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.


Bookends: Los Angeles & San Francisco

When Travis and I arrived in Los Angeles at the start of our vacation, our friend Jeremy picked us up from the airport and played us a mix of songs from LA bands—The Beach Boys, The Doors, Buffalo Springfield—as we drove into the city. Three magical days followed as we ate our body weight in tacos, laid on the beach and, one hilarious night, wore 1970s aftershave from a van-shaped bottle. We were sad to leave LA, but had mountains, elephant seals and seascapes waiting for us on the Pacific Coast Highway. In San Francisco, the revelry continued as we walked around the city until we got lost, took a ferry across the bay and ate sushi in spitting distance of the ocean.

I recently wrote a detailed guide to driving the Pacific Coast Highway, but I also wanted to share some photos from the bookends of our trip: the City of Angels and the City by the Bay. Enjoy.

Getty Villa tile

Midwestern feet with haunting Italian tile at the Getty Villa. Photo by Rose Raymond.

Getty Villa tile

Beautiful Escher-esque tile work at the Getty Villa. Photo by Rose Raymond.


Jeremy, our gracious LA host, chilling in the Getty Villa’s cafe. Photo by Rose Raymond.


Pedra, our other gracious LA host, is enjoying the cafe patio at the Getty Villa. Photo by Rose Raymond.

Pet turtle

Pedra and Jeremy’s pet turtle was the mascot of our LA trip. Here he is taking a stroll at their neighborhood garden. Photo by Rose Raymond.

Golden Gate Bridge

If you visit SF, definitely rent a bike and ride it over the Golden Gate Bridge to Sausalito. There you can catch a ferry across the bay and photograph the bridge at sunset. Photo by Rose Raymond.

Houses in San Francisco

We spotted these Day-Glo houses near Haight-Ashbury in San Francisco. Photo by Rose Raymond.

Rooster pitchers

Rooster pitchers are perched in a San-Fran shop window. Photo by Rose Raymond.

Musee Mechanique carnival game

This is a close-up of a large mechanical carnival arcade game from San Francisco’s Musee Mechanique. I don’t remember the date on this one, but I would guess ’30s or ’40s. We fed the machine 50 cents to watch the wrestlers punch each other while the man out front shouted. This museum is a must-see if you’re in town. Admission is free and each game is 25 to 50 cents. Photo by Rose Raymond.

Musee Mechanique carnival

Here’s another close-up from the carnival diorama at the Musee Mechanique. Fire-eaters and strongmen for 10 cents! Photo by Rose Raymond.

Rose and Travis

San Francisco selfie: I told Travis he looked handsome with a brooding expression on this day, so he made this face in many photos. Photo by Rose Raymond.

Dan and Vicki

Dan and Vicki, our gracious SF hosts, took us to Roti Indian Bistro, where the food was fantastic. Photo by Rose Raymond.

El Toreador

Later that night, we also checked out El Toreador, an SF institution famous for its folk art and reasonable-yet-delicious Mexican food. Photo by Rose Raymond.

Taqueria Cancun

Taqueria Cancun was our last stop on our last night in SF. I felt like I was in college again because the place was cash only and Travis, me and my friend Aaron had to cobble together our dollars and quarters to buy four $2.25 tacos. Good times. Photo by Rose Raymond

Los Angeles to San Francisco on the Pacific Coast Highway: A guide

Pacific Coast Highway sign

A roadside sign on the Pacific Coast Highway north of Monterey, Calif. Photo by Rose Raymond.

When Travis and I planned our February getaway from the ice-encrusted hellscape that would become the coldest winter on record in Chicago, we decided to drive the Pacific Coast Highway from Los Angeles to San Francisco. For inspiration, we watched YouTube videos of the journey, read TripAdvisor and asked our Cali friends for recommendations.

The drive was as phenomenal as everyone said it would be, and I would recommend it to anyone. This is how we did it, and our advice for others.

Trip length: A lot of the TripAdvisor posts we read suggest doing the drive over five days. That seemed excessive to us for a trip that takes, on paper, roughly nine hours. We budgeted three days, which allow plenty of time for eating, sightseeing and relaxing, especially if you, like we did, want to spend some time in LA and San Francisco as well. But after finishing the drive, I do think five days would be better if you can swing it, because you’ll likely take detours, stop at vista points, and want to have several hours at night to get dinner and lounge in your hotel room.

Bowling sign

We stopped to photograph this sign in Oxnard, Calif. Photo by Rose Raymond.

Day 1: Our journey on the Pacific Coast Highway, also known as U.S. Highway 1, began at about 2 p.m. in Santa Monica, which borders LA on the west side. Our friend Jeremy suggested visiting Solvang, the Danish wine hamlet where “Sideways” was filmed. It took us about three hours to drive there, and we deviated from the PCH to go further into the mountains, where the temperature dropped.

We ate dinner at California Tacos, a little strip-mall gem that served us homemade tortillas and chips with heavenly guacamole. This place was amazing and cheap, but if you are looking for resort-town-style ambiance, there are plenty of pricier options in downtown Solvang just a few blocks away, where we headed after dinner to get wine samplers at Carivintas Winery. I tried Barbera wine for the first time. It has a deep, muted, delicious taste. Carivintas donates a portion of their proceeds to animal shelters, and each bottle comes with a painted portrait of a rescue animal on the label.

Highway 1 vista point

Another vista point, another breathtakingly serene view. Photo by Rose Raymond.

Solvang’s city center feels like California’s take on Europe. Lots of Tudor buildings, and everything is a little newer and cleaner. We visited the Hans Christian Anderson museum—a must if you’re in town, it’s free and takes about 15 minutes—and learned a lot about the author of Thumbelina, The Little Mermaid and The Princess and the Pea.

Our first hotel was just a short drive away in Pismo Beach, which a lot of people recommended as a place to sleep. It’s a cute beach town right off the PCH on the ocean. Our room was dirt cheap, but in the off-season Pismo Beach is a bit of a ghost town. We went in the hot tub at our hotel, and the only other people we saw were some sketchy characters in the parking lot. One of them was skateboarding with an empty gas can in his hand until he wiped out spectacularly. We asked him if he was OK, but he just got up and skated away.

I would suggest skipping Pismo Beach in the winter unless you are really in the market for a cheap hotel room.

Day 2:

We started our day in a monarch butterfly grove just down the road from our hotel. We saw hundreds of butterflies clustered on trees and even a few in the throes of an intense mating session on the ground. We learned a lot about the lives of Monarch butterflies: how they travel in packs, migrate south for the winter and can live anywhere from six weeks to seven months, depending on the time of year.

Elephant seals

Some friendly female elephant seals got our attention at the Elephant Seal Vista Point. Photo by Rose Raymond.

Then we started driving. Our first stop was the Elephant Seal Vista Point, which is one of the highlights of the drive. The vista point gives people a chance to see elephant seals in their natural habitat. We probably saw about a hundred of them lounging on the beach, nursing, playing and sleeping. We learned that male elephant seals can be double or triple the size of their female counterparts, and that the males have massive proboscises that make them all look like they’re related to Rodney Dangerfield. We also learned that elephant seals have an “alpha male” system, in that the dominant males, which comprise about 10 percent of the male population, are the only ones that get to copulate.

Maybe half an hour north of the vista point, we pulled over because Travis saw a “Redwoods” sign and a trail. We did some impromptu hiking and saw some gorgeous trees.


A shot from our spontaneous roadside Redwood trek. Photo by Rose Raymond.

Back on the road, raindrops began falling as the landscape grew more dramatic and the drop-offs on the roadside got steeper. A few people had warned me that the hairpin turns and curving mountainside roads of the PCH could be dangerous. However, I was just in Bolivia last October, and the PCH roads have nothing on the Bolivian countryside. These roads may freak you out if you’ve never driven through mountains before, but they had decent guardrail coverage and the pavement is more than wide enough for two vehicles (not the case when I traveled from Corioco, Bolivia to La Paz in the snow and we had to pull over several times to let a bus going the other way pass). My friends said people like to drive fast and recklessly on the PCH, and we experienced a little of that, but just pulled over and let those folks pass us. This may be more of a problem in summer when there are more people on the road, and I could see traffic being a problem. But on weekdays in February, it’s not bad at all.

Several friends recommended Big Sur Bakery, and we got there at the height of the rain. The bakery really delivered, though it should be noted that they only serve meals at lunch and dinnertime. The interior has an elegant log-cabin vibe, and it was a soothing place to escape the weather. We ate a potato frittata, a pumpkin scone and a croissant and washed them down with some very delicious vanilla Rooibos tea.

Point Lobos

The view from the car as we drove through Point Lobos. This is my favorite photo from the trip. Photo by Rose Raymond.

Point Lobos

The Seussian seaside cliffs of Point Lobos. Photo by Rose Raymond.

Point Lobos was our next stop, and by then the rain had cleared up. Point Lobos is another highlight of the PCH. The jutting cliffs, brilliant rain-soaked cypresses and crashing waves will make you feel like you’re in a Dr. Seuss book.

After Point Lobos, we were ready to stop for the night at our hotel in Monterey. We had left all the confirmation info at home, so we actually had to call around to find the hotel we reserved, but it only took a few calls. We stayed at the Colton Inn, which was really nice for the price. They have a sauna that we took advantage of the following morning.

Monterey is known for seafood, and we ate on Fisherman’s Wharf at the Old Fisherman’s Grotto. If this sounds like a cheesy tourist trap, yes, it kind of looks that way from the outside, but inside it is pretty classy and the food was amazing. We ate crabs, scallops, shrimp, clam chowder, crab cake, seafood salad and sourdough bread. Our waiter was one also of the most professional I have ever seen.


Travis is about to feast on crab legs at the Old Fisherman’s Grotto in Monterey. Photo by Rose Raymond.

We ended our day with a beer at the Cannery Row Brewing Company, which has 73 beers on tap. Travis had a sour rye beer and I drank a Firestone Walker IPA. I loved both the restaurant and the brewery, and would definitely suggest stopping in Monterey.

San Carlos Cathedral

We checked out Monterey’s San Carlos Cathedral, built in 1794, on our way out of town. Photo by Rose Raymond.

Day 3:

After a quick stop in the hotel sauna and a quick visit to a 200-year-old church, we drove to Santa Cruz to eat at the Surfrider Cafe, which lured us in with the promise of avocado fries. The “fries” are actually breaded and deep-fried avocado slices, but they were nonetheless delicious. Travis ate a ramen burger, which had a ramen-and-egg bun.

Our next stop was the Fitzgerald Marine Preserve, where we spent an hour wandering around the beach checking out tide pools. We saw sea anemones, starfish, snails, tiny fish and more. If you visit the preserve, check online to see when’s the best time of day to visit. You’ll want to go at low tide. Having said that, while I enjoyed the preserve, it was one of my least favorite stops on our trip.

The inside of San Carlos Cathedral

A peek inside the cathedral. Photo by Rose Raymond.

Then it was time for our farewell stretch of the PCH as we made our way into San Francisco to return our rental car. It’s pretty cool to see the pastoral give way to the urban as you make your way into the city.

After returning the car, our friends Dan and Vicki took us to Twin Peaks to see a night view of the city and then to Beach Chalet, which was a perfect place to end our coastal travels. Beach Chalet is an ocean-side restaurant and brewery inside a stately freestanding building. The first floor, which you walk through to get to the restaurant, features beautiful 1930s frescoes commissioned by the U.S. Works Progress Administration. The paintings are of San Francisco life in the ’30s, and according to the website are in the style of the Arts and Crafts movement. On the second floor are floor-to-ceiling windows for seeing the ocean, which is just across the street, and beer brewed on site.

Everyone should drive the Pacific Coast Highway at least once. Some spots we didn’t check out but are highly rated include the Hearst Castle, the Monterey Aquarium, Pfeiffer Big Sur State Park and the PCH north of San Francisco in Humboldt County. We will be back at some point to hit those!

Vacation portrait

Overcast day + black & white = Vacation portrait perfection. Photo by Rose Raymond.

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