chicago event

Santa Hustle 5k Chicago

December 15, 2021

Santa Hustle Chicago

Ho ho ho! This year I partnered with Santa Hustle 5k‘s Chicago event to recap a fun, festive experience. Held at the iconic Solider Field, my family and I enjoyed 3.1 miles outside at a brisk walking tempo. The course wrapped around the lake for great scenic views! Each Santa Hustle 5k benefits a chosen local charity. This year’s efforts went towards Cal’s Angels, a pediatric cancer foundation based in St. Charles, IL. Their mission is to grant wishes, raise awareness, and fund research.

The Swag

The Santa Hustle 5k had some of the best race swag I’ve ever gotten. Each participant received a red performance zip-up jacket, Santa hat, Santa beard, and a finisher medal that also serves as a souvenir ornament. Additional swag (red tutu, candy cane socks, Santa coat, and more) was available at registration for an additional price.

Future Events

Santa Hustle 5ks are held all over the U.S. Both kids and adults can attend and enjoy the festivities. Registration ranges between $35-$60 depending on how early you purchase. It’s always a good idea to take advantage of early bird pricing! If you’re interested in volunteering instead of running/walking, Santa’s helpers are always needed!

Christkindlmarket Chicago

November 24, 2021

Christkindlmarket at Daley Plaza

This past weekend I kicked off the holiday season with two events: watching the Festival of Lights parade from my window and checking out Christkindlmarket Chicago with my family. This German Christmas market is an annual favorite in the city. Running now through December 24th – downtown and in Wrigleyville – visitors can attend for free while enjoying food, music, and souvenirs for sale. We stayed for about an hour – read below for our experience!

The Traditional Christkindlmarket Mug

Each year a new mug design is featured at Christkindlmarket. These can be bought when purchasing hot cider, spiced wine, beer, chai, or hot chocolate. The mug this year, shown above in forest green, celebrates the event’s 25th anniversary. In my opinion it’s the best design yet!

Experiencing Christkindlmarket Chicago

Aside from having something to drink, we also tried the cherry strudel and traditional pretzels. Make sure to bring plenty of cash – a lot of the booths do not take credit cards! There were also a lot of great ornaments, traditional clocks, and unique gifts for sale. You can find a full list of market vendors here. If you’re looking for something sit-down, you can make a reservation for Stammtisch in the Timber Haus heated tent.

What’s your favorite holiday event in the city? Comment below!

Jack’s Pumpkin Pop-Up 2021

September 28, 2021

My favorite seasonal pop-up is back! Jack’s Pumpkin Pop-Up features Insta-worthy photo opps and a corn maze, as well as food & drink, carnival-style games, axe throwing and pumpkins for an additional cost. This year I attended with my sister, and we got to enjoy some of those add-ons. Read below to learn more about our experience!

Jack’s Pumpkin Pop-Up Photo Opps

This 2-arce pop-up is open now through October 31, 2021 in Goose Island. The best part about the event, in my opinion, are the photo opps. They have so many! Some are fall themed, while others deal more with pop culture. My favorite spots were the pumpkin house featured at the entrance of the pop-up (shown above), the fortune teller’s crystal ball, a black and white angel mural, a pink #freebritney cage, and Winafred’s spell book from Hocus Pocus. There were also some odes to Jack Skeleton, autumn, coffins, and more.

Jack’s Pumpkin Pop-Up Food & Drink

Aside from your usual water and soda, food and alcohol are offered at this pop-up. We ordered a cheeseburger and hot dog. My sister was pleasantly surprised to see that the cheeseburger came on a pretzel bun! The hot dog was pretty good, too. Also on the menu were walking tacos, grilled corn on the cob, elote, hot pretzels, nachos & cheese, Cheetos with cheese, and apple cider donuts. The donuts were delicious! Full bars are offered for those 21+ and up.

My Fall-Inspired Outfit

Although I’m not a fan of colder weather, I do love fall clothing. I was extremely excited to have the chance to wear my latest purchase, featured in my pictures taken at Jack’s Pumpkin Pop-Up. I’ve linked the items here for your viewing!

Go Your Own Way Black Fringe Sweater
Beautiful Sound Cream A-Line Suede Skirt
Similar black heeled boots: Option 1, Option 2, Option 3

Tickets to Jack’s Pumpkin Pop-Up

Jack’s Pumpkin Pop-Up will be open to the public now through October 31, 2021. General admission costs $25, and $23 for kids 5-11 years old. Add-ons include drink tickets, medium pumpkins, apple cider donuts, carnival games, axe throwing, and Smashing Pumpkin alcohol shots. Tickets are offered for timeslots throughout the day and evening.

Chicago’s HideSeek Pop-Up

September 2, 2021

If you know me you know that I really love a good pop-up. They’re always fun and full of great photo ops! My sister and I attended a preview of Chicago’s HideSeek pop-up in Old Town and had the best time exploring their 15 Instagramable rooms of childhood nostalgia. I’m talking big 90’s baby energy. View my favorite rooms below!

My Favorite HideSeek Rooms

HideSeek offers 15 rooms of photo-worthy backdrops. We had a blast capturing content while feeling like a little kid again. My favorite rooms were Slinky Spring (pictured above), Rad Ride, Bubble Trouble, Daydream Days, Pillow Playhouse, and Fuzzy Fix.

Rad Ride

Bubble Trouble

Daydream Days

Pillow Playhouse

Fuzzy Fix

Tickets for Chicago’s HideSeek pop-up are available on their website for designated time-slots now through October 31. Don’t forget to stop by their gift shop on your way out for cute 90s apparel, enamel pins, candy, and toys!

View more Chicago-focused blog posts here.

Tickled Pink: A Bright Pink Fundraiser

March 6, 2020

I recently attended Tickled Pink, an annual fundraiser for Bright Pink, and had a great time! Bright Pink, the organization whom the proceeds of the event went to, is the only national non-profit organization that focuses on early prevention and detection. They were celebrating their 15th year of generating awareness about breast cancer. The event consisted of drinks, food stations, live music, dancing, and raffle prizes.

About Tickled Pink

Tickled Pink was started 15 years ago by Jodi Fyfe in honor of her cousin who passed away from breast cancer. The first event held raised $35,000! Since then Tickled Pink continues to be one of the most popular annual fundraiser events in Chicago. This year the event was held at Rockwell on the River.

The Food and Drinks

The event consisted of an open bar for guests. There was many options to choose from, however my favorite was the specialty drink: The Tickle Tini. I believe it was vodka, sparkling rose, and cranberry juice. Regardless, it was really good! There were also food stations set up, wrapping around the event space. Popular Chicago restaurants such as Barrio, Bar Ramone, Cindy’s, Joe’s Imports, Gene & Georgetti, XO Marshmallow, JoJo’s Milk Bar, and more were there with samples of food.

The Entertainment

For the first half of the event there was a DJ playing a mix of different music. But for the second half the crowd really came alive dancing to live music by The Chicago Players. They were really good! Amazing voices and even better dance moves. I had a lot of fun dancing on the floor!

My Pink Romper

Gotta throw in a shout out to my new favorite romper! I wore a glittery pink pleated romper to the event to go along with the pink theme. You can find it HERE at Nordstrom’s.

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.

Windy City Smokeout 2019

July 30, 2019

There’s nothing better than bbq, music, and Chicago’s beautiful skyline! I attended Windy City Smokeout again this year (check out my experience last year here) and it is hands down now my favorite music festival in the city. The atmosphere is great and the food and music are even better. With new additions and new recommendations, I have listed my tips for attending in the future below.

Attend More Than One Day

I’m not the biggest Country music fan, but I am a fan of a good time. Compared to only going to one day last year, this year we attended two days of WCS; Friday and Saturday. Surprisingly, Friday was the best day to attend! This day had less people than Saturday and had better headliners. This gave more room to dance and walk around! For this reason I recommend attending Friday not for sure.

Activate Your Cashless Wristband

WCS wristbands can be activated with a credit card on file for a fast payment option. I highly recommend doing this BEFORE you go as it was so easy to pay for things without ever having to take a card out! It charges directly to the card on file without any extra processing fees.

Get Margarita Boots from Casamigos

The Casamigos stand has been my favorite place to get drinks the past two years of going to Windy City Smokeout. They have the best, refreshing margs and this year added margarita boots! These were $20 each and so worth it. The amount of drink lasted longer, aka less standing in long lines to get another one. We really should have been Casamigos ambassadors, everyone was asking where we got our boot drinks!

STAY HYDRATED

Due to the time of year that the festival is held, it can get reallyyyyy hot. One of the days we attended was close to 90 degrees! Make sure to wear sunscreen and stay hydrated. There are Yeti canisters stationed around the festival that you can use to fill up your glass or water bottle for free. Use them!

Go With An Appetite

I have made the mistake of eating too close to going to WCS. Go with a fully empty appetite so you can enjoy all of the yummy food vendors stationed there! There are so many mouthwatering bbq options to choose from! The food is a big part of the festival – it’s not all about the music – and i’d say we spent half our time roaming around the different vendors.

Take Lots of Photos

One of the things I love about Windy City Smokeout are their photo ops. They always have cute backdrops that are perfect for snapping an Instagram-worthy shot. Between the famous ‘I Believe in BBQ’ and Happy Camper’s ‘HAPPY’ balloon set up, there was plenty of cute shots to choose from.

Save the Date for Next Year

I love that this festival automatically puts up next year’s dates right when it ends so you can plan ahead. Windy City Smokeout will be coming back to Chicago the weekend of July 10-12, 2020. Mark your calendars!

The Beachwaver’s Make Waves Launch Party

June 19, 2019

The Beachwaver’s Make Waves Launch Party

The Beachwaver has a new hair care line and I am all about it. The Make Waves Collection is women owned, cruelty-free, smells like a tropical vacation, and is for all hair types. Hallelujah. I was able to view the Make Waves collection first hand at The Beachwaver’s recent launch event, hosted at The J Parker rooftop bar in Lincoln Park. Talk about a party with a view! The event featured a Beachwaver-themed cocktail menu, a female-focused panel, cute photo ops, light bites, and the most AMAZING gift bags.

The New Make Waves Collection

You may know The Beachwaver brand for their hair styling tools, however their new Make Waves collection is worth trying! I love the smell of suntan lotion, palm trees, and coconuts – so the signature scent of the hair care products was something that stood out to me right away. Think instant beach getaway. With a great tan. And coconut oil.

My Favorite Products

I was most interested to try the Make Waves Moisturizing Shampoo and Conditioner, as I was looking to help tame my recent hair dryness. Made with coconut milk, they both did the trick! I tried the products the day after the event and loved them. My hair felt silky smooth and smelled like a coconut haven. I also really liked their Great Barrier Heat Protectant Hairspray, which is great for right after you curl your hair!

View me curling my hair using the 1” Beachwaver and Great Barrier Heat Protective Hairspray HERE!

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!

Chicago Rosé Day: A River North Rosé Crawl

June 24, 2018

Aside from champagne, rosé is my favorite choice of beverage. Luckily there is an event for almost everything in Chicago, including this pink bubbly. Read below for my experience at Chicago Rosé Day, a River North Rosé Crawl!

What to Expect

This year’s Chicago Rosé Day, an annual River North crawl party, was an absolute blast. Partakers began their experience picking up their wristband and commemorative wine glass to kick off the festivities. For just a mere $10, the general admission tickets included the souvenir glass, three drink vouchers to be used during certain time frames through out the day, and access to a special $7 rosé deal at participating bars. Compared to other bar crawls I have done in River North, this one gave the most for its $10 price!

Participating River North Bars

Participating bars included a few River North bar favorites: Joy District, Tunnel, Bar Louie, El Hefe, Hubbard Inn, Moe’s Cantina, Bub City, Henry’s, Ironside, Point & Feather and STK. While we weren’t able to make it to every venue, I did enjoy each place we went to and the weather ended up being beautiful. I did, however, have the most fun at bars Joy District and Tunnel! The vibe at these bars were great, and you can’t beat Joy District’s rooftop & flower wall.

What I Wore

Outfit: Romper, LuLu’s // Initial Necklace, 6th Borough Boutique

The theme of Chicago Rosé Day is PINK! Sport your best magenta, blush, and millennial pink in the form of a romper, dress, jumpsuit, dress, or shorts. Since the event occurs in June, I went with a white and blush leaf print romper from Lulu’s that had very light material.

Would I Go Again?

Compared to other River North bar crawls, Chicago Rosé Day is one I would go back to! Mark your calendars for 2019’s event on Saturday, June 22, 2019. Chicago Rosé Day is not an event to miss!

#ChicagoRoséDay