Eat, Drink, Stay – Chicago, Illinois, USA

Eat, Drink, Stay
Chicago, Illinois, USA

No matter where you’re headed, you’re going to need the basics. Chicago offers a broad range of accommodations for the hungry, the thirsty, and the weary; there’s something for most wallets – although you may have to hunt to find a genuine deal – and tastes in every category. Here are some tips from Chicagoland residents and visitors on where to eat, drink, and sleep.


You might vaguely recall Chicago being touted as one of the Fattest Cities in America. Actually, that ranking is assigned annually by Men’s Health Magazine, and Chicago has bounced back and forth in the top five for years; while it never quite edges out Houston, Texas, it comes close. While that particular study may not be entirely scientific, it’s certainly not counter-intuitive. Chicago has fewer junk food places (ice cream shops and the like) than many big U.S. cities, but the favorites are often equally nutritionally devoid. That, of course, doesn’t affect the deliciousness factor, so don’t be deterred.

For that greasy fix, head on over to:

Superdawg Drive-In
Where: 6363 N. Milwaukee Avenue
Open: Sunday-Thursday 11am-1am, Friday-Saturday 11am-2am
How much: ~ $5/meal
Why go: The city’s only drive-in restaurant, Superdawg has a retro 50’s theme and what are reputed to be the best Chicago-style hot dogs anywhere. The atmosphere is great, but the Superfries are unparalleled.
Fun slogan: “From the bottom of my pure beef heart, thanks for stopping.”

In the mood for a neighborhood gathering?

The Fireside
Where: 5739 N. Ravenswood Ave.
Phone: (773) 561-7433
Open: Hours: 11am- 4am Monday through Friday and Sunday; 11am -5am Saturday
How much: $8-$15 entrée
Why go: The friendly service and casual atmosphere, along with the massive all-weather outdoor porch, differentiate this restaurant from a million other little pizza/rib/Cajun/beer joints. Don’t come here expecting to be blown away by anything; the allure is the restaurant’s simplicity.
Best feature: outdoor patio

How about Eastern fare?

Hama Matsu Japanese/Korean Restaurant
Where: 5143 N. Clark St.
Phone: (773) 506-2978
Open: 3-11pm Monday through Saturday; 3-10pm Sunday
How much: $8-$15 entrée
Why go: Hama Matsu is best known for their made-to-order dishes, sometimes composed on the spot by the chef.
Tidbit: They actually have low-carb sushi rolls. Huh.


87th Street Barbecue
Where: 100 West 87th Street
Phone: (773) 846-8829
Open: 11am – 12am every day
How much: ~$5 entrée
Why go: The emphasis is on barbecue, and they do it well here. Fast food, yes, but better than burgers.
Caveat: They only take cash.

Enough with the meat, already.

Chicago Diner
Where: 3411 N. Halsted St.
Phone: (773) 935-6696
Open: 11am-10pm Monday through Friday; 10am-10pm Saturday and Sunday (during the summer, the restaurant stays open half and hour later daily)
How much: ~ $10 entrée
Why go: According to the natives, the Chicago diner is one of the best vegetarian places in the city.
More incentive: Free parking!

So what about those of us with deflated bank accounts?

Brian’s Juice Bar and Deli
Where: 80 E. Lake St.

Phone: (312) 332-3435
Open: 6am-10pm Monday through Friday; 9am-7pm Saturday; 9am-5pm Sunday
How much: <$5/meal
Why go: It’s cheap, it’s fresh, and it’s tasty. You can get everything from the standard deli stuff to Mediterranean specialties to protein shakes.
What’s with the menu: Brian seems to be capitalizing on the enormous health club located right next to his deli.

Spiro and Star (S & S) Restaurant
Where: 823 W. Randolph St.

Phone: (312) 666-6414
Open: 6am-midnight, Monday through Saturday; closed Sunday and holidays.
How much: <$5/meal
Why go: For inexpensive Greek food or a breakfast specialty, it’s a quick stop.
Fun motto: “Avoid tension. Order ahead.”

Where: 3324 N. Broadway

Phone: (773) 868-6262
Open: 10am-10pm Monday through Friday; 9am-11pm Saturday; 9am-9pm Sunday.
How much: <$8/entrée
Why go: Mamacita’s has the warm atmosphere only a small restaurant can have, but serves up healthy and vegetarian fare in addition to traditional Tex-Mex and Mexican staples.

Dude: Like many of Chicago’s restaurants, Mamacita’s has a BYOB policy.


There is no shortage of bars in Chicago. Sports bars, bars with live music, and regular old bar bars are the most common.

Sports bar

Where: 111 E. Wacker Dr.

Phone: (312) 616-3663
Why go: This bar is very popular, not to mention covered in Chicago Bulls paraphernalia. You can’t get much more sports bar-ish than this.

Bar with music
The Cotton Club

Where: 1710 S. Michigan Ave.
Phone: (312) 341-9787
Why go: Not only is this a re-creation of the original Harlem club, it’s one of few places you can get two very different but related types of music. One room features contemporary jazz and blues, while the other features hip hop.

Bar bar
Kasey’s Tavern

Where: 701 S. Dearborn St.
Phone: (312) 427-7992
Why go: This is a neighborhood bar with a whole lot of history – it dates back to 1889.


The most economical way to go is probably with the hostels scattered around the city. Check out BootsnAll’s Chicago hostels page to find one, or BnA’s cheap hotel page. Expect to spend between $12 and $30 a night at a hostel, depending on your preference for rooms and availability. Hotels may run you a little bit more, but can be worth it if you’re not into hostelling. I suggest the Four Seasons Ritz-Carlton downtown. Just kidding. There are plenty of chain hotels and motels in the city and the suburbs that are easily accessed by train or bus.


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