Twenty Things to Do in Chicago in Your Twenties

What I’ve learned from living in Chicago as a young adult is that your twenties are your “selfish years”. While living in the city you must travel, explore, and try new things. After all, it’s important to love yourself and the place that you’re in!

Lucky for Chicagoans and tourists alike, I’ve provided a list of things I’ve enjoyed while living here. Some activities are meant to be enjoyed with friends or family, and others by yourself. You’ll find places to go that are best on weekends versus weekdays, and activities that are more upscale or casual. Nonetheless, this is a list of must-do activities in the city for your average twenty-something, whether you know the streets like the back of your hand or are visiting for the first time.

  • Stroll Around Navy Pier

    Navy Pier is the most popular attraction in the Midwest and without a doubt is one of Chicago’s many claims to fame. This iconic landmark not only offers stunning skyline views but extends over 3000 feet into the Chicago shoreline on Lake Michigan. Drawing nearly two million visitors a year, the pier is home to a myriad of exhibits, restaurants, shops, and activities for people of all ages. If you care to wander along the pier, you’ll find places like Riva Café, Spirit of Chicago Cruises, Chicago Shakespeare Theater, and even a 260-foot-tall Ferris wheel. This is a must-see with friends and families of all ages.

    Navy Pier
    600 E. Grand Ave. | (312) 595-7437

  • Try Deep-Dish at Lou Malnati's Pizzeria

    If you aren’t yet familiar, Chicago and deep-dish pizza go hand in hand. Deep-dish pizza is prepared in a large pan and is nothing like your typical thin sliced restaurant pizza: it’s layered with dough first, cheese and toppings second, and tomato sauce last. It’s also rumored to have been invented right here in Chicago, so if you’re visiting and want the full experience be sure to stop at Lou Malnati’s. Lou’s is dedicated to continuing its family legacy and stays true to the original recipe that Grandpa Malnati created in the early 1940’s at Chicago’s first deep-dish pizzeria. Every pizza is handmade with the freshest ingredients.  Luckily, Lou’s has locations all over Chicago, from the North Side to the South Loop. So, if you ever find yourself in the mood for pizza- they’ve got you covered.

    Lou Malnati's
    1120 N. State St. | (312) 725-7777

  • Take Yoga to New Heights at 360 CHICAGO

    Fact: sky-high views don’t always require a plane ticket. On the 94th floor of the iconic 875 North Michigan building sits the 360 Chicago Observation deck, an observatory offering panoramic views of Chicago’s skyline and Lake Michigan. Equipped with a full bar, and the famous TILT attraction, 360 Chicago also engages residents and tourists with their 360 Chi Series. The 360 Chi Series offers guests an authentic Chicago experience, with weekly activities including live music, private tours, happy hour, trivia, and even yoga.

    Yoga enthusiasts can experience a one-hour weekly class with a one-of-a-kind view at 360 Sky Yoga. Professional instructors invite everyone to witness this incredible yoga backdrop, no matter their skill level. 360 Chicago Yoga instructor, Britta Euman, says, “[We] teach an accessible style of yoga everyone can do.” Although many come for the impressive venue, Euman says guests also come to celebrate special occasions. 360 Sky Yoga is open year-round for guests “old and young, out of town and out of country” who are looking to enjoy themselves. This dream yoga destination is fit for any occasion and will certainly capture those Zen vibes you’ve been searching for.

    Here’s a clip from one of the yoga sessions I attended!

    360 CHICAGO
    874 N. Michigan Ave. | (312) 751-3681

  • Toast at the Top of LondonHouse Chicago

    Perched at the very top (22nd floor) of the LondonHouse Hotel is the LH Rooftop, offering panoramic views of the city, The Magnificent Mile, and Lake Michigan. For many Chicagoans, rooftop season is the best season and by the time you’re 30, you should claim your favorite outdoor dining spot. LH Rooftop is a top competitor with “picture perfect views from the best vantage point,” says Don Barnett, LH Director of Sales and Marketing. Guests can choose to sit outside on the patio or venture back inside to the LH Lounge on floor 21, all while enjoying specially crafted cocktails.

    Despite the rooftop being open seasonally from May to October, guests can still order winter menu items like hot chocolates or ciders from the main bar and take them up to the top to enjoy. The best time for visitors is during the Happy Hour rush or during peak nightlife at around 9 p.m. The busiest nights of the week, however, happen to be on Wednesdays for Ladies Night, with a Christian Louboutin raffle every week. I’m not biased, but nothing beats a free pair of shoes, Instagram worthy views, and signature cocktails all in one night.

    LondonHouse Chicago
    85 E. Upper Wacker Dr. | (312) 357-1200

  • Cheer on "da Cubs" at Wrigley Field

    In the heart of Wrigleyville, in Chicago’s Lakeview neighborhood, the Cubs welcome die-hard fans to Wrigley Field for ball games filled with history, a sense of community, and of course Vienna Hot Dogs. Behind Boston’s Fenway Park, Wrigley Field is the second oldest major league baseball park built in 1914.

    Weeknights are unbeatable for sports fans on a budget, and tickets can easily be purchased online or at the box office, sometimes as low as $12. If you want a 360-degree view of the field and the crowd singing “Take Me Out to the Ballgame,” you might want to check-out the rooftop seats. Either way, you won’t be able to beat the electric energy of a Cubs game, whether you’re in the nosebleeds or behind home plate. Cubs fans have a spirit like no other and for most, your first Cubs game will not be your last.

    Chicago Cubs
    1060 W. Addison St. | (773) 404-2827

  • Hop Aboard the Spirit of Chicago for a Cocktail Cruise

    Why not shake things up? Instead of going out and grabbing cocktails with your gang, head to Spirit of Chicago right off Navy Pier to enjoy a night out on the water. Up your drinking game aboard their special Cocktail Cruise, available on select days during the summer. On board you’ll enjoy craft cocktails, hors d’ Oeuvres, a decadent buffet, interactive games, and a dance floor with a live DJ. Fit for larger and smaller groups, this summer excursion offers a unique view of the city as you drink in the view.

    Spirit of Chicago Cruises
    600 E. Grand Ave. | (888) 957-2634

  • Explore Aquatic Wonders Inside The John G. Shedd Aquarium

    The only decision you and your friends will make when visiting the Shedd is which of the extensive, colorful, and lively exhibits to see first. This attraction offers a dozen experiences and exhibits, from up close beluga encounters to viewing species that dwell in the depths of Lake Michigan. Visiting the Shedd is the perfect weekend activity, and you can spend most of your day exploring their exhibits. The Shedd’s Communications and PR coordinator, Kayley Ciocci, says that all their exhibits are popular, “highlighting unique and beautiful aquatic adaptions.” I make a pact to go the Shedd at least once a year because no visit is the same. Their exhibits are ever-changing and allow guests to come face-to-face with both land and aquatic animals. For visitors, it’s an “opportunity to look nature in the eye” and become inspired by the deep blue sea. 

    Shedd Aquarium
    1200 S. Lake Shore Dr. | (312) 939-2438

  • Spend the Happiest Hour at Beatrix

    Chicago takes Happy Hour to a whole new level. Since dining out can often be expensive, Happy Hour is the perfect reason to go out during the week while staying within your budget. It’s also a perfect place to catch up with friends- an invitation I can never turn down. Beatrix’s modern neighborhood environment provides the perfect meeting spot for you and your friends. The atmosphere is communal, the food is fantastic, and the select wine pours are only $6 during Happy Hour. Their wine menu takes a cue from All-American fare, featuring a variety of classic reds and whites. Beatrix’s Happy Hour runs Monday through Friday from 3-6 p.m., so there’s never an excuse to miss drinks with the gals.

    671 N. St. Clair St. | (312) 642-0001

  • Watch Fireworks from Riva Café and Crabhouse

    Looking for a place to take your relatives or friends that are in town visiting? Riva Café and Crabhouse is located just along the edge of Lake Michigan on Navy Pier and offers both exquisite city and lake views. This two-story, nautically designed space is lined with large floor-to-ceiling glass windows to ensure you have the best view of the Navy Pier fireworks that run from Memorial Day through Labor Day. These elements, together with the exceptional seafood and steak options, will surely impress your guests.

    Riva Cafe
    700 E. Grand Ave. | (312) 644-7482

  • Explore the Exhibits at the Museum Of Contemporary Art Chicago

    Located right near Water Tower Place, the Museum of Contemporary Art is one of the world’s largest contemporary art venues. Filled with thousands of pieces from different eras, the museum is operated gallery-style and includes newly curated exhibits year-round. Past exhibitions have included visuals from both local and global artists like Virgin Abloh, Simon Starling, and Doris Salcedo. Tickets are available online or at the box office; and admission is free for those with membership as well as for Illinois residents on Tuesdays. Suitable for both groups and solo travelers, the MCA is a perfect destination to become connected and immersed in the art community.

    Museum of Contemporary Art Chicago
    220 E. Chicago Ave. | (312) 280-2660

  • Get the Crew Together at Jake Melnick's Corner Tap

    Cubs or Sox? No matter your preference, Jake Melnick’s Corner Tap is home to both local and visiting sports fanatics. As soon as you walk inside, you’re greeted by a roaring atmosphere of fans surrounded by a whopping 27 TVs. You’ll also find that the bar cheers for any sport- baseball, hockey, soccer, football- at any given time. Although Brunch or Football Sundays may be the most popular time to visit, my server added that the after-work crowds fill the restaurant during a corporate event.

    It’s true that Jake Melnick’s is famous for their wings, but not many people know that their group events incorporate both their wings and a little competition. The Get Sauced package isn’t time consuming and it’s engaging for groups of all sizes and all types including corporate events, birthday celebrations, and bachelorette parties. This experience allows for groups to create their own sauce from a choice of 6 different ingredients, all while enjoying welcome cocktails, a two-hour call bar, and appetizers. The groups are split up into smaller teams and once they’ve created their sauces, they’ll be judged by the Chef or Manager. The winning team will receive a basket of their wings tossed in their own sauce, along with a “Get Sauced” T-shirt and a $10 gift card. This all-inclusive event is perfect for larger parties looking for an interactive and unique experience in the heart of the city.

    P.S. When you’re finished with the Get Sauced package, order the Poncho Wings- you won’t regret it!

    Jake Melnick's Corner Tap
    41 E. Superior St. | (312) 266-0400

  • Dance the Night Away at TAO Chicago

    We’ve all wished some night lasted forever. If you and your friends enjoy staying up past midnight, then TAO Chicago is the place for you. A perfect night out includes dinner reservations in their dining room, with endless dim sum and sashimi. Once the nightclub opens at 10 p.m., you can head downstairs to dance the night away- literally. TAO is open Fridays until 4 a.m. and Saturdays until 5 a.m.

    TAO Chicago
    632 N. Dearborn St. 

  • Make Brunch Reservations at Cindy's Rooftop

    Who doesn’t love a good brunch on the weekends? I’ll admit, sometimes I’m way too tired to roll out of bed and make it to my brunch reservations on Sunday morning, but you have to try brunch at Cindy’s Rooftop at least once. Cindy’s Rooftop sits at the top of the Chicago Athletic Association Hotel, offering a communal environment and Midwestern style food ingredients. Chicago Athletic Association’s Marketing Manager, Emmy Carragher, says that, “people come for the experience first and foremost.”

    Beyond the indoor dining area, Cindy’s has a stunning view overlooking the city skyline and Millennium Park, as well as a rooftop patio that’s always open. In the summer, during high volume season, guests can enjoy the open bar, and in winter there are fire pits to keep you warm as you sip on seasonal drinks. Cindy’s impressive food program is what also attracts many brunch-goers, as many items are locally crafted. Their signature cocktails also rotate monthly- just in case a classic mimosa doesn’t satisfy your brunch needs.

    Cindy's Rooftop
    12 S. Michigan Ave. | (312) 792-3502

  • Dine Along the River at River Roast

    Food is good for the soul, right? Or is it music? At River Roast, you’ll find both good music, good food, and even better company nestled into this Midwestern-style restaurant along the Chicago River. This is the perfect place to bring your friends together for a night out, especially during the warmer months. For a more romantic and picturesque dinner, ask to be seated outside on the patio and enjoy delicious cocktails and shared appetizer plates. If you’ve saved room for entrees, the fish, meats, and veggies are roasted and carved table side for all your guests to share.

    River Roast
    315 N. LaSalle St. | (312) 822-0100

  • Shop 'Till You Drop at Water Tower Place

    As you probably know, there are many reasons to visit Chicago. The city, rich in history, is bold in its architecture, museums, restaurants, and yes, even in its shopping districts. The Magnificent Mile is home to both affordable and high-ends shops all within walking distance of one another. Shopaholics like me can rejoice at Water Tower Place, the United States’ first vertical shopping center.

    This diverse shopping destination right in the heart of the city is home to over 100 different shops on 8 levels. It’s perfect for all sorts of shopping experiences, whether it be a long-needed day with the girls or a quick errand for something or someone in particular. 

    Water Tower Place
    835 N. Michigan Ave. | (312) 440-3166

  • Spend Your Saturday at SafeHouse Chicago

    Whenever Saturday rolls around my friends and I make it our mission to find a good restaurant with an even better atmosphere. At SafeHouse Chicago, you’ll find a different type of mission, one that belongs to a secret agent. This spy-themed bar is filled with gadgets, memorabilia, and trinkets from various movies and TV. To enter you have to say the secret password to prove you aren’t a double agent. Once you pass the secret doors, you can enjoy one of their daily specials or treat yourself to a signature burger. Although during the day SafeHouse is open to spies of all ages, after 8 p.m. it becomes a bustling adult-bar with live a DJ, dancing, and specialty cocktails.

    SafeHouse Chicago
    60 E. Ontario St. | (312) 313-1007

  • Face Your Fears at The Great Escape Room

    For thrill-seeking enthusiasts, the idea of being locked in a room for 60 minutes is both terrifying and exciting. The Great Escape Room, a Sherlock- themed escape room, is suitable for teams willing to work together to solve puzzles, participate in a scavenger hunt, and escape before time runs out. With several styles and challenges to choose from, the Great Escape Room can customize events that are perfect for corporate and private parties. They even offer “On the Run,” a portable event that will meet all your team’s needs if you are unable to visit on site. If you’re a young Chicagoan looking for the next best thing to do with a group of friends or coworkers, you’ll want to keep up with this trendy and popular activity that’s become a favorite in Chicago.

    The Great Escape Room
    160 E. Grand Ave. | (312) 281-8915

  • Board a Trolley and Cruise Downtown with Chicago Trolley & Double Decker Co.

    If you’ve ever been to Chicago, you know that some of the best things to do happen after the sun sets. The nightlife scene in Chicago can oftentimes be overwhelming, and sometimes you must venture outside the comfort of your single favorite bar. With Chicago Trolley & Double Decker Co., you can book a private rental and ride around downtown Chicago alongside your best friends. A perfect idea for weddings, pub crawls, or company trips, Chicago Double Decker takes you to several of Chicago’s best spots. Open all year round, this unique night out is only a click away.

    Chicago Trolley & Double Decker Co.
    Michigan Ave. at Pearson | (773) 648-5000

  • Treat Yourself to Stan's Donuts & Coffee

    Sometimes a long workday calls for an afternoon pick-me-up. If you’re like me, there’s no better kick-start to the rest of your day then sipping on a delicious cup of coffee with a tasty donut on the side. At Stan’s Donuts & Coffee, you can indulge in an explosion of flavors with any of their menu items, including milkshakes and cookies. What differentiates Stan’s from other cafes or bakeries is that they live by their mission to serve donuts for everyone no matter their cravings or dietary restrictions. Classic varieties in donuts range from Glazed to Vanilla Sprinkled, or from Nutella & Banana to Caramel Marshmallow. Their specialties also include gluten-free and vegan donuts that are just as tasty as the others. 

    P.S. If you want to enter donut heaven, try the Pistachio Gluten-less donut!

    Stan's Donuts & Coffee
    535 N. Michigan Ave. | (312) 955-3100

  • Enjoy Live Music at the House of Blues Chicago

    You know those moments during a concert when time seems to stop and you’re just present, right there in the moment? Yeah, me too. No matter how many times you listen to your favorite artist, nothing compares to seeing them live. Going to a concert is an experience everyone should have, especially at the House of Blues. Founded in in the 1990's, the House of Blues is chain of live music concert halls that strive to bring all kinds of genres to its local communities. If you’ve got friends in town, be sure to make a stop at the House of Blues to experience live music like no other.

    House of Blues Chicago
    329 N. Dearborn St. | (312) 923-2000

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