Best time to visit Chicago

+89
Chicago

Best time of year to visit Chicago

April to May and September to October is the best time to visit Chicago as the weather is mild and tourist numbers are moderate. In late spring, celebrate local beer culture at the Mayfest. Summer in the city is famous for its hotel rates going through the roof and unstable weather when agonizing heat waves from June to August can hinder your sightseeing experience. However, Chicago is lucky to be located next to the lake, that's why festival goers boldly and enthusiastically attend Lollapalooza and other great summer events. September says goodbye to the summer at the Chicago Jazz Festival and during the Chicagohenge at the end of the month. A freezing and windy period between November and March offers you great deals on airfare and accommodation, just pack your warmest layers. St. Patrick's Day turns the Chicago River green in March, probably one of the best sights of the city!

10 THINGS TO DO IN CHICAGO (JULY 06 - JULY 15)

Summer Fireworks at Navy Pier

Summer Fireworks at Navy Pier

late May–early September • event

For the whole summer you have a chance to see the beautiful fireworks twice a week!

Windy City Smokeout

Windy City Smokeout

July 10–12, 2020 • event

Starting as a local barbecue get-together, the Smokeout has become one of the best festivals in town!

Roscoe Village Burger Fest

Roscoe Village Burger Fest

July 11–12, 2020 • event

The mouthwatering burger festival

Willis Tower (Skydeck Chicago)

Willis Tower (Skydeck Chicago)

all year round • activity

Step to the glass box ledge and walk in the air 1,353 feet above Chicago

Beach Season

Beach Season

July–August • activity

Chicagoans love summers, even though they are extremely hot and humid. Part of this love is surplused by the existance of beaches

Taste of Chicago

Taste of Chicago

July 08–12, 2020 • event

Note down the recipe for an unforgettable food & music festival

Kayaking Season

Kayaking Season

June–October • activity

Take a kayaking trip on the beautiful Chicago River

The Plant Chicago

The Plant Chicago

all year round • activity

A former meatpacking facility is transformed into a human-made ecosystem

Sailing Season

Sailing Season

May–October • activity

Sailing is much time limited in Chicago due to the weather conditions

Kitesurfing & Windsurfing

Kitesurfing & Windsurfing

June–August • activity

Find out if Windy Сity is made for wind sports

56 THINGS TO DO OUT OF SELECTED DATE RANGE

Chicago Air and Water Show

Chicago Air and Water Show

August 15–16, 2020 • event

The oldest and largest show of this kind in the United States

Chicagohenge

Chicagohenge

March 20 • nature

This remarkable urban scene happens twice a year!

4th of July Fireworks & Events

4th of July Fireworks & Events

July 04 • event

Enjoy the most important holiday of the summer on the shore of Lake Michigan

Chicago Thanksgiving Parade

Chicago Thanksgiving Parade

November 26, 2020 • event

One of the biggest fall events in Chicago

Bike the Drive

Bike the Drive

May 24, 2020 • event

Once in a year a lakefront road is closed for cars and open for the cyclists!

Rubber Ducky Race

Rubber Ducky Race

August 06, 2020 • event

50,000 yellow rubber ducks are splashed into the Chicago River to fundraise for the Special Olympics Illinois

Kids and Kites Festival

Kids and Kites Festival

May 03, 2020 • event

The spectacular and beautiful celebration of the spring's arrival!

Chicago Pride Parade & Fest

Chicago Pride Parade & Fest

June 20–21, 2020 • event

A colorful celebration of freedom, diversity and culture

St. Paddy's Day (Green River)

St. Paddy's Day (Green River)

March 14, 2020 • event

St. Patrick's Day in Chicago is definitely a party of a lifetime!

Chinatown Lunar New Year Parade

Chinatown Lunar New Year Parade

February 02, 2020 • event

Chinese New Year is celebrated heavily in Chicago

Chicago Jazz Festival

Chicago Jazz Festival

September 03–06, 2020 • event

A favorite Labor Day Weekend tradition with great music all over the city

BMO Harris Magnificent Mile Lights Festival

BMO Harris Magnificent Mile Lights Festival

November 22–23, 2019 • event

The holiday spirit takes over the Michigan Avenue on that night

Festival Cubano (Cuban Fest Chicago)

Festival Cubano (Cuban Fest Chicago)

August 09–11, 2019 • event

A vibrant celebration of Latin culture in the Midwest

Mayfest (Maifest) at Lincoln Park

Mayfest (Maifest) at Lincoln Park

May 29–31, 2020 • event

As an Oktoberfest's counterpart, this festival offers you plenty of foods and drinks as well as beer gardens!

Memorial Day Parade

Memorial Day Parade

May 23, 2020 • event

Don't miss your chance to see the largest Memorial Day Parade in the country

Chicago Polar Plunge

Chicago Polar Plunge

March 01, 2020 • event

Raising money for a cause is always a good idea, even if it means jumping into the frosty Lake Michigan!

Arts in the Dark Halloween Parade

Arts in the Dark Halloween Parade

October 24, 2020 • event

The most fun fall event loved by kids and adults

Spring Awakening Music Festival

Spring Awakening Music Festival

June 12–14, 2020 • event

A summer gathering of leading DJs from all over the world

East Peoria Festival of Lights

East Peoria Festival of Lights

November 23–December 31, 2019 • event

One of the biggest and brightest holiday events in Illinois

World Music Festival Chicago

World Music Festival Chicago

September 11–27, 2020 • event

Musicians from over 20 countries give about 50 performances with free admission

Winter WonderFest

Winter WonderFest

December 05 2019–January 05 2020 • event

Beloved Chicago indoor winter event perfect for frosty days

Chicago Blues Festival

Chicago Blues Festival

June 05–07, 2020 • event

The largest free blues festival in the world and one of the greatest music festivals in Chicago

Ribfest Chicago

Ribfest Chicago

June 12–14, 2020 • event

One of Chicago's trademarks, the Ribfest attracts crowds annually

Chiditarod

Chiditarod

March 07, 2020 • event

Isn't it your lifetime dream to race in a cart of food between the neighbourhood bars?

Chicago Marathon

Chicago Marathon

October 11, 2020 • event

Check out the scenic course of one of the largest marathons in the U.S.

Dragon Boat Race for Literacy

Dragon Boat Race for Literacy

June 27, 2020 • event

Traditionally ornated Chinese Boats race through Chicago River for Literacy

Chicago Theatre Week

Chicago Theatre Week

February 13–23, 2020 • event

A range of extraordinary theatrical offerings returns to Chicago every year in February

Christkindlmarket Chicago

Christkindlmarket Chicago

November 15–December 24, 2019 • event

​Drink some Glühwein, shop for presents, and enjoy German food delights at one of the largest Christmas markets in the US

May Day

May Day

May 01 • event

Labour Day is always a big deal in Chicago

Chicago Restaurant Week

Chicago Restaurant Week

January 24–February 09, 2020 • event

So many participating restaurants, so little time

Chicago International Film Festival

Chicago International Film Festival

October 14–25, 2020 • event

The longest-running competitive film festival in the USA

Ginza Holiday Festival

Ginza Holiday Festival

August 07–09, 2020 • event

Lots of Japanese food, culture and entertainment

Baconfest

Baconfest

April 18, 2020 • event

A festival dedicated to bacon? Definitely one of the best ideas in the world!

ZooLights

ZooLights

November 29 2019–January 04 2020 • activity

Linkoln Park Zoo is not only one of the biggest and oldest zoos in the USA, but it also boasts some perfect winter scenery

Chicago Food Truck Festival

Chicago Food Truck Festival

June 20–21, 2020 | September 12–13, 2020 • event

The city by Lake Michigan is obsessed with food trucks

Cinco de Mayo

Cinco de Mayo

May 05, 2019 • event

Drink lots of margaritas and cerveza celebrating the Mexican national holiday

Chicago Auto Show

Chicago Auto Show

February 08–17, 2020 • event

The biggest auto show in North America

Riot Fest

Riot Fest

September 11–13, 2020 • event

A legendary rock music event held in Chicago

Pierogi Fest

Pierogi Fest

July 24–26, 2020 • event

Great food and some wacky fun in just 30 minutes from Chicago

Critical Mass

Critical Mass

January 31, 2020 • event

The monthly event to make it clear how many cyclists are there

Chicago Latino Film Festival

Chicago Latino Film Festival

April 16–30, 2020 • event

A great selection of films, documentaries, and shorts from the Spanish-speaking world

Chicago Beer Classic

Chicago Beer Classic

May 02, 2020 • event

The largest beer festival in the city celebrates the beginning of summer season

Lollapalooza

Lollapalooza

July 30–August 02, 2020 • event

One of the oldest and most famous alternative music festivals is a must-visit!

Chicago Museum Week

Chicago Museum Week

January 18–26, 2018 • event

Free events, special programs, and promotions at Chicago's best museums

The Morton Arboretum Illumination

The Morton Arboretum Illumination

November 22 2019–January 05 2020 • event

An enchanted forest filled with dazzling projections and interactive trees that respond to touch and voice

Country LakeShake Festival

Country LakeShake Festival

June 19–21, 2020 • event

A big country music festival on the lakefront

Cupid's Undie Run

Cupid's Undie Run

February 08, 2020 • event

Chicago loves running wearing hardly anything. Of course, for the good cause

Redhead Days Chicago

Redhead Days Chicago

October 26, 2019 • event

The largest redhead gathering in the US

Arlington Million

Arlington Million

August 15, 2020 • event

A perfect opportunity to enjoy live racing, entertainment and fancy group outings

Bud Billiken Parade

Bud Billiken Parade

August 10, 2019 • event

The largest African American parade in the United States

Allstate Hot Chocolate Run

Allstate Hot Chocolate Run

November 08, 2020 • event

The sweetest run in the world takes over the United States from coast to coast

Illinois Craft Beer Week

Illinois Craft Beer Week

May 10–17, 2019 • event

The Illinois Craft Brewers Guild organizes the massive 11 days long craft beer event

Santa Speedo Run

Santa Speedo Run

December 14, 2019 • event

Be merry, be positive, be helpful, be Santa! Thousands of Christmas fans running in the swimming suits.

Journey to the End of the Night

Journey to the End of the Night

June 01–30, 2017 • activity

The urban game that attracts thousands of people

Tour de Fat

Tour de Fat

2019 (caoncelled) • event

The festival of bikes and environmentally conscious people!

Pitchfork Music Festival

Pitchfork Music Festival

July 17–19, 2020 • event

One of the trendiest festivals, Pitchfork sets the music scene

Last updated: