This page lists the biggest and best Chicago events, festivals, and fun things to do in 2014.
Events are listed by starting date, and all dates are confirmed. Mileage is from the Wrigley Building in downtown Chicago, Illinois.
To see more events, please click a month above.
Sketch Comedy Festival
January 9 - 19, 2014
5 miles northChoose from more than 170 shows to watch during Chicago Sketch Comedy Festival at Stage 773. Cost.
January 11 - 12, 2014
17 miles NWThe Chicago Travel & Adventure Show brings together travelers, travel experts, and travel service providers at the Rosemont convention center. Cost.
Chicago Restaurant Week
January 24 - February 6, 2014
Chicago locationsGet a special deal on a fixed-price lunch or dinner at 286 restaurants during Chicago Restaurant Week.
Winter beer festival
January 25, 2014
7 miles northWinter Brew is a Lincoln Square beer fest that features local brew and food at the DANK Haus German American Cultural Center. Cost.
Snow Days at Navy Pier
February 8 - 9, 2014
1 mile eastSee teams sculpt masterpieces from snow during Snow Days in Gateway Park at Navy Pier. Live entertainment, snowboarding, and kids’ activities like snow painting. Free.
February 8 - 17, 2014
3 miles southAdmire new vehicles at the Chicago Auto Show, where exhibits are spectacular due to the large size of McCormick Place convention center. Cost.
Folk music festival
February 14 - 16, 2014
9 miles southCelebrate traditional music from around the world in concerts and workshops at University of Chicago Folk Festival at Mandel Hall, 1131 E 57th St. Cost.
St. Patrick’s Day Parade
March 15, 2014
1.3 miles southThe 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. Free.
Flower and garden show
March 15 - 23, 2014
1 mile eastChicago Flower & Garden Show features 20 gardens, 100 vendors, cooking demonstrations, seminars, and a kids’ activity garden at Navy Pier. Cost.
March 31 - April 6, 2014
Chicago locationsBilled 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. Cost.
Underground film festival
April 2 - 6, 2014
7 miles NWChicago Underground Film Festival (CUFF) shows independent, experimental, and documentary films from around the world at the Logan Theatre, followed by nearby after-parties. Cost.
April 24 - 27, 2014
1 mile westFind fine art, antiques, and jewelry from 100 top dealers at the International Antiques Fair at the Merchandise Mart. Opening night party Wed. Cost.
Comic and Entertainment Expo
April 25 - 27, 2014
3 miles southChicago 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. Cost.
Movies and music festival
May 1 - 4, 2014
5 miles NWThe 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. Cost.
Mayfest & Maifest
May 16 - 18, 2014
Mayfest has bands, festival food, pretzels, and beer. Saturday is kids’ day. Sunday is a pet pageant & expo. At 3100 N Ashland Ave. (5 miles NW) Cost.
May 29 - June 1, 2014
Maifest serves beer, bratwurst, sauerkraut, and music on two stages in Lincoln Square at Lincoln Ave. and Leland Ave. (8 miles NW) Free.
Memorial Day Parade
May 24, 2014
0.5 mile SWA 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. Free.
Bicycle along the lake
May 25, 2014
1 mile southRide your bike up to 15 miles each way on Lake Shore Drive when it shuts down for five hours during Bike the Drive. Enter at S Columbus Dr. and Jackson downtown. Register early. Cost.
Millennium Art Festival
May 30 - June 1, 2014
0.5 mile southThe Millennium Art Festival features artwork, food from local restaurants, and live easy-listening music on Lake Street at Michigan Avenue. Free.
MAY continues in the next column.
Division Street festival
May 30 - June 1, 2014
4 miles NWDo Division Street Fest & 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. Donation.
Craft beer week
May 2014 (undated)
Chicago locationsChicago 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.
June 6 - 7, 2014 (uncertain)
Downtown ChicagoExperience the art, music, dance, and cuisine of Turkey at the Chicago Turkish Festival in Pioneer Court at 401 N Michigan Ave. Free.
Belmont-Sheffield Music Festival
June 7 - 8, 2014
5 miles northCelebrate Memorial Day weekend with local bands, food, drink, and street vendors at the Belmont-Sheffield Music Festival on N. Sheffield from Belmont to School. Donation.
Classical music festival
June 11 - August 16, 2014
Chicago locationsGrant Park Music Festival is billed as America’s only free, outdoor classical music series. Most concerts are at Jay Pritzker Pavilion in Millennium Park. Free.
June 13 - 15, 2014
1 mile southChicago’s biggest music festival, Chicago Blues Festival, brings top-name talent to multiple stages in Grant Park & Millennium Park. After the show, music continues late into the night at city clubs. Free.
Taste of Randolph
June 13 - 15, 2014
1.5 miles westThe highly acclaimed Taste of Randolph offers six blocks of artisan and restaurant booths plus three music stages on W Randolph Street from Peoria St. to Racine Ave. Donation.
Electronic dance music festival
June 13 - 15, 2014
2 miles southSpring Awakening Music Festival draws 75,000 to Soldier field to hear the best in electronic dance music (EDM) by some of the world’s top DJs. Cost.
Old Town Art Fair
June 14 - 15, 2014
3 miles northSee drawings, paintings, photography, ceramics, jewelry, and works in metal, stone, glass, and wood by 250 juried artists at Old Town Art Fair on tree-lined Lincoln Ave. at Wisconsin. Donation.
June 21 - 22, 2014
6 miles northChicago Pride Fest is a huge weekend street festival for gay and lesbian pride with music on two stages, food, drink, arts and crafts vendors, and a pet parade in Northalsted. Donation. Pride parade is June 29.
Southport street fair
June 28 - 29, 2014 (uncertain)
6 miles northSummer on Southport is a mellow event with live music, vendors, food, and a children’s festival on N Southport Ave. at Waveland. Donation.
June 2014 (undated)
Chicago locationsJust for Laughs Chicago is six days of stand-up comedy and sketches by more than 100 comedians.
Wavefront Music Festival
July 5, 2014
6 miles northWavefront Music Festival is an electronic music dance festival that has 100 artists on four stages capped by fireworks at Montrose Beach. Cost.
July 9 - 13, 2014
1.5 miles southA million people get a taste of 35 restaurants and enjoy music & entertainment at Taste of Chicago in Grant Park. Free, except permanent concert seats.
Downtown art festival
July 11 - 13, 2014
0 milesShop from 200 of the best painters, sculptors, and jewelry makers along eight blocks at the North Michigan Avenue Art Festival at Pioneer Court. Free.
Pitchfork Music Festival
July 18 - 20, 2014
2.5 miles westThe free-spirited Pitchfork Music Festival features alternative rock, rap and hip-hop, electronica, and dance music in Union Park. Cost.
Craft beer fest
July 19 - 20, 2014
2.5 miles NWThe Chicago Craft Beer Festival is a Belgian beer fest held on the grounds of St. Michael in Old Town.
Clark Street festival
July 19 - 20, 2014
10 miles northEnjoy multi-cultural food, art, music, and dance at Celebrate Clark Street Festival on N Clark St. from Morse to Estes. Kids’ activities. Donation.
August 1 - 3, 2014
1.5 miles southLollapalooza is a three-day music festival with more than 100 popular alternative rock, punk rock, heavy metal, and hip hop bands; comedy and dance; and craft booths in Grant Park. Cost.
August 8 - 10, 2014
3 miles northGinza Holiday offers Japanese dance, martial arts, drumming, bonsai, craftsmen at work, and teriyaki chicken at Midwest Buddhist Temple. Donation.
Northalsted Market Days
August 9 - 10, 2014
5 miles northNorthalsted Market Days is a gay-friendly street fair and music festival with 400 food, art, and craft vendors plus musical acts on six blocks of North Halsted Street from Belmont to Addison. Donation.
Air and water show
August 16 - 17, 2014
2 miles northThe Chicago Air & Water Show features daredevil pilots, parachute teams, and jets flying in formation, plus water-skiing and boat jumping. See it from the waterfront near North Avenue Beach. Free.
Port Clinton Art Festival
August 23 - 24, 2014
27 miles northPopular Port Clinton Art Festival has 260 artists, a youth division, and kids’ art activities in Highland Park. Taste of Highland Park is Fri. to Sun. Free.
August 28 - 31, 2014
0.5 miles southThe Chicago Jazz Festival is Labor Day weekend at Millennium Park. No dogs. Free.
August 2014 (undated)
3.5 miles SWTaylor Street Festa Italiana has music on four stages, Italian cuisine, a local artisan market, and the Momsay Kids Stage on W Taylor Street between Ashland and Racine. Donation.
September 10 - 12, 2014
1 mile southBerghoff Oktoberfest serves bratwurst, sauerkraut, chicken, pretzels, and apple strudel plus German music at W Adams St. and Dearborn. Free to 9 p.m.
September 26 - 28, 2014
0.5 mile southChicago Gourmet is a premium food and wine event with 100 chefs, cooking demonstrations, beer and food pavilions, and wine tastings in Millennium Park.
Hyde Park Jazz Festival
September 27 - 28, 2014
8 miles southHear 40 jazz performances by top artists indoors and outdoors at the Hyde Park Jazz Festival. Free.
Opera in the park
September 2014 (undated)
0.5 mile southSpectacular singing and orchestral music await at Stars of Lyric Opera at Millennium Park. Free.
October 9 - 23, 2014
0.5 mile eastThe Chicago International Film Festival features more than 100 short and full-length films from 50 countries, free panel discussions, and opening night gala. Films show at the AMC River East 21. Cost.
Marathon & fitness expo
October 10 - 12, 2014
Chicago locationsThe free Chicago Marathon Health & Fitness Expo is Friday and Saturday at McCormick Place. The Chicago Marathon begins and ends Sunday in Grant Park, with an after-festival in Butler Field.
Magnificent Mile Lights Festival
November 22, 2014
Downtown ChicagoThe Magnificent Mile Lights Festival begins midday with family events at Lights Festival Lane in Pioneer Court. The 5:30 p.m. Tree-Lighting Parade starts at Oak Street and runs down Michigan Avenue to the Chicago River, ending in fireworks. All free.
November 27, 2014
1 mile southThe morning Thanksgiving Parade includes giant balloons, floats, and marching bands that go north on State Street from Congress to Washington. Free.
November - December 2014 (undated)
1 mile SWChristkindlmarket is an open-air European holiday market on Daley Plaza featuring traditional art, handmade gifts, German foods, choirs, carolers, and an opening ceremony. Free.
November - December 2014 (undated)
2.5 miles northZooLights 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 some days). Free entry.
December 2014 (undated)
1 mile eastFestival Hall at Navy Pier becomes an indoor Winter WonderFest for the holidays, with music, carnival rides, and entertainment. Expect crowds. Free entry.
New Year’s Eve restaurants
December 31, 2014
Greater Chicago areaThese restaurants offer specials on New Year’s Eve.