17 Chicago Festivals and Events You Don’t Wanna Miss – Mature Woman Solo Travel

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Looking for things to do in Chicago?  Or perhaps you’re a self-professed foodie wanting to check out Chicago festivals such as the “Taste of Chicago” or “Ribfest” but didn’t know much about either one. In this article, I discuss what’s happening in Chicago and 17 festivals that you don’t wanna have the misfortune of missing.  Please note: many of Chicago festivals are free events.

Plan your visit to Chicago NOW.  Don’t miss out on any Chicago festivals or events. Book your room by clicking here. Not sure where to stay in Chicago?  Read my article “Where to Stay in Chicago” for comprehensive information on Downtown Chicago hotels.


chicago festivals

Chicago January Events

It seems crazy to be talking about Chicago festivals in January during which Chicago is experiencing record freezing cold weather.  But this is Chicago and winter doesn’t last forever (although, it feels like it).

If you are fortunate to be visiting Chicago during the winter, there a few Chicago festivals during this time of year you will not want to miss.

Chicago Restuarant Week

If you are a foodie you will absolutely love Restuarant Week.  It is an annual event where fancy-schmancy restaurants (about 350) around the city of Chicago will offer sample plates of delicious multi-course meals that ordinarily would be expensive.  Here are some of the restaurants labeled “Don’t Miss Spots” by the Chicago Tribune:

  • Brindille (534 N. Clark) – French cuisine served in a “refined and sexy ambiance”.  Brindille will be offering a 3-course meal that includes chilled oysters, duck breast with foie grais and coddled duck eggs.  Located in the River North area of Downtown Chicago.
  • City Mouse (311 N. Morgan) – a West Loop neighborhood restaurant located inside the Ace Hotel Chicago.  They offer a seasonal menu inspired by Midwest classic food traditions; meat and potatoes.  They will be offering a 4-course meal for Restuarant Week that includes grilled shrimp in pipian roja, rigatoni with pork and kimchi (yes, kimchi) ragu, swordfish, and a coffee creme brulee.
  • Le Sud (2301 W. Roscoe) – Located in Chicago’s hip Roscoe Village neighborhood, Le Sud features traditional cuisine for Southern France.  It will feature a 3-course dinner that includes salad, steak frites, loup de mer (look it up, people) and chocolate and orange mousse.
  • Oceanique (505 Main St) – Located in Evanston (Home of Northwestern UniversityGo Purple and White!), a northeast suburb just outside of Chicago, Oceanique showcases a menu both “classic and approachable” – “something for everyone” including prime beef, lamb, pork and vegetarian.  They will be offering a 3-course dinner menu which includes calamari and shrimp, Rhodes Island skate and ocean trout.
  • Prosecco (710 N. Wells) – Located in the River North Gallery District; this restaurant features comfort food from 20 regions of Italy and Chicago’s largest selection of sparkling wine.  Prosecco will be offering a 3-course meal of risotto, beef tenderloin and more!

Read reviews from Restaurant Week in the Food and Dining section of the Tribune by clicking here.

To book a ticket at one (or more) of the restaurants featured at Chicago Restaurant Week:

  • Go to the website, “Choose Chicago
  • Choose a restaurant
  • Book a table (via OpenTable)
  • Enjoy!

Where to Stay: Hyatt Regency Chicago (151 E. Wacker Drive).


chicago festivals

Chicago February Events

The month of February begins with Chicago Restaurant Week (ends February 7th).  But you will find plenty of other events to engage in that doesn’t involve your stomach.

Chicago Theater Week

You might be surprised to know that Chicago has an amazing theater scene.  Chicago Theater Week celebrates its 7th year by offering discounts to 100 different productions taking place in theater venues all over the city.  Here are some of the shows in Chicago picked by the critics as “must-see”:

  • Friends – The Musical Parody (Broadway Playhouse at Water Tower Place) – Yes, a parody of the hit TV show, Friends.
  • Photograph 51 (Court Theater, Hyde Park) – About the life and times of the scientist, Rosalind Franklin.
  • Twilight Bowl (Goodman Theater, Chicago Loop) – The play “Twilight Bowl” is about 6 women in a small town in Wisconsin, their struggle of being an adult and the consequences of the choices they make.
  • Anna Karenina (Auditorium Theater, Chicago Loop) – This world-famous ballet is a collaboration between the Joffrey Ballet and the Australian Ballet.

Price of tickets starts at $10. For more information on Chicago theatre events during Theatre Week, click here or go to choosechicago.com.

Chicago Auto Show

This year marks the 111th anniversary of the Chicago Auto Show.  It is the largest auto show in North America.  Women’s Day at the Chicago Auto Show is February 12th for which the cost of admission is $7.00.  For more information: chicagoautoshow.com

chicago festivals

Where to stay: Hampton Inn Majestic (22 W. Monroe)


chicago festivals

Chicago March Events

Ahhh, March in Chicago – not quite winter, not quite spring but we do celebrate the wearing of the green by turning the Chicago River a putrid color of green. It’s a slow thaw. Chicago begins to peel off its layers of cold weather gear and come out of hibernation.  As the city warms up so does the action.

St. Patrick Day Parade and Dyeing of Chicago River

The whole city reeks of booze during this day (and the day after). The streets of Chicago are filled with people in one big city-wide block party.  If you’re an introvert, like myself, you will enjoy people watching folks dressed up in green but you will want to be back in your hotel room before it gets dark and rowdy….and trust me it gets rowdy. It really is a lot of fun…oh, yeah and there’s a parade.

Where to Stay:  Hotel Monaco Chicago (225 N. Wabash)

chicago festivals

Chicago May Events

Technically, spring begins in April but the weather in Chicago can still be quite chilly (and it could snow and has in the past – May 2, 2005).  Anyway, the festival season begins this month regardless of the chill in the air.

Gospel Fest

If Gospel music is your thing, you do not want to miss Gospel Fest.  The Gospel Fest features national and local talent from traditional to contemporary urban gospel music. The festival is held at the Jay Pritzker Band Shell in Millennium Park (201 E. Randolph St). Bring your lawn chair because admission is free.

Lincoln Park Greek Fest

Held in the Lincoln Park neighborhood (2701 N. Sheffield Ave) by St. George Orthodox Church and the local Greek community, Greek fest celebrates the hospitality, food, music, and dance of the Greek culture.  Just like everyone is Irish on St. Patrick Day; everyone is greek during Greek Fest.


Taste of Mexico

The neighborhood of Little Village celebrates south-of-the-border cuisine with the Taste of Mexico.  There will be over 20 neighborhood and local restaurants selling authentic Mexican food, non-stop music, and arts and crafts.

Where to Stay: Palmer House Chicago (17 E. Monroe)


chicago festivals

Chicago June Events

The weather (a major character in the lives of most Chicagoans) is warming up and so is festival season in Chicago. Streets are shutting down all over the city as Chicago neighborhoods celebrate with street festivals and block parties.  There is something going on every weekend up until the kids go back to school in September.

Millennium Park Summer Film and Music Series

Grab a seat or sit on the lawn of the Jay Pritzker Pavillion on Tuesday nights beginning June 6 and watch the City of Chicago salute to the Independent Film Industry.  Some of the movies that will be showcased are Hairspray, High Fidelity, Get Out and many more.  Admission is free.  Click here for more information on upcoming concerts in Chicago.

Also from June through August 2019, the city of Chicago Millennium Park Music series showcases live music on Monday and Thursday evenings at the Pritzker Pavillion.  Admission is free.  Click here for more information.

chicago festivals

Chicago Blues Fest

Chicago Blues Fest is the largest free blues festival in the world and is the largest of the Chicago Music Festivals.  On 4 stages, blues live entertainment will be played for your listening pleasure.  Admission is free.  For more information, click here.

chicago festivals

Chicago Ribfest

Chicagoans love their BBQ ribs and in celebration of that Ribfest showcases the bbq talents of 13 Chicagoland Restaurants along with the musical talents of 25 bands. Donation: $10.  Ribfest will be held on Lincoln Ave; between Irving Park Road and Berteau.  Click here for more information.

chicago festivals

Chicago Pride Festival

The Chicago Pride Fest is a 2-day street festival on the weekend before the Pride Parade (June 30, 2019).  Pride Fest (and the subsequent parade) celebrates LGBTQ life, culture, and community.  The festival features live music, food and drink, dancing and a drag show. This celebration of diversity, equality, and inclusion will be held in Boystown (Halsted and Waveland St).  Click here for more information.

Where to Stay:  The Wit Hotel Chicago (201 N. State)


chicago festivals

Chicago July Events

The city really begins to heat up and the festival season is still going strong in the month of July with the big festival of all festivals…The Taste of Chicago.

The Taste of Chicago

I get mildly nostalgic (and teary-eyed) about the good ole’ days when the “Taste” use to begin the last 2 weeks of June and end with a bang (fireworks) on the 5th of July.  Traffic on Lake Shore Drive would come to a stand-still while folks got out their car to watch the fireworks over downtown Chicago.

Man, the Taste of Chicago has certainly changed a lot during the years. (Sigh).  It’s now a 4-day celebration in the middle of July.  It has slimmed down from over 100 food vendors to about 40 restaurant booths and food trucks.  It still is impressive and a great way to sample some great food from restaurants all over the Chicagoland region.  There will be live music and cooking demonstrations by world-class chefs.  Not to be missed!  And a great time!  Admission: free however food and beverage tickets are sold for $10 for a strip of 14 tickets.  Tickets are used like cash to purchase food or beverage from each vendor.  For more information, click here.

Where to Stay: Hilton Chicago (720 S. Michigan)

Chicago August Events

Things are starting to wind down as the whole city is soaking in the last month of summer.  Beaches are crowded and baseball season is coming to a close.

chicago festivals


Lollapalooza is a 4-day music fest featuring different genres of bands such as alternative rock, hip-hop, heavy metal, and punk rock.  Comedy, dance groups also perform.  It’s all happening in Grant Park, downtown Chicago.

chicago festivals

Chicago Air and Water Show

Chicago Air and Water Show showcases daredevil pilots, parachute teams, air/sea rescue demonstrations and much more.  Watch all the action along North Avenue Beach.  Admission: Free

chicago festivals

Chicago Jazz Fest

Festival season wraps up with a music fest that celebrates jazz.  The Chicago Jazz Fest showcases the greatest jazz artist from Chicago and around the world.  Performances will be held at Millennium Park (201 E. Randolph) and venues across the city. Admission: Free.  For more information, click here.

Where to Stay: Silversmith Hotel Chicago (10 S. Wabash)

Chicago Winter Events

There are a couple of winter events that are worth mentioning that Chicago is known for.  These events are worth coming to Chicago during the wintertime.

chicago festivals

Magnificent Mile Lights Festival

Folks fly in from all over the country for the Mag Mile Lights Festival.  The fest begins with holiday activities (mostly family-oriented) and a Lights Parade that goes down Michigan Avenue from Oak Street to Wacker Drive that is worth hanging out in cold to see.

Christmas Market

The Christkindlmarket is an open-air European-style holiday market featuring traditional art, handmade gifts, choirs, carolers and German food (yum).  The Christmas Market is held at Daley Plaza (50 W. Washington St).  Admission is free.  For more information, click here.

Where to Stay: Loews Chicago Hotel (455 N Park)

For more ideas on what to do during your stay in Chicago, read my article “Perfect Things to Do In Downtown Chicago”.


Please note: Dates, times and venues are subject to change

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