has it all. The best time to visit the Windy City depends on your budget, heat tolerance, and interests. You’ll find cheaper prices in winter, but you’ll have more options in spring and summer.

The Midwest may not be your first thought when planning your next vacation, but Chicago is one of the coolest cities in the country. It’s arguably more quintessentially American than LA or New York. With historic sights and cutting-edge art, there’s always something new to discover in Chi-town.

Picking a time to visit Chicago can be tricky. Bitter cold or high humidity? Compete with throngs of tourists in the peak season or be bored in the off-season? You could be miserable if you don’t time your trip carefully.

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The best times of year to travel to Chicago

If you’re eager to enjoy Chicago’s outdoor activities, then you’ll need to plan your visit during the warmer months: April to September. But if you prefer to spend as little money as possible—or if you don’t like humidity—then you should visit in the off-season: October to March.

Having fun along the Chicago lakefront by diving into the water to cool off on a warm summer day.

Peak season: June to August

The good: Mardi Gras, most activities available

The bad: Crowded, higher prices

The weather: Mid-70s to low 90s, high humidity

July and August are the busiest months for Chicago tourism—and you’ll never forget a Chicago summer.

Start by soaking up the sun with free outdoor activities. Try a group class at

Millennium Park

and then cool down in Crown Fountain. Take a stroll along the

606 Trail

(Chicago’s version of the High Line) and then head to Navy Pier, which puts on a free fireworks show twice a week in the summer.

Patio season is in full swing during the warmer months. Two great patios are Somerset in Gold Coast and Piccolo Sogno in River West. Don’t miss

Maxwell Street Market

, which is bursting with farm-fresh goodies.

Need a reprieve from hot daytime temperatures? Hop on the

Chicago water taxi

(just $6 for a one-way ticket). When the sun goes down, join locals at an outdoor rooftop bar like

Cindy’s

to enjoy beautiful skyline views.

Other high season events include

Chicago Pride

in June,

Taste of Chicago

in July, and the

Grant Park Music Festival

in July and August.

Pro Tip You’ll be competing with both tourists and locals for summer activities, so book as far in advance as possible!

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Off-season: October to March

The river in Chicago dyed green for St. Patricks Day.

The good: Cheaper prices, fewer people

The bad: Cold temperatures, fewer outdoor activities

The weather: Upper teens to mid-50s

While winter in Chicago offers fewer outdoor activities for visitors, there is no shortage of exciting indoor activities. If you don’t mind chilly weather, plan your visit for the off-season to avoid the crowds and save some money.

Chicago has some of the world’s best entertainment, including theatrical shows and comedy clubs. Escape the snow and catch an improv show at

The Second City

. See new works at

Steppenwolf

or snag affordable tickets to a variety of live entertainment during

Chicago Theatre Week

Art museums are less crowded during the off-season—and Chicago is home to some of the region’s best collections. Meet Sue, the famous T-Rex, at the

Field Museum

. Don’t miss the

Museum of Contemporary Art

(open late on Tuesdays).

If you like beer, most breweries are open year-round for indoor tastings and tours. Check out

Goose Island Brewery

or attend

Chicago Ale Fest

in March.

Holiday events are a major attraction in Chicago. Around Halloween, check out the Halloween Parade or take a ghost tour. In December, visit the

Christkindlmarket

and go

ice skating at Millennium Park

beneath the Christmas tree.

St. Patrick’s Day is another fun festival in Chicago—on March 17th, the Chicago River is tinted green!

Pro Tip Snowstorms can cancel events and interrupt your travel plans. For a winter trip to Chicago, bundle up and prepare to be flexible.

Shoulder season: September, April to May

The good: Enjoyable weather, good prices

The bad: Chance of rain, average crowds

The weather: 40s to 60s, depending on the month

Because winter is so extreme in Chicago, the months immediately before and after winter (September, April and May) feel extra special. Shoulder season is the best time to comfortably explore Chicago on foot—without competition from summer tourists.

Get up close and personal with Chicago’s

street art

. Visit the iconic Moose Bubblegum mural at 33 E Congress and take a selfie at the Greetings from Chicago mural at 2226 N Milwaukee Ave.

When Chicago begins to thaw in April, the tulips bloom on Michigan Avenue. This is the perfect time to enjoy the Chicago River. Stroll the

Riverwalk

(starting at DuSable Harbor and meandering west) or hop on a boat for an

architecture tour

to marvel at Chicago’s incredible steel and glass structures from a unique angle.

Curious about crime? Grab a discounted Groupon ticket for a mobster-themed tour and learn about 1920s and 1930s Chicago history. The Victorian-era Graceland Cemetery has a

free self-guided audio tour

Other events include the

Chicago Jazz Festival

in September and the

Hyde Park Jazz Festival

Pro Tip Chicago is a popular spring break destination. If possible, time your visit to avoid the school holiday.

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The cheapest time to travel to Chicago

If you’re looking for the absolute cheapest time to visit Chicago, consider November or January. Low temperatures and fewer seasonal events mean fewer tourists and better prices.

However, if you can’t handle the bitter cold, you can still get some great deals in October and April when temperatures are slightly more friendly. Enjoy Chicago the way most locals do—bundled up with an appreciation for indoor arts and culture activities.

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Find the best month for your visit to Chicago

Not sure when to plan your trip to Chicago? Use this table to find your ideal time to visit the Windy City. Start by finding the activities you’re most excited about in the left-hand column.

Activity	Best month to visit	Why?
Comedy and theater	February to May	Comedy clubs like Second City and renowned theaters like Steppenwolf operate year-round in Chicago—but tickets are cheaper in the off-season.
Pub culture	March	If you’re craving a good brew, come for St. Patrick’s Day and take a brewery tour beside the green-tinted river.
Art	April and May	Take in some of the Midwest’s best art at the MCA or Field Museum , or explore public art on foot.
Architecture tours	May to August	Beat the heat and get off your feet: take a boat tour to learn about Chicago’s incredible architectural history.
Eating	April to September	From farmers markets to “Taste of” festivals, you’ll enjoy incredible food if you visit during the growing season.
Jazz	September	Enjoy world-class jazz in outdoor venues while the weather is still pleasant.
Seasonal memories	October through December	From ghost tours to Christmas markets, there are plenty of opportunities to mark the changing of the seasons.

Pro Tip You’ll find good food, good music, and beautiful architecture year-round in Chicago, so time your trip based on budget and weather if you’re not too concerned about seasonal events.

How to find savings on car and rental insurance

Whether you plan to

rent a car

or drive to Chicago yourself, you’ll need a great car insurance policy. Accidents happen, even on vacation!

Try the

Jerry

app to find out if you have enough coverage and upgrade your policy. It only takes a few seconds and the app is free. Signing up is simple—like, so simple you can do it from your couch on a commercial break.

The average Jerry user saves almost $900 a year on car insurance by shopping and switching.

MORE: 7 ways to save money on car rentals

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FAQ

What is the worst time to travel to Chicago?

There’s no “worst” time to visit the Windy City! Winter in Chicago offers a ton of exciting seasonal events and indoor activities. You’ll save money but you’ll be cold outside. Summer is great for outdoor activities—but it’s crowded and more expensive.

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