Movies like The Great Chicago Adventure (2015)
The best movies like The Great Chicago Adventure (2015) are Playing with Fire (2019), Fireheart (2022) and Adventures in Babysitting (2016). If The Great Chicago Adventure hooked you with its history and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedRon's Gone Wrong (2021)7.8/10 from 2,110 votes
- NewestHenry Danger: The Movie (2025)Released 2025
Playing with Fire (2019)
A crew of rugged firefighters meet their match when attempting to rescue three rambunctious kids.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisFireheart (2022)
The film explores the world of firefighters in 1920s New York City and tells the story of a 16-year-old girl who will have to become a hero in order to save her city.
Why it matches: Recommended by TMDB viewers · both family & comedy
Worth the HypeMovies like thisAdventures in Babysitting (2016)
Two teen rival babysitters, Jenny and Lola, team up to hunt down one of their kids who accidentally ran away into the big city without any supervision.
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisThe Willoughbys (2020)
When the four Willoughby children are abandoned by their selfish parents, they must learn how to adapt their Old-Fashioned values to the contemporary world in order to create something new: The Modern Family.
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisDino Time (2012)
Young daredevil Ernie, his sister Julia, and his best friend Max accidentally trip a time-machine into operation and find themselves transported back in time 65 million years, where they meet a T-rex named Tyra and her rambunctious son Dodger.
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisThe Thundermans Return (2024)
Twins Phoebe and Max are enjoying their superhero lifestyle, but when one 'save' goes awry, the Thundermans are sent back to Hiddenville. While Hank and Barb enjoy their return, and Billy and Nora look forward to a normal high school life, Max and Phoebe are determined to regain their superhero status.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisHappiness Is a Warm Blanket, Charlie Brown (2011)
Linus is pushed to his limits when he learns Grandma is coming to visit and plans on ridding him of his childish security blanket.
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisBlackadder: Back & Forth (1999)
What was a cunning plan from Lord Edmund Blackadder V to fake a time machine on his gullibly incompetent friends, turns out to be the real thing and hurls him and his imbecile underling, Baldrick, through the course of human history.
Why it matches: Recommended by TMDB viewers · both comedy & history
Worth the HypeMovies like thisThe Loud House Movie (2021)
The Loud family travel to Scotland and discover they are descendants of Scottish royalty as they move into their giant ancestral castle.
Why it matches: Recommended by TMDB viewers · both family & comedy
Worth the HypeMovies like thisMinutemen (2008)
When three high-school friends invent a time-machine, they decide to use it to go back in time and prevent other youngsters from making humiliating mistakes.
Why it matches: Recommended by TMDB viewers · both family & comedy
SnoozefestMovies like thisPlanes: Fire & Rescue (2014)
When world-famous air racer Dusty learns that his engine is damaged and he may never race again, he must shift gears and is launched into the world of aerial firefighting. Dusty joins forces with veteran fire and rescue helicopter Blade Ranger and his team, a bunch of all-terrain vehicles known as The Smokejumpers. Together, the fearless team battles a massive wildfire, and Dusty learns what it takes to become a true hero.
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisExtinct (2021)
Op and Ed, two adorable donut-shaped animals - flummels - accidentally time-travel from 1835 to modern-day Shanghai. There they discover traffic, trans fats, and worst of all, that flummels are now extinct. It's up to this bumbling pair to save themselves and their species...and, just maybe, change the course of history.
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisDennis the Menace (1993)
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam comes to town.
Why it matches: Recommended by TMDB viewers · both family & comedy
SnoozefestMovies like thisHenry Danger: The Movie (2025)
Henry Hart meets a superfan—eager to fight crime with Kid Danger—who comes into possession of a device that can open up alternate realities. Facing a wild ride, Henry will need his best friend Jasper and his new superfan sidekick to find his way out or be stuck in another dimension forever.
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisKung Fu Panda: Secrets of the Masters (2011)
Po and the Furious Five uncover the legend of three of kung fu's greatest heroes: Master Thundering Rhino, Master Storming Ox, and Master Croc.
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisRon's Gone Wrong (2021)
In a world where walking, talking, digitally connected bots have become children's best friends, an 11-year-old finds that his robot buddy doesn't quite work the same as the others do.
Why it matches: Recommended by TMDB viewers · both family & comedy
Worth the HypeMovies like thisMinions & More Volume 1 (2022)
This collection of 10 short films produced by Illumination includes: From the "Despicable Me" franchise: Puppy (2013); Minion Scouts (2019); Training Wheels (2013); The Secret Life of Kyle (2017); Santa's Little Helpers (2019). From the "Grinch" franchise: The Dog Days of Winter (2019). From the "Secret Life of Pets" franchise: Norman Television (2016); Weenie (2016). From the "Sing" franchise: Love at First Sight (2017). From the "Lorax" franchise: Forces of Nature (2012).
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisSee Spot Run (2001)
A drug sniffing agent canine is a target for an assassin boss so the FBI calls Witness Protection to send him somewhere else. Meanwhile a single Mom puts her 6 year old boy James in the care of her irresponsible, mailman, neighbor, Gordon, when the babysitter bails on her. Meanwhile, an assassin mob boss hires 2 goons to kill Agent 11. But when 11 escapes from the van when they tried to kill him, he hides in Gordon's Mailtruck that James is in too. And guess what they name him. Spot.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisRugrats Go Wild (2003)
When the Rugrats find themselves stranded on a deserted island, they meet the Thornberrys, a family who agrees to help them escape.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisThe Jetsons Meet the Flintstones (1987)
Elroy Jetson invents a time machine that takes him back to prehistoric times, where he meets the Flintstone family.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisKiss Me, Frog (2000)
Modern version of The Frog King. Out of an impulse, 15-year-old Anna kisses a frog which then turns into a prince. But the curse is not solved that easily.
Why it matches: Similar story and style · both family & comedy
Lemony Snicket's A Series of Unfortunate Events (2004)
Three wealthy children's parents are killed in a fire. When they are sent to a distant relative, they find out that he is plotting to kill them and seize their fortune.
Why it matches: Similar story and style · both comedy & family
Popcorn FlickMovies like thisThe Chipmunk Adventure (1987)
The Chipmunks and the Chipettes go head to head in a hot air balloon race, and the winner gets $100,000. Unbeknownst to the participants, the "race" is actually a diamond smuggling ring!
Why it matches: Similar story and style · both family & comedy
Worth the HypeMovies like thisThe Spy Next Door (2010)
Former CIA spy Bob Ho takes on his toughest assignment to date: looking after his girlfriend's three kids, who haven't exactly warmed to their mom's beau. And when one of the youngsters accidentally downloads a top-secret formula, Bob's longtime nemesis, a Russian terrorist, pays a visit to the family.
Why it matches: Similar story and style · both comedy & family
SnoozefestMovies like thisBiggles (1986)
Unassuming catering salesmen Jim Ferguson falls through a time hole to 1917 where he saves the life of dashing Royal Flying Corps pilot James "Biggles" Bigglesworth after his photo recon mission is shot down. Before he can work out what has happened, Jim is zapped back to the 1980s......
Why it matches: Similar story and style · both family & war
SnoozefestMovies like thisThree Crazy Jerks II (1988)
In 2043, Frank and Xaver have only one big problem with their jobs at a patent office, their boss Dr. Kneitz who's mission it is to make their life miserable. But then an unique opportunity presents itself when an inventor shows up to patent a time machine and they come up with a plan to travel back in time to stop the conceiving of their boss. Accidently Ronny, a night watchman, happens to be in the room with them when they use the time machine and so, in part unwillingly, the 3 of them travel to the year 1988 in Gran Canaria and they only have a couple of days to stop every interaction with potential fathers for the mother to be.
Why it matches: Similar story and style · both comedy
Southland Tales (2007)
Set in the futuristic landscape of Los Angeles on July 4, 2008, as it stands on the brink of social, economic and environmental disaster. Boxer Santaros is an action star who's stricken with amnesia. His life intertwines with Krysta Now, an adult film star developing her own reality television project, and Ronald Taverner, a Hermosa Beach police officer who holds the key to a vast conspiracy.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisThe Visitors (1993)
After a wizard's spell goes awry, 12th-century Gallic knight Godefroy de Papincourt, Count of Montmirail finds himself transported to 1993, along with his dimwitted servant, Jacquouille la Fripouille. Startled and perplexed by modern technology, the duo run amok, destroying cars and causing chaos until they meet Beatrice de Montmirail, an aristocratic descendant of the nobleman, who may be able to help them get back to 1123.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisBack to the Future Part II (1989)
Marty and Doc are at it again as the time-traveling duo head to 2015 to nip some McFly family woes in the bud. But things go awry thanks to bully Biff Tannen and a pesky sports almanac. In a last-ditch attempt to set things straight, Marty finds himself bound for 1955 and face to face with his teenage parents -- again.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisThe Promised Land (1975)
At the turn of the century, Lodz, Poland, was a quick-paced manufacturing center for textiles, replete with cutthroat industrialists and unsafe working conditions. Three young friends, a Pole, a Jew, and a German, pool their money together to build a factory.
Why it matches: Similar story and style · both history
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like The Great Chicago Adventure?
The closest matches to The Great Chicago Adventure are Playing with Fire (2019), Fireheart (2022) and Adventures in Babysitting (2016). Below are 27 more, each with the reason it matches.
What should I watch after The Great Chicago Adventure?
Start with Playing with Fire (2019), the closest match to The Great Chicago Adventure.
What is the highest-rated movie like The Great Chicago Adventure?
Ron's Gone Wrong (2021), rated 7.8/10 by 2,110 TMDB users.
What is the newest movie like The Great Chicago Adventure?
Henry Danger: The Movie (2025) is the most recent release on this list.
Are there English movies like The Great Chicago Adventure?
Yes: Playing with Fire (2019), Fireheart (2022) and Adventures in Babysitting (2016).
How are movies similar to The Great Chicago Adventure chosen?
First come films that Trakt’s viewers watch alongside The Great Chicago Adventure, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.