20 ways to do Chicago for under $20

Garfield Park Conservatory

Truly a tropical oasis in the city, the Garfield Park Conservatory is home to stunning and fragrant botanicals unlike anywhere else in town. As for the kiddos, they’ll thrill for the interior Children’s Garden and the Outdoor Gardens — including the Play & Grow Garden, just perfect for climbing, creating and communing with nature.

Admission is free, with a suggested donation

300 N. Central Park Ave., Chicago

The Signature Lounge at the 96th

Yes, the views from atop the Hancock Tower are amazing, but hanging out a few flights down on the 96th can score a martini for you, a juice for them — and the very same jaw-dropping vistas. 

Reservations suggested

875 N. Michigan Ave., Chicago

North Park Village Nature Center

46 acres of sprawling, glorious woods, savannas and wetlands? It’s never been easier to “get lost” in the city! (Bonus: There’s a terrific hands-on discovery room, an educational facility and rabidly popular day camps, too.) 

5801 N. Pulaski Rd., Chicago

The Original Rainbow Cone

Started in 1926 by a man with a dream beyond chocolate and vanilla, a true Rainbow Cone features decadent layers of chocolate, strawberry, Palmer House (New York vanilla with cherries and walnuts), pistachio and orange sherbet. Baby Cones start at $2.99 and a quart will run you $10.99 — choose wisely. 

9233 S. Western Ave., Chicago

Chicago Riverwalk

This gem along the city’s busiest part of the Chicago River is well worth a stroll any ol’ time, but Free Tours by Foot offers architectural tidbits for the history buffs among you —  and ends near Navy Pier, for the kids (or kids at heart).

Free, with gratuity optional

1 Wacker Drive, Chicago

606 Trail

Once the bustling Bloomingdale train line, the Bloomingdale Trail (also lovingly known as the 606) is one part city park, one part bikeable trail, and about eight parts “I can’t believe how awesome this city is.” 


Between 1800 N. Ashland and 1800 N. Ridgeway, Chicago

‘The Infinite Wrench’ at the Neo-Futurarium

With a run time of 60 minutes- and an attempt to perform as many 2-minute plays as humanly possible in that time frame — the Neo-Futurists bring their brand of hilarious, horrifying, and heartfelt performance to the masses, who are eager to see what’s next for this edgy troupe. (And for a roll-the-die price of under $20, too.)

5153 N. Ashland Ave., Chicago

Chicago beaches

Can’t pick your favorite one? You’re not alone. And with 28 miles of dedicated Chicago beachfront and park grounds to choose from between the South Side to Evanston, nary a person could blame you.


Chicago Trolley & Double Decker Co. Tour

If seeing the city by the light of the moon’s more your thing, Chicago Trolley’s hop on/hop off nighttime tour is just the ticket. From Millennium Park to the museum campuses and back up to the Skydeck, feeling the wind rush through your hair while learning architectural trivia will be the most fun you’ve ever had in Chicago traffic.

$20 for adults, $18 for kids 5-15, 4 and under are free

135 E. Randolph St., Chicago

Lincoln Park Zoo

If it’s been a while since you’ve stomped, scurried, and strolled at the Lincoln Park Zoo, they’ve got some new friends they’d like you to meet (namely, the baby penguin chick at the Pritzker Penguin Cove)! While there are many pay-to-play exhibits at the zoo, like the Penguin Encounter and the AT&T Endangered Species Carousel, the majority of this outdoor wonderland is free — and always has been.

2001 N. Clark St., Chicago


Chicago Theatre Marquee Tour

Refined patrons of the arts and Broadway babies alike will thrill for a behind-the-scenes tour of the iconic Chicago Theatre. Grand architectural highlights abound, of course, but the chance to stand on the same stage as Frank Sinatra after spying his signature in the dressing room? Well, they can’t take that away from you. (On State Street, that great street, no less!)

$15 for adults, children 12 and under are free

175 N. State St., Chicago

Ping Tom Memorial Park

Chinatown is a terrific neighborhood to explore, and Ping Tom Memorial Park’s 12-acre site is a great starting off point. Stroll the walking paths by the river, marvel at the beautiful Chinese landscaping and artwork … and make sure to save room for bubble tea and dim sum at the many nearby hot spots. 


200-322 W. 18th St., Chicago

Chicago SummerDance Festival

Whether you’ve got the rhythm in your heart or two left feet on the floor, the SummerDance folks have got your back. Each summer weekend, the 4,900 square foot dance floor in Grant Park’s Spirit of Music Garden will open up for instructional dance lessons — a different kind each week! — and the chance to shake it with an all-ages, all-encouraging crowd.


601 S. Michigan Ave., Chicago

Chicago River Canoe and Kayak

Hop into the Chicago River (and a kayak) at one of the gentler spots along the water’s edge, right between the Avondale and North Center neighborhoods. Forget bird’s eye view — the best way to see the town is from the point of view of a duck.

Rentals start at $15

3400 N. Rockwell, Chicago

North Shore Channel Trail

Avid biker — but looking to avoid as much of the lakefront congestion as humanly possible? The 13-mile North Shore Trail connects the North Side of Chicago to Evanston and Skokie, as well as many, many parks. Happy trails!


Begins at Ronan Park, 3000 W. Argyle St., Chicago

Art Institute of Chicago

Voted the world’s best museum on TripAdvisor, the Art Institute boasts an impressive amount of classics, hands-on fun, and who can forget about those incredible tiny spaces in the Thorne Miniature Rooms?

$20 for Chicago residents, kids 17 and under are free

111 S. Michigan Ave., Chicago

Movies in the Park

From Berger to Vittum Parks — and with a lineup as varied as the park listings — few things are nicer than watching movies under the stars. And if that span of time also involves your offspring sitting rapt (and quiet)? Ah, bliss.


Various locations across Chicagoland

Maxwell Street Market

A long (long!) running tradition beloved by Chicagoans, Sundays are for the Maxwell Street Market. Bargains, antiques, and globe-spanning cuisine line this open-air treasure trove. Go find your new favorite thing!


800 S. Des Plaines Ave., Chicago

Maggie Daley Park

The city’s biggest playground comes with quite a backdrop: the Chicago skyline, to be exact. But with a skating ribbon, mini golf, and a 3-acre Play Garden (including a 1,200 square foot Watering Hole of epic splashing proportions), who’s even looking at those buildings, anyhow? General park admission is free, $12 for roller blade and scooter rental, $11 for mini golf

337 E. Randolph St., Chicago

University campus tours

From the North Side’s gorgeous Madonna della Strada Chapel at Loyola University Chicago to the South’s unparalleled Frank Lloyd Wright Robie House at the University of Chicago, families can get quite the Chicago walking tour education on the cheap! (Once enrolled? Slightly different price point.)


Loyola University Chicago, 1032 W. Sheridan Rd., Chicago

University of Chicago, 5801 S. Ellis Ave., Chicago

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