Travel: 4 Days in Chicago
I’ve only been to Chicago once before; I was 15 and went with my aunt, cousin and grandmother to visit my other cousin who was studying Sculpture at the School of the Art Institute of Chicago. We stayed mostly in the downtown area and ate at places like Giordano’s and Hard Rock Cafe, so needless to say this second visit with Ed for our one year wedding anniversary was quite different.
Ed came to Chicago last year with a friend, and he thought we should stay in Lincoln Park. I was able to find an absolutely fantastic Airbnb apartment on N. Clybourn Ave. for $110 a night. Photos below—I highly recommend it! We had an incredibly comfortable stay; everything was modern and clean, and it felt like home as soon as we walked in. You can check it out in detail here.
But me being me, I was especially excited to be in Chicago and try new restaurants. We’d made a few reservations beforehand, but we also wanted to be able to pop into someplace on a whim if it looked cool (which we did about half the time). I’ve lined it all out for you by neighborhood, both the excellent and the so-so, below.
Ever been to Chicago? Have some food thoughts of your own? Would love to hear from you in the comments!
SUMMER HOUSE SANTA MONICA
Funnily enough, we started and ended our trip at Summer House Santa Monica. The restaurant eschewed West Coast vibes; it was light and airy, the bar was stocked with rose and the menu was loaded with fresh produce. It was bougie, for sure, but it was also high-quality.
This was our first stop upon arrival on Friday around 2pm, and we were starving as we hadn’t eaten all day. My eyes went first to the Avocado Toast—poached eggs, hass avocado, scallion mascarpone, whole-wheat brioche—but then I audibly gasped at the $16.95 price tag. I don’t care if it’s sprinkled with flecks of gold…I am not paying $17 for avocado toast. A couple of lines below that was the Housemade Green Veggie Burger with white cheddar, avocado and hatch chili mayo for $14. Done and done, and the right choice was made. I’ve never had a veggie burger like this, and it was absolutely incredible. Crispy yet fresh and not greasy at all, the patty was made of chickpeas, cilantro, parsley, green onion, caramelized onion, garlic, salt and pepper. 100% going to try to remake this at home at some point.
On our last day in town, Monday, September 10, we were leaving for the airport at 5pm and wanted to grab a snack beforehand. Back to Summer House, this time for the Guacamole & Housemade Chips. The guac was mixed with corn, cotija cheese, pepitas and cilantro and served with a charred tomato salsa. The chips were amazingly crispy, and both the guac and salsa had fantastic flavors. Well done, Summer House. Hope to visit again soon.
1954 N Halsted St. @summerhousesm
KIBBITZNEST BOOKS, BREWS & BLARNEY
On any trip, whether it’s out of the state or out of the country, I’m always on the hunt for a good bookstore. Ed actually found this one online before our trip. Best part? Kibbitznest is both a bookstore and a bar. Score! Most books were used and I didn’t actually find anything I could’ve live without, but I loved the laid back atmosphere. There’s no Wifi in the joint (which I applaud), but they have a huge collection of board games. We sat for over an hour, playing Guess Who and Connect Four and sipping Cherry Mojitos and Blood Orange Margaritas. They had snack plates, too, but we refrained since we were going to eat pizza later. Next time, though, I’d definitely like to try one of their cheese boards.
2212 N. Clybourn Ave. @kibbitznest
One of the big questions when you visit Chicago is, “Where’s the best deep dish pizza?” It’s a great question, and you’re bound to receive a million different answers. We’d seen the 25-year-old Pequod’s Pizza on The Food Network, and I was particularly drawn to fact that the put additional cheese on the outside of the crust to make it extra crispy and caramelized. And it’s only a few doors down from kibbitznest, so we went there straight away.
Heads up that on a Friday night, even after you’ve waited for your table and have been seated, you might still wait another 45 minutes for your pizzas to arrive. That’s just how it is, and you’ve just got to deal with it. We arrived early, though, at like 5:30pm, so we didn’t have to wait for a table at all and the pizza only took like 20 minutes to make it to our table. Note that this is why your waitress might seem like she’s in a huge hurry to take your order; she wants to make sure she gets it in as quickly as possible to cut down on the wait.
Verdict: crazy good! Deep dish pizza is something I never eat, but I love it whenever I do get to have it. The crust was so incredibly crispy, the sauce had great flavor and the cheese was there in abundance without being over-the-top ridiculous. The actual restaurant was huge, and I liked that it kind of seemed like a dive bar that happened to serve pizza. Highly recommend.
2207 N. Clybourn Ave. @pequodspizza
BLUE DOOR FARM STAND
The thing about Chicago is that most restaurants either close for a few hours between lunch and dinner or they’re only open after 5pm. If you’re wanting a midday snack, like we were the day we were supposed to fly back home, you’re sometimes shit out of luck. But some forward-thinking restaurants like Blue Door Farm Stand thankfully offer happy hour menus so you can still get your grub on at random times of the day.
We went with an order of the Rainbow Hummus—classic, sweet potato and purple cauliflower hummuses served with vegetable crudite—and the Fried Cheese Curds with pickled peppers and herb buttermilk dip. The hummus was fine, but I would’ve preferred it simply with classic hummus (the others were a bit bland) and maybe with a bit of pita or crispy flatbread in addition to the veggies. But on the flip side, the cheese curds were seriously addicting! I loved how the sour/spice of the pickled peppers balanced perfectly with the creamy buttermilk. If we visited again for dinner, I’d love to try the Sweet Potato Empanadas or the Veggie Burger (cannellini beans, quinoa, cilantro, mango and avocado).
2010 N. Halsted St. @bluedoorlp
Our Airbnb had a spring copy of Chicago Magazine, and it happened to be an issue featuring 15 of the best new restaurants in Chicago. The Delta in Wicker Park was rightfully dubbed one such restaurant. It plays homage to the Mississippi Delta region, featuring a variety of tamales and Southern fare along with house cocktails.
The Delta is a restaurant where you walk in and instantly say, “this is cool.” The patrons and staff were practically indistinguishable from one another (no cookie cutter uniforms here), and everyone was super friendly and genuinely seemed glad you were there.
We visited for brunch, and I ordered the Chilaquiles: Vegetarian Red Hot Tamales made with spicy wild mushrooms + a fried egg, queso fresco and crema. Decidedly my favorite meal of the trip. I love my breakfast saucy and served with eggs, and this dish delivered. The chips were covered in sauce yet stayed crispy from start to finish (must be Mississippi voodoo or something), and the sauce itself was flavorful without being too spicy. I ate the whole thing and was full but not stuffed. Perfection all around.
1745 W. North Ave. @thechicagodelta
FAIRGROUNDS COFFEE & TEA
There are two Fairgrounds locations in Chicago (plus one in Los Angeles and Minneapolis), but the one we visited was on N. Milwaukee Ave. in Wicker Park. We stopped in quickly for a tea and to figure out where we were going next, but I easily could’ve hung out there with a good book for a couple of hours. There was tons of comfy seating and the lady who took my drink order kept calling me “sweetie,” which I find endearing as hell. If we hadn’t just eaten I definitely would’ve tried their Breakfast Tacos or Veggie Breakfast Sandwich, but their iced Earl Grey Lavender tea was excellent.
1620 N. Milwaukee Ave. @ourfairgrounds
We stopped in at Lonesome Rose for a couple of quick drinks. It had a very Desperado-meets-Insta celebrity vibe; thinks tons of Millennium Pink, cacti and classic desert saloon music in the background. Again, if I would’ve been hungry, I definitely would’ve ordered some food! Their chips and salsa looked fantastic, and it was difficult to pass up a simple Black Bean & Cheese Taco for $3. The side of Grilled Cactus sounded pretty interesting, too—it came with pepitas, queso fresco, grilled manzano pepper and lime vinaigrette.
2101 N. California Ave. @lonesomeroseforever
So eventually we did get hungry for a snack and stopped in at Revolution Brewpub. I’m not a beer drinker, but I did have a great cocktail (don’t ask me what it was). We slid in just in time for brunch and shared a bowl of Shakshuka. If you’ve never had it before, it’s a stew-like dish that originates from Tunisia and features eggs poached in a sauce of tomatoes, chili peppers and onions. This one was hella spicy (left my nose dripping) and came with pita for dipping. I for sure liked it but wasn’t expecting it to be so spicy. If we came again for a full brunch, I might try the Goat Cheese Frittata.
2323 N. Milwaukee Ave. @revbrewchicago
EMPORIUM ARCADE BAR & LOGAN ARCADE
Chicago loves its arcades! Neither actually offer food (although Emporium allows you to bring in whatever food you want), but I thought both were still worth mentioning if you’re looking for something fun to do in between eating. Emporium had more of the party vibe going on (you could tell it gets pretty wild a night) and they had a variety of games, including Pac Man, pinball, air hockey and pool. They had tons of beers, too (I drank cider).
Logan Arcade, on the flip side, seemed like a place where the true game nerds hang out (reminded me of the arcade from Stranger Things). They kept it classic with tons of pinball machines and games like Tetris and Mario Kart, plus they made a mean gin & tonic. Logan Arcade is a great place for a day hang before heading out at night.
2363 Milwaukee Ave. @emporiumchicago
2410 W. Fullerton Ave. @logan_arcade
OWEN & ENGINE
Ed and I were so excited to come across this proper little British pub. It’s hard to describe how a British pub feels (dark, cramped, mismatched chairs, maybe), but Owen & Engine definitely had it down pat. Ed downed a bunch of British beers while I sipped gin & tonics, and we snacked on chips with malt vinegar mayo (me) and a scotch egg (him). We were going to see Fall Out Boy at Wrigley Field that night and had dinner plans near the stadium, or else we would’ve stayed much longer. I for sure would’ve loved to have tried their Vegetable Korma or Bubble & Squeak!
2700 N. Western Ave. @owenandenginechicago
THE VIOLET HOUR
If you only visit one bar in Chicago (not sure how that’s possible, but anyway), make it The Violet Hour. Basically, if you walk past the bar, you wouldn’t even know it’s there; all you see from the street is a wall with a mural (it changes regularly). But lo and behold, there’s a secret door on the corner with a friendly doorman waiting just behind. You’ll probably see a small (or large) queue hanging around outside, and the door will open occasionally, allowing small groups at a time. Once you do get in, you sit where you’re told. We hung at the bar celebrating Ed’s 34th birthday, drinking and snacking on a soft pretzel, and when we got up to leave the bartender asked if we’d join him in taking a shot (we did). The whole thing had a super cool, swanky, dark & sophisticated speakeasy vibe that I just thoroughly loved.
1520 N. Damen Ave. @violethourchicago. Photos above courtesy of The Violet Hour.
DUTCH & DOC’S
Dutch & Doc’s is a three-story restaurant with views overlooking Wrigley Field—and I think its proximity to this major tourist attraction is why the prices are exorbitantly high. A bottle of Miller Lite was $6, I kid you not.
The food was delicious — I went with the $15 Macaroni + Cheese, made with jarlsburg, grana, white cheddar, cavatappi pasta and breadcrumbs—but portions were small for the price (and I’m not usually someone to complain about portion sizes). Dutch & Doc’s is worth a mention because I do think the quality was there and the atmosphere was nice, but I can’t say I would personally return.
3600 N. Clark St. @dutchanddocs
Beatrix has three Chicago locations, and on our day downtown we dined in River North. This one was connected to the Aloft Hotel, and it was swarming with tourists licking their lips for Sunday brunch. Even so, it seemed like a neighborhood hangout, like the place you’d find both a family with small children and a bougey couple fueling up before international travel.
We had a reservation and slid right into a comfy little table by the window. I ordered the fantastic Quinoa + Poached Eggs, and Ed surprised me by ordering a vegetarian meal, too—Cauliflower Grits & Eggs. This was actually the first time that there were several vegetarian items on the menu that seriously piqued my fancy; I’d love to go back and try the Green Chili Enchiladas or the Pepper & Egg White Sandwich.
519 N. Clark St. @beatrixchicago
PRET A MANGER
I became obsessed with the European fast-casual restaurant Pret when I was studying abroad in London during college. It’s kind of like a Panera Bread but more vegetarian-friendly and with more grab-and-go options. I kid you not, if I lived in London I’d probably eat lunch at Pret every day (and I can’t say that about many restaurants). They’re based mostly in the UK, but they have locations in six American cities, one of which is Chicago. We couldn’t not stop in. The one we visited, on Michigan Ave., was a bit small and a bit sparse on options, but I was more than satisfied with my Egg Salad & Arugula Sandwich + Spinach & Artichoke Mac n Cheese. If you ever come across a Pret, you try it. Trust me.
108 S. Michigan Ave. @pretusa
Also located on Michigan Ave., Free Rein is part of the St. Jane Hotel and has an incredibly alluring logo that is the literal reason why we went inside (it’s also located just down from the American Writer’s Museum, which is well worth a visit). Cocktails only, this time; I went with the “What Would Jane Do?” made with citrus vodka, elderflower, mixed berry, sparkling wine and mint. The coolest part is that $1 from each WWJD sold (it was $13) is donated to the ACLU.
224 N. Michigan Ave. @stjanehotel
GIBSON’S BAR & STEAKHOUSE
Gibson’s is a true Chicago staple. This was Ed’s choice for his birthday dinner, and I was more than happy to play vegetarian-in-a-steakhouse. They didn’t have any specific vegetarian dishes they could whip up, but the highly skilled server talked me into the Double Baked Potato (or twice-baked potato) and a half order each of Spicy Charred Broccolini and Grilled Sweetstem Cauliflower with Lemon-Caper Vinaigrette. I’m definitely not used to steakhouses having such interesting sides, and I loved every single bite. I think my meal was about $25 in total, which certainly isn’t bad for steakhouse prices.
PUNCH BOWL SOCIAL
Remember how I said Chicago loves its arcades? Well, things take an interesting turn in the form of Punch Bowl Social. We arrived at opening time, 11am, on a Monday, and it was no shocker that the place was dead. It was like being in a Dave & Buster’s (but way trendier) after hours. There were lonely looking bowling lanes, shuffleboard tables, pinball machines, table games and a huge stage for karaoke; I seriously got lost in the space trying to find the bathroom.
But let’s talk about the food. I’m a major fan of mushroom gravy, and their Mushroom Biscuits ’N’ Gravy seriously delivered (great hangover food, btw). The buttermilk biscuits were smothered in white gravy and served with a fried tomato, crispy potatoes, avocado and eggs any style (I went with over easy). Beyond delicious and totally worth the genuine bargain of $11.