A guest post from Lynn. Thanks!
Oak Park is the first suburb to the west of Chicago.
See two blocks and then some of Frank Lloyd Wright homes, plus his home and studio. More here: http://www.wrightplus.org/homestudio/homestudio.html
You can take a guided tour or do one of those audio tours with the little phones. IMO, the studio is well worth a tour, and I don’t even like FLW all that much.
The house that he built for his girlfriend when she was still someone else’s wife is here: http://www.oprf.com/flw/Cheney.html
birthplace of Ernest Hemingway, who really didn’t like us (but he didn’t like anybody): You can tour the birthplace home and visit the museum across the street. There are other Hemingway homes in the area (I guess they moved around!) One is now on Chicago Avenue (moved from Euclid, I think?) More about EH here: http://www.ehfop.org/
Other famous people lived here: Edgar Rice Borroughs! http://www.oprf.com/burroughs/
Kathy Griffin! And others still live here, though not the kind you would recognize on sight.
Oak Park is very walkable, though you might want to give your dogs a rest and get a ride with this guy: http://www.rickshawrick.com/ He will also point out areas of local interest/give you a tour if you are so inclined.
Our library is very nice too–the third floor is a nice place to sit and look out the huge windows. Or you can grab a sandwich and have a picnic in Scoville Park across the street (concerts Sunday night) or Austin Gardens, where they sometimes have plays in the park (right now it’s “Fifth of July”)
Other places of Interest (Cheney Mansion) gardens, house belonged to Elizabeth Cheney and then husband) and Pleasant Home on Home Avenue.
Local places to eat: Poor Phil’s (seafood, beer), Philanders (fancier; in same building as Poor Phil’s), New Pot (pan-Asian), Sagano Sushi or Sushi House ($$), Fuego Loco or Maya (mexican-ish), Hemmingways (French bistro-y), Winberie’s, Prairie Bread Kitchen or Erik’s or George’s Lido’s Cafe (super-casual; good for a sandwich), 5 Guys (burgers), The King and I (Thai), Marion Street Grille ($$), Marion Street Cheese Market, and across the street in what looks like a chain restaurant, Pompeii, which I think is wonderful and actually is an offshoot of a restaurant from the Little Italy area of Chicago (Taylor Street). Gepetto’s and Cucina Paradiso are other nice Italian restaurants.
Tasty Dog is a local fast-food hangout that used to be in a grungy place across the street but local kids staged a protest, and given that every other adult at the time worked for some major media outlet, the protest worked, and the village spent something like $1 million on this relatively flashy hotdog stand.
IMO I don’t think Oak Park is a culinary destination by any means, but you won’t go hungry here either.
This is mostly about downtown Oak Park Stuff, between the Oak Park and Harlem stops of the Green Line. There are lots of other things to do South and East, many pools, parks, restaurants (the Depot on Roosevelt, and many other wonderful restaurants there and Cermak Avenue (La Quinta de los Reyes! http://www.yelp.com/biz/la-quinta-de-los-reyes-berwyn), but hard to get to if you are on foot.
If you are taking the Green line to or from Oak Park, you might want to stop off at the Garfield Conservatory, a pretty and peaceful place to see flowers and plants–there is an indoor kids’ play area in the back, and a huge field to romp in. More here: http://www.garfield-conservatory.org/
If you come in on the Blue Line or are up for a walk (or rickshaw ride) you can see our Harrison Street Arts districts, with its studios, glassworks, and boutiques (love Careful Peach) More here: http://www.oakparkartsdistrict.com/
Buzz Cafe is a fixture here, and they have very good food and coffee and show a lot of local artwork: http://www.thebuzzcafe.com/ My personal favorite restaurant there is Trattoria 225: http://www.trattoria225.com/
Also, Oak Park has its own small conservatory, complete with cranky talking parrot George: http://www.oprf.com/conservatory