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Oh Chicago, you sure know how to razzle dazzle us. This is our kind of city: a diverse and cosmopolitan metropolis defined by its phenomenal dining scene, an innovate arts and theater culture, majestic architecture, a truly devoted sports following, and all that jazz. We have mad love for the city of Chicago. Chicago has given us two of our all-time favorite experiences: our number one dining experience and our number one theater experience. So yeah. Chicago holds a pretty special place in our theatrical foodie hearts.

This post is a compilation of several wonderful trips to Chicago and I am already dreaming of when we can return (hopefully during warm summer months!).

Posing at the famous and super touristy Cloud Gate, nicknamed The Bean, in Millennium Park.

EAT & DRINK LIKE A BOSS

Featured first and foremost, because our favorite thing about Chicago is its FOOD.

Alinea

Pop. Six. Squish. Uh-Uh. Cisero. Lipschitz.

Nothing I can possibly write will ever be worthy of this life-changing tour de force, but I thought a reference to my all-time favorite musical song would be a nice touch.

Hands-down our all-time favorite dining experience, but I would be remiss if I didn’t mention that it is also our most expensive. Alinea’s famous tagline is “not a restaurant”, and rightfully so. In fact, to limit Alinea’s ingenuity to the mere title of restaurant seems not only wrong, but downright insulting.  Culinary genius Grant Achatz has created a dazzling theatrical masterpiece where the presentation of each of the innovative and artistically-curated plates is as equally important as its taste. Alinea is true gastronomical theater, folks and something tells me Roxie Hart would be proud. The service is impeccable and the space is hip and minimalistic while unpretentious. Our perfectly orchestrated evening consisted of fourteen meticulously crafted courses paired with mouthwatering wines. Be ready to be wowed, fully satiated and really drunk. This is the epitome of food heaven and no matter how many Michelin-Starred restaurants we dine at, nothing ever seems to compare.

A few things to note:

*Alinea accepts bookings up to two months in advance and when you book your reservation, you will pre-pay for your pre-fixe dining “tickets”. All tickets are non-refundable but fully transferrable.

*Alinea is expensive. Like over $1,000 expensive. I am not so obtuse to know that many people are not in the position to shell out this kind of money for dinner. I’m also fully aware that even if people are in the position to do so, they may wish to spend their money on other things. BUT…if you are a foodie, want a once-in-a-lifetime experience, and/or simply have money to burn, I promise you this will be one of the most incredible dining experiences of your entire life. To us foodies, this extravagantly lavish night was worth every penny. P.S. Our menu is framed and prominently featured in our home. Have I mentioned that Alinea was life-changing?

One of only 13 U.S. restaurants to earn 3 Michelin Stars & currently ranked #21 in the world. 

 

The first of our fourteen courses: butternut squash, muscovado, lime goodness

T’s lamb course with sixty accompaniments. Um, that’s right. SIXTY.

 

Hot Potato, Cold Potato: This incredible black truffle snack literally changes temperature in your mouth. It’s mind-blowing and all kinds of amazing. 

The famous and completely-edible green apple taffy balloon course. Besides its surprising delicious flavor, the best part is when all of your fellow diners join you in talking in that annoying yet hilarious helium-infected voice.

If you watch Netflix’s Chef’s Table (and if you don’t, you should!), you’ve seen this famous dessert presented.  Essentially, for your final course, a tarp is laid out over your table and chefs channel their inner Jackson Pollack by splashing streaks of chocolate, birch syrup, and all other kinds of deliciousness. To top it all off, a block of frozen mousse that gradually turned into a more mousse-like texture as it defrosted, is centered on this delicious canvas and cracked just waiting to be devoured. To watch this piece of edible art unfold is truly mesmerizing. If you’re so inclined, you can watch a video of this delectable magic here.

Avec

We really loved this Mediterranean and Midwestern inspired restaurant. The small plates theme is perfect for a group, as is the cosy communal seating setting. Every single dish we ordered was delicious.

 

The Aviary

Where the gin is cold and the piano’s hot.

Grant Achatz is clearly a man after my own heart. This revolutionary cocktail lounge is one of the coolest and most creative of its kind, where intricately crafted cocktails are concocted and uniquely presented in an ultra-posh swanky setting. There are no bartenders here–at least not by typical standards–the ingenuity that comes out of this cocktail kitchen can only come from the likes of mastermind cocktail chefs and brilliant ice sculptors.

Fun fact: A second Aviary branch is opening soon in Manhattan.

You might say that I’m a little excited about my cocktail:

Cafe Spiaggia

Pepper my raggoo…

The lower-key sister spot of famed fine-dining restaurant Spiaggia (a long-time favorite of President Obama’s), we loved this intimate cafe. Although the food is identified as “casual”, it’s nothing short of excellent, and the wine list is spectacular. This was a perfect choice for lunch.

Over the years, Spiaggia has consistently earned 1 Michelin Star along with countless other accolades.

CH Distillery

Find the flask we’re playing fast and loose…

Because one epic Chicago cocktail bar can’t possibly be enough, CH distillery is a cocktail-meets-lounge distillery gem. Chic, trendy, and cutting-edge, this hotspot is the perfect place to enjoy unique cocktails made from on-site stills. The sleek industrial feel makes for a snazzy yet welcoming setting.

Enjoying some cocktails with family before dinner at Avec:

Giordano’s

That means somebody everyone knows…

Sometimes highly-touted touristy spots are famous for a reason. Similar to Pat’s and Geno’s Steaks in Philly and Ben’s Chili Bowl in DC, Giordano’s is somewhat of a Chicago pizza institution. I hate when people instantly dismiss these kind of spots just because they’re touristy. They’re usually popular and touristy for a reason, people. The stuffed pizza deliciousness I had at Giordano’s was enough to make me a stuffed pizza believer and follower for life, y’all. The atmosphere is a bit kitchey and cheesy (see what I did there?), but the pizza is the stuff (yet another witty pun by yours truly) that dreams are made of.

 

Girl and the Goat

They’re gonna wait outside in line to get to see…

Reservations at Stephanie Izard’s (formerly of Top Chef) hot spot eatery are highly coveted…so highly coveted that when I made a reservation over six months in advance for a Tuesday night, I could only score a 9:30 table. Defined by its delicious and creative small plates in a dramatic open space, Girl and the Goat is absolutely fantastic. Loved this restaurant.

I still dream about their chickpea fritters:

 

Goddess and The Baker

You want some advice, well here’s a piece of advice from me to you, lay off the caramels.

We loved having this fabulous cafe across the street from our downtown hotel. Their delicious (and many are vegetarian!) breakfast and lunch options are perfect for the quick bite or for the occasional lingering session.

 

Publican

I wanted to like this place more than I did. Almost every top restaurant list in Chicago features Publican and I don’t really understand why. Now I will fully acknowledge that their pork-focused menu is not necessarily catering to me and my non-meat-eating ways, but no-one in our party (including the carnivores) was overly impressed by their meals. I will say their extensive beer selection is pretty fantastic and I loved their hip and open beer hall setting with communal seating.

 

Roister

It’s just a noisy hall…

Clearly we have a thing for Grant Achatz. His most recent restaurant is yet another work of brilliance. Much more casual (and affordable!) than Alinea, Roister has a convivial vibe where interesting music playlists along with sounds of the boisterous open kitchen fill the long narrow dining room. Steeped in Southern, Brazilian, and Korean roots, the interesting yet approachable comfort food will satisfy your soul while tantalizing your taste buds.

Fun fact: Roister is next-door to the Aviary…the perfect recipe for the perfect night!

One Michelin Star

 

TRU

A luxurious restaurant that serves lavishly French-inspired fare, this restaurant is one for the foodie books. This is the epitome of fine dining and the sublime pre-fixe menu is sure to wow. Full disclaimer: TRU can feel a bit pretentious and it’s definitely not a cheap restaurant. But the food is delectable, the extensive 1,500+ wine selections are fantastic, and the service is outstanding. So again, for us, it was absolutely worth it.

Two Michelin Stars

 

THINGS TO DO

Architecture Tour

Chicago’s stunning architecture sure has some stories to tell. I highly recommend taking an architectural tour of some sort to learn about its fascinating history. Our last trip to Chicago was in early March so we opted for the weather-friendly interior and pedway tour. This two hour walking tour allows you to meander throughout the underground tunnels, passages and corridors of the downtown loop. In addition to exploring the pedway, the tour takes you to stunning interiors including a beautiful church atop of a skyscraper and the impressive landmark of the Chicago Culture Center. I would love to take an architecture river cruise next time we’re in Chicago during the warmer months.

 

 

Art Institute of Chicago

With more than 300,000 works in its permanent art collection, The Art Institute of Chicago is so massive (it’s the second largest art museum in the country!) that it can send you reeling.  At the very least, plan to allocate several hours to wander through the countless mazes of galleries and ancient displays of pottery.

 

Landmarks & Parks

As with any cosmopolitan city, there are an abundance of “must-see” landmarks, parks, and sites to visit while exploring Chicago. Below I only scratch the surface of must-visits, ones we’ve particularly enjoyed visiting during our multiple trips to the Windy City.

Living in Washington, DC, I sometimes miss imposing skylines, where skyscrapers perfectly puncture the looming sky. Well, there is certainly no shortage of towering buildings like the Willis Tower (where the city views from the top are amazing), and the notorious John Hancock Center in Chicago, where I’m more than happy to get my fix for a bit.

The lofty and impressive Willis Tower:

I absolutely love a good urban park, I mean, what’s not to love? An expansive green oasis enveloped within a bustling metropolis? Yes, please. Chicago’s Grant Park is the quintessential city park that’s chalk-full of so much beauty and activity. The very popular Millennium Park is a favorite among locals and tourists alike due its wide green spaces, ice skating rink (we had a blast ice skating and drinking hot chocolate years ago–and yes, you better believe it was cold), and iconic Cloud Gate structure. Grant Park is also home to the recognizable Buckingham Fountain, thanks to its prominent feature in Married With Children’s opening credits, and the majestic Art Institute of Chicago (highlighted above).

Millennium Park:

Buckingham Fountain:

The Magnificent Mile

I don’t care about expensive things, cashmere coats, diamond rings…(yeah, right)

It’s nearly impossible to travel to Chicago without visiting the Magnificent Mile, the posh stretch of Michigan Avenue that’s lined with luxurious boutiques and department stores, upscale eateries, and high-end hotels. Shopping galore awaits on this quintessential Chicago avenue.

 

Navy Pier

With its carnival rides, food court, and souvenir shops, truthfully the Navy Pier can be a bit touristy and tacky, but it’s still a fun and scenic place to stroll along Lake Michigan’s shoreline.

 

ARE YOU NOT ENTERTAINED? 

Come on babe, why don’t we paint the town…

Comedy

Funny Honey…

Cannot recommend enough catching a comedy show at Chicago’s famed Second City. Known for its numerous celebrity alums including Tina Fey, Bill Murray, Amy Poehler, and Steve Carell (and many, many, many more), this hot spot puts on crying-out-loud hilarious comedy sketches, political satires, and improv shows. Soooo much fun here.

Sports

Growing up about seventy-five minutes outside of Philadelphia and consequentially becoming a devoted Eagles fan at an early young age, I have an affinity towards sports cities like New York and Chicago. Combine that with our goal of visiting every NFL stadium (hitting stadium #12 in Denver this fall!), we just had to attend a Bears game at the legendary Soldier Field. And clearly we became Bears fans for a hot minute while we were there. #posers

Theater

Give ’em act with lots of flash in it…

I began this post with a life-changing event (um, duh, Alinea), and I will end it with another life-changing event: H A M I L T O N. As with Alinea, words fail to describe the utter brilliance that is Hamilton. To quote Michelle Obama (because, really, her opinion is the only one that really matters) “It’s the best art I have ever seen in my life”. And she ain’t never lied (p.s. If you disagree with that statement, please refrain from commenting. Thanks.).

But seriously, all of the plays, operas, dance performances, symphonies, and musicals (including Chicago)—and Lord knows that we have certainly seen our fair share—can’t even hold a candle to Hamilton. Seriously, it’s that good. And yes. It’s worth every ten dollar bill.

 

I hope to see you soon, Chicago. And believe you me, I’ll be ready.

I’m gonna rouge my knees and roll my stockings down. 

And all that jazz.

 

Related Reads: Detroit, Charleston, New York City, DC Winter 2017 Dining