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After our month-long Route 66 roadtrip a couple years ago we planned for a few days to explore Chicago, Illinois. We LOVE New York City, so were looking forward to exploring another large and bustling city. And it helps that Chicago is known for a couple food items we’re fans of… hotdogs and pizza! As a budget traveller I always look for budget friendly and cheap ways to explore new places. Chicago is a city ripe with budget-friendly options, so I’ve put together this list of cheap things to do in Chicago so that you can explore some of the awesome things we loved. Take a look, and make note so that you can plan your visit to Chicago on a budget!

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Cheap Things to do in Chicago

1. Eat at Portillos

2 words: CHICAGO DOG. I didn’t even know this was a thing until I arrived in Chicago. But now that I do, it has become my personal mission to make sure everyone tries one! Yes, they are THAT delicious! Without a question, this is my top recommendation for cheap things to do in Chicago!

So, a Chicago-style Dog is typically a boiled vienna hotdog, served in a poppyseed bun. (yes, the poppyseeds are important!). It is then topped with a generous amount of mustard, relish, diced onions, tomatoes, 2 ‘sport peppers’, a dill pickle wedge, and celery salt. And NO KETCHUP! Seriously, it’s basically a sin to add ketchup in Chicago.
Full disclosure.. I HATE mustard, relish and pickles. So I was a little skeptical on trying something that was pretty much full of things I hate. So I compromised and opted to ask for no pickle, and half the mustard and relish.
OhmiGAWD I am officially a convert!! These babies are amazing!

Portillo’s is a seriously funky establishment. You feel like you’re walking into a little town when you enter. If you’re lucky, there will only be a few people in line. But even if it’s packed, they work hard to take your order quickly. And I promise, it’s worth the possible wait!!!

FOODIE TIP: Try their chocolate cake shake ;). I’m sorry, and you’re welcome. 

Read More: Pack for the perfect road trip with my road trip packing check list 

2. Go for deep dish pizza

There are a few things Chicago is famous for, and the most popular one is deep dish pizza! Now, if you didn’t know, Chicago does pizza differently. Crust goes on the bottom, as it should. But then, they add cheese BEFORE the sauce! We tried 2 different restaurants… Pequod’s, who are famous for their ‘burnt cheese’ crust (pictured to the right), and Lou Malnati’s, who is just plain famous. To be honest, neither were our favourite… We’re pretty hooked on NYC thin crust! But given that it’s a MUST TRY in Chicago, I definitely have to include it in my recommendations. Given the options, I prefer Lou’s over Pequod’s. BUT, Pequod’s has an awesome $5 lunch special that really makes trying them a ‘can’t lose’ situation (and you know how much I love a good deal!).

3. Walk Navy Pier

I’ll be honest, this wasn’t our favorite thing to do in Chicago. While Navy Pier is a great place to see the sunset over the skyline, the rest of it is mostly overpriced restaurants and souvenir shops. We are glad we made the walk down to the end, as it is a nice walk with all the boats docked along the walkway, but I don’t feel a need to go back. BUT, it truly is worth a visit, even just to say you’ve been there. Go for sunset and you won’t be disappointed!

4. Get a transit pass

Driving around downtown can be terrible, depending on what time of day you head in. But even if traffic is decent, parking is horrendous!! It’s hard to find, and seriously a fortune (one place wanted to charge us $28 for a 20 min stop!). So I highly recommend public transportation! The train and bus system is excellent and your pass works for both. We tend to go for unlimited passes, because they let us travel around without having to check our balance, and it always proves to be cheaper than paying by the trip.

5. Take an architectural boat tour

Everyone I asked about what to do in Chicago told me I HAD to go on an architectural boat tour of the city. And having done it, I definitely agree with the recommendation! It’s a great way to see the city from a different angle, and we learned quite a bit about the buildings and the city from our guide.

Before you book, make sure you look for discounted tickets on Groupon. We booked tickets with Chicago Line Cruises and saved about $10 each!

Budget Tip: Start watching Groupon ahead of time, and use a 10% off coupon or $ off discount to save even more!

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6. Have a giant potato at the French Market

Seriously, it was the size of my head!! Where else are you going to find a stuffed baked potato big enough to feed you for 3 meals?! (Seriously though.. Where else?? Because if I can eat this somewhere else, I need to add it to my travel list!) While you’re there you can take a wander around the market and pick up some goodies to take home. It’s not a big market, so you won’t spend hours there. But it’s a nice little walk around inside, and worth the stop!

7. Tour a brewery

Chicago has an amazing microbrewery scene, so it’s no surprise that this makes my list of cheap things to do in Chicago. We took a free tour at the Haymarket Pub & Brewery. It’s a small microbrewery west of downtown, and it was a great stop after the Maxwell Street Market! There are several brewery tours in and around Chicago, so pick one and enjoy!

TIP: Check out this post to see some of the brewery tours offered here!

8. Get a good view of the Chicago skyline

Like many cities on a waterfront, the skyline is best viewed from the water. 2 of the best options in the city are at Navy Pier and on the drive to the Adler Plantetarium. Both are easy to get to from downtown, whether you’re driving, taking transit or walking.

9. Pose at the Bean

Can’t leave the Windy City without having the quintessential tourist experience at the Bean at Cloud Gate! It’s always pretty busy around there, so you’ll have a hard time getting tourist-free photos. But if you feel so inclined, get there around 6:30am for your best chance at some! The bean is just a few minutes from the Crown Fountain, Buckingham Fountain, Navy Pier and a Garrett’s popcorn, so make an afternoon of it!

Read More: Plan the Ultimate Summer Road Trip with this guide

10. Play in the water at Crown Fountain

This is a fountain that we just stumbled upon one afternoon, and it’s a pretty funky place to visit! It features a big screen at either end of a courtyard. The screens feature a face making different faces, and every few minutes they turn into a fountain. Hard to describe, but definitely worth a stop on your way to Cloud Gate!

11. See Buckingham Fountain

Buckingham Fountain in Grant Park is one of the largest fountains in the world, so definitely a must see while you’re here! The fountain pumps more than 14000 gallons of water every minute during its hourly light and water shows! It operates mid-April to mid-October, so be sure to fit it into your schedule if you’re looking for things to do in Chicago during those months.

12. Get a view from the top

Chicago is home to two 100+ story buildings that both offer a beautiful view of the city. Head to the John Hancock Tower to view the city from the lounge of the Signature Room on the 96th floor, the Signature Room restaurant on the 95th floor (food/drink purchase required at both of these), or the 360* Observation Deck on the 94th floor. Form 1000 feet up, you can see 55 miles on a clear day, and 4 states! If you’re brave, try the new ’tilt ride’ on the observation deck!
Or head the the 103rd floor of the Willis Tower to step out out on the ledge on the Skydeck! Both towers offer an amazing view, but make sure to go up on a clear day or you might be disappointed!

13. Try some Garrett’s popcorn

You can’t leave Chicago without trying some REAL Chicago Popcorn Mix! If you haven’t been living under a rock the last several years, chances are you’ve had some of the famous blend.. A wonderful mix of cheese and caramel coated popcorn. Whether you have or haven’t, you can’t leave the city without stopping in for a sample and a bag to take home!

Fun Fact: the name ‘Chicago Mix’ has actually been trademarked by a St Paul, Minneapolis candy store! Having been sued a few years ago for their use of the name, Garrett’s actually doesn’t call their mix ‘Chicago Mix’ anymore!

14. Visit the Pilsen neighbourhood

If you’re a fan of street art (which I am) and Mexican food (which I definitely am) Pilsen is an awesome neighbourhood to visit! Head down for an afternoon wander and grab dinner at one of the many local Mexican restaurants! Don’t forget to have a churro!

Read More: Pack for any trip with my essential packing list

15. See the Route 66 start & end sign

This was actually one of our main stops in Chicago, because we were in Chicago to finish our Route 66 roadtrip. Because Route 66 used to only be a single lane in either direction, and the streets are now one ways, the start and end points are actually a block apart.

The start and end points are downtown, right across from Grant Park and Cloud gate, so this is a great place to start a day of wandering around downtown!

16. Get a ‘Depression Dog’ at Gene & Jude’s

For those that aren’t into the ‘dragged through the garden’ style of the Chicago Dog, the original ‘depression dog’ might be more appealing… This dog was potentially the ORIGINAL version of the Chicago dog, and it comes with much less toppings- typically just mustard, onions and sport peppers. And possibly some relish… But still NO ketchup! But wait…. The most important topping? French fries! You’ll get them piled on top or wrapped up with the dog as an all-in-one meal. If you’re a foodie, this is definitely a worthwhile stop on the Chicago food scene! Henry’s Drive In gave this meal the tagline ‘it’s a meal in itself’, which couldn’t be more accurate! Add this to your plan for visiting Chicago on a budget!

17. Visit Monster Toys

There isn’t much to see here (sadly there’s no actual toy factory to go into!), but if you’re looking for a cute photo op (and have a car or an unlimited bus pass) it’s an easy and quick stop to make! Look close… You might miss it!

18. Wander around the Chicago Botanic Garden

Chicago’s Botanic Garden gives a nice break from the bustling city streets. Walk through the gates and you’re stepping into a whole different world! Catch here is that it’s actually a ways north of downtown.. about 40 minutes by car or 90 minutes with transit. So while it IS a great thing to do in Chicago, be prepared to dedicate a whole day to the Botanical Garden.

19. Score some deals (and sweet Mexican food!) at the Maxwell Street Market

Maxwell Street Market is a once a week market every Sunday. The street shuts down to vehicle traffic, and vendors and shoppers take over the 2 block span of Maxwell Street. Vendors are mostly ‘flea market’ style, and you’ll find a full block of Mexican food stand and trucks. You won’t spend more than an hour or 2 here, but it’s a fun start to your Sunday! And there’s a Portillo’s a few blocks away, so head over there for lunch 😉

20. Walk the Chicago Riverwalk

Whether you want to just go for a walk, or grab a bite or a drink, Chicago’s Riverwalk is the perfect place to do this. You’ll be surrounded by stunning, world-class architecture, and have amazing views of the city. Several river cruises depart from along the Riverwalk, and there is a water taxi you can take to get to a different section. Spend an hour or an afternoon… But definitely add this to your list of things to do in Chicago on a budget!

21. Wander the Magnificent Mile

North Michigan Ave, or the Magnificent Mile as it is known, is home to many of the areas top places to shop. Budget shoppers will agree that most of the stores don’t qualify to be on a list of cheap things to do in Chicago, but if you don’t go inside, it still makes for an entertaining (FREE) afternoon! The views are impressive, and worth the time. Several of the tallest towers in the United States call this street home, so be sure to look up! Pop into Lindt chocolate and Garrett’s Popcorn Shops for a free sample 😉

Read More: Visit all the best diners on Route 66!

22. Take a free guided walking tour

One of my favorite things to do in New York City is to take a free guided walking tour with Free Tours by Foot. So, naturally, when we got to Chicago I had to check out if they were in this city, too. And they are! You can choose from a variety of guided tours around the city. As the name implies, the tours are completely free. You just decide at the end whether to give your guide a tip. We generally tip $5-20, depending on how long the tour is, how much we enjoyed the tour, and whether we both attend or not. If you’re wanting to learn about the city of Chicago, these tours should definitely make your list of cheap things to do in Chicago.

23. Count the bricks on the Tribune Tower

The Tribune Tower is on the south end of N. Michigan Ave, or the Magnificent Mile. It was built in 1925, after a contest was held to design the building. The base of it is dotted with stones and bricks from historically important sites around the world, brought back by correspondents for the Chicago Tribune newspaper in years previous. There are a total of 149 of these relics on the building. We had fun walking around it and seeing where each came from! Portillo’s is only a 10 minute walk away, so head over there for lunch afterwards for one of our favourite cheap things to do in Chicago!

Now… it’s time to start planning!

I hope this list helps you make the most of your time in Chicago, and helps you to stay on budget when planning your visit to the city! There are many cheap things to do when visiting Chicago on a budget, these are just our favorites!

Do you have an idea for cheap things to do in Chicago?

Leave a comment below so that I can add it to my visit for my next visit!

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