Best time to visit Chicago

+111
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!

9 THINGS TO DO IN CHICAGO (SEPTEMBER 15 - SEPTEMBER 24)

Chicagohenge

Chicagohenge

March 20–March 23 | September 20–September 23 • nature

This remarkable urban scene happens twice a year!

World Music Festival Chicago

World Music Festival Chicago

September 2021 • event

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

Hummingbird Migration

Hummingbird Migration

May–September • nature

Entice these buzzy flying jewels into your yard

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

Kayaking Season

Kayaking Season

June–October • activity

Take a kayaking trip on the beautiful Chicago River

Riot Fest

Riot Fest

September 17–19, 2021 • event

A legendary rock music event held in Chicago

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

Sandhill Crane Migration

Sandhill Crane Migration

mid-September–mid-November • nature

Sandhill cranes make a stop at northern Illinois marshes on their way to Florida

68 THINGS TO DO OUT OF SELECTED DATE RANGE

Chicago Air and Water Show

Chicago Air and Water Show

mid-August 2021 • event

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

4th of July Fireworks & Events

4th of July Fireworks & Events

July 4 • event

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

Bike the Drive

Bike the Drive

late May 2021  • event

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

Rubber Ducky Race

Rubber Ducky Race

early August 2021 • event

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

Chicago Thanksgiving Parade

Chicago Thanksgiving Parade

November 26, 2020 • event

One of the biggest fall events in Chicago

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!

Kids and Kites Festival

Kids and Kites Festival

May 1, 2021 • event

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

Windy City Smokeout

Windy City Smokeout

July 9–11, 2021 • event

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

Chinatown Lunar New Year Parade

Chinatown Lunar New Year Parade

February 21, 2021 • event

Chinese New Year is celebrated heavily in Chicago

St. Paddy's Day (Green River)

St. Paddy's Day (Green River)

March 13, 2021 (virtual) • event

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

Chicago Pride Parade & Fest

Chicago Pride Parade & Fest

mid-June 2021 • event

A colorful celebration of freedom, diversity and culture

Roscoe Village Burger Fest

Roscoe Village Burger Fest

July 10–11, 2021 • event

The mouthwatering burger festival

Chicago Jazz Festival

Chicago Jazz Festival

early September 2021 • 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, 2020 • event

The holiday spirit takes over the Michigan Avenue on that night

Festival Cubano (Cuban Fest Chicago)

Festival Cubano (Cuban Fest Chicago)

mid-August 2021 • event

A vibrant celebration of Latin culture in the Midwest

Mayfest (Maifest) at Lincoln Park

Mayfest (Maifest) at Lincoln Park

May 28–30, 2021  • 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 29, 2021 • event

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

Spring Awakening Music Festival

Spring Awakening Music Festival

June 11–13, 2021 • event

A summer gathering of leading DJs from all over the world

Chicago Restaurant Week

Chicago Restaurant Week

March 19–April 4, 2021 • event

So many participating restaurants, so little time

Chicago Polar Plunge

Chicago Polar Plunge

March 7, 2021 (virtual event) • 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

East Peoria Festival of Lights

East Peoria Festival of Lights

November 26–December 31, 2020 • event

One of the biggest and brightest holiday events in Illinois

Illinois Fall Colors

Illinois Fall Colors

October • nature

Enjoy the best fall colors across the state

Chicago Blues Festival

Chicago Blues Festival

early June 2021 • event

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

Chiditarod

Chiditarod

March 6, 2021 • event

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

Winter WonderFest

Winter WonderFest

canceled in 2020 • event

Beloved Chicago indoor winter event perfect for frosty days

Ribfest Chicago

Ribfest Chicago

June 11–13, 2021 • event

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

Chicago Theatre Week

Chicago Theatre Week

February 25–March 7, 2021 (virtual) • event

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

Chicago Marathon

Chicago Marathon

October 10, 2021 • event

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

May Day

May Day

May 1 • event

Labour Day is always a big deal in Chicago

Critical Mass

Critical Mass

Last Friday of every month • event

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

Baconfest

Baconfest

April 10, 2021 • event

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

Dragon Boat Race for Literacy

Dragon Boat Race for Literacy

June 26, 2021 • event

Traditionally ornated Chinese Boats race through Chicago River for Literacy

Christkindlmarket Chicago

Christkindlmarket Chicago

November 1–December 31, 2020 • event

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

Ice Shards on the Great Lakes

Ice Shards on the Great Lakes

mid–February–late March • nature

The ice cover gets shattered to knife-sharp pieces as spring takes over winter

New Year's Eve in Chicago

New Year's Eve in Chicago

December 31 • event

Color blasts illuminate the iconic Chicago skyline

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

Chicago International Film Festival

Chicago International Film Festival

October 14–25, 2020 • event

The longest-running competitive film festival in the USA

Richardson Adventure Farm Corn Maze

Richardson Adventure Farm Corn Maze

September 12–November 8, 2020 • activity

Come out and get lost in the world's largest corn labyrinth

Chicago Food Truck Festival

Chicago Food Truck Festival

August 29, 2020 • event

The city by Lake Michigan is obsessed with food trucks

Ginza Holiday Festival

Ginza Holiday Festival

August 07–09, 2020 (virtual event) • event

Lots of Japanese food, culture and entertainment

Taste of Chicago

Taste of Chicago

early July 2021 • event

Note down the recipe for an unforgettable food & music festival

Pierogi Fest

Pierogi Fest

July 23–25, 2021 • event

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

Skiing and Snowboarding in Wisconsin

Skiing and Snowboarding in Wisconsin

December–March • activity

Discover some of the best ski areas of the Midwest

ZooLights

ZooLights

November 21, 2020–January 3, 2021 • 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 Auto Show

Chicago Auto Show

February 13–21, 2021 • event

The biggest auto show in North America

Cinco de Mayo

Cinco de Mayo

May 5, 2021 • event

Drink lots of margaritas and cerveza celebrating the Mexican national holiday

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 2, 2020 • event

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

Arlington Million

Arlington Million

August 14, 2021 • event

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

Lollapalooza

Lollapalooza

late July–early August 2021 • 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 20, 2020–January 3, 2021 • 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

Kitesurfing & Windsurfing

Kitesurfing & Windsurfing

June–August • activity

Find out if Windy Сity is made for wind sports

Fall Colors in and near Chicago

Fall Colors in and near Chicago

early to mid-October  • nature

Absorb the bright season without leaving the Windy City

Lilacia Park

Lilacia Park

late April–early May (Lilac Time events have been canceled for 2020)  • nature

Discover a safe haven abundant with flowers just on the outskirts of the Windy City

Cupid's Undie Run

Cupid's Undie Run

February 13, 2021 • 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

Bud Billiken Parade

Bud Billiken Parade

August 14, 2021 • event

The largest African American parade in the United States

Naperville Ale Fest

Naperville Ale Fest

late February | mid-July 2021 • event

The only outdoor winter and summer beer festival of Midwest

Allstate Hot Chocolate Run

Allstate Hot Chocolate Run

November 08, 2020 (virtual event) • event

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

Chicago Labor Day Weekend

Chicago Labor Day Weekend

September 3–6, 2021 • event

Wrap up the summer season with a bang

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 1–30, 2017 • activity

The urban game that attracts thousands of people

Tour de Fat

Tour de Fat

July 30, 2018 • event

The festival of bikes and environmentally conscious people!

Pitchfork Music Festival

Pitchfork Music Festival

mid-July 2021 • event

One of the trendiest festivals, Pitchfork sets the music scene

Last updated: