Often overshadowed by the coastal juggernauts of New York and LA, Chicago is one of those cities that many international visitors simply fly over. The 3rd largest city in the United States is well worth a visit though.
Chicago is a vibrant city with amazing architecture, food, music, sports, and so much more! With one of the most impressive skylines in the world set along the beautiful Lake Michigan, Chicago sure is easy on the eyes.
In addition to admiring the world-class buildings, backpacking Chicago means digging into the incredible culinary, art, sports, music, and nightlife scenes.
Whether you’re checking out the free public art, catching a Cubs game, hitting up a craft brewery, rocking out to some live music, or just biting into a slice of deep-dish Chicago pizza, you’re sure to enjoy all that this city has to offer.
I’m thrilled to share this jam-packed guide with you guys on how to make the most of your trip to the Windy City. Read on for tons of information on the best things to do in Chicago, where to stay, and some Broke Backpacker money-saving tips.
Table of Contents
What to expect from Chicago?
One of the best parts about traveling in Chicago is without a doubt the friendly Midwestern hospitality that you experience there. People smile and greet each other, hold doors open, and all that good stuff.
It’s a big city that somehow manages to feel like a small town at times. People are genuinely nice here, and that’s not something you hear very often about other big cities.
Having traveled all over the US, I can say without a shadow of a doubt that Chicago is my favorite American city. I can’t even count how many times I’ve been there, but I keep coming back.
Since the city is quite big, you’ll find yourself having to decide between districts, neighborhoods, and a lot of attractions. In order to have a successful trip, we’d suggest coming up with a rough itinerary. Walking around without a clue often leads to wasted time, wasted money, and the stressed feeling of missing out.
Do yourself the favor and plan ahead!
If you are traveling the USA, then Chicago makes an awesome stop. Visiting Chicago in three days is definitely possible. You’ll be able to fit in the main hotspots of the city and still have a relaxed stay. However, if you want to experience Chicago properly, you’ll need to stay for at least a week.
There are many awesome things to see in Chicago, on and off the beaten track. If your budget and time allow it, explore the city for a bit longer!
Day One in Chicago: The Highlights
For the first of three days in Chicago, you’ll want to head straight downtown to take in some of the highlights of this great American city.
Make your way to Grant Park, where you have tons of options for your first day in the city. This is the perfect place for a stroll along Lake Michigan with excellent views of the city’s famous skyline.
Walking north along the lake, you’ll soon find yourself in Millennium Park. Stop here to pose for funky photos with the Cloud Gate, otherwise known as The Bean. It’s just one of several examples of the awesome public art that’s spread across the city. This is a great point to jump in on the self-guided Loop Art Tour that I mentioned earlier in the guide.
After you’ve had your fill of the parks and the public art, it’s time to walk along the Chicago River. Here you’ll see plenty of the city’s world-famous buildings that make Chicago an architecture lover’s dream come true. If your feet are tired and you don’t mind splurging a bit, you can hop on a river cruise instead.
Surely you’re hungry by now, so it’s time to try the classic Chicago-style hot dog. They’re not hard to find, but some are definitely better than others.
One of your best bets is Portillo’s, which has several locations throughout the city. If you’re a vegetarian, never fear – there are plenty of excellent options for you in the city as well.
With a full belly, it’s time to take in the views of Chitown from above. Head to the Willis Tower and buy a ticket to go up to the observation deck. I’m usually not one to spring on these expensive tickets, but I think this one is definitely worth it if you’ve never been. The views of the city and Lake Michigan are absolutely incredible up here.
If you timed your day right, you’ll be coming down from the observatory at the start of Happy Hour. Chicago is a city that loves to booze it up, and there are bars around every corner here.
Going out early means you can score some great deals and get a little buzz on while the rest of the city goes about its daily rush hour thing.
What you decide to do with your evening in Chicago is entirely up to you and your style. The options are seriously endless for a night out in Chicago. You can book a table at one of the city’s amazing restaurants and enjoy a nice dinner. Chilled seafood tower for two, anyone?
You could also catch a musical or comedy show at one of Chicago’s many theaters. If you’re more into sports, chances are there’s a game you can try to attend live or just watch from a bar.
Of course, you can always just gather up some fellow party animals from the hostel and head out on a pub crawl. Whatever you do, have fun out there!
Day Two in Chicago: Museums and Parks
If you had a big night out, go ahead and sleep in a bit. This city loves brunch, so go ahead and enjoy a nice casual meal to start day two in Chicago. One of my favorite places is Yolk, which is right downtown and a short walk from the Museum Campus.
Take your pick between the Shedd Aquarium, Adler Planetarium, or the Field Museum. All three are great, so it really just depends on your interests.
Personally, I think the Field Museum offers the best bang for your buck. I’ve been several times and still jump at the opportunity to go back and learn something new. You can easily spend half a day in there and not get even the least bit bored.
Hopefully, you’re backpacking Chicago on a nice, warm day, because that’s when the city is its best. For your afternoon, I recommend heading up to Lincoln Park. This large green space is home to a free zoo, which is actually quite good. In the summer months, you can hit the beach and go for a refreshing swim in Lake Michigan.
For dinner, you should probably dig into some Chicago deep-dish pizza. I’ve sampled the city’s famous pizza on countless occasions and would personally recommend Giordano’s, Pizzeria Uno, and Lou Malnati’s. Hopefully, you have some friends to share the pie with, because they sure are filling.
If you want to feel like you’re on a tropical getaway in the middle of a big city, head to Three Dots and a Dash. This excellent tiki bar will transport you to Hawaii in no time with their delicious tropical cocktails.
From here, you’ve got plenty of options to keep the party going. I’d suggest trying to find a place with some live music, preferably one without a cover charge so you have more money to spend on drinks.
Day Three in Chicago: Choose Your Own Adventure
After those first two days, you’ve already seen a lot of Chicago’s best places. As a result, you can choose your own adventure for day three in Chicago. I’m not going to leave you hanging though! Here are a few ideas for how to spend your last day in the Windy City.
If it’s a nice day, a great place to go kill a few hours is Navy Pier. This little strip of land jutting out into Lake Michigan has a big ferris wheel that gives you awesome views of Chicago. It’s also a pleasant place for a stroll, and there are plenty of cafes and restaurants along the way if you want to sit down for some food or a drink.
Another good idea for a beautiful Chicago day is a bike ride. There are kiosks all over the city where you can rent some wheels for 24 hours for about $15, so jump on and start peddling. If you’d rather not bother with trying to navigate your way around the city, you can always join a bike tour.
Depending on when you’re visiting, you may not want to spend that much time outside. If it’s a cold and rainy day, you can choose from one of the several museums that you’ve yet to visit. I really enjoy the Art Institute of Chicago and I’m not even that big of an art guy.
Perhaps you don’t want to do any kind of sightseeing today at all. That’s totally fine as well! There’s nothing wrong with just eating and drinking your way around the city on your last day. If you’re a beer lover, I’d recommend checking out the taproom at Lagunitas or Goose Island.
The former hails from California and opened a Chitown location a few years ago, while the latter is a Windy City original. Both make solid beer and are fun places to hang out.
If you’ve still got any gas left in the tank, you can go out and catch a show or just hit a few more bars. That does it for a pretty epic three days in Chicago. While you covered some serious ground with this itinerary, you’ll surely be left wanting more and planning your return visit. Trust me; it happens every time!
Chicago off the Beaten Track
In a city as large and diverse as Chicago, it’s not too hard to get off the beaten track. You can plan on seeing plenty of tourists along the lakefront and on the riverboat tours. Ditto for the big attractions like the Willis Tower and Navy Pier.
Head a bit out of the downtown area to any local neighborhood though, and you’ll already be off that beaten path.
In this massive city, you’ll find a wide variety of neighborhoods. There are plenty of ethnic enclaves, such as the city’s famous Chinatown. Very few tourists make it down here, so this is a cool place to explore minus the crowds.
You could also check out the Pilsen area in Chicago’s Lower West Side. Dive into Mexican culture here at the National Museum of Mexican Art and the area’s countless authentic restaurants.
If you’re just looking for cool local ‘hoods to walk around in, you can check out Lincoln Park, Logan Square, and Wicker Park. All are hip parts of the city with plenty of options for dining and nightlife that serve more locals than tourists.
- Free Breakfast
- Café & Bar
Where to stay in Chicago?
Figuring out where to stay in Chicago can be tricky. It’s a huge city that’s quite spread out with many unique neighborhoods. That being said, you don’t really have a ton of options as a backpacker. Many backpackers are surprised to find that American cities don’t really have a lot of hostels, and Chicago is no different.
You don’t even need to bother searching for hostels in Chicago because we’ve done it for you!
To make your life even easier, I’ve narrowed it down to the top three choices for the best overall hostel, best for solo travelers, and best party hostel in Chicago.
Those who prefer a bit more privacy and comfort may want to search for places on Airbnb. While it’s pretty expensive to book an entire place, you can find a private room in a shared apartment for as little as $40-60.
Overall Best Hostel in Chicago – Freehand Chicago
Freehand is an easy choice for the best hostel in Chicago. This hostel has a great location in the vibrant River North neighborhood just a few blocks from the famous Michigan Avenue.
The dorms are nice and only have four beds in each room. With free breakfast and a shared kitchen, it’s easy to save money on food by staying here. There’s also a fitness centre and a bar here, which you should hit in that order.
Highlights include: Amazing location, small dorms, free breakfast, shared kitchen, on-site bar.
Best Hostel for Solo Travelers in Chicago – HI Chicago Hostel
This is the 2nd largest hostel in all of the USA with over 500 beds. That means plenty of opportunities to meet your fellow backpackers! They make being social easy here with free walking tours and other daily activities, such as pub crawls or group outings to jazz clubs.
You also get a great free breakfast, WiFi, and a common TV area with movies. It’s hard to top the location of this hostel, which is just a block away from Grant Park and Lake Michigan.
Highlights include: Very social atmosphere, amazing central location, lots of free activities, breakfast and kitchen.
Best Party Hostel in Chicago – Wrigley Hostel
Chicago loves to party, and nowhere is that more true than in Wrigleyville. This excellent party hostel is right by historic Wrigley Field – home to the defending champion Chicago Cubs. You can pre-game at the hostel bar with a game of pool, darts, and ping pong.
They also host free weekly BBQs and lead guests on some epic pub crawls. Within blocks of the hostel, you can find countless restaurants, bars, and clubs. A free breakfast ensures you don’t have to drag your hungover ass out of the hostel too early.
Highlights include: Great area for going out, walking distance to Wrigley Field, cool bar and common area, free breakfast.
Chicago Accommodation Travel Hacks
Chicago is not a cheap place to stay, and there is no way around it. Even a hostel here can set you back $60-70 a night just for a dorm room. That being said, there are a few accommodation hacks you can use to try and save a few bucks:
- Couchsurf: There are plenty of people in Chicago who are on Couchsurfing. If you’ve got some good reviews and you’re not travelling with a big group, it’s worth it to reach out to locals and see if anyone can host you. Even a night or two saves a lot of money.
- Free breakfast and a kitchen: If you decide to go the hostel route, try to find one that has both a free breakfast and a shared kitchen. If you get fed in the morning and can cook at least one meal for yourself, you won’t spend much on food.
- Avoid events: If you end up in Chicago the same weekend as the marathon or a giant music festival, those dorm beds are going to be in short supply and the price will be jacked up. Do your research and find out what’s going on in the city before you plan your visit.
- Stay in local ‘hoods: It’s great to stay right downtown near Michigan Avenue and the lakefront, but it will cost you. Look for accommodation in local ‘hoods to save some cash.
- Weekly discounts: There’s definitely enough to do in Chicago to keep you busy for a week. Most Airbnb hosts will give a weekly discount automatically, and some hostels will as well if you ask.
There are seemingly never-ending amounts ofthings to see and do in Chicago. I’ve been going to the Windy City for about thirty years now and always find something new to do when I visit.
Here’s my list of the top 10 things to do in Chicago to show you some of the best that the Windy City has to offer:
1. Admire the architecture
In the city that invented the skyscraper, one of the best things to do is simply wander around with your head pointed up. If you can fit it in your budget, it’s worth considering a boat tour on the river to take in and learn about the city’s famous buildings. This is definitely one of the most popular things to do in Chicago.
Don’t worry if you can’t swing a boat tour in your budget. I’ve been to the city about a hundred times and have never even done one myself. You can easily follow this DIY walking tour map to take in some of Chicago’s architectural highlights.
2. Hit the museums
Chicago is home to some amazing museums, so you should definitely try to hit at least one on your trip. If I had to recommend just one, I’d go with the Field Museum. This natural history museum has a vast and impressive collection and it’s tons of fun to explore.
You could easily spend a full day in there if you wanted to. Other great choices include the Art Institute of Chicago and the Museum of Science and Industry.
3. Free public art
Not all of the art in Chicago is locked away inside museums. The city has a ton of great public art on display, including sculptures by famous artists such as Picasso. All you’ll need to see Chicago’s public art is a good pair of walking shoes. There’s even an itinerary on Wikitravel called the Loop Art Tour that you can follow.
One of the coolest things you’ll see on this self-guided tour is definitely the Cloud Gate – one of the best places in Chicago to visit. More commonly referred to as the Bean, this funky stainless steel sculpture gives off a funhouse mirror effect that makes for some awesome photos.
4. Explore ethnic neighborhoods
Chicago is one of the most diverse cities in the US, meaning there are several ethnic neighborhoods where you can experience the culture of the immigrants who founded them.
There’s Chicago’s large Chinatown with dim sum restaurants, a Nine Dragon Wall, and bustling markets. In other parts of Chicago, you can experience Polish, Mexican, and Vietnamese culture, among others.
5. Fun on Lake Michigan
No visit to Chicago would be complete without a nice stroll along the scenic Lake Michigan. A great place to begin a walk is in Grant Park, where you can check out the Buckingham Fountain before walking along the lakefront. If you’d rather cruise than walk, you can rent bicycles or even join a Segway tour.
During the hot summer months, Chicago’s beaches are bumping. You’ll find people playing frisbee and beach volleyball or just cooling off in the lake. Unfortunately, you can’t legally booze it up on Chicago’s beaches. That being said, nobody has to know that that’s not really water in your water bottle, wink wink.
6. Visit the Willis Tower observatory
When it was completed in 1973, the Sears Tower (as it was then called) surpassed the World Trade Center to become the tallest building in the world.
It’s now called the Willis Tower, and while it’s no longer the tallest building in the world, it’s still an impressive architectural achievement and a great place to visit in Chicago. The observation deck at the top of this 110-story skyscraper provides incredible panoramic views of the city and Lake Michigan.
7. Take in some live music
Chicago boasts one of the best live music scenes in the world with venues of all different shapes and sizes. Here, you can see everything from a symphony orchestra to a ripping blues band, to a massive rock show, to an underground rave.
There are shows every night of the week all throughout the year, meaning you can catch some live music regardless of when you visit. I had one of the best musical experiences of my life in Chicago when we saw the Fare Thee Well shows that celebrated 50 years of the Grateful Dead. Be sure to check the calendar and see what’s playing so you too can experience musical euphoria in Chicago.
8. Hot dogs and pizza, Chicago style
While it’s true that the city is home to countless fancy restaurants, us Broke Backpackers will opt for the cheap local classics. That means munching down on a Chicago style hot dog or a deep dish pizza.
The dog is loaded with chopped white onions, a slice of tomato, a pickle spear, pickled sport peppers, and yellow mustard. In my humble opinion, it’s the best freaking hot dog in the nation.
A Chicago deep dish pizza is loaded with an excessive amount of gooey melted cheese. It’s so filling, you really only need one slice. Some of the best places to go for a deep dish pizza include Pizzeria Uno and Lou Malnati’s.
9. See a sports game
To say that Chicago is a sports-crazed city is an understatement. Chicagoans are die-hard supporters of their teams, including the Bulls (NBA), Blackhawks (NHL), Fire (MLS), and Bears (NFL). The only divide here comes with baseball, as the city is home to two different MLB teams – the Cubs and the White Sox.
Since Chicago has teams in every major professional sport, you can attend a game year-round. Attending a sporting event is something that should definitely be high on your list when backpacking Chicago.
Having been to all of the sporting venues, I can say from experience that nothing beats a Cubs game at Wrigley Field. Opened in 1914, it is the 2nd-oldest ballpark in the United States.
10. Party it up
If you’re looking to have a good time, you’ve come to the right place. From dive bars to high-end nightclubs and everything in between, there’s no shortage of places to wet your whistle in the Windy City. You can find craft beer joints, classy wine bars, and even tiki bars pouring some delicious tropical drinks.
Some of the best neighborhoods in Chicago for partying in include Wicker Park, Bucktown, and Wrigleyville. Wherever you end up, be sure to try a few Chicago classics, such as a tall boy can of Old Style and a shot of Malort. For many years, the label on the latter actually read, “our liquor is rugged and unrelenting (even brutal) to the palate.” Take one shot and you’ll see why.
Best Time of Year to Visit Chicago
The best time to visit Chicago depends on your tolerance of two things – cold and crowds. During the dead of winter, it can get painfully cold in Chicago.
While there’s plenty to do inside, Chicago just isn’t nearly as much fun when it hurts to step outside. This is the case between December and March, generally speaking.
On the other hand, summers tend to be nice and hot in Chicago. They’re also super crowded, especially on weekends when there’s a big festival going on. Unless you’re going to attend said festival, it’s worth avoiding those crowds.
Whenever you visit in summer, be sure to book accommodation in advance to avoid disappointment.
If you ask me, the best time to visit Chicago is probably May-June or September-October. Most kids are in school in these months, so you don’t have quite as many tourists flooding the city. The weather is also pleasant enough to spend a majority of the day outside without dripping sweat or freezing your ass off.
Books to read on Chicago
Before backpacking Chicago, you might want to read up on the city a bit to plan your trip. Below are 5 books and guides to add to your Chicago reading list:
- The Backpacker Bible – Get it for free! Learn how to ditch your desk and travel the world on just $10 a day whilst building a life of long-term travel with an online income. To inspire and help the next generation of Broke Backpackers, you can now grab ‘How to Travel the World on $10 a Day’ for free! Get your copy here.
- Lonely Planet Chicago Travel Guide – All you need to know about backpacking Chicago can be found in the most recent Lonely Planet guide.
- Not for Tourists Guide to Chicago – You’re not a tourist – you’re a backpacker! This is a great guide for getting off the beaten path and seeing a more local side of Chicago.
- History of Chicago: A Captivating Guide to the People and Events that Shaped the Windy City’s History – Chicago is a city with a fascinating history, and this is the book to read if you’re interested in learning about it.
- The Third Coast: When Chicago Built the American Dream – Author Thomas Dyja says “Understanding America requires understanding Chicago,” and he helps you do just that in this excellent book.
Staying Safe in Chicago
If you’ve Googled “safety in Chicago,” you might be terrified of visiting the city. While it’s true that the city has a huge problem with violence – there were 765 people murdered in Chicago in 2016, more than New York and LA combined – most of the city is completely unaffected by this.
It’s sad but true that almost all of the violence in Chicago takes place on the south side of the city. As a backpacker, you have absolutely no need to venture south.
Downtown Chicago is an incredibly safe place to visit. Just take the same precautions that you would in any other major city. Keep an eye on your valuables, especially when riding public transport or walking in crowded areas.
Be mindful of your fancy iPhone if you insist on looking at it while riding the train. The city has plenty of “apple pickers” who will gladly snatch it and jump off the train right before doors close. Don’t get super fucked up and wander around dark alleys at 3AM. You’ll be just fine if you follow that simple advice.
Get Insured before Backpacking Chicago
Do you need Travel Insurance for your trip? Even if you’re only going for a few days, that’s more than enough time to get buggered by wicked men or smote by wrathful angels. Have fun in X, but take it from us, overseas medical care and canceled flights can be seriously expensive – insurance can, therefore, be a life-saver.
Travel mishaps can and do happen and it is well worth thinking about insurance before you leave home.
We have used World Nomads for years now and I have personally made several claims. Why not get a quote from them yourself?
Do be sure to read the terms and conditions to make sure that the policy covers your needs.
Getting an estimate from World Nomads is simple – just click the button or image below, fill out the necessary info, and you’re on your way!
Chicago Travel Guide – Getting In and Around
Arriving in Chicago
Chicago is served by two airports – O’Hare and Midway. Most international flights arrive at O’Hare, which is about 30 km northwest of downtown. Flights are notoriously delayed here, so don’t be surprised if that happens to you. You can ride the Blue Line to the city in about an hour from O’Hare.
Midway is located in the southwest part of the city and is accessible by the Orange Line. This airport mostly serves low-cost carriers like Southwest for domestic flights. I’m pretty sure the only international flights here go to Mexico.
It’s also possible to get in and out of Chicago by bus or train, although your options are somewhat limited. I’ll get to train travel in a second, but as far as buses go you should check out Megabus. This no frills bus company has super cheap fares if you book in advance. I’ve traveled between Chicago and my native Detroit several times for just $1.
Of course, you can always rent a car to get yourself to Chicago. Just be warned that parking is a major pain in the ass in the city and it will cost you a pretty penny. Honestly, a car is just a liability in the city and you’re much better off relying on public transportation.
How to get around Chicago
As I just mentioned, you really don’t need a car to get around Chicago. The city has a solid system of trains and buses in place to get you everywhere you need to go. You can use the handy RTA trip planner to figure out how to get around if you’re not too familiar with the city.
Most Chicagoans refer to the train system as the L because many of the trains are on EL-evated tracks. Get it? The different lines are identified by color, and most of them hook up downtown in “The Loop.” The red and blue lines both operate 24/7, making Chicago the 2nd city in the US (other than NYC) to have round-the-clock public transportation.
If you’re spending a few days in Chicago, you should just pick up the 3-day CTA pass. It will cost you $20 and is good for all the trains and buses. Google Maps works fine in Chicago and will give you good directions on using the public transportation. You can also use both Uber and Lyft here, which can be quite reasonable for short trips outside of rush hours.
Onwards Travel from Chicago
Train travel in the United States is quite lackluster. Your options are limited, and they usually aren’t cost-effective. For example, the train from Chicago to Detroit often costs about the same as a flight, but takes six hours instead of one. It’s pretty sad because Chicago is basically the rail hub of the US and even here train travel isn’t great.
If you do want to give train travel a shot, here’s what you’ll need to know. Trains arrive and depart from Union Station in downtown Chicago. The only train operator is Amtrak, so you can check their website for times and prices.
From Chicago, you can take a train to other major cities like New York, Washington DC, New Orleans, and Denver. If you’ve got the time and the money, you should consider riding The California Zephyr line all the way to San Francisco. It’s supposed to be one of the most scenic train journeys in the world.
There’s no doubt that big American cities aren’t exactly known as top backpacker destinations. They also aren’t the cheapest places to travel, that’s for sure. In this section, we’ll take a look at how much you can expect to spend when backpacking Chicago.
Daily Budget for Chicago
At the lower end, you’ll probably spend about $70-80 a day when backpacking Chicago. At this amount, you can get a dorm bed in one of the cheaper hostels, get around on foot or the city’s great public transportation, take advantage of free activities, and stick to simple food and drink.
If you can afford to up that daily budget to around $100-110, you’ll probably still be staying in a hostel dorm. Hotels are freaking expensive in Chicago! With the extra money, you can add an extra fun activity each day like going to a museum or seeing a ball game.
So just how far does your dollar go in the Windy City? Here’s a breakdown of a daily Chicago budget:
Tips for visiting Chicago on a budget
It’s definitely easy for your money to disappear into thin air in a place like Chicago. That being said, there are still some strategies you can follow to try to minimize the damage to your wallet.
- Visit in spring/fall: Summer is peak tourist season in Chicago, which means big crowds and higher prices. Winter is downright painful, meaning you won’t be able to spend that much time outside. You’ll spend more on entrance tickets and transportation as a result. Visiting in the spring or fall means you can enjoy the relatively nice weather and smaller crowds.
- Avoid big event weekends: If you really want to go to Lollapalooza or a Chicago Bears game, that’s great. Go for it. If not, you won’t want to be traveling to Chicago on a weekend. Hostels and hotels jack up their rates and the downtown area is somewhat of a cluster fuck.
- Buy a CTA card: If you want to explore all that Chicago has to offer, it’s worth it to pick up a CTA transport card. For just $20 you can get a pass good for 72 hours on all trains and buses. It’s very easy to get your money’s worth on these.
- Do the free things: You can burn through a lot of money in Chicago quickly by buying entrance tickets and joining tours. You can also entertain yourself with plenty of awesome free activities. Walk around the city in search of all the awesome free public art, visit the free Lincoln Park Zoo, and stroll along Lake Michigan without spending a dime.
- Be a Happy Hour Hero: Chicago is well-known for its amazing restaurants and bars. These can burn a hole through your wallet if you’re not careful, though. Keep an eye out for Happy Hour deals and take advantage of them. After all, you’re on vacation. Go ahead and have a drink at 4 o’clock on a Tuesday and pay less for it than everyone who shows up after work.
Volunteering in Chicago
Long term travel is awesome. Giving back is awesome too. For backpackers looking to travel long-term on a budget in Chicago whilst making a real impact on local communities, look no further than World Packers. World Packers is an excellent platform connecting travelers with meaningful volunteer positions throughout the world.
In exchange for a few hours of work each day, your room and board are covered.
Backpackers can spend long periods of time volunteering in an awesome place without spending any money. Meaningful life and travel experiences are rooted in stepping out of your comfort zone and into the world of a purposeful project.
Worldpackers opens the doors for work opportunities in hostels, homestays, NGOs, and eco-projects around the world. We’ve tried and approved them ourselves – check out our Worldpackers in-depth review here.
If you’re ready to create a life-changing travel experience and give back to the community, join the Worldpacker community now. As a Broke Backpacker reader, you’ll get a special discount of $20. Just use the discount code BROKEBACKPACKER and your membership is discounted from $49 a year to only $29.
Make Money Online Whilst Backpacking Chicago
Traveling in Chicago long-term? Keen to make some cash when you are not exploring the city?
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In addition to giving you the qualifications to teach English online, TEFL courses open up a huge range of opportunities and you can find teaching work all over the world. To find out more about TEFL courses and how you can teach English around the world, read my in-depth report on teaching English abroad.
Broke Backpacker readers get a 35% discount on TEFL courses with MyTEFL (simply enter the code BACKPKR), to find out more, please read my in-depth report on teaching English abroad.
Whether you are keen to teach English online or looking to take your teaching game a step further by finding a job teaching English in a foreign country, getting your TEFL certificate is absolutely a step in the right direction.
Must-Try Experiences in Chicago
Eating and Drinking in Chicago
Many people travel to Chicago specifically to eat and drink their way across the city, and there is absolutely nothing wrong with that. The city has a world-class culinary scene that’s well worth digging in to. You can find every type of restaurant imaginable here, from greasy spoon diners to Michelin-star restaurants.
The three most iconic dishes in the city are definitely the Chicago style hot dog, deep dish pizza, and the Italian beef sandwich. Be sure to try them all when you visit. You can diet later.
I can personally recommend Portillo’s for dogs, Lou Malnati’s for deep dish, and Al’s Italian Beef for their namesake. One night when you’re nice and drunk and got the munchies, do yourself a favor and visit the Wiener Circle. It may be the funniest dining experience you ever have.
Whether you seek a smoothie, coffee, a cup of tea, craft beer, fine wine, or a cocktail, Chicago has got it for you. I would highly recommend going out of your way to frequent Ipsento in the morning. Their namesake is seriously the best cup of coffee ever. I wish I could have it every day. It’s espresso with coconut milk, honey, and cayenne pepper. You can thank me later.
Chicago is quickly developing a reputation as a beer city thanks to its many craft breweries. Be sure to try some local brews or even visit the tap rooms of places like Goose Island, Three Floyds, and Half Acre.
No discussion of Chicago drinks would be complete without mentioning Malort. This Chicago liquor is interesting, to say the least. Give it a try at least once and then never again.
Nightlife in Chicago
Chicago is a city that loves to party. Most bars do their last call around 1:45 and close at 2am here, but that doesn’t mean you have to go home. There are over one hundred “late night bars” in Chicago that stay open until 4. Some of them even go until 5 on the weekend! Epic nights out are definitely the standard when partying in Chicago.
The Windy City is home to countless bars, breweries, music venues, and clubs. There are dive bars, hidden speakeasies, trendy cocktail bars, craft beer joints, gay bars, blues clubs, underground house music venues, and everything in between. Seriously – the sky is the limit when it comes to going out in Chitown.
For me, a great night out in Chicago would go something like this. Start out with a solid Happy Hour somewhere with a cheap drink or two and some appetizers.
Grab some dinner and then hit another bar or perhaps a local brewery for a few more drinks. Find out what’s going on and check out a show, whether it’s comedy, jazz, hip hop, electronic – whatever tickles your fancy.
Grab a late-night slice or a Chicago dog then keep the party going. Wind down the night at some random dive bar that will serve your drunk ass another drink at 4 AM. Yep – that’s a good night in Chicago alright!
Best Walks in Chicago
Despite being a massive metropolis and somewhat of a concrete jungle, Chicago is actually a very walkable city. Here are a few great choices for a casual stroll in the Windy City:
- The Loop Art Tour: Take in some of Chicago’s best public art on this self-guided walking tour around the Loop. There’s even a Wikitravel page about this walk that you can follow.
- Museum Campus to Navy Pier: On a nice, sunny day in Chitown, it’s hard to beat a nice stroll along Lake Michigan. If you start somewhat early, you can hit a museum, walk through the parks, cut across the river, and end up at Navy Pier.
- Lincoln Park: This park is so big that you could easily spend half a day just walking through it. There’s a free zoo, a conservatory, and even a beach.
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Need More Inspiration???
- Backpacking New York City Travel Guide
- Backpacking Los Angeles Travel Guide
- Backpacking USA Travel Guide
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Sasha is an English teacher, language student, blogger, and video producer. He and his wife run Grateful Gypsies, where they write about life abroad, long-term travel, and live music.