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! 

Pizza

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 Deep Dish

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.

Chicago Pizza and Oven Grinder

This place — made famous for its pizza pot pies — is NOT all it’s cracked up to be. However, it’s damn delicious. We got there at 10:30 pm on a Friday night, thinking we could avoid a long wait. Nope. Got quoted an hour and a half, so we left for no more than 45 minutes to take a Malort shot (obviously). When we got back, the teenager who was taking people’s names on a tiny notebook said he already called us, and since we left, he can add us back on the list. Sir, you quoted an HOUR AND A HALF and we were gone 45 minutes. Who was wrong here??? Anyways, we took a seat at the bar and got some wine. I had to hit the ATM twice because this place is CASH ONLY. Ugh, such a tourist trap. We didn’t end up sitting down until midnight, so right on par with that quote after all. (And only because I made the pimply teen look me in the eyes — a thing he was avoiding — and actually take us to the immediate next table.) Rant over.

The actual food was pretty incredible. Note: Pizza pot pie is NOT deep dish. The crust is literally like a pot pie’s and it’s so different and delicious. The surprise star was the oven grinder, which is basically like a sandwich. Holy crap. Best sandwich I’ve ever had?

Giordano’s Deep Dish

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

Ann Sather’s

Ann Sather has been on my list to visit for SO LONG. It’s very diner-esque, but the true star is the cinnamon rolls, which are a side and come in pairs. We ordered one pair to split, and our server brought us two orders, because he is an angel sent from heaven. Bonus: Ann Sather is BYOB and NO corking fee.

Those were the real stand outs. There are a lot of typical breakfast things, and you might have to wait on a busy weekend day.

Bar Roma

Bar Roma is such a steal of a bottomless — an entree and bottomless mimosas is $24. I got the carbonara and it was so freaking good. The croissant sandwich also looked great.

The Hampton Social

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

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

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

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

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!

Au Cheval

Heralded as THE BEST burger in all of Chicago, Au Cheval does not disappoint. However, this was another place to expect a 3-hour wait. But…. not for us. Tiny brag moment. We walked into the restaurant on a whim and with very low expectations. We heard the woman in front of us get quoted 3 hours for her party of 3, and we were just going to ask our wait and see if the bar was first come, first serve. The guy said he had a table no-show so we actually got to sit immediately. WHAT LUCK.

The actual food: We split the burger (double, add bacon) and some fancy fries with the best sauces ever. We ate every single bite of this meal, with no regrets, and feeling like the luckiest girls alive.

Crisp

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.

Hopleaf

This is a bit of a neighborhood joint, but if you’re in the area, check it out. Great beers and heavy wine pours, plus innovative sandwiches that come with a mountain of fried and mac and cheese that’s pretty great.

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

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!

Ballast Point Brewery

Ok, this is NOT a Chicago-based brewery. (It’s actually based in California.) But, it does have a new outpost in Chi-town, and it has a few special beers brewed on site. Highly recommend those, but they actually have the LARGEST beer menu I’ve ever seen.

Out on the town

My two favorite things to drink in Chicago are glogg (warm wine with brandy) and Malort. Wait, I know everyone talks about how Malort is gross and all, but it really wasn’t that bad and is basically a rite of passage in the city. It’s got a long history in Chicago and is made there. It’s a digestiv — like negroni — and has a citrus flavor (more grapefruit than orange). It’s a tough shot, for sure, and there’s almost like a recoil of the flavor hitting you. You’re make a face. That’s called the Malort Face.

If you’re down to hit the town, 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!