago’s Thanksgiving Parade is one of the largest parades in the country. It takes place on Thanksgiving Day in downtown and features floats, marching bands, and giant balloons. It’s a fun way to kick off the holiday season.
November is also a great time to get your ice skates out and head to one of the several ice skating rinks in the city. Located in the heart of downtown Chicago, the Millennium Park Ice Skating Rink is a popular destination for locals and tourists alike. It’s open from November through March and offers stunning views of the city skyline. Further ahead, lies the Maggie Daley Park Ice Skating Ribbon This unique outdoor ice skating rink is in the shape of a ribbon, winding through the park’s rolling landscape.
Chicago weather in November
Visit Chicago in December
The traditional German Christmas market, Christkindlmarket, opens in mid-November and really picks up pace in December before closing on Christmas Eve. The original location is in Daley Plaza with a second location added in recent years at Gallagher Way at Wrigley Field. Visitors can shop for unique gifts and crafts, sample traditional German food and drink, and enjoy live music and entertainment. I loved the beet soup from Prince of Pierogi and of course Bob’s Belgium hot chocolate last year.
The Zoolights at Lincoln Park is a great way to get into the holiday spirit and experience the beauty of the zoo in a unique and memorable way. You can explore the zoo after dark and enjoy a variety of holiday activities like ice carving demonstrations, musical performances, holiday snacks and beverages, and visits with Santa Claus. There are also plenty of opportunities to see the zoo’s animals, including the big cats, primates, and penguins.
Wrap up the year in style at Navy Pier. There’s a ticketed New Year’s Eve Party at Aon Grand Ballroom with live entertainment, a dance floor, a midnight countdown, and fireworks. Or if you’re on a budget, you can skip the party, bundle up and simply ring in the new year on the pier as colorful fireworks sparkle over Lake Michigan at midnight.
Chicago weather in December
Phew! As you can see, Chicago has so much to offer all year round. I’ll be perfectly honest, I’ve been to many of these events and yet there’s always a new one that I can find to attend. You can never get tired of living in Chicago because there’s always something new and fun to do.
Take that first Chicago trip using this month-by-month guide, and I guarantee you will want to return to the city. This list is by no means comprehensive but I’ve done my best to highlight the biggest or most unique experiences. If you’re headed over to Chicago with your partner, don’t forget to check out this guide for the best things to do in Chicago for couples.
Let me know what’s your favorite month from this list in the comments below. And if I’ve missed anything that you think should be on here, please don’t hesitate to share.