Scroll to Explore

Loews Chicago Hotel

Chicago, IL

Annual Events

Chicago Annual Events


Gold Coast Art Fair (June)

Known as “the granddaddy of American art festivals.” More info

Pride Parade (June)

The Chicago Gay and Lesbian Pride Parade starts on the corner of Halsted and Belmont at noon and ends in Lincoln Park. Awards are handed out to participants and the parade is free for the public to attend. More info.

Wavefront Music Festival (July)

Wavefront Music Festival is an electronic music dance festival that has 100 artists on four stages capped by fireworks at Montrose Beach. More info.

Wicker Park Music Festival (July)

Wicker Park Fest brings cutting-edge local and national acts to three stages on Milwaukee Ave. from North Ave. to Paulina St. Go early for the best shopping and best-behaved crowd. More info.

Taste of Chicago (July)

The 10-day event features over 60 restaurants and free concerts by local and world known music artists. The main entrance is Michigan Avenue at Congress Drive. More info.

Downtown Art Festival (July)

Shop from 200 of the best painters, sculptors, and jewelry makers along eight blocks at the North Michigan Avenue Art Festival at Pioneer Court. More info.

Pitchfork Music Festival (July)

The three-day event at Union Park showcases over 40 bands on three stages. The annual event was created to showcase independent bands in a big festival setting while maintaining low ticket prices. More info.

Clark Street Festival (July)

Enjoy multicultural food, art, music, and dance at Celebrate Clark Street Festival on N Clark St. from Morse to Estes. More info.

Lollapalooza (August)

The biggest annual music event in Chicago takes place in Grant Park. The three day and night event attracts big musical performers as headliners. More info.

Northalsted Market Days (August)

It's the largest two-day street fair in the Midwest and lives up to its reputation as one of the country's finest festivals featuring big-name musical performers. 

Air and Water Show (August)

Over two million people watch the annual Air and Water Show, which takes place along North Avenue Beach the second weekend of August. More info.

Chicago Jazz Festival (August)

The annual Chicago Jazz Festival is held the week before Labor Day in Grant Park. Free admission. More info.


Berghoff Oktoberfest (September)

Berghoff Oktoberfest serves bratwurst, sauerkraut, chicken, pretzels, and apple strudel plus German music at W Adams St. and Dearborn. More info.

Andersonville City Made Fest (September)

Featuring Chicago-based musicians, brewers and artisans, this new festival is a celebration of all of the great stuff being made right here in our city. The festival is held on Clark Street between Argyle & Carmen. More info.

Chicago Gourmet (September)

Chicago Gourmet is a premium food and wine event with 100 chefs, cooking demonstrations, beer and food pavilions, and wine tastings in Millennium Park. More info.

Marathon & Fitness Expo (October)

The free Chicago Marathon Health & Fitness Expo is held on a Friday and Saturday at McCormick Place. The Chicago Marathon begins and ends Sunday in Grant Park, with an after-festival in Butler Field. More info.

SOFA Chicago (October/November)

The 20th Annual Exposition of Sculpture Objects & Functional Art Fair is a gallery-presented, international art exposition dedicated to bridging the worlds of design, decorative and fine art. More info.

ZooLights (November–January)

ZooLights at the Lincoln Park Zoo features millions of holiday lights, ice carvings, music, carousel and train rides, food and gift shopping (plus photos with Santa). More info.

Magnificent Mile Lights Festival (November)

Since 1959, the holiday season has kicked off with this annual event where Grand Marshall Mickey Mouse taps his wand and lights up more than one million lights on 200 trees along Chicago's famous Magnificent Mile. More info.


Winter WonderFest (December–January)

Festival Hall at Navy Pier becomes an indoor Winter WonderFest for the holidays, with music, carnival rides, and entertainment. More info.

New Year's Eve Fireworks (December)

Welcome the new year with New Year’s Eve Fireworks at Navy Pier at midnight. More info.

Sketch Comedy Festival (January)

Choose from more than 170 shows to watch during Chicago Sketch Comedy Festival at Stage 773. More info.

Winter Brew Festival (January)

Winter Brew is a Lincoln Square beer fest that features local brew and food at the DANK Haus German American Cultural Center. More info

Chicago Auto Show (February)

Chicago's first Auto Show took place in 1901 at the Chicago Coliseum and showcased vehicles for an entire week in March. Currently, the Chicago Auto Show is held at McCormick Place, which has 1.2 million square feet to showcase 1,000 vehicles in February.  More info

Snow Days at Navy Pier (February)

See teams sculpt masterpieces from snow during Snow Days in Gateway Park at Navy Pier. Live entertainment, snowboarding, and kids’ activities like snow painting.More info.

Folk Music Festival (February)

Celebrate traditional music from around the world in concerts and workshops at University of Chicago Folk Festival at Mandel Hall, 1131 E 57th St. More info.


St. Patrick’s Day Parade (March)

The Chicago River flows green at 10 a.m. near Michigan Ave. & Wacker Dr. The St. Patrick’s Day Parade begins at noon, rain or shine, at Balbo Ave. and goes north on Columbus Dr. to Monroe St. 

Chicago Flower & Garden Show (March)

Chicago Flower & Garden Show features 20 gardens, 100 vendors, cooking demonstrations, seminars, and a kids’ activity garden at Navy Pier. More info

Chicago Improv Festival (March/April)

Billed as the world’s longest running festival of improvisational theater, the Chicago Improv Festival includes music, song, comedy, story, and puppetry performances in multiple locations. More info.

Underground Film Festival (April)

Chicago's best annual event for movies is the Underground Film Festival which is held at Gene Siskel Film Center. The largest underground film festival in the nation belongs to Chicago where people enjoy independent features, documentaries and experimental films. Anyone can submit a film for consideration to be shown. Awards are given out for best narrative feature, narrative short, experimental, animation and more. More info.

Chicago Comic and Entertainment Expo (April)

Chicago Comic and Entertainment Expo (C2E2) is a convention for fans of comics, graphic novels, anime, manga, video games, toys, movies, and pop culture at McCormick Place. More info.

Antiques Fair (April/May)

Find fine art, antiques, and jewelry from 100 top dealers at the International Antiques Fair at the Merchandise Mart. Opening night party.  More info.

Chicago International Movies & Music Festival (May)

The Chicago International Movies & Music Festival (CIMMfest) is “where movies and music meet.” See films with a music connection by day, and hear live music with a film connection by night at Wicker Park and Logan Square. More info.

Craft Beer Week (May)

Chicago Craft Beer Week features hundreds of craft beer events in the greater Chicago area, from special $4 tastings of rare beers to beer dinners. It’s sponsored by the Illinois Craft Brewers Guild. More info.

Mayfest & Maifest (May)

Mayfest has bands, festival food, pretzels, and beer. Saturday is kids’ day. Sunday is a pet pageant & expo. At 3100 N Ashland Ave. Maifest serves beer, bratwurst, sauerkraut, and music on two stages in Lincoln Square at Lincoln Ave. and Leland Ave  More info.

Memorial Day Parade (May)

A wreath laying ceremony is 11 a.m. at the Eternal Flame on Daley Plaza. The Memorial Day Parade at noon has high-school marching bands, drum and bugle corps, veterans’ groups, and active duty military on State St. from Lake to Van Buren.

Millennium Art Festival (May/June)

The Millennium Art Festival features artwork, food from local restaurants, and live easy-listening music on Lake Street at Michigan Avenue. 

Division Street Festival (May/June)

Do Division Street Fest and Sidewalk Sale has rousing live music, a sidewalk sale, a fashion show, and a family fun fest (Sat. & Sun.) on Division Street between Damen and Leavitt. More info.

Printers Row Lit Fest (June)

This festival attracts over 200 booksellers from across the country displaying new, used and antiquarian books and featuring more than 200 authors participating in panels, discussions and a variety of other programs. More info.

Ribfest Chicago (June)

Visit dozens of rib and food vendors, enjoy a rib-eating contest and ennjoy family entertainment and live music. Proceeds of the festival are utilized to fund community activities. More info.

57th Street Art Fair (June)

Come down and participate in the popular Art Buying Boot Camp, a guided tour through the fair with art-buying experts. Held in Chicago’s historic Hyde Park neighborhood. More info.

Chicago Blues Festival (June)

The largest free blues festival, held annually at Grant Park. Since 1984, the festival has evolved to four days of blues music on six stages. Admission is free. More info.

Wells Street Art Festival (June)

The Wells Street Art Festival transforms Wells Street—the heart of Chicago’s historic Old Town—into an open air fine arts museum. The Festival also features the cuisine of 20-plus neighborhood restaurants, a music stage, kids’ activity area, and an elaborate silent auction. More info.

We are Working on Your Reservation
Please Wait