There are easier ways to see Chicago. You could book a lovely hotel, spend a week eating deep-dish pizza, take approximately 847 photos of the skyline and fly home feeling like you've conquered the Windy City. Or (and hear me out) you could actually live there for a while.
Get a job. Find a room. Figure out the public transport. Make friends with people you've only just met. Learn which neighbourhoods you love, which ones you keep getting lost in and where to find food after a late shift.
Suddenly, Chicago isn't just somewhere you're visiting. It's somewhere you're living. And that's what makes seasonal work such a fun way to experience the city. So, what can you actually do for work? The good news is that you don't need to have your entire career mapped out before heading to Chicago.
Seasonal and temporary work comes in all sorts of flavours, from hospitality and retail to events, warehouses and construction. Your best option will depend on your experience, what sort of hours you want and, frankly, how much physical exertion you're prepared to tolerate before you start complaining about your aching feet.
Restaurants, cafés, bars and hotels are obvious places to start.
There are waiting jobs, kitchen roles, housekeeping, reception work, hosting and plenty of other positions where being friendly, reliable and reasonably good with people can get you a long way.
The hours can be antisocial, admittedly. You may find yourself working when everyone else is heading out for the evening.
The upside? Your colleagues can become your social life surprisingly quickly. When you've all survived a chaotic Saturday shift together, friendships tend to happen rather naturally.
Retail is another option if you'd rather spend your working hours somewhere slightly less frantic than a restaurant kitchen.
Depending on the employer, temporary jobs can range from shop-floor assistants and cashiers to stockroom positions.
And there's a bonus: you'll probably get very good at pretending you aren't tempted to spend your entire pay cheque shopping.
Chicago is a big events city, so temporary work connected with venues, conferences, festivals and entertainment can be worth looking into.
These jobs can be fun if you like busy environments and don't mind working evenings or weekends.
They're also a decent way to meet people - which matters more than you might expect when you've just arrived in a new city and your social circle currently consists of your flatmate and the person who sold you your coffee that morning.
If sitting behind a desk all day sounds like your personal version of hell, warehouse and logistics work could be worth considering.
These roles can involve packing, sorting, stock handling and loading, and some positions offer shift patterns that can leave chunks of your day free for exploring.
Just be honest with yourself about the physical side of the job. "I'll get used to it" sounds very optimistic until you're halfway through your third consecutive shift wondering why you ever thought lifting boxes was character-building.
Construction is another possibility, particularly if you already have relevant experience or qualifications.
Suddenly, Chicago isn't just somewhere you're visiting. It's somewhere you're living. And that's what makes seasonal work such a fun way to experience the city. So, what can you actually do for work? The good news is that you don't need to have your entire career mapped out before heading to Chicago.
Seasonal and temporary work comes in all sorts of flavours, from hospitality and retail to events, warehouses and construction. Your best option will depend on your experience, what sort of hours you want and, frankly, how much physical exertion you're prepared to tolerate before you start complaining about your aching feet.
Hospitality: the classic choice
Restaurants, cafés, bars and hotels are obvious places to start.
There are waiting jobs, kitchen roles, housekeeping, reception work, hosting and plenty of other positions where being friendly, reliable and reasonably good with people can get you a long way.
The hours can be antisocial, admittedly. You may find yourself working when everyone else is heading out for the evening.
The upside? Your colleagues can become your social life surprisingly quickly. When you've all survived a chaotic Saturday shift together, friendships tend to happen rather naturally.
Retail jobs
Retail is another option if you'd rather spend your working hours somewhere slightly less frantic than a restaurant kitchen.
Depending on the employer, temporary jobs can range from shop-floor assistants and cashiers to stockroom positions.
And there's a bonus: you'll probably get very good at pretending you aren't tempted to spend your entire pay cheque shopping.
Events and entertainment
Chicago is a big events city, so temporary work connected with venues, conferences, festivals and entertainment can be worth looking into.
These jobs can be fun if you like busy environments and don't mind working evenings or weekends.
They're also a decent way to meet people - which matters more than you might expect when you've just arrived in a new city and your social circle currently consists of your flatmate and the person who sold you your coffee that morning.
Warehouses and logistics
If sitting behind a desk all day sounds like your personal version of hell, warehouse and logistics work could be worth considering.
These roles can involve packing, sorting, stock handling and loading, and some positions offer shift patterns that can leave chunks of your day free for exploring.
Just be honest with yourself about the physical side of the job. "I'll get used to it" sounds very optimistic until you're halfway through your third consecutive shift wondering why you ever thought lifting boxes was character-building.
Construction and other physical jobs
Construction is another possibility, particularly if you already have relevant experience or qualifications.
It can be a good way to earn while gaining practical experience, but this is one area where it's particularly important to take the job (and your safety) seriously.
Ask what training you'll receive. Understand the work you'll be expected to do. Find out what protective equipment is provided. And don't be tempted to play the hero if you're asked to do something you haven't been trained to do.
No temporary job is worth an avoidable injury.
Then comes the fun part: finding somewhere to live. By "fun", I mean something that may involve scrolling through listings late at night and questioning whether a bedroom the size of a cupboard is really worth that much money.
Chicago has plenty of different neighbourhoods and accommodation options, but your first priority should probably be where you'll be working.
A slightly cheaper room isn't necessarily cheaper if your daily commute takes forever and costs a fortune. Before signing anything, check:
If you're only staying for a season, short-term or shared accommodation can make much more sense than signing up for a long lease you'll immediately regret.
And keep some emergency money aside. Future You will be extremely grateful.
Here's the real reason to consider working in Chicago rather than simply visiting. You get days off. And when you're on holiday, a day off can feel like wasted time if you spend it doing laundry and watching Netflix.
When you're living somewhere, that's just life.
You can have a lazy morning, wander around a neighbourhood you've never visited, grab lunch somewhere random, walk along Lake Michigan and still feel like you've had a pretty great day.
Of course, there are the big Chicago attractions: there's the architecture, the museums, the lakefront. The skyline. The sports. The food. And yes, you should absolutely try the deep-dish pizza.
But don't make the mistake of thinking you have to spend your entire season behaving like a tourist. Some of the best bits of living somewhere are the little discoveries.
Your favourite coffee shop. A brilliant cheap lunch. A park you stumble across. A bar where everyone seems to know each other. A particular view of the skyline that you start taking for granted - until you leave. That's the stuff you'll probably remember.
Let's be realistic: you aren't going to have an Instagram-worthy adventure every single day.
Some days you'll work a long shift, come home exhausted, eat something questionable and fall asleep fully clothed. That's fine. Actually, it's probably inevitable.
Ask what training you'll receive. Understand the work you'll be expected to do. Find out what protective equipment is provided. And don't be tempted to play the hero if you're asked to do something you haven't been trained to do.
No temporary job is worth an avoidable injury.
Finding somewhere to live without losing your entire pay cheque
Then comes the fun part: finding somewhere to live. By "fun", I mean something that may involve scrolling through listings late at night and questioning whether a bedroom the size of a cupboard is really worth that much money.
Chicago has plenty of different neighbourhoods and accommodation options, but your first priority should probably be where you'll be working.
A slightly cheaper room isn't necessarily cheaper if your daily commute takes forever and costs a fortune. Before signing anything, check:
- how long the commute is;
- whether public transport is convenient;
- what's included in the rent;
- whether the room is furnished;
- how long you're expected to stay;
- whether there's a deposit;
- and whether there are additional fees.
If you're only staying for a season, short-term or shared accommodation can make much more sense than signing up for a long lease you'll immediately regret.
And keep some emergency money aside. Future You will be extremely grateful.
Chicago is your playground: when you're not working
Here's the real reason to consider working in Chicago rather than simply visiting. You get days off. And when you're on holiday, a day off can feel like wasted time if you spend it doing laundry and watching Netflix.
When you're living somewhere, that's just life.
You can have a lazy morning, wander around a neighbourhood you've never visited, grab lunch somewhere random, walk along Lake Michigan and still feel like you've had a pretty great day.
Of course, there are the big Chicago attractions: there's the architecture, the museums, the lakefront. The skyline. The sports. The food. And yes, you should absolutely try the deep-dish pizza.
But don't make the mistake of thinking you have to spend your entire season behaving like a tourist. Some of the best bits of living somewhere are the little discoveries.
Your favourite coffee shop. A brilliant cheap lunch. A park you stumble across. A bar where everyone seems to know each other. A particular view of the skyline that you start taking for granted - until you leave. That's the stuff you'll probably remember.
The secret is finding a work-life balance
Let's be realistic: you aren't going to have an Instagram-worthy adventure every single day.
Some days you'll work a long shift, come home exhausted, eat something questionable and fall asleep fully clothed. That's fine. Actually, it's probably inevitable.
The trick is not to treat every day off as an opportunity to cram in ten attractions. Give yourself permission to do absolutely nothing occasionally.
Go for coffee, sleep until late, call home. Watch something rubbish. Then, when you do feel energetic, go and explore! That balance is what makes seasonal work different from a holiday. You're not constantly chasing the next experience. You're building a little temporary life for yourself.
It's easy to get caught up in the excitement of moving somewhere new and forget that you're still going to work every day.
If your job is physical (particularly if you're working in construction, around machinery, at height or near vehicles) workplace safety needs to be taken seriously.
Know the procedures. Use the equipment you're given. Ask questions if you're unsure. And don't let anyone convince you that being cautious makes you difficult.
It doesn't. It makes you someone who would quite like to finish their seasonal job with all their limbs intact.
If you are injured while working in construction, it's also worth knowing where you can turn for information about your rights and potential options. Having the contact details of a Chicago construction accident attorney can be useful if you're seriously injured, particularly because workplace accidents can involve complicated questions about workers' compensation, contractors and other potentially responsible parties. You should seek appropriate medical attention and report the accident through your workplace's required process first; legal advice can then help you understand your particular situation and what options may be available.
Please note that this is general information, not legal advice. Workplace injury laws and potential claims depend on the circumstances of each accident.
Here's something nobody particularly enjoys talking about when they're planning a working adventure: money. Yes, you're going to Chicago to earn. Yes, you're going to have fun.
No, this does not mean your entire first month's wages should disappear on restaurants, nights out and things you absolutely did not need but somehow couldn't leave the shop without buying. Before you arrive, work out roughly how much you'll need for:
Also remember that your first few weeks can be expensive. Deposits, accommodation, getting set up and everyday costs all add up rather quickly.
Having a financial buffer gives you something extremely valuable when you're living abroad: options.
One of the strangest things about moving somewhere temporarily is the pressure to make it amazing.
You start thinking every weekend needs to involve a road trip. Every evening needs to involve going out. Every photograph needs to look like it belongs in a travel magazine.
It doesn't. Your Chicago experience might include incredible nights out, but it might also include boring shifts, homesickness, bad weather, awkward flatmate situations and eating cereal for dinner because you're too tired to cook.
That's normal. The adventure isn't about making every moment perfect. It's about giving yourself the chance to experience a completely different version of everyday life.
If you're after a straightforward holiday, probably don't get a job. If you're looking for something a little more chaotic, challenging and memorable, however, seasonal work could be exactly what you're after.
You'll work. You'll earn. You'll probably get tired. You'll meet people you never would have met at home. You'll discover places you didn't know existed. You'll learn how to navigate a huge city without constantly checking your phone.
And somewhere between the early shifts, cheap dinners, spontaneous nights out and days spent exploring, something funny happens.
Chicago starts to feel a little bit like home. Not permanently. Not perfectly. But enough.
And when the season ends and it's time to pack your suitcase again, you'll realise you didn't just visit Chicago. You lived there.
Go for coffee, sleep until late, call home. Watch something rubbish. Then, when you do feel energetic, go and explore! That balance is what makes seasonal work different from a holiday. You're not constantly chasing the next experience. You're building a little temporary life for yourself.
And then there's the less glamorous side: staying safe at work
It's easy to get caught up in the excitement of moving somewhere new and forget that you're still going to work every day.
If your job is physical (particularly if you're working in construction, around machinery, at height or near vehicles) workplace safety needs to be taken seriously.
Know the procedures. Use the equipment you're given. Ask questions if you're unsure. And don't let anyone convince you that being cautious makes you difficult.
It doesn't. It makes you someone who would quite like to finish their seasonal job with all their limbs intact.
If you are injured while working in construction, it's also worth knowing where you can turn for information about your rights and potential options. Having the contact details of a Chicago construction accident attorney can be useful if you're seriously injured, particularly because workplace accidents can involve complicated questions about workers' compensation, contractors and other potentially responsible parties. You should seek appropriate medical attention and report the accident through your workplace's required process first; legal advice can then help you understand your particular situation and what options may be available.
Please note that this is general information, not legal advice. Workplace injury laws and potential claims depend on the circumstances of each accident.
Budget like you're sensible - even if you don't always feel like it!
Here's something nobody particularly enjoys talking about when they're planning a working adventure: money. Yes, you're going to Chicago to earn. Yes, you're going to have fun.
No, this does not mean your entire first month's wages should disappear on restaurants, nights out and things you absolutely did not need but somehow couldn't leave the shop without buying. Before you arrive, work out roughly how much you'll need for:
- accommodation;
- food;
- transport;
- your phone;
- work clothes or equipment;
- entertainment;
- travel;
- and an emergency fund.
Also remember that your first few weeks can be expensive. Deposits, accommodation, getting set up and everyday costs all add up rather quickly.
Having a financial buffer gives you something extremely valuable when you're living abroad: options.
Don't wait for the "perfect" adventure
One of the strangest things about moving somewhere temporarily is the pressure to make it amazing.
You start thinking every weekend needs to involve a road trip. Every evening needs to involve going out. Every photograph needs to look like it belongs in a travel magazine.
It doesn't. Your Chicago experience might include incredible nights out, but it might also include boring shifts, homesickness, bad weather, awkward flatmate situations and eating cereal for dinner because you're too tired to cook.
That's normal. The adventure isn't about making every moment perfect. It's about giving yourself the chance to experience a completely different version of everyday life.
So, is working in Chicago worth it?
If you're after a straightforward holiday, probably don't get a job. If you're looking for something a little more chaotic, challenging and memorable, however, seasonal work could be exactly what you're after.
You'll work. You'll earn. You'll probably get tired. You'll meet people you never would have met at home. You'll discover places you didn't know existed. You'll learn how to navigate a huge city without constantly checking your phone.
And somewhere between the early shifts, cheap dinners, spontaneous nights out and days spent exploring, something funny happens.
Chicago starts to feel a little bit like home. Not permanently. Not perfectly. But enough.
And when the season ends and it's time to pack your suitcase again, you'll realise you didn't just visit Chicago. You lived there.
And honestly, that's a much better story to bring home! (Photo credit: Bo Zhang, Drew Gilliam)
