Last Updated on 11/12/2024 by Rany Burstein
Chicago isn’t just a city—it’s the ultimate playground for all ages. From world-class museums to epic concerts, thrilling sports games, and shopping districts that’ll make any fashionista swoon, there’s something here to satisfy every taste.
And if you’re looking to bond with your roommate or hang out with your pals in the city, you’re in for a treat. Here are some of the absolute best things to do in Chicago that’ll make every moment unforgettable!
Chicago: The Ultimate Sport City
Thinking of a city that has all the sports for every fanatic? You won’t find one better than Chicago. Known for its legendary basketball team (Bulls), two baseball teams (Cubs, White Sox), football team (Bears), and hockey team (Blackhawks), Chicago is a city brimming with sports traditions.
Snagging Cheap Tickets
Now, let’s talk about scoring those tickets without breaking the bank. Check out Facebook groups for sweet deals, especially for weekday games or when the big shots aren’t in town. And if you’re still using that student email, you might just snag some sweet discounts.
If you are up for watching college football leagues, you don’t have to worry about getting tickets beforehand. If you reach the stadium an hour before the game starts you can just buy the tickets at the gate.
Sports Bars
If you’re not up for dropping serious cash on tickets, no worries! Chicago’s got plenty of spots to catch the game without draining your wallet. Think cozy sports bars with good vibes and even better company.
Here are some of our faves:
- Michael’s Tap: Cheap drinks? Check. Happy hour? Double check. Plus, it’s super easy to get here from the Red Line.
- Fatpour Tap Works: With a beer selection that’ll make your head spin (in a good way) and a vibe that screams game day, Fatpour Tap Works knows how to party.
- Murphy’s Bleachers: Nestled near Wrigley Field, this spot is a local legend. It’s the perfect place to catch a Cubs game and soak up that classic Chicago sports atmosphere.
- Lottie’s Pub: If you’re all about that dive bar life, Lottie’s Pub has got you covered. It’s always buzzing on game days, so grab your crew and get ready to cheer.
Quick tip: Bars might hike their prices when the game’s on, so don’t get caught off guard. And if you want a seat, make sure you get there at least an hour before kickoff. Oh, and downtown bars might cost a bit more, but they know how to bring the sports bar vibes.
So whether you’re a die-hard fan or just in it for the good times, Chicago’s got something for everyone. Get ready to make some memories with your roommates in the ultimate sports city!
Entertainment Extravaganza: Theatre, Comedy, Music Venues, and More
The Performance Arts Scene
You don’t know fun until you are sat with your friends enjoying a great comedian’s bit, which leaves you in bits.
And Chicago has some great comedy clubs.
Check out the iconic Laugh Factory, known for its great selection of local and big-name comedians. How do they always hit the mark?! Tickets start at a reasonable $30, but it’s first come, first served, so don’t dawdle.
Or if you want double the fun, head to ComedySportz. Like everything else, Chicagoans have turned comedy into a sport form as well. Two teams battle it out for your laughter, delivering double the jokes and double the fun. Shows start at $5, but the better ones go for $25.
Lastly, whether you’re a drama geek or just looking for a night of entertainment, there’s something for everyone. Check out Theatre in Chicago for all the latest plays and shows, or immerse yourself in the true Steppenwolf Theatre vibe for a night to remember. Tickets may start at $70 and above for some shows, but you can also find great options at Berger Park Coach House, Nederlander Theatre, or Goodman Theatre for as low as $15.
….& The Music Scene
Of course, comedy isn’t the only game in town. Chicago’s music scene is legendary, offering live performances that’ll have you dancing all night long. You have the usual big names coming to Chicago all the time performing at the United Center or Soldier Field. But let’s face it, that is not a daily occurrence most of us can afford to enjoy with our roommates.
Places like The Hideout are always packed with top-notch acts, while spots like The Empty Bottle host local shows, many of which are free. The city’s top rock stars emerge from this place, so expect them to go big any time soon. And don’t forget the bonus of pairing live music with some of Chicago’s famous pizza—now that’s a winning combo!
Enjoy the Foodie Hotspots in Chicago
What better way to bond with your roommate than dining out together, right? Chicagoan Travel Blogger, Lily shares some of her favorite foodie hotspots in all of Chicago. Some of her top picks are:
- Tortello: Tortello is a little slice of Venice right in Wicker Park. With fresh pasta made right before your eyes, it’s like Italy in a bowl. Trust us, the taste is chef’s kiss-worthy! Prices start at $23, and while the menu is limited, every bite is packed with flavor.
- Spacca Napoli: This Ravenswood pizzeria that’ll have you coming back for more. Because let’s be real, what’s better than pizza with your roommate? While Chicago’s deep dish gets all the fame, Spacca’s pizza gives Naples a run for its money any day of the week. And don’t even get us started on their tiramisu—it’s a total game-changer!
While the rest aren’t Lily-approved, they are definitely Diggz-approved:
- Redhot Ranch: If you are looking for a late-night snack with a roommate, Redhot Ranch will not disappoint. It has two locations at Bucktown and Lakeview. From classic Chicago dogs to crispy fries, everything on the menu is priced between $1 and $10, making it the perfect pit stop for a post-night-out bite.
- Goree Cuisine: This Senegalese gem in Hyde Park is perfect for groups. With everything on the menu priced between $10 and $18, it’s a budget-friendly option for trying something new. Their stews are legendary, but the dibi chicken is equally drool-worthy.
Shopping Spree in Chicago
1. Magnificent Mile
Sure, it’s known for its luxury brands like Gucci, but don’t let that intimidate you. You’ll find everything from high-end splurges to affordable steals like Zara. And for a one-stop shopping extravaganza, head to 900 N Michigan, where you’ll discover a fantastic food court and plenty of cool, budget-friendly shops. Don’t forget to check out the thrift stores too—places like North Shore Exchange offer some serious treasures.
2. Thrift Stores: Reduce, Reuse, and Score Big!
When being eco-friendly and snagging incredible finds, Chicago’s thrift stores are where it’s at. And if you’re a couple of dudes sharing an apartment, why not make shopping together a bro-bonding experience? Head over to Richard’s Fabulous Finds, the only all-men thrift store in the city. From vintage luggage to plaid blazers, this place guarantees a fun day hunting for treasures.
And if you’re looking to spruce up your apartment with your roommate, Root Consignment Company is your go-to spot. While they’ve got a bit of everything, they’re best known for their killer furniture, art decor, and home goods.
For more thrifting adventures, swing by The Brown Elephant with locations across Andersonville, Lake View, and Oak Park. This place is known for its tidy layout and top-notch goods, so you’re bound to find something special.
3. Armitage Avenue
Now, let’s talk about Armitage Ave, nestled in Lincoln Park – Diggz’s top neighborhood pick in Chicago. This strip is a shopaholic’s dream, with beauty stores like Lush, Benefit, Aesop, and L’Occitane lining the streets. But it’s not just about cosmetics—there are also plenty of indie shops selling everything from stationery items to cozy cashmere sweaters. So grab your roommate and get ready to explore all the cool independent shops and salons it has to offer!
4. Outlet Malls
Looking to score some major deals on designer threads? Just a short trip from downtown Chicago, you’ll find two top-notch outlet malls waiting to be explored.
Fashion Outlets of Chicago: This place is a fashionista’s paradise, with outlets for high-end designers like Gucci, All Saints, Coach, Jimmy Choo, Karl Lagerfeld, and many more—all offering incredible discounts.
Chicago Premium Outlets: This sprawling outdoor mall is a shopper’s dream, with outlets for Ann Taylor, Armani, BCBG, Calvin Klein, Max Mara, Restoration Hardware, and countless other stores offering unbeatable deals you won’t want to miss out on.
Go For a Cultural Escape: Museums and Galleries
Chicago wears its cultural heart on its sleeve, boasting a plethora of world-class museums that cater to every taste.
Take the iconic Art Institute of Chicago, for instance. Here, you’ll find a mesmerizing blend of the old and the new, from timeless classics to cutting-edge contemporary works. With so much art to explore, it’s no wonder you might feel compelled to make it a two-day affair—after all, why resist a second visit?
But the Art Institute is just the beginning. Dive into history at the Field Museum, explore the wonders of the universe at the Adler Planetarium, or immerse yourself in contemporary art at the Museum of Contemporary Art Chicago.
For a taste of something new, check out the American Writers Museum, a tribute to over 100 of the nation’s literary greats. With interactive displays that let you contribute to a collective story, it’s an experience unlike any other. And with tickets starting at just $16 per adult, it’s an affordable way to dive into the world of American literature.
The best part? Visiting museums with your roommates is not only enriching but also mostly free, allowing you to enjoy quality time together without breaking the bank. So grab your roomies and get ready for a cultural adventure unlike any other in the vibrant city of Chicago.
Explore Chicago’s Amazing Architecture
Get ready to discover some of the coolest spots in the city with easy walking tours from GPS My City. They’ve got tours for every vibe—whether you’re a beginner, a shopaholic, or just love checking out cool buildings.
- Start your Friday adventure strong with a visit to the iconic Willis Tower. It’s been dubbed one of the 7 wonders of Chicago by readers of the Chicago Tribune. With 110 stories, it offers some seriously jaw-dropping views on clear days. Just make sure to check the visibility before you head out—if it’s less than 5 miles, maybe save the trip for another time.
- After taking in the sights at Willis Tower, take a quick stroll over to the Rookery Building. You’ll have a blast spotting rooms from famous movie sets. And if you’re up for it, join a walking tour led by the Frank Lloyd Wright Trust. They run tours Monday through Friday from 10 am to 1 pm, and tickets range from $10 to $17.
- Next up, head over to The Chicago Theatre, aka the Wonder Theatre of the World. This place is seriously cool—it’s one of the first of its kind to pop up after the Great Fire of Chicago. Plus, you might even catch a play or musical while you’re there. Tickets are $20 per adult at Ticketmaster.
- And when you’ve had your fill of sightseeing, wrap up your day with drinks at a local bar or grab a sandwich from Goodwins. Here’s to exploring Chicago’s incredible architecture with your awesome roommate!
Free Things to Do in Chicago
As one of America’s largest cities, Chicago offers many free outdoor activities that are as fun as budget-friendly. Cruise along the Lakefront Trail on bikes or by foot, stopping to enjoy beaches, playgrounds, public art installations, and more—it’s like strolling through an open-air museum!
For animal lovers, a visit to Lincoln Park Zoo is a must. With over 200 species to marvel at, it’s an experience that’s sure to delight both kids and kids-at-heart alike.
Summertime in Chicago is simply unbeatable. With two stunning waterfronts—Lake Michigan and the Chicago River—locals enjoy kayaking, paddle boating, or simply basking in the sun by the water’s edge. Don’t forget to check out the 606 Trail for biking, hiking, or a refreshing morning jog. Who knows? You might just find yourself making it a regular part of your routine!
But the fun doesn’t stop there—Chicago is also home to a vibrant art scene, with iconic installations like the Bean and Sankofa for the Earth waiting to be discovered. The 16th Street Art Murals located in Pilsen is also great for catching a mix of small-time and bigger artists.
And if you are not a morning person, we got you! Navy Pier has a firework show every Wednesday and Saturday at 9 pm and 10 pm respectively, from May to September.
Prefer indoor adventures? Many of the city’s museums offer free admission on select days, although be prepared for crowds. Make sure to take advantage of Chicago’s free festivals, including the Grant Park Music Festival, Jazz Festival, and World Music Festival, which offer unforgettable experiences throughout the year. So gather your friends and roommates and get ready to explore all the free fun Chicago has to offer!
Look Out for More Exciting Events
Keep your eyes peeled for upcoming happenings with the help of sites like Eventbrite or Reddit threads. These gems are perfect for discovering small, casual events that might otherwise fly under the radar. Think chess nights, walking tours, or cycling clubs—everything that makes Chicago truly shine, courtesy of its residents.
Bottom Line
There you have it—Chicago’s affordable and free fun served up on a silver platter! And the best part? These experiences are all nestled in some of the top neighborhoods in Chicago.
Whether you’re hitting the trails, exploring Lincoln Park, or indulging in a shopping spree on Armitage Avenue, you’re just a short drive away from the hottest spots in the city for young professionals.
So, grab your roommate and make a date out of it. With so many exciting adventures waiting to be had in the beautiful city of Chicago, the possibilities are endless!