The Cheapskate Guide To: Chicago

Want some cheap travel to Chicago? Click through for a local's recommendations on $34 Airbnbs, $5 Chicago-style pizza, and $7 comedy shoes at Tina Fey + Amy Poehler's alma mater! >> yesandyes.org
Chicago is one of my favorite long weekend destinations. The public transport is easy and cheap, there’s tons to do AND THERE IS A GIANT LAKE IN THE MIDDLE OF THE CITY. Today, local Windy City-er BreAnna is telling us all about $7 comedy shows, free brewery tours, $5 Chicago-style pizza, and a clever way to get to the top of the John Hancock building for $9!


Hi! I’m BreAnna, the lady behind 
Crafty Coin, a frugal lifestyle blog. I’m all about teaching others how to live frugally without sacrificing quality. Hailing from North Dakota, I’ve lived in Chicago for nearly three years. Given my passion for saving money, you better believe I know how to navigate the Windy City on a budget!

Cheap Lodging in Chicago

The Cheapskate Guide To: Chicago // yesandyes.org

Get a bed at HI Chicago – $34/night per person
This hostel is located right in the heart of downtown. You can’t get much cheaper than this when you’re only a 10-minute walk from Millennium Park! They often have coupon codes on their site, so be sure to look for one before booking.

Park your RV at McCormick Place – $35/night
Camping sites that are less than an hour from downtown Chicago are basically non-existent. However, if you’ve got an RV, you can park it at McCormick Place, then hop on the #3 bus to be downtown in 15 minutes.

Rent a room through AirBnB – $35-$65/night
AirBnB is my go-to these days wherever I travel. You could stay in this swanky bedroom downtown for $65 or stay on this futon for $35. Whatever your budget (and comfort) needs, you can find it. My suggestion: Look someplace north of downtown, preferably off the Red Line. It’ll save you money and expose you to other Chicago neighborhoods!

Cheap Things to Do in Chicago

The Cheapskate Guide To: Chicago // yesandyes.org

Take in a concert or movie with a picnic at Millennium Park – Free
This iconic Chicago park has free events all summer along. But did you know you can bring your own food and drinks into the pavilion? Whether you’re taking in a jazz concert or watching Grease on the big screen, be sure to grab a blanket and pack some sandwiches and a bottle of wine! They also offer free yoga and fitness classes. Check out the full events schedule to find out what’s going on during your stay.

Enjoy the view of the Chicago skyline from the Signature Lounge – Cost of a drink (cheapest is $9)
The Observation Deck on the 94th floor of the John Hancock building costs $20 per adult. For an equal and cheaper view of the city, head up two more floors to the Signature Lounge and snag a table by the windows. It’s free to get in and instead of paying for a ticket, you’ll be paying for a drink. Doesn’t that sound like a better deal?

Catch some rays at Oak Street Beach – Free
If you’re staying downtown, Oak Street Beach is just footsteps away. The Chicago beaches are my favorite. It always amazes me that I can be lounging in the sand overlooking the fifth largest lake in the world with a bustling city right behind me. It’s the best of both worlds! If you’re looking for a less crowded beach, Montrose and Foster are great options that are about 5 miles north.

The Cheapskate Guide To: Chicago // yesandyes.org

Go for a run along the Lakefront Trail – Free
Or walk. Let’s be real, you’re on vacation. This trail is 18.5 miles long, following the shoreline of Lake Michigan. You’ll be sure to get some great views of the water and beautiful snapshots of the city skyline. There are also many parks along the way!

Hang with the party animals at Lincoln Park Zoo – Free
Lions, and tigers, and bears, oh my! Boasted as being one of the oldest zoos in the US, Lincoln Park Zoo is one of the best free things in Chicago. If you’re visiting over the winter holidays, be sure to check out ZooLights, where the entire place is decked out with holiday music and lights!

Fun fact: One of my favorite childhood movies, Baby’s Day Out, had scenes filmed here.

Peruse the local goods at Green City Market – Free
This is Chicago’s only year-round farmers market. It’s also the biggest! Head here for everything from artisan breads to homemade tamales to beeswax candles.

The Cheapskate Guide To: Chicago // yesandyes.org

Learn about beer with a tour at Revolution Brewery – Free
If you’ve stepped inside any Chicago restaurant, you’ve probably found Revolution beers on tap. It’s a local favorite! Hit up this free brewery tour and try some samples along the way.

Get your laugh on with improv at Second City – $7
Chicago is well-known for its improv scene. Countless comedians have been Second City trained, including Chris Farley, John Candy, and Tina Fey. But here’s a cheapskate secret: buy your tickets online through Goldstar. You can often find comp tickets (aka free) and after fees, you’ll be paying a mere $7 for a night of laughs. Who knows – you might be seeing the next big star of comedy!

Dance the night away to 90’s music at the Holiday Club – No cover, $2.50 can-tastic beer of the month
The thing I like best about this place is that the front half has a sports bar feel, but walk through the back doors on a Saturday night and you’re transported into a 90’s music flashback. Not a TLC or Britney fan? Then come on a Friday for 80’s night, complete with music videos.

Cheap Food in Chicago

The Cheapskate Guide To: Chicago // yesadyes.org

Cafecito – $6 Cuban Sandwich
I could literally eat these Cuban sandwiches every. single. day. My favorites are the Pavo and Guava-Q. And while you’re there, be sure to get some of the best coffee of your life. Their cortadito is to die for!

Bonus: If you’re staying at HI Chicago, this place is right next door.

Flub a Dub Chub’s – $5.50 Chicago Dog
There’s obviously great debate over who serves the best hot dog in the Windy City, but one thing is for sure: no true Chicago dog comes with ketchup. Try asking for some and you’ll be given a hard time! Flub a Dub Chub’s serves true Vienna beef and even has vegetarian options for the meatless folks. Their dogs come with a ginormous order of fries, so for $5.50, you’ll be plenty full. Go for the classic Flubby or spice it up with the Speiser.

Pequod’s Pizza – $4.95 Chicago Deep Dish Pizza
I have yet to make my way to Pequod’s, but word on the street is that you can get a 7” deep dish cheese pizza and fountain soda for under $5 any weekday from 11am-3pm. It’s definitely on my Chicago food bucket list!

Big & Little’s – $4 Truffle Fries and $2.99 Tacos (plus it’s BYOB!)
Known all over the world thanks to the Food Network, this place is a cheapskate’s dream. Their tacos are one of a kind, especially the Mango Chutney and Bahn Mi options. I pair these with truffle fries, and don’t even care that it’s a weird combination, because they are just too good to pass up. The best part? This place is BYOB! Save money on drinks by bringing your own.

Tip: Many Chicago restaurants have the option to bring your own beverages. Search BYOB on Yelp to find a place near you.

Billy Goat Tavern – $3.35 Cheezborger “Original”
This place may be a bit of a tourist trap, but there’s good reason – it’s the cheapest burger you can find off the Mag Mile! Don’t get lost on your way if going to the original location. It’s UNDER Michigan Avenue. To get a better feel for the joint, check out this SNL skit based on Billy Goat Tavern.

The Cheapskate Guide To: Chicago // yesandyes.org

Lickity Split Frozen Custard – $4.50 Concrete
These things are HUGE! The regular size can easily be split by two people. Lickity Split’s concretes are the equivalent to Dairy Queen’s blizzards but 1,000 times better because they are made with homemade rich and creamy custard. I’m torn between OMG and Crazy Cake – both make me drool! To top it off, the atmosphere of this place is cute to boot! It’s got a 50’s candy shop vibe, including every sweet you could imagine.

Toni’s Patisserie – $1 Macarons
Located between Millennium Park and State Street, this place is a dream when your feet are tired from a long day of shopping and being touristy. Stop in on Thursdays for $1 macarons (regularly $1.75), grab a $2.75 cup of coffee, and take a load off. They’ve also got Happy Hour specials Monday – Friday from 4-7pm!

Cheap Transportation in Chicago

The Cheapskate Guide To: Chicago // yesandyes.org

A word on transportation in Chicago: I haven’t driven a car in three years. I use the trains and busses everywhere I go. I promise it isn’t scary!

The L costs $2.25 per ride whereas the busses are $2 (transfers within 2 hours are $.25). For $20, you can get a 3 day pass. The pass is definitely worth it if you’re planning to go anywhere outside of downtown (which you should!). Skip the Ubers and stick with public transportation. There’s no greater feeling of accomplishment than mastering a big city’s transit system!

Tip: Use the Google Maps app to find out what route you need to take to get to your destination. Click the train between the car and person to switch to public transportation directions. It’s what I use every day to get around!

Thanks so much for sharing your tips, BreAnna! I’m sure there are plenty of Chicagoans who can weigh in. What would you add to this list?

P.S. Did you know I have an entire Pinterest board devoted to budget travel? There’s tons of great tips for saving money, cheap destinations, and finding awesome, affordable lodging!

photo credits: jeremy keith // hi-chicago // johnpickenphoto // don sorsa // ashleigh nushawg // shutter runner // opacity // tom campone // jared unzerzagt // john w. iwanski // meligrosa // sxates // toni’s patisserie // ryan // michael kappel // cc

4 Comments

Anonymous

The Ho Club is the best!!! Friendly people, awesome music and dancing, plus el palmar is right next door for cheap, late night, delicious Mexican food!

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taylor

Seeing this post made me so happy! I just moved to Chicago a month ago. I will definitely be visiting those restaurants you recommend, especially the custard one. 🙂

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