I Moved Away from Chicago After 14 Years and These Are the 20 Places I Miss the Most

Chicago is a massive city—the third largest in the U.S., in fact, right behind New York and L.A. So needless to say there is a treasure trove of restaurants, stores and bars to explore, with seemingly a million more opening by the day. Until 2022, I was one of the Toddlin’ Town’s longtime residents, exploring its hidden gems one by one, from the newest music venues to the most beloved bookstores. But now that I’ve moved 186 miles away, with another 990 to go on my way to sunny Florida (sorry not sorry), I’m finding that the places I miss the most aren’t the hippest haunts (they’re always too crowded, anyway) or the most publicized. No, it’s the everyday unassuming spots that slowly became a part of my weekly, monthly or even yearly routine that made their mark on my heart. Below, the 20 places in Chicago I miss the most after moving away.

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1. Unabridged Bookstore

  • Neighborhood: Lakeview
  • Yelp Rating: 4.5 Stars

Chicago has its fair share of bookstores, but this is the one I came back to time and time again, regardless of what neighborhood I found myself living in, and the one that I miss most now. Despite its small size, it always seems to have what you’re looking for, be it fiction, nonfiction, travel or something in between. Better yet, the books are all neatly displayed with *actually* helpful card descriptions from store employees who’ve read and adored them. Owner Ed Devereux’s picks are particularly on-point—if I saw a card with “Ed LOVED,” I knew I was in for a good read. An admitted book hoarder, I also appreciated the store’s discounted selection on the left side of the store, where you can find great titles for roughly $5 to $7 (and ease your guilt about blowing your whole paycheck on novels when you’ve got a stack of 30 waiting to be ahead of them at home. Just me? Oh.)

773-883-9119, 3251 N. Broadway St., Chicago, IL, 60657;

2. Cozy Corner

  • Neighborhood: Rogers Park
  • Yelp Rating: 4 Stars

One thing about me: I’m obsessed with diners. I will take a basic bacon-and-eggs combo platter over any fancy brunch the city’s culinary artists can dream up. The problem? There are far too few of them in Chicago. Look up “brunch” and you’ll find yourself inundated with spots for dandelion, shallot and leek omelets (m.Henry), prosciutto and egg tartine (Maple & Ash) and smoked trout scramble (Lula Cafe). Which is great! …If that’s your bag. Mine, however, is far more simplified, and I found my holy trifecta—scrambled eggs with cheese, toast and mimosas—at this Rogers Park staple. More than serving up the essentials (plus a mean plate of chilaquiles when I wanted to switch it up), the staff is so friendly, they feel like old friends, offering up their names and a warm greeting every time you step inside. The Rogers Park locale was also centrally located right across the street from my house, so I know that no matter where I go, the setup isn’t likely to be nearly as convenient.

773-274-1100, 6349 N. Clark St., Chicago, IL, 60660,

Places I'll Miss Most in Chicago: A bright restaurant with a floral background and glass counters
Jacob Hand

3. Venteux Cafe

  • Neighborhood: The Loop

Venteux is a place I was introduced to just before my move, much to my chagrin: It’s everything I’ve ever dreamed of finding in a coffee shop. Inspired by a Parisian bistro, the space is incredibly bright and airy (40-foot windows tend to have that effect), with the cutest little velvet sofas you ever did see and coffee that’s *actually* good. There’s also the croque monsieur, which is pretty much to die for. After just a handful of visits, I loved this place so much, I went out of my way to frequent it the last time I was in town—and I suspect I’ll be doing the same during any future trips to the Windy City.

312-777-9003, Pendry Hotel, 224 N. Michigan Ave., Chicago, IL, 60601;

Places I'll miss in Chicago: A dimly lit tent with candles and cushions
Allyu Spa

4. Allyu Spa

  • Neighborhood: River North
  • Yelp Rating: 4.5 Stars

When it comes to Chicago spas, I tried a good number, from the high-end (Waldorf Astoria Spa, Spa @theWit) to the corner nail type, but none sucked me in quite like Allyu. I fell in love with this place from the moment I walked in. Everything about it, from the warm, welcoming shop at the front, which is chock-full of everything from boho jewelry to energizing crystals (yes, I bought several), to the meditative waiting room weaves a kind of spell while you’re here. I have no idea how they managed to make such an enchanting space out of a few hanging drapes and pillows, but by god, they did—I almost look forward to lounging in the waiting room more than I do the actual services (almost). I also sincerely appreciate its affordable prices. The last time I came, I got a lash tint and a 60-minute massage for less than $200, plus a turn in the private shower, which comes free of charge (though you’ll need to book it as a separate service to reserve the time). Honestly, how am I supposed to enjoy a regular old spa after this?

312-755-1313, 600 W. Chicago Ave., Chicago, IL, 60654,

Places I miss most in Chicago: A rose garden with a statue in the background
Chicago Botanic Garden

5. Chicago Botanic Garden

  • Neighborhood: Glencoe
  • Yelp Rating: 4.5 Stars

Alice in Wonderland is my favorite book of all time, and the closest I ever got to falling down the rabbit hole during my time in Chicago was while strolling through the rose garden at the Chicago Botanic Garden. Riddled with 5,000 blooms and tall trees overhead that make you feel as though you’re walking through a plant maze, it’s a sight to behold come spring. Equally enchanting is the Japanese garden, where you’ll see short pine trees, a zig-zagging bridge, stone lanterns and monstrous fish swimming in the sparkling water below. While it’s not technically within Chicago’s borders, it was always well worth the 25-minute drive North to Glencoe. Now, the Everglades will have to do, and I’ve heard tell that the mosquitoes are far from “enchanting” there.  

847-835-5440, 1000 Lake Cook Rd., Chicago, IL, 60022,

6. Hala Kahiki

  • Neighborhood: River Grove
  • Yelp Rating: 4 Stars

Ironically, Hala Kahiki was the place I went when I wanted to escape Chicago and its dreary, unending snow in favor of a more tropical locale. Now that I’m gone, however, it’s a place I long to get back to. The bamboo-covered bar, Hawaiian statues, festive servingware and flaming (!) drinks really make you feel like you’ve been transported somewhere more…White Lotus-esque, even in the dead of winter. The themed cocktails tend to be quite strong, so I highly recommend going with a DD, since it’s a bit of a drive in River Grove. There’s also a little gift shop where you can grab souvenirs from your “trip”—something I’m kicking myself for not doing now.

708-456-3222, 2834 N. River Rd., River Grove, IL, 60171,

7. The Signature Lounge at the 96th

  • Neighborhood: Magnificent Mile
  • Yelp Rating: 3.5 Stars

The moment someone tells me they’re visiting the Windy City, I direct them to make a trip to the Signature Lounge, which became one of my favorite spots in Chicago from the moment I first stepped foot in it circa 2003. Not the Signature Room, mind you, which is the building’s restaurant on the 95th floor, but the actual lounge and bar one floor above. Maybe it’s because I had my first-ever sip of wine here (the stories my mom could tell!), or maybe it’s the little stomach flip l I always got flying 96 stories up in the lightning-quick elevator, but this is one place I’ll never *not* be nostalgic for. The food is every bit as good as the restaurant below (and far cheaper, albeit with a far smaller selection), but more importantly, the view is the best you’ll find in the city on a clear day—even better than the Sears Tower. (Seriously—I took this photo from the ladies’ bathroom.)

312-787-9596, 875 N. Michigan Ave., Chicago, IL, 60610;

8. Sultan's Market

  • Neighborhood: Lincoln Park
  • Yelp Rating: 4 Stars

I never knew it was possible to deeply crave falafel—let alone a specific falafel—and yet, here we are. My boyfriend introduced me to Sultan’s Market circa the early 2010s, and it’s something I’ve been longing for since our move. It’s deliciously crispy, free of the heavy chickpea flavor so many recipes have and surprisingly affordable for the quality. And, when you feel like switching it up, there’s always the smoky eggplant-based Baba Ganuj or the baked spinach pie. This is not somewhere you go to leisurely dine (it’s super small and the tables are rather cramped), but trust me when I say that the food is worth the trek for takeout. Beyond that, while it tends to accumulate a line, particularly around lunchtime, the service is so consistently speedy, you can be in and out in ten minutes or less.

312-638-9151, 2521 N. Clark St., Chicago, IL, 60614;

9. Anthony Cristiano Salon

  • Neighborhood: River North
  • Yelp Rating: 4.5 Stars

I tend to make my hair appointments on Saturdays, which means I’m giving up a significant chunk of one of my two days off to watch hair dye turn colors on my head. In exchange, I expect to be really and truly pampered, and Anthony Cristiano truly delivers. While my stylist, Lauren Ashley, has since moved to Arsova Salon (another fantastic space, BTW), I loved coming here because they readily offered up mimosas from the bar upstairs, used one of my favorite color lines (Wella) and had floor-to-ceiling windows with stellar views of the Chicago river. Coming here felt like a treat instead of a chore, and I’m not sure any I’ll find in Florida will quite compare.

312-268-2440, 401 N. Wabash Ave., Chicago, IL, 60611,

Places I Miss Most in Chicago: A bright lobby in the LondonHouse hotel
Photo via LondonHouse

10. Bridges Lobby Bar at LondonHouse

  • Neighborhood: The Loop
  • Yelp Rating: 3.5 Stars

I loved bringing my laptop down to this beautiful space at the Bridges Lobby Bar and setting up shop in one of the window seats. The views of the river from the floor-to-ceiling windows are unparalleled, there are cozy seats (and convenient outlets) and you can even indulge in a delightful tea service while you’re there. (It sure as heck beat the overcrowded Starbucks.) I also loved bringing guests to this spot for happy hour after 5 p.m., since it also has a decent cocktail menu. Which brings me to the question at hand: Where will I find such a perfect combo again?

312-357-1200, 85 E. Wacker Dr., Chicago, IL, 60601,

Places I Miss Most in Chicago: An exterior shot of a bar with an L&L awning

11. L&L Tavern

  • Neighborhood: Lakeview
  • Yelp Rating: 3.5 Stars

You may have heard tell of Chicago’s infamous L&L Tavern: It’s been heralded as the “creepiest bar in the U.S.” for its ties to former serial killer patrons Jeffrey Dahmer and John Wayne Gacy, both of whom are said to have frequented its four walls. And naturally, as a true crime junkie, it proved to be irresistible to me. While I never witnessed any criminal or paranormal activity here, it did have many eccentricities that somehow endeared it to me. The diviest of dives, it’s pitch black after sundown (though its glass block windows ensure as little light as possible gets in during the day), its seating is extremely limited. If you ask for a lemon drop, they’ll literally chop a lemon in half and push a shot of vodka your way. But when you want a no-frills drink and a jukebox full of classic rock, it’s a fun place to post up at the bar and get just the slightest bit skeeved out. 

773-528-1303, 3207 N. Clark St., Chicago, IL, 60657

Places I miss most in Chicago: A seal pats his belly
Photo via Lincoln Park Zoo

12. Lincoln Park Zoo

  • Neighborhood: Lincoln Park
  • Yelp Rating: 4.5 Stars

There aren’t many zoos that allow you to visit nearly 365 days a year completely free of charge (something that was key for date nights in my less lucrative days). I also spent plenty of time here solo, enjoying the nearly 200 species of animals it's home to (you’ll see everything from an African lion and penguin to my personal favorite, the Asian small-clawed otter). And when my feet got tired of walking, I took quiet respite in the natural surrounding gardens. A pro tip? The food court offers up a birds-eye view of the Swan Pond waterfall outlook—something I have a sneaking suspicion will be far more lovely than, say, Sea World.

312-742-2000, 2001 N. Clark St., Chicago, IL, 60614;

Places I miss Chicago Metro
Photo via Metro Chicago

13. Metro Chicago

  • Neighborhood: Wrigleyville
  • Yelp Rating: 4.5 Stars

Chicago’s music venues are rivaled only by its restaurants, but Metro is the only one still causing me serious FOMO when I see a killer band on the bill.  Unlike, say, the Huntington Bank Pavilion Northerly Island, which holds about 30,000, the Metro is a space with room for just 1,100—and that’s between its main floor and balcony. That means if you happen to be lucky enough to get tickets to one of its private shows, which draw acts like The Foo Fighters, Metallica, The Smashing Pumpkins, and most recently, Fall Out Boy, you’re in for a very, very special and intimate evening. It’s also a great spot to discover new local acts and simply be in the company of other music lovers.

773-549-4140, 3730 N. Clark St., Chicago, IL, 60613,

Places I miss most in Chicago: A room full of crystal balls, sprays and more
Ruby Room

14. Ruby Room

  • Neighborhood: West Town
  • Yelp Rating: 4 Stars

As a gal who grew up obsessed with The Craft, I’ve always had a healthy interest in all things otherworldly. And the Ruby Room has an intriguing mysticality about it—only without all those Nancy Downs-post-villain vibes. Rather, the charming shop downstairs is filled with incense, tarot cards, gemstones, crystal balls and pendulums, and when you’re ready to take things one step further, you can head upstairs for an intuitive reading or healing massage from the establishment’s masters. It’s a genius blend of spiritual offerings and more traditional spa care, and a supremely unique space that I’ll surely miss dropping into on a whim.

773-235-2323, 1743 W. Division St., Chicago, IL, 60622,

Places I miss the most in Chicago: An aerial shot of the Pier
Navy Pier

15. Navy Pier

  • Neighborhood: Streeterville
  • Yelp Rating: 3.5 Stars

Yes, it’s a tourist trap. Yes, the line of screaming children at the McDonald’s is enough to make you want to rip your hair out. But Navy Pier remains, hands-down, one of my most-loved spots to spend a day in Chicago. The beer garden toward the end of the pier, from which you can see both the lake and the skyline behind you, is the picture-perfect area to sip on a cold one (which you can conveniently grab from the window vendors in the summer). There’s plenty to do, thanks to the copious restaurants (Tiny Tavern is a favorite for wine), live music and boat rides, which range from architecture cruises to dinner voyages. And the summer fireworks show Navy Pier puts on every Wednesday and Saturday rivals most town’s 4th of July display. There’s also that nearly 200-foot Centennial Ferris wheel, inspired by the similar 150-feet creation on display at the 1893 World’s Fair, to tackle. All in all? I’d call it downright magical. While Disney has its (many, many) charms, I know I’ll be longing to stroll Navy Pier’s boardwalk next summer, anyway.

312-595-7437, 600 E. Grand Ave., Chicago, IL, 60611;

16. Vines on Clark

  • Neighborhood: Wrigleyville
  • Yelp Rating: 3 Stars

Vines on Clark holds a special place in my heart—namely because I waitressed there on and off for the better part of seven years. (Or was it eight? It’s all running together.) Located directly across from Wrigley Field, it was often crowded with Cubs fans. And sure, it’s not as flashy as some of the other bars that have gone up in the neighborhood since my departure. But as the Cheers song goes, sometimes you really do want to go where everybody knows your name, and this was that spot for me for a long, long time. There is a comfort in grabbing a seat at the end of the bar, getting exactly what you want (typically without having to ask) and knowing that at any moment, your friends and newly off-duty coworkers will be dropping in to join you. Since most of the staff and management has turned over since I left, I’ll miss this one mostly in memory, but the roof and monstrous patio deck are still great spots to be when the sun is shining, the Cubs are winning and the DJ’s blasting the jams.

773-327-8572, 3554 N. Clark St., Chicago, IL, 60657,

17. Metamorph Studios

  • Neighborhood: Wicker Park
  • Yelp Rating: 4.5 Stars

I know what you’re thinking: You miss a tattoo parlor? But strangely enough, the answer is yes—yes, I do. I like getting ink on a whim, and for that, this place was the absolute best. Four of my nine tattoos were done here, all by different artists, and they’re all among my favorites (something that can’t exactly be said for all of my artwork). In addition to being able to trust in the collective talent of the artists at any given moment, this was a cool place to just…hang out. Which is a good thing, because sometimes, tattoos can take a hot minute. There’s always plenty of room for anyone you might want to bring along for an added boost of confidence or even entertainment (a huge plus in my book), and everyone is nice and friendly, so you could make a full night out of it should the ink urge strike.

773-384-9788, 1456 N. Milwaukee Ave., Chicago, IL, 60622,

Places I Miss most in Chicago: A dive bar with Christmas lights
Liar's Club/Facebook

18. Liar’s Club

  • Neighborhood: Lincoln Park
  • Yelp Rating: 4 Stars

My boyfriend Kevin is a musician. My friends are also musicians (shoutout to Blood People and Hawley Shoffner). It probably goes without saying that I spent a lot of time taking in live music in my Chicago years, and Liar’s Club is a cool, low-key place where you can not only catch a show, but the crowd is filled with talented people who could easily jump onstage at any moment. The eclectic decor means there’s always something intriguing to look at, and you’re always in for a treat if bartender Gary Kessler happens to serve you— he’s welcoming, warm and friendly, and, as my pal Aly so aptly puts it, “He’s a fashion icon.”

773-665- 1110, 1665 W. Fullerton Ave., Chicago, IL, 60614;

Places I miss Chicago Pequods

19. Pequod's

  • Neighborhood: Lincoln Park
  • Yelp Rating: 4 Stars

It’s basically a prerequisite for Chicagoans to have a favorite deep-dish pizza, and while many will cite Lou Malnati’s or Giordano’s as their go-to spots (two respectable choices, to be sure), I’m here to report that Peaquod’s has both beat. The pan-style pie is cooked in a cast-iron pan to create its famous caramelized edges, the likes of which crunch perfectly in your mouth (no doughy centers here!). Even my full-blown Italian boyfriend, who has *opinions* on all things pizza, will wolf this down with verve. Frankly, there’s nothing like it, and on the nights I’m stuck choosing between Domino’s and Papa John’s for the 100th gazillion time, I long for this mouthwatering delight.

773-327-1512, 2207 N. Clybourn Ave., Chicago, IL, 60614;

Places I Miss the Most in Chicago: A curved road next to a lake near skyscrapers

20. Lakeshore Drive

OK, so this isn’t really a destination, but on a cloudless day, when the sun is shining down, driving South toward the twinkling city on LSD or Jean Baptiste Point DuSable Lake Shore Drive (as Lori Lightfoot and Lori Lightfoot alone insists on calling it), really wasn’t half bad—yes, even in traffic. When the waves of the lake are crashing to your left, the skyscrapers are looming overhead and your favorite song is on the radio, it’s a grand day, indeed.

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Commerce Director

Nicole is the former commerce director at PureWow. With a Bachelor of Arts in Journalism from Michigan State University and more than 15 years of experience writing and editing...