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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!

94 things to do in Chicago

Critical Mass

Last Friday of every month Event

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

Chinatown Lunar New Year Parade

February 9, 2025 Event

Chinese New Year is celebrated heavily in Chicago

Windy City Smokeout

July 11-14, 2024 Event

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

Chicago Air and Water Show

August 10–11, 2024 Event

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

Chicagohenge

March 20–23 | September 22–25 Nature

Even the most hurried drivers don't mind stopping to gaze at the unique solar spectacle

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!

Bike the Drive

September 1, 2024 Event

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

Kayaking Season

June–October Activity

Take a kayaking trip on the beautiful Chicago River

Ribfest Chicago

June 14-16, 2024 Event

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

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

Summer

June, July, August Weather

The wettest and warmest time of the year is the most attractive for visitors

Mayfest (Maifest) at Lincoln Park

May 17-19, 2024 Event

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

Rubber Ducky Race (Duck Derby)

August 7, 2024 Event

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

Lollapalooza

August 1-4, 2024 Event

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

Winter

December, January, February Weather

The nights can get frosty, but there is not much snow

Pitchfork Music Festival

July 19–21, 2024 Event

One of the trendiest festivals, Pitchfork sets the music scene

Sailing Season

May–October Activity

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

Santa Speedo Run

December 7, 2024 Event

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

Dragon Boat Race for Literacy

June 22, 2024 Event

Traditionally ornated Chinese Boats race through Chicago River for Literacy

Roscoe Village Burger Fest

July 19-21, 2024 Event

The mouthwatering summer festival with great food and music

Chicago ZooLights

November 15, 2024–January 5, 2025 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 Polar Plunge

March 3, 2024 Event

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

St. Paddy's Day (Green River)

March 16–17, 2024 Event

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

Spring

March–May Weather

More sun and warmth, but with occasional rains and tornadoes

Chiditarod

March 4, 2023 Event

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

Chicago 4th of July Fireworks Shows & Events

July 1–July 5 Event

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

Chicago Restaurant Week

January 19–February 4, 2025 Event

So many participating restaurants, so little time

Chicago Jazz Festival

August 29-September 1, 2024 Event

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

The Wintrust Magnificent Mile Lights Festival

November 23, 2024 Event

The holiday spirit takes over the Michigan Avenue on that night

Chicago Food Truck Festival

July 20–21, 2024 Event

The city by Lake Michigan is obsessed with food trucks

Willis Tower (Skydeck Chicago)

all year round Activity

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

Chicago Thanksgiving Parade

November 28, 2024 Event

One of the biggest fall events in Chicago

World Music Festival Chicago

September 20–29, 2024 Event

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

Chicago Latino Film Festival

April 13-23, 2024 Event

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

Memorial Day Parade

May 24–26, 2024 Event

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

Turkey Testicle Festival

November 27, 2024 Event

Are you ready to eat lots of turkey testicles and listen to hours of live music?

Arts in the Dark Halloween Parade

October 19, 2024 Event

The most fun fall event loved by kids and adults

Ginza Holiday Festival

July 26-28, 2024 Event

Lots of Japanese food, culture and entertainment

Chicago Pride Parade & Fest

June 22–23, 2024 (Fest) | June 30, 2024 (Parade) Event

A colorful celebration of freedom, diversity and culture

Chicago Blues Festival

June 6–9, 2024 Event

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

Chicago International Film Festival

October 16–27, 2024 Event

The longest-running competitive film festival in the USA

Taste of Chicago

September 6–8, 2024 Event

Note down the recipe for an unforgettable food & music festival

Chicago Theatre Week

February 6–16, 2025 Event

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

Chicago Marathon

October 13, 2024 Event

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

Chicago Auto Show

February 8-17, 2025 Event

The biggest auto show in North America

Christkindlmarket Chicago

November 22–December 24, 2024 Event

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

The Morton Arboretum Illumination

November 16, 2024–January 4, 2025 Event

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

East Peoria Festival of Lights

November 23, 2024–January 5, 2025 Event

One of the biggest and brightest holiday events in Illinois

Light Up The Lake (Winter WonderFest)

November 29, 2024–January 5, 2025 Event

Beloved Chicago indoor winter event perfect for frosty days

Riot Fest

September 20-22, 2024 Event

A legendary rock music event held in Chicago

Cinco de Mayo

May 5, 2024 Event

Drink lots of margaritas and cerveza celebrating the Mexican national holiday

May Day

May 1 Event

Workers' Day is always a big deal in Chicago

Spring Awakening Music Festival

July 9–10, 2023 Event

A summer gathering of leading DJs from all over the world

Redhead Days Chicago

October 26, 2019 Event

The largest redhead gathering in the US

Pierogi Fest

July 26-28, 2024 Event

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

Arlington Million

August 14, 2021 Event

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

Bud Billiken Parade

August 10, 2024 Event

The largest African American parade in the United States

Kitesurfing & Windsurfing

June–August Activity

Find out if Windy Сity is made for wind sports

Naperville Ale Fest

February 12, 2025 Event

The only outdoor winter and summer beer festival of Midwest

Allstate Hot Chocolate Run

November 3, 2024 Event

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

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

Chicago Labor Day Weekend

August 31–September 2, 2024 Event

Wrap up the summer season with a bang

Illinois Fall Colors

October Nature

Enjoy the best fall colors across the state

Chicago Fall Colors

early to mid-October Nature

Absorb the bright season without leaving the Windy City

Lilacia Park

late April–mid-May Nature

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

Richardson Adventure Farm Corn Maze

September–October Activity

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

Skiing and Snowboarding in Wisconsin

December–March Activity

Discover some of the best ski areas of the Midwest

New Year's Eve in Chicago

December 31 Event

Color blasts illuminate the iconic Chicago skyline

Hummingbird Migration

May–September Nature

Entice these buzzy flying jewels into your yard

Sandhill Crane Migration in Illinois

mid-September–mid-November Nature

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

Lake and River Cruises

April–November Activity

Whatever cruise you choose, Windy City won't leave you unsatisfied

Halloween in Chicago: Events, Parades & Activities

October 16–31, 2024 Event

From an art parade to booze cruises—Halloween is a great time to explore Chicago

Chicago Christmas Lights

mid-November–early January Event

Get into the festive spirit while walking or driving through spectacular holiday lights

Cherry Blossom in Chicago

late April–early May Nature

Find the best spots to enjoy beautiful cherry blossoms in Chicago

Chicago Comic & Entertainment Expo (C2E2)

April 11-13, 2025 Event

The biggest geek gathering in the Midwest

Fan Expo Chicago

August 16–18, 2024 Event

The massive fan gathering which was previously known as Chicago Comic Con

Stargazing

all year round (best in September–May) Nature

Absorb the starry skies in the vicinity of Chicago

Oktoberfest Chicago

September 6-8, 2024 Event

Rejoice in an amiable atmosphere at Chicago German-American Oktoberfest

FOBAB

November 22–23, 2024 Event

America's biggest barrel-aged beer festival

Plainfield Fest

June 28-30, 2024 Event

Enjoy great food, music, and street fun in a suburb of Chicago

St. Alphonsus Oktoberfest

September 27-29, 2024 Event

Join thousands of beer lovers at St. Al's Oktoberfest

Revolution Oktoberfest

September 13, 2023 Event

Beer Under Glass, which is hosted by Revolution Brewing, marks the start of Illinois Craft Beer Week

Fox Lake 4th of July Fireworks & Parade

June 29, 2024 Event

A relaxing Independence Day celebration at The Chain O’Lakes

Palatine Hometown Fireworks, Festivals & Shows

July 3–7, 2024 Event

One of the best small-town 4th of July celebrations in the greater Chicago area

Wheaton 4th of July Fireworks, Parade & Shows

June 29–July 4, 2024 Event

A community celebration with fireworks in the Chicago suburbs

Crystal Lake Fireworks

July 7, 2024 Event

A spectacular 4th of July celebration in the Chicago suburbs

Waukegan Fireworks

July 4 Event

One of the multiple fine options to make some 4th of July memories near Chicago

Evanston 4th of July Fireworks & Parade

July 4 Event

A historic celebration near Lake Michigan

Geneva Christmas Walk

December 6, 2024 Event

Get into the holiday season with traditional festivities in Downtown Geneva, IL

Fox Lake Festival of Lights

November 30, 2024 Event

Start the holiday season with a vibrant parade, holiday market, and the annual Christmas tree lighting

Lincoln Square Apple Fest

October 5–6, 2024 Event

A beloved community event on the North side of Chicago

Great Highwood Pumpkin Festival

October 4-6, 2024 Event

Take in pumpkins galore and explore the town invaded by hundreds of skeletons!

Gold Coast Art Fair

mid-June 2025 Event

The Granddaddy of American Art Festivals has been around since 1957

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