Eat Out / Travel There

Where to Eat and Drink in Chicago

Every time I visit Chicago, I come back with a few extra pounds as a souvenir! I’m not even that mad about it… from deep dish and hot dogs to beer and brunch, the Windy City has a lot to offer in terms of calories!

When you’re not eating, check out this weekend guide to the city! 

Deep Dish

Deep dish is a MUST! But fair warning: It’s a whole experience. The pizzas take 45 mins to make, so order up and tuck in. There’s a whole debate in Chicago between Giordano’s and Lou Malnati’s. Both are good for different reasons and both have locations across the city. Tho, if I had to pick…. Giordano’s is my fave.

Lou Malnati’s

Though I loved Giordano’s, Lou was my first bite of deep dish and I’ll always love it for that. We got the classic (and added green peppers). It was cheesy and delicious. A total knife-and-fork dish — hands would be impossible. I ate two pieces, with no shame. But I will say, those two pieces were super filling. One pizza and one bottle of wine later, I was obsessed and ready to be rolled right out of the restaurant.

Giordano’s

There was a long wait at Giordano’s in downtown Chicago during St. Paddy’s Day, but we got to order our pizza while we waited for our table, so we were eating within five minutes of sitting down. The crust is really what sets it apart for me — I ate twoish pieces and wanted so badly to be able to cram more in because so delish!

Brunches

The Hampton Social

Chicago

You’ve seen this one on Instagram. It’s got the “rosé all day” sign and the cutest nautical decor. I went for brunch, but it’s definitely cute for dinner or lunch too. I got the fish tacos (not exactly a Chicago specialty) and they were surprisingly good. You gotta go for the rosé, but I also loved the frosé.

Troquet

Chicago

For just $27, you can get 2 hours of bottomless mimosas and an entree at this lovely downtown eatery. 10/10 would recommend. That’s probably one of the best bottomless deals. It’s French food, and pretty delicious at that.

El Mariachi Tequila Bar & Grill

El Mariachi Tequila Bar & Grill

I know, I know… Mexican in Chicago? It’s honestly a sin…. HOWEVER. Mariachi has a $25 entre + bottomless mimosa deal that is WORTH turning your back on Tex-Mex for. We sat outside midday in summer and wow it was hot. But our server was truly great and let us move to a shadier table when one became available!

The mimosas were great — never did we see the bottom on the glasses! I got a skillet dish with steak and eggs. It was pretty good, but I barely made a dent in it! The french toast and steak omelet were also very good — and very large sizes! Be prepared to be rolled out of Mariachi — from being so full of food and mimosa!

Zella

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Zella is a little more expensive but it’s all you can drink AND eat. For $50, you can literally spend hours at Zella. And we did. We got there around noon and closed the brunch down at 3. Zella, which has a beer garden patio that was closed and covered in snow when I visited, usually has a line out the door. But we sat inside (obviously) and near the TVs (the Texans were on).

The food was ehh, aside from the mac and cheese. That was some of the best mac I’ve ever had. The mimosas were also just solid (although my table must have split a dozen carafes, so we didn’t hate it), but Zella’s saving grace was its throwback playlist. So many great tunes — the kind you forget you know all the words to. Everyone in the bar was so, so drunk and so, so happy.

My faves

Portillo’s

Chicago

Portillo’s is another rite of passage in Chicago. You gotta get the beef sandwich and/or the chicago-style hot dog — this is a specialty: yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt all on a poppy seed bun.

I also loooove the chili cheese dog and the cheese fries, and no I do not have any problem putting that away! YUM. Also it’s a casual $6 for a huge beer, but like $3 for wine and $4 cocktails. Such a great life you can live in Portillo’s.

Warning: You will wait in a line then you will wait again to get your food ESPECIALLY if you’re going to the downtown location. If you have a car, some of the locations have drive throughs!

Crisp

crisp chicago

The quick counter service Korean fried chicken place is a new fave! They have bowls and sandwiches, but the real treat is their wings or boneless tenders in one of their specialty sauces! I loved their BBQ sauce — it had a kick to it — and their Seoul Sassy, which tasted like nothing I’ve ever had before!

Feeling famished, I actually ordered the Foodie’s Choice Crisp sandwich that had my choice of sauce boneless chicken and blue cheese, bacon, mayo, spinach and more! It was absolutely incredible, so I highly recommend that if you don’t just want wings.

Little Bad Wolf

I’ve gone to Little Bad Wolf a couple times now: once pre-drinking and once post. It’s great for both the late night snacking as well as for brunch/lunch! My fave thing about LBW: They put bacon on everything. I recommend a burger or a bao, but if you’re really brave, like I was, I just got three sides for a meal. (It was an overwhelming amount of food!!!) The mac n cheese was the real winner — seriously the side could be an entre! And the brussel sprouts were a close second. Fries and mashed potatoes are super yum too. The best most filling lunch in town!

Bongo Room

Best for breakfast or brunch, Bongo Room is in the cutie neighborhood of Andersonville. We went before Lollapalooza and had the best pre-music fest meal.

Ok, I’m not the biggest sweets for breakfast person but I am still drooling over the pancakes I had. If you’re going in a group, you gotta split one! Their sandwiches are also top notch! There’s also a full coffee bar menu and tons of local beers. It’s not the cheapest meal around town, but it’s definitely one of the tastiest!

Purple Pig

We got super lost finding The Purple Pig, and when we did find it, there was a line out the door, which wasn’t great for us, since we were in a rush to get to Second City. Thankfully, there were exactly two free barstools, so we grabbed them. A quick Yelp search informed us that the pork shoulder was one of the best things on this earth, so we ordered that, a half bottle of wine and some spanakopitas!

All the stress and craziness finding the place was so so so worth it. The pork literally fell apart on the plate, and the mashed potatoes were amazing. Honestly, one of the best meals of my life.

Breweries

Begyle

ChicagoI have no clue how known Begyle is on the craft brews scene in Chicago, but I discovered them on Instagram and fell in love! We hung out there for a few hours playing Uno and Skip-Bo. Beers are pretty cheap — $5-7 and you try three at a time for a flight. I liked their Blonde the best and their Boogie Pijamas was a pretty great and boozy IPA. If you like coffee beers, they have a pretty amazing one.

Half Acre

This was a busy spot when we went. I feel like Half Acre is the Karbach of Chicago: The beer is great and it has a great place to hang. I got two flights (because I thought I was sharing). Unfortunately, there weren’t any labels, but I liked all the different beers! I definitely recommend going on a Saturday morning to do the tour!

Out on the town

During the winter months, Chicago peeps don’t go out too much and definitely don’t do the whole bar crawl thing. Brr. Apparently though in the summer or late spring, everywhere is popping. There are a few bar-centric hoods of Chi-Town. Here were our options:

  • Division and State: Lots of divey fun bars.
  • Old Town: Midwest bar central, meaning all the sports bars.
  • River North: More upscale — people dress up!

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