things to do

Things to Do in Chicago: Winter 2023

November 16, 2023

Let’s hear those sleigh bells ringing! The holiday season is here, which means there are a lot of great events to check out in Chicago. My favorites from past years have included festive pop-ups such as Jack Frost Winter Fest Pop-Up and local markets like Christkindlmarket. Below you will find a list of recommended things to do in Chicago this winter!

Jack Frost Winter Fest Pop-Up

Date: November 30, 2023 – December 31, 2023
Location: Fulton Market
Cost: Admission $18-$34 + Selected Activities
View my 2022 Jack Frost Winter Fest Pop-Up review here!

ZooLights at Lincoln Park Zoo

Date: November 17, 2023 – January 7, 2024
Location: Lincoln Park Zoo
Cost: Mondays are free, other dates $7-$10 admission, possible drinks available for purchase

Christkindlmarket Chicago

Date: November 17, 2023 – December 31, 2023 (locations vary)
Location: Daley Plaza (Loop) & Gallagher Way (Wrigleyville)
Cost: Free admission, Food/Drink/Shop items available for purchase
View a recap of my past experience at Christkindlmarket here!

Santa Baby Christmas Bar

Date: November 17, 2023 – December. 31, 2023
Location: Bamboo Club in Wrigleyville
Cost: $5 cover charge on certain dates, Food & drink available for purchase

Pink Wonderland Pop-Up Bar

Date: December 2, 2023 – December. 30, 2023
Location: 324 W Chicago Ave
Cost: $25-$40 admission

Ice Skating at Maggie Daley Park

Date: November 17, 2023 – March 10, 2024
Location: Maggie Daley Park
Cost: $16-$22 admission, Locker rentals $3-$5, Skate aids $10

Things to Do in Chicago: Fall 2023

August 14, 2023

Who’s ready for spooky season? I definitely am! I absolutely love Fall time in the city. From festive pop-ups to pumpkin-flavored treats to Halloween, there’s nothing better than the cozy aesthetic that comes with it. Looking forward to scheduling plans? Make sure to add the ones listed below to your calendar! This post will be updated as events arise.

Jack’s Pumpkin Pop-Up

Date: September 21 – November 3, 2023
Location: Goose Island (1465 N. Elston Ave.)
Cost: $22 for GA, food/drink & extras available for purchase
View my 2022 Jack’s Pumpkin Pop-Up recap post (this is my favorite fall event!)

Harry Potter Magic at Play

Date: Now – September 4, 2023
Location: Water Tower Place (835 Michigan Ave.)
Cost: $42.50 per ticket, treats & souvenirs available for purchase
View my Harry Potter Magic at Play recap post

Rooftop Cinema Club

Date: Now – September 4, 2023
Location: The Emily Hotel (311 N Morgan St.)
Cost: $22.50+ per ticket

Chef BBQ at Green City Market

Date: September 7, 2023
Location: Lincoln Park (1817 N Clark St)
Cost: $159 for GA, $289 for VIP
View my 2022 Chef BBQ recap post

Taste of Chicago

Date: September 8-10, 2023
Location: Polk Brothers Park (600 E Grand Ave)
Cost: Free admission, food available for purchase

Oktoberfest at the Zoo

Date: September 16, 2023
Location: Lincoln Park Zoo
Cost: $15 admission (early bird price), food & drink available for purchase

Chicago Gourmet

Date: September 21-24, 2023
- Sep 21: Tacos & Tequilas ($110)
- Sep 22: Hamburger Hop ($130)
- Sep 23: Grand Cru ($255)
- Sep 24: Prost! In the Park ($99)
Location: Harris Theater Rooftop (205 E. Randolph St.)
Cost: $99-$255 + tax
View my 2019 Chicago Gourmet recap post

Green City Market

Date: Now – November 2023
Location: Lincoln Park, West Loop, Avondale
Cost: Free admission, vendors selling items for a cost

The Exhibit House

Date: Indefinitely
Location: Water Tower Place (835 Michigan Ave.)
Cost: $30 per ticket
View my The Exhibit House recap post

ZooLights

Date: November 17, 2023 – January 7, 2024
Location: Lincoln Park Zoo
Cost: TBD

Things to Do All Fall

Things to Do in Chicago: Summer 2023

April 16, 2023

Summer in Chicago is the best time of year. Whether you’re a local or just visiting for a weekend, there’s always something to do to enjoy the city (and nice weather). Plenty to keep your calendar full! Read below for things to do in Chicago this summer, May through September! This post will be updated as events are announced.

May 2023 Events

Green City Market

Date: May – November 2023
Location: Lincoln Park, West Loop, Avondale
Cost: Free admission, vendors selling items for a cost

Pixar Putt

Date: May – September 2023
Location: Polk Bros Park outside Navy Pier (600 E. Grand Ave.)
Cost: $22-$33 per ticket
View my 2022 Pixar Putt Chicago recap post

Harry Potter Magic at Play

Date: May – September 4, 2023
Location: Water Tower Place (835 Michigan Ave.)
Cost: $42.50 per ticket, treats & souvenirs available for purchase
View my Harry Potter Magic at Play recap post

Sueños Music Festival

Date: May 27-28, 2023
Location: Grant Park
Cost: $179+ per ticket, view lineup

Millennium Park Summer Workouts

Date: May 27 – September 2, 2023
- 8–8:45am Pilates (no classes 7/1)
- 9–9:45am Yoga (no classes 7/1)
- 10–10:45am Cardio Kickboxing (no classes on 6/10, 7/1, 9/2)
- 11–11:45am Zumba® (no classes on 6/10, 7/1, 9/2)
Location: Great Lawn in Millennium Park (201 E. Randolph St.)
Cost: Free admission

The Exhibit House

Date: Indefinitely
Location: Water Tower Place (835 Michigan Ave.)
Cost: $30 per ticket
View my The Exhibit House recap post

June 2023 Events

Malibu Barbie Cafe Chicago

Date: June 7 – September 15, 2023
Location: TBA, Downtown Chicago
Cost: $35 for kids, $49 for adults (each ticket includes reserved seating, entree & side item)

Heatwave Music Festival

Date: June 10-11, 2023
Location: Huntington Bank Pavilion at Northerly Island
Cost: $99+ per ticket, food & drink available for purchase

Grant Park Music Festival

Date: June 14 – August 19, 2023
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free seating, first come first serve

Millennium Park Summer Music Series

Date: Mondays & Thursdays, June 22 – August 21, 2023 – 6:30-9pm (Gates open at 5pm)
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free admission

Pride in the Park Chicago

Date: June 23-24, 2023
Location: Grant Park
Cost: $75+ per ticket, food & drink available for purchase
View my 2022 Pride in the Park Chicago recap post

Joffrey Ballet’s “Joffrey for All Celebration”

Date: June 25, 2023 – 5:30pm
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free public performance

Chicago Symphony Orchestra’s “Concert for Chicago”

Date: June 27, 2023 – 6:30pm
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free public performance

July 2023 Events

NASCAR Chicago Street Race Weekend

Date: July 1-2, 2023
Location: Grant Park (337 E Randolph St.)
Cost: $269+ per ticket

Millennium Park Summer Film Series

Date: Tuesdays, July 11 – August 29, 2023 – 6:30pm (Gates open at 5pm)
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free admission

Windy City Smokeout

Date: July 13-16, 2023
Location: United Center parking lot
Cost: $55+ per ticket, food & drink available for purchase
View my 2022 Windy City Smokeout recap post

Chicago SummerDance

Date: July 15 – September 10, 2023
Location: Grant Park & Millennium Park
Cost: Free admission

Sad Summer Festival

Date: July 21, 2023
Location: Huntington Bank Pavilion at Northerly Island
Cost: $49.50+ per ticket, food & drink available for purchase

Pitchfork Music Festival

Date: July 21-23, 2023
Location: Union Park (1501 W Randolph St.)
Cost: $109+ per ticket, food & drink available for purchase

August 2023 Events

Lollapalooza

Date: August 3-6, 2023
Location: Grant Park
Cost: $125+ per ticket, food & drink available for purchase

Stan’s Donut 5k

Date: August 19, 2023
Location: Solider Field
Cost: $40 per registration
View my 2022 Stan’s Donut 5k recap post

Chicago Air and Water Show

Date: August 19-20, 2023
Location: North Ave Beach & along the Lakefront
Cost: Free admission, reserved viewing at certain businesses for a cost

September 2023 Events

Chef BBQ at Green City Market

Date: September 7, 2023
Location: Lincoln Park (1817 N Clark St)
Cost: TBD, tickets required
View my 2022 Chef BBQ recap post

Taste of Chicago

Date: September 8-10, 2023
Location: Polk Brothers Park (600 E Grand Ave)
Cost: Free admission, food available for purchase

Chicago Gourmet

Date: September 21-24, 2023
- Sep 21: Tacos & Tequilas
- Sep 22: Hamburger Hop
- Sep 23: Grand Cru
- Sep 24: Prost! In the Park
Location: Harris Theater Rooftop (205 E. Randolph St.)
Cost: TBD, tickets required
View my 2019 Chicago Gourmet recap post

Things to Do All Summer

Chicago Attractions

Chicago Museums

Things to Do in Chicago This March

February 5, 2020

Time to come out of hibernation! Us Chicagoans will (hopefully) get a glimpse of Spring this month and I can’t wait. It’s about time for all the fun, festive events to make a come back. I have rounded up all the worthy things to do in Chicago this March for your viewing below. Which of them will you be trying out?

Charm’d: The Magical Irish Pop-Up Bar

March 1 – 14, 2020

True to the spirit of St. Patrick’s Day in Chicago, Charm’d is an Instagram-worthy pop-up bar in Chicago’s Wrigleyville neighborhood. The pop-up will be held inside Deuce’s and The Diamond Club, one of my favorite party spots. Events offered at the Irish themed pop-up include Paint n’ Sip, Bingo n’ Booze, Karaoke Night, Magic Mondays, and Sunday Funday. It is recommended to buy a ticket ahead of time online to make sure the day you want to attend does not sell out (tickets are also more expensive at the door). Themed food and drinks will be available for purchase.

Chicago Flower & Garden Show

March 18 – 22, 2020

Who else thinks flowers are absolutely beautiful? How about life-size gardens all in the same place? This year the Chicago Flower & Garden Show is hosting their annual event during a small part of March. Tickets can be bought here. The show will also offer Special Events throughout it’s debut, including a Chicago Reader party and networking event!

St. Patrick’s Day Chicago Green River Dyeing & Parade

March 14, 2020

One of the events Chicago is most notorious for is the green dyeing of the Chicago River for St. Patrick’s Day. This usually happens in the morning on the Saturday of St. Patrick’s Day festivities in the city (bar crawls, bar parties, etc.). This year it is occurring March 14, 2020 at either 9 or 10am. I recommend going to Upper Wacker for a good view of the river being dyed green! The Chicago St. Patrick’s Day Parade will start at Grant Park for the North Side. If you’re looking for a good bar crawl, I’m going to the one in Wrigley!

Macy’s Flower Show

March 22 – April 5, 2020

The Macy’s Flower Show is always a Springtime favorite. The event features beautiful flower installations all focused around a hand-picked theme. This year’s theme is Voyage to Oceanum – featuring floral aquatic beauty. I can’t wait to see the spread for the 2020 event at Chicago’s Macy Flagship location on State Street! Free to the public.

Chicago Beer Festival

March 14, 2020

Calling all beer lovers! Have a taste of Chicago’s best brews at the Chicago Beer Festival, held at The Field Museum. Those attending will receive 40 beer tasting vouchers to try. VIP also includes specialty beers poured during a special VIP session. The event is 21+ and tickets can be purchased here.

Uncorked: Chicago Wine Festival

March 21, 2020

Uncorked, a Chicago wine festival held at the Museum of Science and Industry, highlights over 200 wines and champagnes from around the globe. VIP tickets include an extra hour of tasting (4 hours), compared to general admission tickets for three hours of tasting. Dress or cocktail attire is recommended.

Things to Do in Chicago This November

October 11, 2019

*Updated for November 2019

Things to Do in Chicago This November

The temperatures have dropped and the city is buzzing with seasonal events and specials leading up to the holiday season. Who else is beyond excited to add all of these festive events to their social calendar?? Make sure to take a look and mark down dates for things to do in Chicago this November!

Christkindlmarket Chicago

One of my favorite seasonal events in Chicago comes back this November. Christkindlmarket is a festive holiday tradition in the city that graces Daley Plaza and Wrigleyville. Featuring vendors from all over the world, German food and drinks, and holiday entertainment, this event offers free general admission with food and drink available for purchase. Christkindlmarket is known for their souvenir boot mugs, which features a new design each year, are perfect for collecting, and perfect to have hot spiced wine in! This event is open to the public November 15 – December 24, 2019.

Meals on Wheels Celebrity Chef Ball

Enjoy an evening of food and philanthropy on November 8, 2019. Meals on Wheels Chicago‘s signature fundraiser, Celebrity Chef Ball, brings Chicagoans and chefs together to nourish homebound neighbors. Guests doing the VIP Chef’s Table option will enjoy a six-course dinner with cocktail pairings, desserts, and a live auction. Those doing the Chef’s Tasting Party will sample dozens of different chef stations, enjoy cocktails, a live auction and dancing.

MSI After Hours: Naughty or Nice

Time to get naughty. Just kidding. But actually. This 21+ holiday party at Chicago’s Museum of Science and Industry features spiked hot chocolate, Santa Claus and Krampus to decide what list you’re on, over 50 holiday trees and decorations, and a 45-foot Christmas tree to take selfies with. Tickets are required ($30 each) and includes free parking, coat check, a complimentary drink, and access to MSI’s exhibits.

Walnut Room Tree Lighting

Located inside of Macy’s on State St., The Walnut Room will have their annual tree lighting ceremony this November. The Walnut Room was the first restaurant to open inside of a department store, making it the perfect historic place to start off the holiday season in Chicago!

Zoolights at Lincoln Park Zoo

Another one of my favorite annual events to look forward to is Lincoln Park Zoo’s Zoolights. I love looking at the different light up displays synced with favorite holiday tunes while drinking a tasty hot chocolate. Admission into the zoo is free, however special events, like the zoo’s Holiday Market and Adults Night Out event, require a ticket.

Vegan Feast at Sunda

This River North (my neighborhood!) feast at Sunda offers guests a taste into Southeast Asia cuisine, on November 12, 2019, in celebration of World Vegan Month. Example dishes to try include Burmese Tea Salad, Shiitake Edamame Dumplings, and Filipino Mushroom Adobo. YUM. Guests will also have the special chance to try Sunda’s new vegan sushi menu, which launches November 1, 2019. Items on this menu includes Sweet Potato Caterpillar Roll and Beets Gunkan Maki. Tickets for Vegan Feast are $45 and can be purchased HERE.

The BMO Harris Magnificent Mile Lights Festival

On Saturday, November 23, 2019 enjoy a night holiday parade lead by Mickey Mouse and friends down North Michigan Ave. to Wacker Drive. Featuring one million lights, gaze upon a procession of decorated floats, marching bands, well-known Chicago mascots, and live entertainment all leading up to a firework show over the Chicago River. Join the celebration early the night before (Friday, November 22, 2019) for live music and sample treats from Chicago favorites including Garett’s Popcorn, The Eli’s Cheesecake Factory and more.

Heated Domes at City Winery Riverwalk

If you are worried about enjoying the Chicago River’s gorgeous views in Chicago winter weather, City Winery Riverwalk’s heated domes are your answer. Now until December 16th, reserve your own private heated dome for your next dining experience. Price is $85/guest: a non-refundable $25 rental fee per guest plus $60 each for food and drink minimum. Heated domes are 21+ only and include 2.5 hours inside the climate-controlled setting. Make your seasonal reservations here!

Writer Wednesdays

About Last Knife (ALK) has partnered with the American Writers Museum this season for Writer Wednesdays. Anyone who donates a book, starting on Wednesday 11/6, to neighboring Hotel Julian‘s library will receive a complimentary drink from ALK’s new literary-inspired menu! View some of the eight “Novel Approach” cocktails below:

Hemingway Daiquiri with rum, maraschino, grapefruit, and lime
Eventide – the name of Gwendolyn Brooks’ first published poem – with gin, americano, violette, and bitters
The Giving Tree – inspired by Shel Silverstein’s infamous children’s book – with sherry, cherry, and demerara
Bandit of Hell’s Bend – a Western fiction novel by American writer Edgar Rice Burroughs – with rye, cardamaro, and vermouth

Black Wednesday Turkey Bar Crawl

There’s always a bar crawl going on in Chicago, even right before Thanksgiving! This festive Black Wednesday bar crawl is only $10 and includes admission into Wrigleyville bars, a dinner buffet, gift cards to use during the crawl, drink specials, and more. Bars featured are Moe’s Cantina, Old Crow, Country Club, and Stretch with drink specials including $4 Bud Light, $5 Goose Island 312, and $6 Jameson at most bars.

Frosty’s Christmas Bar

Frosty’s will be back this year, and I’m guessing better than ever! I went to last year’s event and had a blast. This pop-up bar features themed drinks and 3 levels of all the holiday, Christmas decorations you can physically fit in a room. It is down right amazing. There’s even snow confetti canons. Make sure to wear something festive! Check out some inspiration from my visits here and here.

Christmas Around the World

View a floor-to-dome Grand Tree at this annual exhibit at Chicago’s Museum of Science and Industry. Featuring more than 50 trees, with decorations representing holiday traditions and cultures around the world, attend this event from November 14 – January 5, 2019.

Seasonal Chicago Food & Treats

Now to the good stuff; FOOD. There are multiple places to put on your check out list this November (and December) for seasonal food and treats. Dine in with The Walnut Rooms’ Great Tree Buffet and enjoy a view of their giant Christmas tree!

Things to Do in Chicago this May

April 26, 2019

Who else is still recovering from the event scene come-back in April?? Now that the weather is starting to show hope towards #patioseason, events for Spring and Summer are in full swing. Read below for a roundup of things to do in Chicago this May! Listed in order by date 🙂

Fyre Festival Pop-Up

May 3 – 19, 2019

Replay Lincoln Park‘s newest pop-up experience is themed around the infamous Fyre Festival (celebrity models not included). Some “luxury” items that will be featured include “gourmet cheese sandwiches” and yummy frozen cocktails. Admission is free!

National Fitness Day @ Athleta Oak Street

May 4, 2019

Photo: aSweatlife Ambassadors – Eventbrite

Celebrate National Fitness Day with aSweatlife Ambassadors and Athleta’s Oak Street location! Two fun classes will occur: HIIT Bootcamp and Yoga Sculpt. There will also be an Instagram scavenger hunt challenge to participate in for the chance to win prizes! Grab your ticket here.

Celebrate Derby Day

May 4, 2019

Before celebrating Cinco de Mayo, it’s time to bring out your best Kentucky Derby Day hat! Derby Days is upon us, and many Chicago bars are celebrating. Not sure which one to go to? Check out the lineup before!

Celebrate Cinco De Mayo Weekend

May 4-5, 2019

It’s time to Cinco de Drinko! There are many festivities occurring around the city for Cinco de Mayo, including bar crawls and bar parties. You can find a list of them below!

It’s Britney Brunch

Every Saturday in May (4, 11, 18, 25)

It’s Britney…Brunch! Sounds like the best brunch ever to me. Join AceBounce every Saturday in May from 12pm-3pm for Britney karaoke led by house DJ, bottomless mimosas, and unlimited ping pong. For just $39 you can rock out to one of the most iconic artists of our time for a three hour package. Make sure to book your reservation to attend!

Yoga & Brunch at Pinstripes Chicago

May 5, 2019

Start your morning off right with bottomless brunch and an hour Corepower Yoga class at Pinstripes! Your $5 ticket includes the class, one complimentary mimosa, and $5 off Pinestripe’s bottomless brunch. Reservations for brunch are strongly recommended and it is BYOM (bring your own mat)!

Food Truck Social

May 11, 2019

This food truck soirée features over 15 popular restaurants – including some I love like La Cocinita and DaPizzaDude – perched at the Lincoln Park Zoo. What could be better than roaming around the zoo and trying different food from a variety of trucks?? General Admission for the 6pm time slot is sold out, but you can still grab a 7:30pm spot for only $10!

Celebrate Mother’s Day

May 11 – 12, 2019

Photo: Mother’s Day Brunch at The Metropolitan – Eventbrite

Chicago is known for having great brunch spots, especially when it comes to celebrating a holiday. This includes Mother’s Day! Find a quick list below of where to have Mother’s Day brunch in the city.

Lincoln Park Wine Fest 2019

May 17 – 19, 2019

Photo: Lincoln Park Wine Fest – Eventbrite

Do you like wine? Of course everyone does! Lincoln Park Wine Fest is back with their 5th annual wine fest for Chicagoans to cheers to summer. Located at Jonquil Park, this festival features over 90 different wines to taste with your 12 drink tickets. Make a note – Friday’s night will focus on rosé and sparkling wines only!

Gourmet Puerto Rico

May 18, 2019

First off, YES. As a fellow Puerto Rican, I was so excited to see Latinicity’s Gourmet Puerto Rico event. This nighttime event will feature five food stations cooking up the best fare to celebrate Puerto Rico’s finest chefs, cuisine, music, culture, and more. Proceeds benefit the Segundo Ruiz Belvis Cultural Organization and the Dia de la Mujer Latina Organization. Purchase your tickets here!

Sweat Cause: Namaslay for ABTA

May 18, 2019

Who’s ready to namaslay for a cause?! Join Sweat Cause for their official launch at Yoga Six. The event’s proceeds will benefit the American Brain Tumor Association, the charity that motivated Sweat Cause to form. Choose to do either a $40 yoga or yoga sculpt ticket!

Zoo-ologie 2019

May 18, 2019

Zoo-ologie is an annual cocktail party supporting the Lincoln Park Zoo – one of my favorite Chicago landmarks. Proceeds will benefit the Auxiliary Board of the Lincoln Park Zoo’s efforts towards their capitol campaign, The Pride of Chicago. Attendees will enjoy open bar, bites from Chicago’s favorites, a silent auction, and dancing at this festive event. Come party with the animals! VIP tickets are sold out. General Admission is available for $125.

Namas-tea (Yoga & Tea)

May 19, 2019

Photo: HollisticRX & Tiesta Tea – Eventbrite

Tiesta Tea says it best: There’s nothing better than Sunday than savasana and sipping tea mimosas! Love it. Hoping to go this event myself! Hosted by HolisticRX & Tiesta Tea, $10 will get you a goodie bag, tea mimosa samples, a 45-minute all-levels Vinyasa Flow, snacks, and services from local Chicago companies.

Summer Cocktails Fest on the Beach

May 24, 2019

Yum, summer cocktails! My favorite thing aside from champagne. Summer Cockails Fest on the Beach will be held at the Shore Club off Lake Shore Drive. Your $50 ticket will include 3 hours of cocktail tastings, giveaways, and more. Sounds like a great event to kick off summer to me! Make sure to use my code below for a discount 🙂

Use code ALYSSA at check out for a ticket discount!

Crawl of Thrones

May 25, 2019

Join other GOT fans at this one-day bar crawl in River North! The crawl is based off HBO’s popular Games of Thrones TV show and is in honor of it being in it’s last season. For less than $20 you get general admission, an LED bracelet, 16oz color changing cup, and access to photo ops and giveaways.

Celebrate Memorial Day Weekend

May 27 – 28, 2019

Ahoy! It’s time to plan your beachy, sunny Memorial Day Weekend plans in Chicago. From yacht parties to bar crawls, there’s something for everyone to relax and have fun. Read a list of things to do below!

Wine Fest on the Beach

May 31, 2019

Shore Club is a great beachy spot located at Fullerton Beach. What better place to hold a wine fest by the water! The event includes three hours of wine tastings and giveaways, all while welcoming Chicago’s summertime weather. Pre-sale tickets are currently $50!

The Next Collective Women’s Conference

May 31, 2019

Join other #bossbabes at this one-day, women-only conference in Chicago. If you are interested in entrepreneurship or a career pivot, this is the event for you. The topic will be finding a personal purpose through listening to a panel of inspirational speakers. Early bird tickets go for $165. Hurry and buy yours before they go up to $180!

Which of these great events will you be going to? Comment below and let me know!

Things to Do in Chicago This December

November 28, 2018

It’s the most wonderful time of the year in the most wonderful city! As if I didn’t love Christmas time enough, Christmas in Chicago is truly spectacular. The city comes alive with holiday cheer and the most festive events. There are many things to do in Chicago during Christmas. Read a list of them below!

Christkindlmarket Chicago

One of my favorite seasonal events in Chicago is Christkindlmarket. This Christmas market is a festive holiday tradition in the city that graces Daley Plaza and Wrigleyville. Featuring vendors from all over the world, German food and drinks, and holiday entertainment, this event offers free general admission with food and drink available for purchase. While Christkindlmarket is known for their souvenir boot mugs, which features a new design each year, this year’s featured mug is in the shape of a heart! This event is open to the public now until December 24.

Ice Skating at Maggie Daley Park

The ice skating ribbon located in the Loop has been an annual tradition for Chicagoans to partake in each winter. With the beautiful city skyline as your backdrop, cozy up with a cup of hot chocolate and a few laps around the rink. Admission is free, however skate rentals range from $12-$15. Fast Passes are available for those impatient to wait for a turn!

Frosty’s Christmas Pop Up Bar

Chicago’s favorite Christmas themed pop up bar, Frosty’s, is back this year! I went to last year’s event and had a blast (see picture above). This pop-up bar features themed drinks and 3 levels of all the holiday decorations you can physically fit in a room. It is down right amazing. There’s even snow confetti canons. Make sure to wear something festive! Tis’ the season for ugly sweaters.

Ride Chicago’s Holiday Train

While not the easiest to catch, every year Chicago’s L trains and buses feature festive holiday trains. These dressed up transit options are only available for on certain days and times. The full schedule can be found here. You might be one of the lucky people to get a ride from Santa and his helpers!

Holiday Tea at The Drake

If you have never had afternoon tea, The Drake’s Palm Court is a great place to start. This year’s Holiday Tea was my birthday outing wish with some of the women in my family, and boy was it worth it! Holiday Tea included a three-tier selection of tea sandwiches & deserts, your tea of choice, and festive carolers singing festive Christmas tunes.

Have a Drink at Butch McGuire’s

Locals know that come December, this family-owned bar in Gold Coast is the place to be whether it’s after-work or on a weekend outing. Featuring fun holiday decorations around the whole bar, Butch McGuire’s is a great place to grab a drink and get into the holiday spirit with decor from all your favorite Christmas movies.

Zoolights at Lincoln Park Zoo

Another one of my favorite annual events to look forward to is Lincoln Park Zoo’s Zoolights. I love looking at the different light up displays synced with favorite holiday tunes while drinking a tasty hot chocolate. I mean, who wouldn’t? Check out this picture from my first time at Zoolights in 2015! Admission into the zoo is free, however special events, like the zoo’s Holiday Market and Adults Night Out event, require a ticket.

Santa Baby Christmas Bar

Brand new this year is Wrigleyville’s Santa Baby pop-up bar, hosted at the popular Deuce’s and the Diamond Club. From what I have seen from pictures, this Christmas bar looks like a really fun time! The bar will feature festive drinks, ugly sweater competitions, Santa appearances, movie nights, karaoke, and human tree decorating. The festivities will run through January 6th.

Holiday Buffet at The Walnut Room

Located inside of Macy’s on State St., The Walnut Room features a huge Christmas tree each year for Chicago locals to admire. I recently went to see the tree for myself and my was it magnificent! There was even a cool Chicago-themed display around the bottom featuring local landmarks. One thing to note: reservations to The Walnut Room will get you a table at your requested time, however DOES NOT get you a table next to the tree. That is a separate list that you will have to put yourself on when you check in for your reservation.