I’m not here to fight over the origin of the nickname “Windy City” with you, don’t worry. (I still side with the politics version BTW). I just wanted to share some of my favorite restaurants and tips for visiting Chicago. I went in September a while back for a long-weekend and exceptionally enjoyed my stay.

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Think: New York City hustle, with Midwestern kindness, mixed with straight up Cleanliness. Yeah I said it.

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For my first time in Chicago, I was told to stay in their (and I’m cringing while typing this) “Times Square” area. Luckily for me it resembled nothing to the shithole I’m used to in NYC, but a cute (decently touristy) area. I guess this would be referred to either River North / West Loop / New East Side.

Kinzie Hotel


I managed to snag a room at the Kinzie Hotel – an adorable boutique establishment right in the River North area, easily walkable to main attractions. You can bet your ass I went every morning to the included breakfast, mostly to stock up on portable peanut butter packets and OJ for the impending hangovers.


Free Tours By Foot – Day

Whenever traveling to a new city, whether domestically or abroad, I always try to look for a free walking tour. You obviously tip the dude doing all the work, so it’s not really free, but I feel they work a lot harder to keep you entertained and not just spit out facts no gives a shit about.


I’ve used this company Free Tours By Foot a few times in other cities and really enjoyed it. There were a few types of tours to chose from but first thing I did was the Architecture Tour.


I work every day in  Midtown Manhattan and I can tell you straight up – there is nothing like the architecture you find in Chicago.


Each building has its own wealth of history attached, just as every sculpture has its own function. The overall beauty of these dominating constructions can really only be appreciated in person.


The facades, the compositions, the little nuances – they are all worth a closer look.


Ok so let’s get back to what we really came here for – the food.

Lou Malnati’s


There are quite a few locations of Lou Malnati’s, but don’t let that you veer away just yet. Known for their deep dish pizza, I have (surprisingly) heard rave reviews of their Caesar salads. I’m not even joking you.


For my first deep dish pizza in Chicago, I was pretty sold. The salad, though, words cannot describe. I need the recipe for this dressing seriously. For a somewhat chain restaurant, they definitely deliver.




Oh hey, it’s me! Back to Chicago…


The Bean / Millenium Park


What’s more quintessential Chicago than “The Bean”? Situated in the AT&T Plaza at Millennium Park, it’s technically named “Cloud Gate”. But, let’s be honest, “The Bean” just sounds so much more fitting.


Honestly, it’s nothing more than a horrendous tourist trap. I mean, don’t get me wrong,  the actual “Bean” is a beautiful piece of art. The reflection of the nearby buildings in the stainless steel’s curvature is beyond impressive. But – trust me – go on an off time, take your obligatory reflection pic, and then bounce.


Millennium Park as a whole I’d probably just do a walk through so you can tell everyone you did it. (Crowds are not my thing, can you tell?)


Free Tours By Foot – Night
You gotta throw in a late night stroll and admire the architecture in different light (preferably after a few Goose Islands if you know what I mean).


Side note: I did try to do a general Chicago walking tour during the day (along with the Architecture one I had that morning), but found it a little drab, as a lot of the information overlapped. So I unfortunately left that one early.

But I did take the night tour (all 3 were from the same company) and really enjoyed the contrast.


It’s such a beautiful city to wander aimlessly at night. The lights from the skyscrapers reflect off the river, giving this illumination you can’t find in many other places. (I dare any NY’er to tell me where you can find something like this).


Chicago Pizza Tour

The following day I did a Chicago Pizza Tour. I honestly found it on Groupon on a 20% off day and said why the hell not. Unless you have the dough (pun!), I would probably Google shit and do it yourself. Not saying I had a bad experience whatsoever, just saying I didn’t get enough pizza for the amount of money I paid. (But bonus points: My tour guide was most def high AF and extremely hilarious).


First stop was the OG – Uno’s Pizzeria. Did they create the deep dish, or did Malnati’s? We’ll never know. Either way, their sauce was a bit more bitter than expected, but I think it really helped mild out the amount of cheese hidden underneath. I liked it, just wish the crust wasn’t as crunchy.


Second stop was Quartino – a more refined establishment with mostly Italian-based pizza. If I wanted thin crust sparse cheese pizza I woulda just grabbed it at my local pizzeria in NYC – I’m just sayin.


Last stop, and probably everyone’s favorite, was Giordano’s (insert every tongue-out/drooling emoji possible). Yup, cheese, sauce, bread – that’s all you need. And they do it well. The marinara sauce is so much more different in Chicago than NYC, but I’m not complaining. If there’s that much bread involved, I think a tangy sassy sauce is required.


Definitely want to come back just for this bad boy.



Anyone who knows me knows I love me some craft beer. Luckily Chicagoans get to venture to both Lagunitas and Goose Island breweries – which I made a point to visit both on my trip.


They’re equally somewhat out of the way of downtown, so Uber might be your best bet. Definitely check the brewery tour dates beforehand, because they vary per season and day of the week. Also schedule beforehand if you can, since I know they do fill up during the busy season.

Lagunitas Brewery


For a beer that I thought was only bottled and sold from California, I was really thrown off on this one. Plot twist: The brewery originated in California but the owner wanted to open up a larger distribution center in the city he was from – Chicago. They’ve opened up a few more locations since, but a lot has probably changed since my visit a while back.


Tour guide was thoroughly knowledged; I never felt bored. For a free tour (which it was then – I can’t find any update now), it surpassed my expectations. Plus, I mean, I’ve loved this brand of beer for years. Seeing how it was made and distributed met my heart’s content.


Such a funky building with a lot of flair. You know damn well my ass bought a bunch of trinkets to take back.

Goose Island

As impressed as I was with the originally California-based brewery, I think Goose Island takes my win. Named after a local landmark (the actual Goose Island being about a mile or two away), it has always been my go-to beer at any bar that serves it on draft.


Their IPA has seen me through my good, my bad, and most definitely my ugly. But I wouldn’t trade those memories for anything. Even if it meant allowing their employees to force me to wear these nasty ass boots before going on the brewery tour. Apparently my open-toed sandals were a risk for falling beer cans or something, I don’t know.


Their tour was just as in-depth as Lagunitas was (but let’s be honest, they’re all for the most part the same). Hops and hops and barrels and shit – we get it. They did provide an adequate amount of beer tasting though, which I did enjoy.


Da Lobsta


Why they spelled this location’s name based off Mark Wahlberg’s accent I don’t understand. But the food was good. Not enough lobster for my liking, but it did the job for a somewhat take-out kind of restaurant.


Shoreline Sightseeing

What would Chicago be without a boat tour, right? The city is situated around many rivers and if you’ve ever watched “The Break Up”, you’d know that the Grobowski’s wanted to take the city by bus, boat, and air.


I chose the Shoreline Sightseeing tour, as suggested by my pizza tour guy. It’s a bit expensive (maybe $20ish a person), but I used my Chicago Go Pass – More on that below. Either way, I think it’s quintessential thing to experience.



Under bridges and around prominent architecture, the boat tour took us throughout and then outside of the Chicago River. The tour guide depicted stories of histories past and elaborated on decorations found on some of the buildings.


Oh, and there’s beer on board – always a plus in my book.


Basically you get to see Chicago in a way that can’t be done by foot. Plus you get some really cool photo ops.


Eataly Chicago

I want to give this shoutout to my Eataly Flatiron in Midtown NYC – You still the real MVP. While the concepts of both Eataly’s are identical, I found the food and prices a little inferior to that of NYC’s. I would, however, like to give Chicago’s Eataly some bonus points for not being so overwhelmingly crowded and not so fucking confusing to navigate.


But alas, when in Rome.. Had to get some snacks while I was here. Of course all the usual suspects were found.

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With a few local touches that I appreciated (Lagunitas IPA!).


Skyscraper Observatories

Which competing skyscraper’s visitor center should you visit? I guess it depends on what you’re looking for – but both are worthwhile in their own rights. At about the same price, they are equally opportune spots for that next Facebook pic. I will however jump to the chase and say my honest opinion would be 360 CHICAGO just because it’s less crowded and has more views of the cityscape.


John Hancock Center / 360 CHICAGO

Located on the 94th floor of the John Hancock Center is what is now known as 360 CHICAGO. As implied by the name, it boasts a 360 degree view of Chicago (and up to 4 states as well, which I find unlikely but heyy).


I went at night due to limited timing, but it truly was a breathtaking view. Right in the center of the city, you can really see all the skyscrapers and dazzling lights. Below is a night shot of the Navy Pier for reference how close it is to the center.


They also have a small restaurant bar where you can grab your drinks and perch against the window tables. As expected, it’s expensive AF.

Willis / Sears Tower

Ask any local Chicagoan they’ll probably still refer to this place as the Sears Tower. For nearly 25 years it was the tallest building in the world, and still holds the second tallest building title in the US.


On the 103rd floor is the Skydeck, where I’m sure we’ve all seen our Facebook friends post photos of them posing on this see-through box. It’s actually called “The Ledge”, and prepare to push your way through hoards of tourists trying to get the perfect shot. I’d honestly estimate a solid half hour, depending on the time of day, to stand there waiting in line behind the cute-kissing-photo-couple or the oh-no-I’m-falling-shot.

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Chicago Hot Dog

Trust me, I love my NYC water dogs. But where these Chicago dogs take the upper hand is in the extra textures. “Dragged through the garden” in most scenarios seem disgusting, but I’ll take it here. Pickles, peppers, and mustard are right up my alley. And no, I don’t miss the ketchup you Yanks.


Navy Pier

Navy Pier – Chicago’s number one tourist attraction. That should already be enough information to plan accordingly.

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I went exactly when it opened at 10AM because I ain’t messing with any of the crowds. My Chicago Go Card gave me access to all the rides, which I happily used to my advantage.

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Just note that if it was mid-summer, scorching hot weather, packed like sardines, I would be nowhere near this area. But again, I went during an off-season and went immediately while opening so it worked out for me. Actually I was probably the only one riding the ferris wheel at one point.

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I honestly don’t know how or why I got here, but it’s apparently called the Crystal Gardens and situated right outside of the Navy Pier entrance. I’ve seen my fair share of botanical gardens, so this one can be a pass for me.

The Art Institute of Chicago

If you’ve taken a history class or have any common knowledge of recent popular culture, you should at least recognize these paintings. I wouldn’t personally be able to tell you the name of the artist if it wasn’t already there, but they’re apparently “famous” and that’s the whole point right?

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If you’re an art-fiend or just trying to get some free air conditioning, by all means cough up the $25 entry fee and enjoy. Again, this was included in my Chicago Go Pass, so I weaseled my way in, took a lap around, then quickly left. Most likely I was hungry at that point.

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Dick’s Last Resort

Do you like being berated? Do you like unwarrantedly being called names? Well boy do I have a place for you!


Located right in the Marina City Towers, this restaurant boasts an almost 180 degree view along the river. It really is a prime location and perfect for people-watching. The food isn’t half bad either. But, as with the rest of the Dick’s chain of restaurants, the wait staff’s goal is to basically treat you, like, a dick.


I don’t think my waitress could have called me a “fat ass” any more if she tried. I took it with pride, as I ordered cheese tots, fried alligator, and an entire tray of nachos.


Eating along the river was the perfect way to end off my trip to Chicago. Carrying a doggy bag of my fried leftovers onto the plane however was not ideal.


I also probably forgot to mention I bought a Chicago Go Card. Depending on what you’re looking to do, there are different prices that either reduce the cost for local attractions, or some are absolutely free with the card. I suggest you tally the things you definitely want to do before buying it. Worked out for me because I’m a nerd and made a thorough spreadsheet of everything I wanted to see.


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Posted by:Talei Rukstad