While Chris Farley wearing a grass skirt and coconut bikini might be the first thing that comes to mind when you think of Chicago, there’s more to the Windy City beyond Polish Sausage, the Bears and Ditka- just don’t think of taking his name in vain within city limits. While it might not get the same attention as NY or LA, event just a quick weekend trip will show you plenty of reasons why Midwest is best.
PUT EM BACK
HOPLEAF BAR || 5148 N. Clark St., Chicago, IL 60640
This place is first on our list because it feels like quintessential Chicago. Oh, it also has one of the best draught beer lists we’ve ever seen. This bar has been slingin’ beer for 25 years, and recently added onto the kitchen to satisfy any of your stick-to-your-ribs bar food needs.
MAP ROOM || 1949 N. Hoyne Ave., Chicago, IL 60647
Map Room is kind of what it sounds like it would be. It’s a bar with a beer selection from all over the map. Is that what you thought it was? Well, you’re right. It’s a casual bar with beer you’ve never heard of and probably could never pronounce.
THE DRIFTER || 676 N Orleans St., Chicago, IL 60654
Underneath the historic Green Door Tavern lies this odd little bar. Their motto is “Come as you are. And leave the way you want to be.” It’s dark and it’s eerie inside, and that’s what the owner was going for. The big attraction to this bar is the dark, almost gothic, entertainment which is specially curated to match the image of the bar.
THREE DOTS AND A DASH || 435 N. Clark St., Chicago, IL 60654
When you find yourself in Chi-town it might be cold, windy, and rainy. Three Dots and a Dash is the cure for that. It’s a Hawaii themed lounge with awesome cocktails made with fresh fruit juice. The food served is light and tropical. Every city should have a bar like this.
WEINER'S CIRCLE || 2622 N Clark St, Chicago, IL 60614
While this should technically be under the Good Eats header, if you end up at the Weiner’s Circle- which we strongly suggest you do- it’s likely been at the end of a loooooooong evening at some of the above watering holes. Hot dogs, fries, burgers, you name it, they’ve got it. Famous for berating their customers, you’re sure to end your night with some quality entertainment; especially if you order the Chocolate Shake...please order the chocolate shake.
SUPERDAWG DRIVE-IN || 6363 N Milwaukee Ave., Chicago, IL 60646
Not too far from Edgebrook Golf Course is this drive-in hot dog joint. It’s a super casual and classic experience that’s hard to find anymore. Pull up, order, and eat this classic American food. Oh, they were founded in 1948, so you can bet this place makes a mean authentic Chicago hot dog.
JOE’S SEAFOOD, PRIME STEAK, AND STONE CRAB || 60 E Grand Ave., Chicago, IL 60611
The name says it all. Joe’s is the place to go for a classic steak house dinner. This is an awesome date spot, one that you’ll thoroughly enjoy too. If you’re having trouble deciding between a steak and seafood, allow us to suggest the fried chicken.
PORTILLO’S ||100 W Ontario St, Chicago, IL 60610
While they can be found all over the city, a trip to Chicago without a stop at Portillo’s is near sacrilege. Tough to find outside of Chicago, the highlight here is the Italian Beef Sandwich- part french dip, part New Orleans Muffuletta, all delicious.
AU CHEVAL || 800 W Randolph St, Chicago, IL 60607
Self described as a “diner style bar and restaurant with a passion for eggs,” Au Cheval is currently getting most of their acclaim from their top notch burger which many claim is the best in the country. While the food will satisfy no matter what path you choose, you’ll also want to ensure you arrive thirsty with an unrivaled cocktail and shot list that also featured root beer floats and the three dollar tall boy of your choosing.
LOU MALNATI’S || a few locations in the city
There's not much more iconic than Chicago Deep Dish pizza and while everyone has their favorite, for us no one has been doing it better than Lou's. It might get knocked by the New York City crowd, but a thick, sausage topped, cheese filled slice of Lou's satisfies like the best of the Big Apple.
GET YOUR FIX
SAWADA COFFEE || 112 N Green St., Chicago, IL 60607
Did you know there are world renowned baristas? Apparently one of them owns this place and his name is Hiroshi Sawada. This dude makes killer caffeine concoctions for you to enjoy in this industrial yet comfortable building.
MILLENNIUM PARK || 201 E Randolph St., Chicago, IL 60602
Millennium Park, maybe better known as the home of that giant reflective thing that looks like a bean. Go and snap a few pics with “The Bean” then head over to Wrigley Square for a relaxing time in the park smackdab in the middle of Chi-town.
NAVY PIER || 600 E Grand Ave., Chicago, IL 60611
Take a boat tour of Lake Michigan. See a play at Chicago Shakespeare Theater. Take a ride on the Centennial Wheel. Navy Pier is the perfect place to kill a few hours between meetings and obligations. There is always something going on here that you’ll want to check out.
OFF THE GRID
BURNHAM PARK || 5491 S Shore Dr., Chicago, IL 60615
Burnham Park is a great place to go if you’re looking for some r&r. There’s an awesome lakefront beach that’s slightly outshined by Northerly Island which grants some incredible views of the city.
FILL YOUR BAGS
State Street is a historic shopping area located in the heart of the Windy City. There’s loads of shops to pick up great clothes and trinkets on State Street. It’s also scattered with art installations and landmarks, including the original Playboy Mansion.
HANG YOUR HAT
CHICAGO ATHLETIC HOTEL || 12 S Michigan St., Chicago, IL 60603
Everything about this hotel is badass. It might look like a cigar lounge, but don’t blame us when they tell you to put out your stogie. If you’re trying to stay in for a night while here, wander down to the Milk Room for a classic cocktail, then hit up the Game Room for a gentlemanly game of bocce ball.