Diner Grill – Lakeview
Nights out in Wrigleyville are likely to end late, and even more likely to end in a quest for lots of greasy food. On your next trip, look no further than Diner Grill, a 24-hour old-school diner built inside a rehabbed train car. Enjoy all your egg, bacon and pancake favorites, or try your hand at their legendary Slinger: this monstrosity includes two burger patties, two eggs sunny-side-up, cheese, hashbrowns, onions, chili and a side of toast. It will definitely sound like a good idea at 4 am, and if you manage to finish it, you get your very own certificate of victory.
1635 W Irving Park Rd, Chicago, IL, USA, +1 773 248 2030
Max’s Place – Uptown
In a north-side neighborhood that often gets either overlooked or favored for its jazz clubs and concert venues rather than its bars, a bar like Max’s brings a different kind of nostalgic feel to Uptown. It comes with all the dive requisites: family-owned and operated for over 35 years, cheap beer, an old-timey jukebox and a hesitancy to accept anything but cash. Stop in for a cold $1 OldStyle and have a chat with a bartender, who may tell you a tall tale about Al Capone free of charge.
4621 N Clark St, Chicago, IL, USA, +1 773 784 3864
White Palace Grill – Loop
White Palace Grill is the all-star of Chicago diners, and the rest of the country has taken notice. It was featured on an episode of the famed Food Network series Diners, Drive-Ins and Dives, where Guy Fieri himself chatted with patrons of the packed house and sampled its best dishes, which are almost all made from scratch. White Palace Grill has been open continuously on the south edge of the Loop since 1939, as it operates 24 hours a day, 365 days a year. Whether you’re here to end your night or start your day, it’s sure to rival some of the tastiest diner food you’ve ever had.
Southgate Market, 1159 S Canal St, Chicago, IL, USA, +1 312 939 7167
K’s Dugout – Andersonville
Head a few blocks west of Clark Street for K’s Dugout, a quaint neighborhood bar that gives off all the right vibes. It’s a great spot to catch a Cubs or a Blackhawks game on a weeknight, with the cheapest drinks around and a side of free popcorn. They do monthly open-mic nights, raffles and watch parties for all the big games. But come with your competitive side geared up, because they also offer trivia, darts, shuffleboard, Pacman and pool.
1930 W Foster Ave, Chicago, IL, USA, +1 773 561 2227
Jeri’s Grill – Lincoln Square
If you’re looking for a good, cheap meal at any time of day with no frills or fancy expectations, Jeri’s is the place for you. It stays open 24/7, which makes it great for late-night pig-outs, but it’s just as tasty for breakfast, when you’ll see a crowd of locals who keep coming back. Sit in a booth or at the bar and pick your favorite tune on the jukebox, because Jeri’s has a classic old-school charm that just can’t be beat by the onslaught of fancy brunch joints across the city.
4357 N Western Ave, Chicago, IL, USA, +1 773 604 8775
Ed & Jean’s Tavern – Bucktown
In a neighborhood feeling the presence of yuppie cocktail bars and expensive boutiques on every corner, Ed & Jean’s remains an oasis of dive-bar calm. Come for the free pool and laid-back sports bar atmosphere, but stay for the cases of PBR and cheap apple pie shots. If that’s too straightforward for you, live on the edge and spin their drink wheel that sits behind the bar for a surprise every time. Everything’s cheap and everyone’s friendly, which makes it the best place to while away a weekend.
2032 W Armitage Ave, Chicago, IL, USA, +1 773 851 8054