First, let’s get one thing clear: Chicago is an expensive city to live in, but it doesn’t have to be an expensive city to enjoy.
We’ve all been there, looking at a bank account that’s screaming for help while still wanting to actually leave the house. So, we turned to our Facebook community of locals to ask: where do you send friends when you’re “super broke” but still want a world-class day out?
If you are planning a trip soon or just trying to survive until payday, here is where Chicagoans go for a steakhouse-level experience on a hot dog budget.
1. The Lakefront Trail & Picnic Staples
Hands down the runaway winner for a cheap date. Locals suggest grabbing a “cheap bottle of wine” or hitting up a Jewel-Osco for snacks and a drink, then heading to the lakefront.
Whether you are walking from the South Loop up to Lincoln Park or renting a Divvy bike to cruise the path, the people-watching and skyline views are “next level.”
Pro move: find the concrete steps between Lincoln Park and the north side to enjoy the sunset without the “downtown circus.”
2. Garfield Park Conservatory
If you only have time for one activity, this is it. It is free, beautiful, and feels like a tropical escape even when Chicago weather isn’t cooperating.
It’s a “neighborhood gem” that locals recommend to everyone from tourists to long-time residents.
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3. The CTA Brown Line “Architecture Tour”
Forget the triple-digit price tag of some boat tours. For just $2.50, you can hop on the historic Brown Line.
It’s an elevated train that’s over 100 years old and circles the Loop before heading over the river for a stunning view of the city’s skyscrapers.
It is the “quintessential Chicago experience” for the price of a coffee.
4. Lincoln Park Zoo & Conservatory
One of the few free zoos left in the country, and a “clear favorite” for a low-cost afternoon.
Right next door is the Lincoln Park Conservatory, making it easy to double up on the greenery without spending a dime.
5. Free Museum Days & Mindworks
Think you can’t afford the big names? The Shedd Aquarium, Adler Planetarium, and Field Museum are “top tier” and offer frequent free days (the Shedd is a popular Tuesday go-to).
If you want something interactive and always free, check out Mindworks downtown. You can even participate in behavioral science studies to earn points for the gift shop.
6. Grant Park Music Festival
When summer hits, locals head to the lawn at Millennium Park. You can catch the Grant Park Music Festival for free while surrounded by the skyline on one side and the lake on the other.
Pack a picnic, be “discrete” with your wine, and enjoy the show.
7. Chicagoland Games (Dice Dojo)
Tucked away in Edgewater, this is a “sleeper” spot that doesn’t get enough love. You can play any of hundreds of board games completely free.
It’s a great way to spend a rainy afternoon, though locals suggest calling ahead to find the slowest days so you can “snag a table” easily.
8. The Riverwalk & Buckingham Fountain
For a “damn epic” summer night, just walk. The Riverwalk and a stroll past the Buckingham Fountain (especially when the water is on) are classic for a reason.
It costs nothing to soak in the “glamorous” atmosphere of the city.
9. Montrose Point Bird Sanctuary
If you want to “discover the Chicago you don’t know,” head to Montrose Point.
It’s a fun outdoor area to explore that feels miles away from the city noise, and it’s a “reliable winner” for nature lovers.
10. Federal Money Museum
Located right downtown, this museum is “always free.” It’s a quick, interesting stop that won’t “break the bank”, mostly because they literally show you how the bank makes the money you’re trying to save.
11. Neighborhood Hopping & Street Fests
Take the L or a bus to neighborhoods like Pilsen, Wicker Park, or Andersonville. Depending on the weekend, you’ll likely stumble into one of the city’s many neighborhood fests.
The entry is usually just a small suggested donation, making it “perfect for out-of-towners” and locals alike.
12. The 606 & Navy Pier Views
While locals usually say “don’t bother going inside” Navy Pier, walking to the very end of the pier offers a “beautiful view in all directions.”
For a more active vibe, hit The 606 trail for a walk or bike ride through the heart of the northwest side neighborhoods.
13. Cheap Seats: White Sox & Cubs
If you’re a sports fan on a budget, look for the “cheap seats.” The White Sox often have “Baseball and Brews” deals or $5 tickets.
It’s a “solid classic option” to see a game without the “triple-digit” price tag of the premium boxes.
14. Live Music at The Green Mill
For a “sexy, old-school vibe,” take the Red Line to Uptown. The Green Mill has covers that are usually around $10 for world-class jazz.
Pair it with some “cheap Asian restaurants” on nearby Argyle Street for a full night out that feels like you’re “in on a secret.”
