The windy city is one of the must-visit cities in all of the United States! It’s a city full of diverse cultures, music, and art, and I love it.

Going to Chicago is like going to a big playground with so much to explore, and wow, don’t even get me started on the things to eat. You’re gonna have a killer time in Chi-Town.

When visiting Chicago, there are a few iconic things that you must do — and if you don’t, did you really even go to Chicago?

First, you must catch a game at Wrigley Field and enjoy a Chicago hot dog. Don’t miss the chance to take a selfie at the Bean and take a boat cruise on the Chicago River.

Going to a new city requires you to be a tourist, at least for a little bit. But once you’ve seen all the sights, it’s time to get down Chicago style and join in on the festivals.

Consider yourself lucky if you’re in town during one of these events!

Festivals in Chicago

There are all sorts of awesome festivals to enjoy when visiting Chicago. From the world-famous Lollapalooza to the more locally based events like The Windy City Smokeout and the Air and Water Show, you’ll definitely get your fill of Chicago eats and treats.

So on that note, let’s take a look at some of the best Chicago festivals.

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    Chicago Blues Festival

    Chicago Blues Festival
    Still can’t believe this festival is free
    Photo: Jennifer Morrow (Flickr)

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    • When: June
    • Where: Millennium Park, Chicago

    The Chicago Blues Festival is one of the biggest music festivals in the world, and it happens in Millennium Park every June.

    Chicago has been dubbed the Blues Capital of the World, and this festival celebrates the deep-seated blues music tradition of the city. This free event has been going on since 1984, and it attracts thousands of people worldwide every year.

    The lineup for this festival is filled with some of the biggest names in blues music, both past and present. Some of the most famous acts that have played at this festival include B.B. King, Buddy Guy, Koko Taylor, and Etta James. I can’t imagine seeing them live; the atmosphere must have been booming.

    With an event that has been going on this long, they didn’t get there by chance. With the help of the public and the support of blues lovers, the Chicago Blues Festival will continue to be a highlight of the city’s summer music season.

    Support the festival by buying food and drinks from local vendors. Not only is the food top-notch, but it’s also a great way to keep the festival alive and flourishing.

    Where to Stay:

    Have insane views when you stay at this Hilton chain hotel. With floor-to-ceiling windows, you can take in the sights of Chicago while having a restful night’s sleep before and after the festival.

    Logan Square Arts Festival

    Cheers to Beer
    • When: June
    • Where: Logan Square, Chicago

    The Logan Square Arts Festival is one of the best cultural festivals in Chicago. It’s an outdoor event that takes place in the heart of Logan Square every summer.

    The festival celebrates the city’s diverse culture, from music and art to food and fashion. There are live performances throughout the weekend, as well as art installations, activities for kids, and a wide selection of vendors selling handmade goods.

    Within the park, you will find skilled merchants and artists from the area who bring vibrancy to the event. While you shop, you can enjoy live music from popular bands on two stages while indulging in tasty local food and drinks.

    So, grab a beer and stroll through the festival grounds to have a memorable weekend in Chicago.

    The event celebrates the unique characteristics of the neighborhood, which is known for its friendliness, diversity, and eclecticism. It’s the perfect event to get involved with the locals and experience the culture of Chicago in its fullest form.

    Additionally, since it began in 2009, the festival has raised significant money for nonprofit organizations in the community.

    Where to Stay:

    If you’re traveling on a budget or traveling solo and hope to meet new friends, stay at the Wrigley Hostel. You can enjoy walking tours of the nearby Wrigleyville neighborhood with other travelers.

    Wicker Park Fest

    Wicker Park Fest Chicago
    Photo: Mike (Flickr)
    • When: July
    • Where: Wicker Park

    The Wicker Park Fest is one of the most popular festivals in Chicago. This festival is so popular because it reflects the cultural liveliness of the neighborhood, including its musical heritage, exciting nightlife, and diverse cuisine.

    In July, the three-day street festival goes all out in Chicago. They have four stages that offer live music and entertainment.

    Wicker Park is one of the nicest places to stay in Chicago. A lot of families head out to Wicker Park for the weekend to enjoy the music, browse vendors, and eat some of Chicago’s best food.

    The festival features over 50 musical groups, and a designated art area showcases additional installations and events. You can also get your grub on at one of the 80 food vendors. It’s the perfect way to support local artisans, boutiques, and restaurants — and it only costs $10!

    For those of you who don’t have kids, or even if you do and need a babysitter, Wicker Park Fest throws an after-dark fest with lots of booze, food, and even more music every year. You gotta be 21 to get in, though!

    Where to Stay:

    Enjoy easy access to the festival by staying at the Hyatt Place in Wicker Park. With a beautiful city view and a delicious breakfast buffet, your time in Chicago will be perfect.

    Pitchfork Music Festival

    Pitchfork Chicago
    Photo: IncaseFollow (Flickr)
    • When: July
    • Where: Chicago

    The Pitchfork Festival is a three-day summer event in downtown Chicago held at Union Park on Randolph St.

    The festival features a mixture of art, music, and food at an affordable price. The lineup usually includes popular music artists and over 50 food vendors from around the city, making it worth every penny.

    The Festival is a great way to experience Chicago’s unique culture through its music, art, and food. The open atmosphere allows attendees to explore different genres of music while providing plenty of space for dancing.

    In 2010, the festival organizers bought carbon credits to offset the musicians’ travel and urged attendees to recycle, use eco-friendly transportation, and buy their own carbon offsets. The world at large is always at the forefront of this festival’s vision.

    From the amazing music to the supportive atmosphere, Pitchfork is a must-visit for any Chicagoan looking for an unforgettable experience. Whether you come solo or with friends, the festival will be sure to leave you with memories that will last a lifetime!

    One-day passes cost $109, and three-day passes cost $239.

    Where to Stay:

    The Hotel Versey is slightly out of the center but has a king room and easy access to the subway. It’s a great hotel to save a little money at and explore a different part of the city.


    Lollapalooza Chicago
    Photo: BluEyedA73 (Flickr)
    • When: August
    • Where: Grant Park, Chicago

    You can’t have a best festivals list and not include Lollapalooza! This four-day music festival takes place in the heart of downtown Chicago every year, and it brings together some of the biggest names in music.

    This Chicago music festival offers the opportunity to enjoy live music performances by world-renowned artists and groups against the backdrop of a beautiful lakefront during a summer in Chicago. With nine stages and 170+ artists, this festival goes WILD.

    Past headliners include Chance The Rapper, Ariana Grande, Paul McCartney, The Weeknd, and Travis Scott. The lineup is always packed with the hottest names in hip-hop, electronic, and rock music, so you never know who you’ll see.

    Lolla first started in Chicago in 1991 and has since become one of the biggest music festivals in the world. The festival is so successful that other cities like Berlin, Paris, and Buenos Aires host their own versions of Lollapalooza as well. It’s for sure one of the best things to do in Chicago if you’re there in August.

    General Admission starts at $385 for a four-day pass, and VIP starts at $1,600. You can also purchase one-day passes if you’re on a budget or have a specific artist you’re trying to see.

    Where to Stay:

    If you spent all your money on tickets — oops! Stay at the Chicago Getaway Hostel to stay a few bucks and meet other festival goers!

    Have you sorted your accommodation yet?
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    Chicago Air and Water Show

    Chicago Air and Water Show
    • When: August
    • Where: Chicago Lakefront

    Nothing screams summer quite like the Chicago Air and Water Show. Every August, the Windy City puts on an incredible show featuring some of the best pilots from around the world.

    The event takes place along the Chicago lakefront and features thrilling aerobatic performances from stunt planes, helicopters, jet teams, and more. You can expect to see jaw-dropping stunts such as loops, rolls, formation flying, and inverted flat spins.

    And while the air is full of crazy pilots, the water is filled with boats and jetskis pulling professional skiers on ropes while they are doing all kinds of acrobatic stunts and pyramids. Don’t try these at home, kid!

    The show has been taking place every year since 1959, and it attracts over two million people each year. It’s one of the most popular events in Chicago.

    You can see the event from almost anywhere on the lakefront. Make sure to get there early to grab a good seat.

    Visiting is free for everyone. So pack a picnic and make a hot summer day out of it.

    Where to Stay:

    Request a high-rise room at the Arlo Chicago and get views of the planes soaring over the lakefront.

    Chicago Jazz Festival

    Chicago Jazz Festival
    Photo: Joan (Flickr)
    • When: August
    • Where: Millenium Park, Chicago

    Every year during Labor Day weekend, Millennium Park hosts the Chicago Jazz Festival, where renowned and up-and-coming jazz musicians from all over the globe take the stage. It’s one of the most anticipated festivals in Chicago.

    For over 40 years, the Chicago Jazz Festival has been a part of Chicago’s summer music events. The festival features a wide range of artists, including jazz legends, influential modern masters, and new voices contributing to the genre’s ongoing development.

    The Chicago Jazz Festival aims to make jazz music accessible to everyone and continue to educate the masses about this incredible art. The festival has previously showcased legendary jazz musicians like Duke Ellington and John Coltrane.

    This is the perfect summer festival in Chicago because you can attend it for free, and because it’s held in Millenium Park, you can bring a blanket, pack a picnic, and enjoy a day in the city. You’ll have warm weather and the sounds of jazz around you while you get to know some incredible musicians.

    Where to Stay:

    Enjoy views of the river and be within walking distance of Millennium Park at the Allegro Royal Sonesta. It’s the perfect place to get to and from the festival.

    Travel with peace of mind. Travel WITH a security belt.
    Active Roots Security Belt

    Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

    It looks exactly like a normal belt except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

    Hide Yo’ Money!

    Taste of Chicago

    Taste of Chicago
    Who’s hungry?
    Photo: freeflight046 (Flickr)
    • When: September
    • Where: Chicago

    Chicago is famous for its delicious food, so what better way to experience the best of Chicago cuisine than at the Taste of Chicago? This massive food festival takes place over three weekends in the summer and then finishes out with a huge event in September in Grant Park.

    For over 40 years, Taste of Chicago has been a popular event for food enthusiasts. The festival hosts free-admission pop-ups in three different neighborhoods leading up to the classic lakefront festival in Grant Park. The pop-up events feature some of the city’s best local food, live music, and other activities.

    At Taste of Chicago, you can enjoy all of the Chicago classics, from that cheesy deep-dish pizza to Chicago-style hot dogs, cheesecake, and much more.

    This festival is the world’s largest free outdoor food festival, attracting over three million visitors each year.

    Chicago’s food scene is huge, and trying all the amazing restaurants is impossible, especially on a time crunch. But with Taste of Chicago, you’ll be able to try ’em all. Every year, the Taste of Chicago includes many top-rated restaurants from Chicago and food trucks, making our job as foodies much easier!

    Where to Stay:

    Stay downtown at the HI Chicago Hostel, snag a dorm bed for around $50 a night, and meet a group of people to get your grub on at the festival!


    Christkindlmarket CHicago
    Christmas in Chicago <3
    Photo: Marcin Wichary (Flickr)
    • When: December
    • Where: Chicago

    If you haven’t noticed, most of the festivals in Chicago take place in the summertime. The winter weather in Chicago can take the fun out of any outdoor event, but to get in the holiday spirit, you must check out the famous Christkindlmarket on the Daley Plaza.

    During December, the German-themed Christkindlmarket takes place in downtown Chicago and brings in over 1 million visitors each year. This festival celebrates Christmas and German culture with live performances, traditional food, unique gifts, festive decorations, and more.

    Best of all, it’s free for everyone to attend! Buy some mulled wine and a fresh pretzel, and enjoy the holiday season. It will feel as if you’re in a real German market with all the trimmings.

    The Chicago Christkindlmarket is an amazing way to get into the holiday spirit, and it’s definitely worth checking out if you’re ever in Chicago during December and is sure to bring out your inner child and remind you of the magic of this special season!

    Where to Stay:

    This ultra-modern boutique hotel is located right on the Magnificent Mile in the center of all the city’s action. It’s a great place to stay if you want to be close to shopping, restaurants, and attractions.

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    An eSIM works just like an app: you buy it, you download it, and BOOM! You’re connected the minute you land. It’s that easy.

    Is your phone eSIM ready? Read about how e-Sims work or click below to see one of the top eSIM providers on the market and ditch the plastic.

    Grab an eSIM!

    What To Pack For Your Chicago Trip

    Trust me on this one. These little extras accompany me on EVERY trip now. Take ’em and you’ll find out.

    Don’t Let Snorers Keep You Awake!
    Don’t Let Snorers Keep You Awake!

    Ear Plugs

    Snoring dorm-mates can ruin your nights rest and seriously damage the hostel experience. This is why I always travel with a pack of decent ear plugs.

    Keep your laundry organized and stink free
    Keep your laundry organized and stink free

    Hanging Laundry Bag

    Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.

    Stay Dry With a Micro Towel
    Stay Dry With a Micro Towel

    Sea To Summit Micro Towel

    Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.

    Make Some New Buddies…
    Make Some New Buddies…

    Monopoly Deal

    Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.

    Reduce Plastic – Bring a Water Bottle!
    Reduce Plastic – Bring a Water Bottle!

    Grayl Geopress Water Bottle

    Always travel with a water bottle! They save you money and reduce your plastic footprint on our planet. The Grayl Geopress acts as a purifier AND temperature regulator. Boom!

    Don’t Forget Travel Insurance!

    Before you go wild at one of these Chicago festivals, make sure you’re insured. Good travel insurance is ALWAYS a wise idea.

    ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.

    They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

    SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

    Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

    Final Thoughts on Festivals in Chicago

    What’s not to love in Chicago, deep dish pizza, The Cubs, and incredible architecture? After all, It was just named the best big city in the US for the 6th time in a row.

    From large-scale festivals like Jazz Fest and Pitchfork to smaller, more localized celebrations like Christkindlmarket and the Logan Square Arts Festival, you’ll get a taste of all that Chi-town has to offer.

    If you’re a music lover like me, then I can not stress enough how much you need to buy tickets to Lollapalooza. In my opinion, it’s the can’t-miss festival in Chicago. It’s become one of the biggest events in the music world and is worth every penny.

    Let me know which your favorite festival is in Chicago in the comments below. 🙂