Few things hit harder than realizing your home of five years is just that now. A home of five years. While I do not regret leaning into my hunger for travel, I will always have a special place in my heart for my first non-Florida home. This likely will become a regularly updated rolodex of goodies. Mind the dust, I recognize this list comes from a place that has not explored Chitown since March of 2021. Which was right on the cusp of things reopening.

As there are a balance of city culture musts along with personal recommendations, with the most traditional and iconic in bold. This will be a living document updated regularly as there’s so much to recommend even with a few years of discernment under my belt.

Full list of recommendations are on a nifty Google Map linked here. If you can’t tell Chicago is a food-city. I left out the Michelin star and other fancier spots because let’s be honest–everyone knows about these.

Quick jumps as follows:

Must Eat

✶ Susie’s Noon Hour Grill, Rodger’s Park, Chicago, IL (Cash Only)
✶ Korean omelet’s were a college addiction. One of my friends here was actually a server in a college Korean diner I would go so far as to read there, skip class there (senioritis is real), and drag friends there avidly. I have never found a place that could make omelets like those, not in Seoul, not in another city, nowhere. But damn does Susie’s come close. Close enough that I was impressed and comforted with every bite. The owner of the restaurant is a sweet elderly woman who is a one person show. She cleans, she cooks, she serves, and you can feel her dedication to her cooking in it. As it’s a one person operation, approach with patience or good company to pass the time. Pre-pandemic it was cash only, may still be so.

✶ Rice’N Bread, Wrigleyville, Chicago, IL
✶ Two Korean diner’s on a list?! Mish are you okay? Frankly, I’d be mad not to talk about Rice’N Bread. This diner has a cult-like following. There’s magic in their rice and gravy. I said what I said. No matter whether you came for a burger, bulgolgi plates, buldak, or any other dish, make sure you have a side of rice and gravy. There’s magic in this deceptively unassuming combo of fresh hot rice and with thick, flavorful gravy. I’ve had friends come ready to laugh me out who’ve folded at the first bite.

✶ Tamale Guy Wickerpark, Chicago, IL
✶ Words cannot fully form how deeply ingrained in local culture this man is. Yes, the tamale guy is a person. The tamale guy has saved many a drunken night, a hungry night, and enrichened countless denizens throughout the year. He’s gone from being your typical tamale man to a brick and mortar restaurant, to a person who community will and has rallied behind. When the tamale guy opened his brick and mortar store, his partners almost immediately tried to freeze him out of the business while profiting from his recipes. While the lawsuit persisted the community rallied. Restaurants found offered kitchens to allow him to make his recipes as he decoupled from the restaurant, and he migrated to Wickerpark where his main fan base resides. Chicago is passionate about many things, and the Tamale Guy is one of them.

✶ Portillo’s, various locations, Chicago, IL
✶ To be frank, I would be stoned if I didn’t mention Portillos for the Chicago Dog. An everything but ketchup Polish or Italian beef hot dog on a poppy seed bun. My favorite place was a mom and pop shop that didn’t survive the lockdowns…but Portillo’s is definitely an icon of successful local Chitown joy. Now a national chain, you can’t say no to grabbing the famous hot dog and washing it down with a Chocolate Cake Shake. A shake that has slices of their chocolate cake in it, making it a marriage of milkshake slurping and spooned out chomping.

✶ Lou Malnatis Deep Dish, various locations, Chicago, IL
✶ A local chain that many born and raised Chicagoans swear is the deep dish pizza place. If you’re in a hurry order ahead of time, unlike other pizzas, deep dish really does need 45 minutes to bake…it’s the depth and size of a lasagna, you don’t see that finishing in an oven in 10 minutes. Sausage is a must if you’re being a proper local. Unlike the rest of the US that cherishes peperoni as the one topping on their pizza, Italian sausage rules the hearts of locals. And honestly, they make a solid pizza to argue it.


✶ Maxwell Street Market Mangonadas & Tacos, UIC Area/Near West Side, Chicago, IL (Cash Only)
✶ Probably one of the only street markets that gets physically moved due to the popularity of both the road and the market itself, not once, but twice. Thankfully this home is more permanent, having been it’s Sunday recurrence since 2008 (the market has been documented since the mid-1800s). What keeps this as an “eat” and not a “do” is that, while the market has occasional performances and a vast spread of things to buy, all the lines, hustles, and energy comes from the food. There are people who swear by Ruby’s tacos, I love La Paz. The tacos are oblong and filled to the brim. The salsa is refilled frequently and every drop screams of fresh tomatillos for salsa verde, while the peppers really bite in the salsa roja. If it’s the summertime, treat yourself to a mangonada. It’s a fun tower of tamarind candy stick to place by the Sears Tower for a picture. It’s also layered with fresh mango, mango sorbet, and lots of tajin (chili limon powder) to boot.

✶ Delilah’s (for those 21+) Lincoln Park, Chicago, IL
✶ Whiskey lovers rejoice! Delilah’s is open again. All grunge, pool tables upstairs, and an ample wall of whiskey–Delilah’s is the one place you see people in business suits next to your neighborhood hipster. This place brings all whiskey lovers together. They have some house whiskies as well but if you’re not looking for downtown prices and Rivernorth/Loop vibes, this is a great alternative. I honestly used the proximity to Delilah’s as a factor in the last Chicago home I lived in. No regrets.

✶ Demera, Uptown, Chicago, IL
✶ One of the best Ethiopian places year over year in the city. Great for vegans and meat eaters alike (all vegetable dishes are vegan) and group meals. You can go solo, just expect leftovers. It’s a great experience. There are other Ethopian places in the city but so many options to choose from.

✶ Uncle Mike’s Place, West Town, Chicago, IL
✶ Filipino breakfast here we come! This is a favorite of many folk, the portions are huge, the food is cheap, and the service is super fast. I go for the spicy spam silog or tocino silog as an immediate fall back–spam silog is soooo popular and sometimes sells out! FYI–Silog is basically rice and eggs, a trend that seems to have not reached the parts my mother was in before she immigrated to the US, or at least calling it silog, I’m sure rice and eggs is a staple that’s practically timeless.

✶Nutella Cafe, Loop, Chicago, IL (the first one in the world!)
✶ If you love Nutella or Ferroro Rocher…you just have to. It’s a cute cafe along the way to/from the Bean. Indulge in one of the first Nutella cafe’s in the world. Truly a short and sweet description to a place that explains itself.

✶ Kai Zan, Ukranian Village, Chicago, IL
✶ I hemmed and hawed about sharing this one. I love Kai Zan. I really do. And even after moving to PNW where seafood and Asian food really puts a high standard in place, this place pans out on top still. Which is why it’s hard to put in on here. Their food is phenomenal, the price is reasonable for the caliber, and the reservations are a battle. Their omakase is one of my favorite in the city (with Sushi-san‘s omakase as a close second, I know scandalous). If I recall it is 7 courses and they’re delightful. Shown is the scallop and oyster shooter course of their omakase.

✶ QXY Dumplings, Chinatown, Chicago, IL
✶ These dumplings are so good, they opened up a more functional location in the Loop called Jiao. From the day they’ve opened they have dominated their dumpling competition and kept a steady stream of customers in no matter the state of the world. I personally consider it the niche that keeps places like Din Tai Fung at bay (delicious don’t get me wrong but they would likely compete head to head on their dumpling quality). Given it’s location–wander around Chinatown while you’re at it! This is the only city I’ve seen be concerned enough about the small details for tourism to do a multi-year construction to move the road so you can “drive right into” old Chinatown’s Gateway without having to bend around Cermak first. It’s not a thing anyone visiting now can see but it was wild to process the work that went into removing half a block so Clark St would drive unencumbered into it. I lovingly call Chicago’s Chinatown functional, as it has some of the expected Chinatown appeal with all the authenticity of the strip layout of being back in China proper.


✶ Sawada Coffee, West Loop, Chicago, IL
✶ Tired from all the eating? Perk yourself up with Sawada Company’s Military Latte. A Matcha Latte with a shot of espresso dappled through it. Take a seat and absorb the vibe of a mix of business folk working, creatives designing, and folks meeting up and mingling nearby. There are plenty of plugs and table space so if you need to be plugged in and planted, you can. Sawada Coffee Tokyo screams skater vibes turned (world renowned) barista–because frankly it is–and it’s popularity has survived the test of time. Circa 2015, Sawada coffee has been a pocket of city peace and punk in a side pocket of modern-West Loop bourgeois.

Must See

✶Sears Tower, Loop, Chicago, IL
✶ Part of the Chicago tourist pass, and well worth it. I have so many photos from taking out of town friends here and honestly the view never gets old. I don’t have any photos of just the view, so here’s a broody picture of the tower staring down at me instead. FYI, Chicagoans are very stubborn at accepting renamed things, so even if Google maps says Willis Tower…it’s still the Sears to most folk.

✶Mag Mile, River North (+More), Chicago, IL (Uniqlo…trust me)
✶There are many views of the Mag Mile, and many ways to experience it. Each one with it’s own charm. But if you want a peaceful but idyllic viewpoint that I don’t think many tourism callouts would be aware of, go to the Uniqlo on Michigan Ave and grab a beverage from Starbucks, as the south facing window from there has seating and overlooks the Water Tower and the strip.


✶Cloudgate aka The Bean, Loop, Chicago, IL
✶ A selfie tool before selfie’s were trendy. A meeting spot. A group photo. A common wedding group spot. The Bean is such a popular installation you’d think it’s been there for tale as old as time, however it was finished in 2006! While it looks like a singular metal bean, it’s actually composed of many panels. A clear testament to how quick the city and its visitors are quick to iconize cool things.

✶Outside Adler Planetarium, Loop, Chicago, IL (skyline view of the city)
✶ In the summer, combo this with a leisure walk or city bike along the way and join the tradition people of all ages partake in. Occasionally you’ll find engagement photos or wedding photos underway, and who can blame them? This phone capture hardly does the view justice!


✶The Robey Rooftop View, Wickerpark, Chicago, IL
✶ Grab a seat or lean on a wall and catch up with a beverage in hand as you soak in the downtown views from the side of Chicago full of great food and bars.

✶Greetings from Chicago, Logan Square, Chicago, IL
✶Frankly a chill 20 minute walk, or speedy 10 minute train ride from the previous must see. I’m not quite sure when these became an expectation of cities, but the best part of this one is it’s near a lot of older murals that pre-date the newer B-Line Murals (see below!)

✶B-line Murals, Fulton Market, Chicago, IL
✶One of the more recent art movements of the city. As a way to revitalize the city and show it’s many personalities, the B-Line Murals, while with recent updates, is actually a movement that started in the ’70s. Watching the recent murals come together and build community was fascinating, especially given how active the Instagram community of artists were in documenting this.

✶ Bahai Temple, Chicago Botanic Garden, & Home Alone House (All Northern Burbs)
✶To be honest, these are so close and popular spots I’d be a poor hostess to not mention them. Go to the Bahai temple to see the oldest temple still in use by the Bahai. As such a famous site, it is well maintained and stunning to see in person. The Botanic Garden is the only thing on this bullet that costs money, they have such a renowned Orchid show and overall greenery they’re all worth the visit. And for those with penchant nostalgia, the Home Alone house isn’t too far away–although I’d give it space if you do go see it as it is an actual home, much like the Painted Houses of San Fran.

Must Do

✶ Chicago Cubs Game in Wrigley Field, Wrigleyville, Chicago, IL
✶ Home games are in Wrigley Field, America’s 2nd oldest ballpark. Even for those not into baseball, there’s charm in this city’s field. If you’re really into baseball don’t forget Southside’s Guaranteed Rate Field, home to the Chicago White Sox. Just don’t mention you hopped between fields, the rivalry has been known to spark intense conversations in almost any environment

✶ Bulls Game at United Center, West Loop, Chicago, IL
✶ Bulls’ fans are great. And during this time period, the Bulls’ are having a PHENOMENAL season. I like to joke that any team I want to win loses, so self-fulfilling prophecy here by being far away. However even when seasons are a less than fair weather, Benny the Bull, the events team, and the players all give phenomenal efforts. Lots of fun themed home games and free swag.

✶ The Art Institute of Chicago, Loop, Chicago, IL
✶ The downtown art museum, in a city full of museum’s this one still takes the crown. With a healthy rotation of traditional art, catch anything from Monet to analog Van Gogh (the virtual experience is cool, but seeing his works in person is something else) to anything the museum has curated for the time.

✶ Ride the Brown Line Loop/Merchandise Mart, Chicago, IL
✶ Cheapest view of the city with a plethora of wonderful views. Honestly one of the simple indulgences I miss is seeing the neighborhood go by and catching the view as of the river.

✶ Peep into Replay Lincoln Park’s Latest Pop-up, Lincoln Park/Lakeview, Chicago, IL
✶ This spot took some time to recall as, per earlier, it’s hard to remember it’s new name. This was original a Headquarters bar that branched off into it’s own thing. This unassuming garden level bar is almost always doing a theme. I’ve sat on the Iron Throne there, drank warm Malort for a Pokemon Soul Badge, and done a Pickleback in honor of Pickle Rick. If you’re 21+ and enjoy a good theme bar, this place almost always will scratch that itch.

✶ Catch the sunset from London House Rooftop Bar, River North, Chicago, IL
✶ Cool view of the river and bridges, good drinks, and great tables if you’re coming as group.

✶ Catch a Second City Show, Oldtown, Chicago, IL
✶ All their shows are funny and if you want to kill time pre-show, you can drink at the Irish bar across the street, the bar in the building, or wander (and/or drink) throughout the neighborhood. As the historic old Germantown, you can see nuances of old German culture that built up the now young urban professional dominated community.

✶ Get Lost in Myopic Bookstore, Wickerpark, Chicago, IL
✶ Bibliophiles rejoice! This may not be like the Portlandian Powell’s but it sure is a Chitown treasure. The walls are all books, even along the stairs, giving it a treehouse/book maze vibe. If you like spooky things, all mystery books are in a room in the basement. If you need to hit up a coffee shop after in the area go to Wormhole for an 80s gamer inspired ambiance, with a whole DeLorean DMC-12 to boot. They recently opened a second location…but nothing beats the original.

Seasonal Musts

✶ Expo Chicago, Navy Pier, Chicago, IL
✶ Personally one of my favorite events. It’s a giant art expo with curations from around the world out for Chicago to see. Part of it is done in Navy Pier, but it’s bigger than just that. Curators and artists have forums, sessions, and even occasionally tea ceremonies to express their art and the Expo’s different annual themes. A lot of moving protest pieces and environmental statements from around the world can really grip you. If you’re an art lover. This is a must.

✶ St Patrick’s Day River Dyeing (St. Patrick’s Day Weekend), River North, Chicago, IL
✶They dye the river green. People are profusely drunk, if it’s not your jam it’s still green the next day. Can you tell I’m no longer in my 20s?

✶ DO312’s ACTIVATE Series (Summers), Loop, Chicago, IL
✶ Link sadly varies annually but they turn different alleys and underappreciated places into themed forms of expression. I’ve seen them cover what “community” is with each alley (they do one a month) covering how people come together. Neighborhoods captured in an alley space. It’s the best free-99 deal of the summer.


✶ Zumba in the Park (Summer weekends), Loop, Chicago, IL
✶ If you’re here over the weekend in the summertime and don’t feel that walking/commuting around is cutting it for you, gear up and bring a towel! The city encourages movement with free workouts in the park. Zumba is a common staple, however everything from cardio, tai-chi, and yoga have been scheduled in years past.

✶ Oktoberfest (September), Lincoln Park (+ More Locations), Chicago, IL
✶ St. Alphonsus hosts one of the largest Oktoberfests I’ve been to and volunteered for in my time there. So many communities throw on this festival to celebrate a good harvest and a have a good time with fresh beer. And to be frank this city loves any excuse to drink, so you’ll be around some pretty “have a good time” folk. If you don’t plan on hitting up Bavaria, you have a great Midwestern second in Chicago.

✶ Open House Chicago (October), Everywhere, Chicago, IL
✶ Is a giant architecture open house. Basically you get to see iconic and typically private/off limits locations for free. There is a member’s only group too, which you can either pay for or (if you’re local enough or just trying to do this on a budget) volunteer a day towards to get access for free the other days. It’s usually a 3+ day affair so volunteering one day won’t hurt if you really want to access the premium things for free.

✶ Christkindlmarket (Fall-mid-December), Loop (+ More Locations), Chicago, IL
✶ The original is in the Loop, however a few other ones throughout the city have sprung up in recent years to offset the demand. Wrigleyville boasts of one with a skate rink that goes through the end of the year. Much like Oktoberfest, it can scratch an itch for those who want to experience aspects of the EU without leaving the country.

✶ Butch McGuire’s (December), Gold Coast, Chicago, IL
✶ Probably this city’s worst kept secret. You love Christmas? You miss the sensation that an elf has thrown Santa’s workshop into a nearby pub? Well it’s okay if you only said yes to one of the two, Butch McGuire shall provide. Grab a Hot Toddy inside to fight the winter chill.

Call me nostalgic but writing this brought up so many more places I’d recommend. The gems that are the coffee shops in town. The tea shops that prove to the world Chicago has some historic afternoon teas that still deliver and newer ones that bring a fun twist.

Hopefully this was useful, I tried to balance it since there’s a lot of staples but the truth is, Chicago is a highly diverse city. There are some communities that have left their mark and migrated within and throughout the area, and there are communities who have held steady on their geographic roots within the city limits. There’s a lot of charm, and I hope if you get to go, you feel that energy while there.

Stay Hungry
XOXO
Mish ♥