Get your tourist on: Chicago

Chicago skyline

Sky, city, surf: The Chicago skyline, as seen from in front of the Adler Planetarium. iPhone photo by Rose Raymond.

When I was 20, my best friend Preethi had just moved to Wrigleyville, and we were in the habit of spending broke summer weekends eating the cheapest food we could find and walking around the city for hours. One 90-degree June evening, we had splurged on Flaming Lips tickets at the Aragon. We trekked the two-plus miles in the sweltering heat—it felt a lot further—and arrived at our destination sweaty, thirsty and already sleepy. After the show, we used Preethi’s U-Pass to get on the El, where we ran into several fellow concertgoers and Lenny, a drunk busker.

Lenny introduced himself to us on the platform, then boarded the train with us, where he began to play.

“Girls, this is a song I wrote. It’s about what happens when a man loves a woman, and they’re two different colors,” he said.

He proceeded to play an amazingly heartfelt rendition of Hot Chocolate’s “Brother Louie.” Of course, this was long before the song re-entered the cultural lexicon via Louis CK. We loved the song and, in our naivete, had no idea that it wasn’t original.

“That was a classic Chicago moment,” Preethi said to me as we exited the train and said goodbye to Lenny. Months later, we would discover his ruse, which would only make the exchange even more legendary to us.

This memory still stands out as one of my favorites of the city, but I’ve added many others to it over the years by visiting museums, eating and drinking in various neighborhoods and listening to live music all over the city. Inspired by my friend Mathilde’s guide to Atlanta, I wanted to write my guide to the City of Big Shoulders—an easy list to share with visiting friends and anyone else interested in exploring Chi-town.


Chicago has more tourist attractions than I could possibly list here—this is just a brief rundown of my personal favorites.

Architecture boat tour (located in the Loop/River North): This is, hands down, my favorite sightseeing pastime in the city. Ride a boat down the river for an hour or 90 minutes and learn about the origins of the Merchandise Mart, the Willis Tower, the Trump Tower and the Carbon & Carbide Building.

Kids under the Bean

My cousin Fred and his friend Zak having fun under the Bean. Photo by Rose Raymond.

Millennium Park (located in the Loop): The result of the city’s 2004 downtown revitalization project. Highlights include the Pritzker Pavilion (amazing acoustics for outdoor shows) and Cloud Gate, also known as the Bean, where you can photograph a wavy reflection of the city skyline and yourself upside down. If you’re in town on a Monday, definitely check out Downtown Sound. There are other free events throughout the week as well, such as yoga on some mornings.

The Art Institute of Chicago (located in the Loop): See Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, Georges Seurat’s A Sunday On La Grande Jatte and countless other iconic paintings and works of art. The 2009 addition, the Modern Wing, provides an airy, light-filled space to hang out in and a nice view of the city skyline.

Second City (located in Old Town): The comedy club that produced Tina Fey, Steve Carell, Tim Meadows, Chris Farley and Bill Murray. I’ve laughed until my face hurt every time I visited. Definitely pop in the Old Town Ale House on your way home if you go and check out the unique artwork.

Chicago skyline

The Chicago skyline as seen from Montrose Beach. iPhone photo by Rose Raymond.

Montrose Beach (located in Uptown): Our favorite beach in the city. Expansive grassy space for grilling, views of the city from the lake, usually not too crowded.

Museum of Contemporary Art (located in River North): A pretty comprehensive modern art museum. You can find lots of unusual goodies in their gift shop, too.

Chicago Cultural Center (located in the Loop): A free museum that has interesting rotating exhibits as well as a nice free hangout area and the world’s largest Tiffany stained glass dome.


Again, Chicago is a hugely musical city and contains more venues than I could possibly name here—below are the spots in which I most enjoy hearing live tunes.

The Green Mill (located in Uptown): A former speakeasy and hangout of Al Capone, this jazz club has a well-preserved ’40s feel, beautiful wood-carved walls and great musicians.

Schuba’s (located in Lakeview): A tiny bar and club that often hosts indie, alt-country and singer-songwriter acts. They have a restaurant next door called The Harmony Grill, where you can get baked mac & cheese with 17 different toppings, including black beans, mushrooms and veggie chili.

Lincoln Hall (located in Lincoln Park): A sister venue of Schuba’s that opened in 2009. It’s bigger than Schuba’s, but still intimate. The best thing about this venue is the rich, acoustically almost-perfect sound.

Food and drink by neighborhood

Chicago is famously a city of neighborhoods—no trip is complete without at least one adventure outside the bounds of the Loop. Here’s a list of my favorite hoods, and the places I love to eat and drink in them.

Wicker Park

Visit the intersection of Milwaukee, Damen and North, also known as “The Crotch,” for your fill of hipsters, mustachioed cyclists and some of the best food and drink in the city.

Antique Taco's indescribably delectable fish taco. iPhone photo by Rose Raymond.

Antique Taco’s indescribably delectable fish taco. iPhone photo by Rose Raymond.

Antique Taco: Delicious, somewhat reasonably priced hipster tacos! Their fish taco—smoky and deep-fried with the perfect amount of Sriracha tartar sauce and cabbage—is the best I’ve ever had.

Piece Pizza: Currently my favorite pizzeria in the city. The pizza is New Haven style, not Chicago style. My favorite: the white pizza with clams, a New Haven classic.

Big Star: An iconic Chicago bar that also serves hipster tacos. Strings of lights hang over the massive outdoor patio.

The Violet Hour: Beautifully crafted cocktails likely to contain exotic ingredients such as tobacco bitters and rosewater. Swanky, fancy interior. No sign out front, and people often wait an hour to get in. But once you’re in, you’ll get your own table, and the drinks are worth the wait!

Emporium: Play ’80s and ’90s arcade games and drink craft beer. Dig Dug, Tetris, Frogger, pinball. Super fun.

Logan Square

Adjacent to Wicker Park, Logan Square serves as its hipster overflow zone by offering cheaper rents. Logan Square, which has Mexican grocers and cheap diners alongside its trendy bars, feels a little more authentically Chicago to me.

Revolution beers

Revolution brews. iPhone photo by Rose Raymond.

Revolution Brewing: One of Chicago’s best breweries. Their Anti-Hero IPA is probably my favorite local beer. Their food is delicious too.

The Boiler Room: Delicious pizza, cheap drinks, old movies with the sound off, usually ’90s rock on the speakers, booths to sit in … what more could you want?

Longman & Eagle: Epic brunch. Fancy drinks & expertly made omelets. Expect the wait to be long, but worth it.

Ukrainian Village

A neighborhood near and dear to me, as I lived there for two and a half years (I just moved to Albany Park/Ravenswood … more on my new hood in a future post!). Neighborhood residents are a mix of hip kids and Ukrainian immigrants that came over in waves from the 1870s to the 1990s, after the fall of the Soviet Union. Home to a number of beautiful Ukrainian churches; you’ll see several if you walk down Oakley Street from Division Street to Huron Street.

Ukrainian church mural

The mural gracing Sts. Volodymyr and Olha Ukrainian Catholic Church at Oakley and Superior Streets. Photo by Rose Raymond.

Fatso’s Last Stand: Classic Chicago greasy spoon fare. Think Chicago hotdogs, gut-busting burgers and crispy fries. They also serve the elusive vegetarian Chicago-style hotdog, which I haven’t tried yet, but it’s on my list.

Happy Village: Probably the best outdoor drinking area in the neighborhood. Ping pong tables indoors. Cheap drinks.

Bite Cafe: A cozy little BYOB spot with a nice brunch. They serve breakfast bebimbap, which is my favorite.

The Lockdown: A prison-themed heavy metal bar that serves unbelievable burgers. Expect to have your ears blasted by Slayer while you foodgasm from the culinary delights. Half-priced burgers on Tuesdays.

Lincoln Park

To be honest, Lincoln Park technically isn’t one of my favorite neighborhoods, but a few of my favorite restaurants live there, and it’s a convenient hood for out-of-towners to visit, as it’s near the Loop and it houses the Lincoln Park Zoo.

Pequod's pizza

Pequod’s deep dish. I ate it for breakfast on this day, which explains the vitamins. iPhone photo by Rose Raymond.

Pequod’s: Chicago-style pizza at its best. I’m honestly not a huge fan of the deep dish, but I love taking out-of-towners here. The pies are spot on and I love the homey, chill atmosphere as well.

Banh Mi hotdog

The Banh Mi dog from Franks ‘N’ Dawgs. iPhone photo by Rose Raymond.

Franks ‘n’ Dawgs: Super-fancy artisan hotdogs and sausages served on Texas toast.


Encompasses Wrigleyville and Belmont & Clark, a mecca of thrift stores and specialty stores selling goth and punk apparel. I loved this area when I was in high school and early college. Think mid-20s baseball fans from the suburbs, rebellious teenagers and young professionals. Nowadays I prefer hanging out on the city’s West side, but again, a few of my favorite eateries are here.

House of Sushi & Noodles and Wasabi Cafe: Why eat sushi in the Midwest? Because all you can eat. These sister restaurants know how to do it. Wasabi Cafe is a few dollars more, but also is BYOB and has a bigger dining room. It’s better for groups.

Headquarters: If you love old arcade games, this is the place for you. Much bigger than Emporium, and the games are all free. In return, you pay more for drinks, but they serve a lot of good craft brews.

Crisp: Korean-style fried chicken. If you haven’t had it, it’s lighter, juicier and more spice-infused than American fried chicken. Crisp was highlighted in Travel & Leisure’s “America’s Best Fried Chicken” back in 2010. Take that, the South!

Soupbox: Nothing but lots and lots of heavenly soups. I practically fainted when I had the lobster bisque—the perfect amount of cream and lobster, with just a touch of mint. Swoon.


A Mexican neighborhood on the city’s West Side. Famous for good Mexican food, art galleries and thrift stores.

The Skylark: This was my favorite hangout in the city when I was 22. It’s a classic Chicago dive with booths, dim lighting, cheap drinks and amazing tunes on the jukebox. But what elevates it above the other Chicago dives? Soul food! In particular, tater tots with three dipping sauces. PBR + tots = Every college kid’s dream.


A fun South Side hood. Encompasses U.S. Cellular Field, and is thus a good neighborhood to check out after a Sox game.

Maria’s Packaged Goods & Community Bar: A super-chill bar that serves craft beer and fancy cocktails. Out of the way for most, but worth the trek. It has two epic outdoor seating areas.

The Polo Cafe: I haven’t tried it yet, but it’s on my list. Has a ’50s atmosphere and is the No. 14 restaurant in Chicago on TripAdvisor. Standard American fare. Surf and Turf.

Nana: A cute little vegan-friendly eatery. Heavy on the local, organic and sustainable fronts. I had the chickpea fries and they rocked my world.


A historically Swedish neighborhood famous for brunch, bakeries and antiques.

Hopleaf: A Belgian-style bar inspired by the Cadieux Cafe, my favorite establishment in Detroit. Bounty of Belgian brews on tap, double-fried French fries, light and airy dining room.

Simon’s: An old Swedish-themed bar that feels like stepping back into the ’70s. Has live jazz on occasion and a fantastic jukebox. (Full disclosure: I haven’t actually been here, but Travis loves this place and provided this review.)


Also on the South Side, near Bridgeport. A fun place to walk around, especially if you are in the area. Definitely make the trek to Chinatown Square, an outdoor-mall-like strip that really feels like Asia (says the girl who lived there for two years!).

Hing Kee: Soups and stews with homemade noodles. Reasonably priced and delicious.

Aji Ichiban: The Chicago branch of a chain candy store based in Hong Kong. Worth visiting just to see the plethora of random Asian candy they have on offer as well as the dried squid.

Dim sum: Chinatown is famous for dim sum. I haven’t tried it yet here, but my friend Iris recommends Phoenix and Triple Crown.

Out of bounds

Here are a few places I love that didn’t fit in any of the neighborhoods on my list.

The Signature Lounge (located in River North): A must for visitors lucky enough to catch the city on a clear day. It’s a bar on the 96th floor of the John Hancock building. Enjoy the city from above while drinking an $8 Budweiser.

Lincoln Square Lanes (located in Lincoln Square): An old-school bowling alley complete with an Abe Lincoln mural, pool tables, shuffleboard and a rowdy clientele.

Surviving winter in Chicago: Polar vortex edition

Millenium park

On New Year’s Day, we took our friends Jeremy and Pedra to Millennium Park in the snow. Photo by Rose Raymond.

By the time I read that Chicago’s 2013-2014 winter has been the city’s coldest in 30 years, I wasn’t surprised. I knew it was bad the day my work was closed because wind chills were threatening -45 degrees. The actual temperature that day? -12. What does that feel like? No matter how bundled up you get, cold seeps through your hands, feet and face almost instantly. On that day, I threw a cup of boiling water into my boyfriend’s yard and watched it vaporize into steam on impact with the frigid air.

Cloud gate

Snow falls on Cloud Gate on New Year’s Day 2014. Photo by Rose Raymond.

As Bob Dylan would say, “You don’t need a weather man to know which way the wind blows.” But in January, I got in the habit of checking the 10-day forecast on anyway, hoping to see respite from the deep freeze on the horizon. Then I lost track of how many days running I saw nothing higher than 29 in the forecast. When things finally started to look good—highs in the 40s!—the forecast reminded everyone that another polar vortex was on the horizon.

Devastating? Yes. A total bummer? Uh-huh. Strength-building? Absolutely.

In 2010, I moved to south Florida with a lifetime of brutal winters under my belt, including many in Chicago and D.C.’s 2010 Snowpocalypse. I got to West Palm Beach in August, and it was December before I needed to wear a long-sleeved shirt outdoors. On Halloween, it was 75 degrees and humid at midnight. In the streets of West Palm Beach, my fellow revelers took full advantage of the warm weather to show some serious skin. If you haven’t seen thongs in the street, you haven’t experienced a south Florida Halloween. But that’s another story.

The balmy winter was nothing short of heavenly, but I was shocked the first day the temperature dropped below 40 degrees—I think it was in January. I was in the habit of going to the gym after work with three of my coworkers. That day, they all said it was too cold to go anywhere. When I got to the gym by myself, I was one of the few exercisers “foolish” enough to venture out in the chilly 37-degree weather.

Over the following 18 months that I stayed in South Florida, I noticed a trend: If the weather was ever-so-slightly unpleasant, people would stay indoors. Once, I was the only person besides the team captain to show up for a kickball practice when it was cloudy and drizzling. Another time, a Friday night bar outing was canceled because of heavy rain.

Had I stayed much longer in Florida, I’m sure I would have joined the ranks of weather pansies dominating the state. But after this winter, I feel invincible. A few weeks ago, I had plans to go out with friends on a Friday night. When I saw that the windchill was -5, I thought to myself, “That’s not so bad,” and my buddies and I wandered around the city, visiting no less than five establishments that night. We walked about a mile total traveling from place to place. I might be out sunbathing when we see 45 degrees.

Presumptuously, I now consider myself something of a cold-weather expert. Here are my tips on surviving a 30-year cold spell in Chicago, or anywhere really:

Go on a spending freeze.

The coldest months of the year are usually January and February—conveniently, right after the holidays, when we’re all broke and burned out on socializing, eating out and celebrating. I decided to restrict my spending from January 21-February 21. I didn’t go out unless I had previous plans to do so, and I avoided buying nonessential items. This was my first ever spending freeze, and it was really hard, but the abysmal weather made it a little easier to stay home and cook or have dinner at friends’ houses instead of going out.


One of our staying-home winter projects was making homemade blueberry scones. iPhone photo by Rose Raymond.

Get out of the house.

I’m fully aware this item directly contradicts the previous. My boyfriend, Travis, and I avoided going out when we didn’t have set plans, but we ventured into the sub-zero many times. Usually it was because we had concert tickets or out-of-town guests, but the act of going out, even in the raw cold, was always a refreshing break from a solid week of nesting.

But if we didn’t have anything going on, we almost always stayed in, and probably would have even if we weren’t trying to save. So my advice would be to buy concert or theater tickets and invite friends to visit well in advance of the crappy weather—you won’t want to go out, but once you do, you’ll be glad you did.

Dr. Dog

We faced frigid temps to see Dr. Dog at the Riviera Theater in Uptown. Amazing show. iPhone photo by Rose Raymond.

Cheese fries

We ended another winter night out at Chicago institution Weiners Circle. The cheese fries are fantastic. iPhone photo by Rose Raymond.

Cans at Maria's

A wall of vintage cans from the wall of Maria’s, one of the places we sojourned during the deep freeze. iPhone photo by Rose Raymond.

Wear snow boots and long underwear.

After one of our early January arctic blasts, the temperature inexplicably rose to 38 degrees, prompting rain and the mountains of piled-up snow around the city to flood the streets. On this day, Travis was nearly the unhappiest I’ve ever seen him—we went to a birthday dinner, and his shoes and socks got soaked through on his way to the party. Luckily, my feet were dry, so I was in a better mood. I cheered him up by reminding him of our upcoming travel and making a list of all the other things we had to look forward to (Outdoor dining! Going to the beach! Ice cream!).

Commuting and going out in inclement weather is brutal, but wearing the right stuff works wonders. My staples this winter? Snow boots, fleece-lined leggings and mittens made from recycled wool sweaters.

Leave town.

At the beginning of January, Travis and I bought plane tickets to California for the last week of February. Knowing we were escaping really helped us get through the dreary subzero days. Travel is expensive, but in my opinion, it’s worth every penny—and you can go on a spending freeze to save up for your trip!

For the past six weeks, as Travis and I traversed the city in the heinous cold, wearing our excessive layers, we reminded each other that we were escaping. That soon, we’d be on a beach in flip-flops and T-shirts.

What are your tips for surviving merciless winters?

Frozen river

The partially frozen waters of the Chicago River make a beautiful design. iPhone photo by Rose Raymond.

Cool running: Seeing the city at 6 mph


This is one of the oldest outdoor murals in the country, according to WBEZ. It’s on North Avenue and it’s called “La Crucifixion de Don Pedro Albizu Campos” and features portraits of nine Puerto Ricans instrumental to the island’s development and independence. iPhone photo by Rose Raymond.

When I lived in D.C. in 2009, my Saturday runs were on the National Mall. I’d run north through my neighborhood to get there, then past the Smithsonian Castle, the Washington Monument and the Lincoln Memorial. Sometimes I’d take detours past the Vietnam Veterans Memorial and the Jefferson Memorial. Occasionally other runners joined me, but I mostly dodged throngs of tourists mesmerized by the monuments, snapping shots of the capital of the free world.

Had I not been an outdoor runner, I would have visited the Mall about 25 fewer times than I did the year I lived in the District. I would have known much less about the geography of the area and the patterns of weekend tourists. Running is a great way to learn more about your neighborhood and your city. And you don’t have to go crazy—I’m by no means a serious runner. I max out at 7 miles. I have no interest in doing a marathon. But I do go running at least once a week, and everywhere I’ve lived, I’ve learned something about my home by running around it.

In Chicago, I often run in Ukrainian Village and Humboldt Park. On my Saturday runs here, I’m most struck by the murals I encounter. Some of them are political. Others are commercial. Most of them are beautiful. They all make my run, and the area, a little more intriguing.


Chicago-area hot dog joints are often called “red hots.” This is Odge’s Old-Fashioned Red Hots on Damen. I haven’t eaten there yet. iPhone photo by Rose Raymond.


I really enjoyed this spine painting. Only later did I realize that my legs were in the picture. iPhone photo by Rose Raymond.


A portrait of Puerto Rican baseball player Roberto Clemente is on the grounds of a high school that bears his name at Western and Division. iPhone photo by Rose Raymond.


Palms on California Avenue near Division, I think. iPhone photo by Rose Raymond.


Flamingos on California Avenue near Division, I think. iPhone photo by Rose Raymond.

Bright lights, big shoulders: My own private Chicago


A piece of Chicago’s skyline, as seen from a river architectural tour, August 2011. iPhone photo by Rose Raymond.

For most of my life I have had a feverish love affair with the city of Chicago. It started when I was 5 years old and saw the city from the (then) Sears Tower for the first time. I remember trying to find my house beyond the skyscrapers. We lived in Oak Park at the time.

Later, as a high school student, my friends and I leapt at any chance to escape our hometown (no longer Oak Park at this point; the less-cool Woodridge) and drive into the city. Sometimes we had a reason, such as a shopping trip at The Alley or an exhibit at the Art Institute. Other days, we’d linger over coffees in Greektown diners or people-watch in Grant Park.

When I was a college student, the city came to represent everything the suburb where I went to school lacked: diversity, grittiness, vibrancy, excitement (sorry, Naperville …). A few of my friends had moved there by then. I discovered neighborhoods I’d never seen before, each with their own personality: Pilsen, Andersonville, Bridgeport. I went to shows at Metro, the Vic and the Double Door, and back then I kind of relished the fact that a trip to the city tacked a couple hours onto the night—the driving in and the driving home. Of course, I often slept on my friends’ sofas, too. In the morning, we’d stuff ourselves with pancakes from Lou Mitchell’s, the Golden Nugget or Cozy Corner.

Mexican wrestlers

Mexican wrestlers at Humboldt Park’s Riot Fest, September 2012. iPhone photo by Rose Raymond.

When I left the country in 2005, I missed Chicago terribly. I walked the streets of Seoul, loving the narrow alleyways, well-dressed pedestrians and cheap noodle shops, but missing Chicago’s diners, laid-back passersby and comparatively wide open spaces (I looked it up once: At the time, Seoul and Chicago shared roughly the same land area, but Seoul’s population was three times Chicago’s.).

But my love for Chicago was conflicted by my desire to attend graduate school. So off to Missouri I went. I learned to love Missouri, but that’s another story. How was it easier to live halfway across the world from Chicago than a six-hour drive from it? I was visiting the city more frequently now and discovering new neighborhoods, bars and even friends.

I lined up unpaid internships in the city for the summer of 2008. I was as psyched to live in the city as I was stressed about the fiscal black hole I was about to fall into. Then a company in Florida offered me a paid internship. Financially, it was the only responsible decision to make. And a similar opportunity came up in Washington, D.C., in 2009. In 2010, I was offered a job in Florida. At this point, I’d been away from the city for five years, and the extended near-poverty of graduate school and internships was starting to wear on me. A job? With benefits? By the beach? Yes, please.

My two years in South Florida were an extremely fun blur of Cuban food, tiki bars and beach runs. They gave me an appreciation for warm weather that has, I fear, forever diminished my tolerance for Chicago winters. But in 2012, I decided that 1,300 miles between myself and my favorite city was 1,300 too many. An opportunity presented itself, and I moved to the city in August. A friend from college needed a roommate in the Ukrainian Village. Years earlier, I couldn’t have known that so many of the places I’d loved visiting – Club Foot, the Empty Bottle, the Rainbow Club – were in the first Chicago neighborhood I would live in.


Storefront on Western Avenue in Ukrainian Village, circa October 2012. iPhone photo by Rose Raymond.

As ecstatic as I was/am to finally call Chicago home, my relationship with the city changed when I moved here. When you don’t live in a city, you’re not spending your time in it buying groceries, commuting and doing your laundry. So it’s easy for the city to retain 100 percent of its magic. Before moving here, I associated Chicago with adventure, wild nights out, 4 a.m. burritos at Flash Taco before a RedBull-fueled drive back to the ‘burbs.

Moving to the city you’ve always loved from afar is like finally going on a date with the high-school crush you’ve had eyes on since junior high. Or maybe it’s like skipping the courtship and moving in with that person. Now that this is my home, I’m privy to all of Chicago’s burps, farts and dramatic weirdness.

I know that it’s not the best city in the world for commuting, and it might have the most abysmal weather of any place I’ve ever lived, and yet … I love that I can see the John Hancock building from my neighborhood. I love riding the El and living in a city where you can get by without a car. I love that, a short walk from my apartment, there’s a prison-themed heavy metal bar that serves unbelievable turkey burgers, and I’m about to go eat one.

This blog will serve as my attempt to capture what I can of the magic of Chicago. It’s my reminder to keep exploring, to keep finding new things to love about this city. If you’re reading, feel free to send me suggestions of places to go or things to do!