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Best Time of Year to Visit Chicago

Updated: October 28, 2023

This is a guide to choosing the best time of year to visit Chicago, based on hotel prices, weather, events and activities, and crowds, and is updated for 2023.

We provide a month-to-month comparison, with suggestions of the best events to attend on the month you plan to be here.

The Quick Answers

The best time to come to Chicago depends on what you want out of your trip.

When is the cheapest time to visit Chicago?

If you want short lines and cheaper hotel and flight rates, and don’t mind cold weather, coming in January, February, or November might be the best choice for you.

These are considered the low season months when deals such as Chicago Restaurant Week take place.

Things to Do for Free in Chicago

If you want to visit Chicago in the summer to take part in food and music festivals, boat cruises, outdoor dining and rooftop bars, the beaches and lakefront trails along Lake Michigan, and enjoy the architecture, then June through August are the most popular months.

If you want something in-between, coming in mid-March-May or September-October means fewer crowds, average prices, and still plenty to see and do!

We break down the month-to-month guide in this article so you can take part in the best of Chicago no matter which month you decide to visit.

If you are coming with kids, you are likely to come during peak tourism periods in the city.

Consider visiting in August, when it's less humid and morning and evening temperatures are more bearable, the city is still busy with kid-friendly activities, and prices are a bit better than in July.

And be sure to check out what the members of our Chicago Travel Tips Facebook group have to say about when the best time to go to Chicago is.

We have over 15k members and growing, including locals, regular visitors, and those planning a trip.

It's a public group, so no need to join to read the comments and suggestions.

Cheapest Hotel Rates

The average nightly stay in Chicago costs $202.

The months of January through March were the cheapest months to book a hotel.

The months of July through October were the most expensive.

Staying downtown will always cost more than hotels near the O'Hare or Midway airport, but you can learn how to utilize Chicago’s public transportation near any hotel to get to our top attractions and neighborhoods.

You can utilize sites such as and TripAdvisor and filter the reviews for the lowest price first.

Cheapest Time to Fly to Chicago

Airfare cost is one of the top deciding factors for many of us when planning a trip, so using a tool like Google Flights is a great way to see the best times to save money flying to Chicago. 

Here you can see a 5-day roundtrip cost from London to Chicago in August would cost you nearly double what the same trip would cost at the same time in September. 

Cheapest Time to Fly to Chicago
screenshot from Google Flights (2022)

Prices tend to follow the weather, so the higher the temperature, the higher the ticket cost.

Holidays will also play a factor in increased airline ticket prices.

Here are a few tips when booking tickets:

  • Utilize search engines to compare prices between airlines, such as and
  • Sign up for airline loyalty programs to get frequent flier points.
  • Plan to visit after a holiday.
  • Fly during off-peak hours, such as a red-eye flight.

Best Season to Visit Chicago Weather-Wise

It’s no secret that the Windy City is known for having both hot and cold seasons.

And it’s important to know what the weather will be like during your vacation or trip to pack appropriate clothing.

Here is a breakdown of the temperature and weather conditions in Chicago in each season.

Most people enjoy the summer months the most, specifically late June through September.

But, there are two small periods of time in the year that are equally enjoyable, in late May and early October, when crowds are small and the temperature is comfortable. 

Winter (December - March)

Beginning in December the average high temperatures begin to drop into the 30s F and stay in the range of mid-20s F throughout January and February.

Statistically, January tends to be the coldest month of the year, and also the snowiest and is commonly accepted as the center point of the worst weather of the year.

Temperatures in March will return to the 30s, but traveling with a winter coat, boots, hat, and gloves is a must during all winter months.

Light snowfall between 1-2 inches is typical.

How cold is Chicago in January

Spring (April-May)

Chicago springtime is only two months long, but it’s a beautiful time to see the city.

With comfortable temperatures averaging in the low 50s during both April and May, you can pack a light jacket and dress in layers.

Don’t forget your umbrella and rain boots, with as much as 3 inches of rainfall occurring 12 days out of the month. 

Summer (June-September)

Chicago has beautiful summers to make up for our long winters and wet springs, with an average high of 74F and a low of 62F between June and September.

June is typically the wettest month of the year in Chicago, with roughly 4 inches (10 cm) of rain on average.

But, July and August offer clear skies perfect for outdoor concerts, festivals, and pay-what-you-like walking tours. 

Fall (October-November)

Autumn is a wonderful time to see Chicago.

The cooler weather of October and November with less precipitation means you can enjoy temperatures in the 40 - 50s F without the snow or rain that begins in December. 

Best Months to Visit the Museums and Indoor Activities

Chicago museums are open year-round for visitors to enjoy and are an excellent option when the weather is cold or rainy, or when you need to beat the heat for an afternoon.

So no matter when you visit, consider purchasing a museum ticket. 

If the skies are clear, our observation decks offer impressive views of Chicago year-round.

These viewing spaces tend to be most popular in the summer, so travelers coming outside of those months will enjoy shorter lines and fewer crowds.

Choose between the Willis Tower Skydeck or 360 Chicago at the John Hancock Tower.

Best Months for Theater, Comedy, and Live Entertainment in Chicago

While you can see great theater, comedy, or live music anytime in Chicago, there are a few special events to be aware of when planning your trip.

The annual four-day music festival Lollapalooza is hosted every late July/early August.

December offers seasonal holiday shows, such as the Goodman Theatre’s long-running A Christmas Carol. Other popular theatres include:

Music lovers can enjoy the Blues Festival in June each year, or live performances all year round at our most popular clubs:

  • The Green Mill
  • The House of Blues
  • Buddy Guy Legends
  • Blue Chicago
  • Andy’s Jazz

Laughter is a year-round event in Chicago at the legendary Second City or iO Theater! 

Highlights of Each Month


The holidays may be over, but the winter events are still open, such as ice skating at Millennium Park’s McCormick Tribune rink, or the ice ribbon at Maggie Daley Park.

We recommend exploring our museums, theaters, and the interior of the free Chicago Cultural Center to get the most out of your time.

Chicago Restaurant Week, where you can get great deals on 3 -5 course meals, begins mid-January and lasts 17 days.


The weather is still very cold in February, so indoor experiences such as museums and restaurants will be a worthwhile way to spend your time.

If you like cars, the Chicago Auto Show is annually held at the McCormick Place convention center for anyone looking to see or test drive the latest models from major worldwide manufacturers. 


St Patrick’s Day is the highlight of March when the Chicago River is dyed a bright green color on the Saturday before the holiday to celebrate the Irish heritage in Chicago.

Chicago River dyed green for St. Patrick's Day

Pub crawls and parades give us the first taste of Spring fun, although the weather is still very cold. 

The Major League baseball season begins in late March, so you can watch a Cubs or White Sox game between now and late September. 


If you visit Chicago in April, be sure to see the beautiful tulips that bloom along Magnificent Mile and State Street in the Loop neighborhood just after the Easter holiday. 

It's also the first month where the weather is consistently warm enough for other outside activities, such as the Lincoln Park Zoo, which offers free admission.

Take a walking tour to have an expert guide show you any of these neighborhoods:


Celebrate Cinco de Mayo at the start of the month, or visit during Memorial Day weekend to mark the official start of summer with a parade on State Street and fireworks at Navy Pier every Saturday at 10 pm and Wednesday at 9 pm.


June is a big month for festivals, including The Chicago Blues Festival and Taste of Chicago.

The Blues Festival is a free citywide festival that occurs in the early weeks of June at Millennium Park, with a range of headliners from the past and present of the jazz, soul, R&B, gospel, rock, and hip hop scenes. 

Taste of Chicago is a multi-week summertime event that offers tastings from our city’s best restaurants.

Bring cash or a credit card for the individual menu items, though the event itself is free of charge to enter.  

It’s also Pride Month, with the annual Chicago Pride Parade happening at the tail-end of the month on the North Side along North Halsted Street in the ‘Boystown’ neighborhood. 


The Fourth of July fireworks is best seen at Oak Street Beach or on Navy Pier.

July is the month to experience the Taste of Chicago Food Festival, which takes place from July 7-9.

Enjoy up-and-coming music performances at Pitchfork Music Festival at Union Park in mid-July.

The Square Roots festival in Lincoln Square is another option for anyone looking to party like a local listening to live music with a craft beer in hand!  


Outdoor events continue to be popular, including the free Chicago Air and Water show that usually occurs in mid-August along North Avenue Beach and the Lakefront. 

Foodies should check out the annual Ribfest in Northcenter in the latter half of the month for an irresistible BBQ with plenty of live music and culture; an average of 50,000 pounds of pork is consumed annually at this event. 


Live music at Millennium Park continues with the Chicago Jazz Festival in early September before the weather gets too cool.

Labor Day Weekend is the last chance to see the weekly fireworks in Chicago.

The Chicago Gourmet food festival takes place from September 23-24.

The NFL season begins, so you can go to a Bears football game at Soldier Field while you’re in town. 


October isn’t just for pay-what-you-like haunted history tours, though it is a fun way to celebrate the spooky Halloween season.

The Bank of America Chicago Marathon occurs in the middle of the month, with the annual participation of up to 40,000 runners.

Chicago Ghost Tours

Hotels will be fully booked the week of the marathon, so book early if you’re coming this month. 

The NHL and NBA seasons begin, so you can attend either a Bulls or a Blackhawks game at the United Center and cheer on the local teams!

And this year, the Chicago International Film Festival takes place October 11-22.


As the weather cools, the tourist season is officially over. November is a quiet month to visit and explore Chicago like a local.

At the end of the month, The Chicago Thanksgiving Parade runs along State Street on Thanksgiving morning to kick off our holiday season. 

And don't miss the Magnificent Mile Lights Festival, which begins in mid-November.


Enjoy the holiday season in the downtown Loop neighborhood. Go ice skating at Millennium Park beside our city’s Christmas tree.

Visit Macy’s for shopping and a meet-and-greet with Santa Claus or visit our German-themed Christmas market, Christkindlmarket, at Daley Plaza.

There are several holiday performances around town, including Charles Dickens’s A Christmas Carol at the Goodman Theatre.

Want to see it all? Join our seasonal Holiday Tour with one of our jolly tour guides!

Ring in the New Year on the Magnificent Mile at one of the many hotel ballrooms, like The Drake Hotel or London House.  

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About The Author

Andy Meholick

Andy has been a Chicago tour guide with Free Tours by Foot since 2015. He loves guiding groups around the Windy City telling stories of the past, offering tips to enjoy your visit, and showing off the city's world-class architecture. Andy is also the host of the Free Tours by Foot Chicago Youtube Channel, offering traveler tips and virtual tours.
Updated: October 28th, 2023
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