Chicago is a fascinating city full of world-class architecture, theater, restaurants, museums, and bars. It’s a diverse city that always has something new to do and see. Chicago has much to offer, but as Woody Guthrie once sang, you won’t think it’s so hot if you ain’t got the do-re-mi.
The New York Times’ “36 Hours in Chicago” recommended $25 martinis, a $30 architecture walking tour, and $44 miso black cod (its mid-level accommodation option has rooms starting at $204 per night), and never ventured more than a mile or two from the lakefront. In United Airlines’ Hemisphere magazine, “Three Perfect Days: A Trip to Chicago,” suggested the West Side consisted of Wicker Park, Logan Square, and Ukrainian Village.
As a cheaper, broader alternative, here’s our guide to seeing as many of our 77 neighborhoods as you can — on a budget. It’s Chicago for the rest of us.
TUESDAY: The North Side
Wake up in the Apache Motel on Lincoln Avenue. This mid-century gem, which still has a vertical sign topped with an American Indian head, dates back to the pre-Interstate days, when U.S. 41 was the main highway in and out of town. Best of all, rooms are only $77, which is cheaper than most Airbnbs around here. The Apache doesn’t have a pool or a gym. So to get your morning exercise, head down Lincoln to Welles Park, named for Abraham Lincoln’s Secretary of the Navy, Gideon Welles. The park’s indoor pool is open every morning for lap swimming between 7:30 and 8:45 a.m.
After you’ve worked up an appetite, eat breakfast at the Diner Grill on Irving Park Road. The Diner Grill is most famous for the Slinger — a huge pile of crispy hash browns topped with grilled onions, two cheeseburger patties, two over-easy eggs and three ladles of chili — but you really have to be drunk to appreciate it. Try a plate of fresh fruit pancakes for $8.95.
Next, if you’re an art lover, make your way to Rogers Park, which has a collection of murals painted on L viaducts, including one of the city’s musicians, from Benny Goodman to Chance the Rapper. While you’re in the neighborhood — and if you’re particularly tight on cash — enjoy a free lunch at A Just Harvest, which has been serving meals to the hungry for nearly 20 years. If you’re lucky, you’ll visit on hot dog day. Be sure to leave a donation on the way out the door.
After lunch, freshen up with a $7 haircut at A New Image Hair Salon on Clark Street. Later in the day, try a free trapeze lesson at Broadway Armory Park, then go for dinner at Ghareeb Nawaz, a Pakistani restaurant on Devon Avenue, Chicago’s “Little India,” where the chicken biryani will run you $7.99 and last for two meals.
Finally, enjoy a nightcap at Sovereign Liquors on Broadway, which specializes in $3 cans of domestic beers.
WEDNESDAY: The West Side
To prepare for your day on the West Side, stay at the Ohio House Motel, downtown Chicago’s only motor inn. It’s another mid-century masterpiece that opened in 1960, and still maintains its New Frontier charm and decor. A standard king room is $115. The highlight of Chicago’s West Side is Route 66, which begins at the corner of Michigan and Jackson, then angles southwesterly along Ogden Avenue.
It’s essential to eat breakfast at Lou Mitchell’s, a 102-year-old neon diner that serves a $6.75 bowl of cooked cereal. Since Chicago is famous for public art, stop and take a look at the Route 66 mural in Douglass Park, which features depictions of a car, a guitarist, and the Art Institute lions, which are across the street from the route’s starting point. Then take a snapshot of the Castle Car Wash, an abandoned gas station at Ogden and Hamilton avenues.
For lunch, you’ll have to venture beyond the city limits to Henry’s Drive-In in Cicero, where a corn dog is $3.75. Invented in Illinois, the corn dog is the state’s essential delicacy, combining Downstate corn with Chicago meat. Head back into the city for a visit to Out of the Past Records in West Garfield Park, where you can find “dusties” on vinyl — blues, soul, jazz, R&B — for prices that are negotiable at the counter.
If you’re looking for something to read, try Plot Twist Used Books in Portage Park, which has a good selection of mysteries. Then, head back to West Garfield Park for a true West Side feast at MacArthur’s, where you can heap your plate with fried chicken, collard greens and macaroni and cheese for $9.99.
Finally, enjoy a late-night drink at the Lakeside Bar in East Garfield Park, which has a pool table, a mural of famous Chicago bluesmen, and domestics on tap for $1.75.
Thursday: The South Side
Today’s lodgings are at the Cicero Hotel (actually a motel), which is only a mile from Midway Airport (particularly convenient if you flew in on Southwest Airlines). A Queen Ada guestroom is $139.
For breakfast, try Valois Restaurant in Hyde Park, a cafeteria-style joint that was once patronized by Barack Obama and has a sign displaying his favorite breakfasts. Two eggs with bacon or sausage are only $10.95. Valois gives you the most food for the least money – music to any bargain traveler.
If you’re an art lover, you’ll want to visit the Gage Park Field House, which has an impressive collection of murals illustrating the early contact between pioneers and Native Americans. For lunch, try the Skyway Dog House on the East Side, where a Chicago-style dog with fries (an essential treat for any visitor) is only $3.29. (It’s on 95th Street, not far from the bridge the Bluesmobile jumped.) Take your food down to the beach in nearby Calumet Park, where it’s possible you’ll see a freighter heading toward the mouth of the Calumet River.
You can’t leave Chicago without learning some of its history, so visit the Southeast Side Historical Museum in Calumet Park, which is open every Thursday between 1 p.m. and 4 p.m. and is free. There’s a diorama of Commercial Avenue during the neighborhood’s heyday, when the now-demolished U.S. Steel plant employed 20,000 workers.
West of Midway Airport is Pticek & Sons Bakery, known for its hearty cake donuts. Wash that down with a beer at Marianna’s, on 63rd Street, where cans of Stroh’s are only $1.50.
Finally, enjoy dinner at Soul Veg City, a vegan soul food restaurant on 75th Street, where the stir fry vegetable plate is $10. (If that’s too expensive, or if you like meat, you can get a cheeburger at Hyde Park’s Woodlawn Tap, a.k.a. Jimmy’s, for $4.50.)