''A Long Way from Chicago'' is a series of short stories by Richard Peck. Set between the 1920s to 1940s, two children - Joey and Mary Alice - find themselves uprooted every summer from their city-slicker lives in Chicago, in order to live with their eccentric Grandma Dowdel in rural Illinois. While the two are initially not very happy with this arrangement, each summer has some wacky adventure happen, usually instigated by their grandmother. It won the 2001 Newbery Award for children's literature.
In the sequel, ''A Year Down Yonder'', Mary Alice is sent to live with her grandmother for a full year, due to the Great Depression hitting her family hard. Now a teenager, she must learn to survive in a hick town where life is much different than where she grew up. It won the Newbery Medal in 2001
A third book, ''A Season of Gifts'', tells the story of a new family who moves in next door to Grandma Dowdel. The protagonist is Bob Barnhart, whose father is the new preacher in town.
!! Tropes found in this work:
* AdultFear: Issues like losing one's home are touched upon in the series. There's also a chapter in ''A Year Down Yonder'' where Mary Alice experiences her first tornado, and the whole thing is terrifying.
* BatmanGambit: Grandma is very good at pulling these.
* CoolOldLady: Grandma Dowdel
* DarkerAndEdgier: To a degree. While ''A Year Down Yonder'' isn't all depressing, it is less comical than ''A Long Way from Chicago'' and deals with more adult things (Mary Alice having to live away from her family for a full year, the TheGreatDepression, a tornado, and so on).
* DeadpanSnarker: The Dowdels in general are pretty snarky.
* DefeatMeansFriendship: Subverted in general. Grandma often outwits various townspeople, particularly the snobby Weidenbachs, but she doesn't think any better of them, nor they with her. The best that can be said is that they learn it's better to simply leave her alone, rather than tangle with her. Implied to be the case with Effie Wilcox though, as the two seem to have at least some grudging respect for each other. [[spoiler:At least enough for Grandma to get the banker to give Effie her foreclosed house back.]]
* HotGuyUglyWife: The opinion several ladies hold of Franklin and Eleanor Roosevelt (though it's not so much that Eleanor's ugly as that she's really plain).
* HypocriticalHumor. In the first book, Grandma warns Joey and Mary Alice not to listen to Effie Wilcox's gossip, because they shouldn't trust what an ugly woman tells them. Joey internally notes that Grandma herself isn't exactly an oil painting.
* IWasQuiteTheLooker: Implied in one story, where Joey and Mary Alice are digging up old outfits for a festival being held in town. While searching Grandma's attic, Mary Alice unearths a beautiful dress that fits her quite well. When she wears it downstairs, Grandma is stunned and can only remark how the dress used to be her's. While her exact appearance in the dress isn't told, the plump Grandma of the books wouldn't fit in a dress that her teenage granddaughter could pull off.
* NakedPeopleAreFunny: In ''A Year Down Yonder'', Mary Alice's study session with Royce comes to an abrupt halt when [[spoiler:the postmistress runs out of the house, buck-naked, screaming. It turns out the New York painter boarding at Grandma's place was painting her nude, and a snake kept in the attic to eat mice fell on her.]]
* TeenPregnancy: Turns out, [[spoiler:this is one of the reasons Mildred Burdick never came back to school after the first chapter.]]
* TheGreatDepression: Sets the stage for the second book. Mary Alice is sent to live with Grandma Dowdel because the Depression hit her family hard.
* WorkingClassPeopleAreMorons: Played with. Many of the townsfolk are shown to be hicks, but plenty are shown to be clever enough to try to outwit each other on various occasions. Grandma Dowdel, who shuns modern technology, outright subverts the trope by being the most cunning and resourceful person in the series. Joey and Mary Alice, meanwhile, are often clueless and taken advantage of by the townspeople at first, and can only hold their own once they start thinking the same way.