If you’ve ever found yourself torn between visiting New York City or Chicago, you’re not alone. If we haven’t met, I’m Gina, and I’m an aesthetic traveler who’s learned that no two cities make you fall in love quite the same way. While NYC and Chicago have a lot of similarities, their differences will be the deciding factor in which one you choose. Whether you’re looking to visit or move, this post offers insight into the city layout, vibe, food, people, and more. As always, use the Contact Me form at the bottom or message me on Instagram if you have questions!
You could say I’m a frequent flier when it comes to NYC and Chicago. I have been to both cities multiple times and have come to know the ins and outs and develop my own personal likes and dislikes about each one. However, my favorite thing about Chicago and New York are the once-in-a-lifetime experiences I’ve had in each city. In fact, this is my favorite part about visiting a big city in general – anything can happen, and you will almost always walk away with at least one epic story to tell (and to read about some of my best stories, check out my Storyteller section). The question is – will your story take place in New York or Chicago? Let’s find out!
Exploring The City Layout of NYC and Chicago
New York City is technically comprised of 5 boroughs: Manhattan, Brooklyn, Queens, The Bronx, and Staten Island. However, when most people talk about NYC, they’re referring to Manhattan…which is the area I’ll be focusing on in this post. In contrast, Chicago is made up of a large city center surrounded by dozens of suburban neighborhoods.
Chicago and NYC are the 2 of the most urban cities in the United States. IMO, they’re both relatively easy to navigate because they’re laid out in a grid-like fashion. Both cities have skyscrapers, bridges, rivers, and iconic landmarks that help you figure out where you are. One of my favorite things about NYC and Chicago is it’s super easy to walk almost everywhere. Both cities also have extensive public transportation options, the most popular being the subway system.
Navigating New York City
For me, the easiest way to orient myself in NYC is to memorize where the different Manhattan neighborhoods are. When I come to the city, I almost always stay in Midtown because it’s right in the middle. From here, I know that Central Park, Upper East Side, Upper West Side, and 5th Avenue are all north of me. I also know that I can go southwest to get to SoHo, Chelsea, and Greenwich/West Village. I tend not to spend as much time in the southeastern neighborhoods (Lower East Side, East Village, etc) but that’s just me.
- Pro Tip: Many New York neighborhoods get their names from nearby landmarks or street locations. For instance, SoHo stands for South of Houston Street.
A lot of NYC streets and avenues are organized by numbers (5th Ave, 6th Ave, West 34th St, etc) and run perpendicular to each other. The avenues run north-south, and the streets run east-west. Just when you start to think “this is easy!” – many of the streets also have actual names (Park Avenue, Canal Street, etc), and it also varies depending on the neighborhood you’re in. Eventually, I started to get the hang of it and learned which streets were known for what. For example, Greene Street in SoHo is lined with some of the city’s best shopping.
NYC is the largest city in the United States, and it’s even more obvious how large it is when you’re there. Sometimes, walking a block in New York feels like you’re walking half a mile. Don’t get me wrong: I love walking around here. But sometimes, it seems like it takes forever to get anywhere!
In New York, there are nice restaurants, swanky rooftop bars, boutique shops, and rustic cafes that are spread out all over Manhattan. Despite being so walkable, there’s a good chance you will have to take at least a 30 minute subway ride or Uber to the different places you want to go. It’s also entirely possible that you could stumble upon a really chic restaurant or shop that has been placed right in the middle of a random building on a random street that’s not entirely obvious. The takeaway: There are countless places to eat and shop here…it’s just that some are tucked away and easy to miss if you don’t already know where to look.
Taking the Subway in New York City
New York’s subway system is the best in the world. There’s just no comparing it. You are able to take the subway system in New York to get literally anywhere, anytime, 24 hours a day. This is the city that never sleeps, remember?
The Best Iconic Instagram Spots in New York City
But because it’s so extensive, it can also be confusing. There are multiple different trains you can take to get to the same destination. There are also a lot of trains going different places that come through the same station, so it’s easy to accidentally get on the wrong one by mistake. Ask me how I know 🙃. I like using the Citymapper or Transit app when I’m here because they tend to give more reliable information about train cancellations, routes, and wait times.
Navigating Chicago
Chicago is also a huge city, but the way it’s laid out makes it seem less big and intimidating. For starters, a city block in Chicago is shorter than a city block in New York, so I feel like I can walk to places a lot quicker. Many of the bars, restaurants, shops, etc. in the city center are concentrated in the River North/Streeterville/Gold Coast area, which are all right next to each other.
Additionally, many locals would vouch that the West Loop is the new go-to neighborhood, with a ton of shops, bars, and restaurants on Randolph Street and Fulton Market. The West Loop is only a 10 minute Uber ride away from River North, and has become my new favorite place to go out in Chicago.
The “Loop” is Chicago’s business hub in the city center where you’ll find the Riverwalk and many industrial skyscrapers. I often use The Loop to orient myself in the city, similar to how I use Midtown in NYC. Although there are some bars and restaurants here, this part of the city tends to shut down after working hours and can be somewhat desolate. But OMG is it ever beautiful to walk through, especially at night when it’s all lit up:
Outside of the city center, you’ll find some of Chicago’s popular neighborhoods: Lincoln Park, Bucktown, Logan Square, etc. If you have time, I would definitely recommend exploring some of these places just to see how they’re different from the more urban areas. You will need to Uber or take public transportation, since these are far to walk.
To summarize, although Chicago is a huge city, I tend to spend the majority of my time in River North and West Loop. This makes Chicago feel less overwhelming and less stressful to navigate than New York, where I tend to neighborhood-hop more.
Taking the Subway in Chicago
Chicago’s subway system is not quite as extensive as New York’s, but will still get you just about anywhere in the city that you want to go. Locals call it the “L,” short for elevated, because parts of it are above ground. The lines are named after colors (Blue Line, Orange Line, etc). There are also way less different subway trains compared to NYC, making it a simpler system to navigate.
- Pro Tip: When taking the L, I have been told by multiple locals to avoid the Red Line, since this train connects directly to Chicago’s infamously dangerous South Side neighborhoods. However, many popular routes in the city center also involve the Red Line. Use increased caution, especially at night or when the train is less crowded.
The Aesthetics: NYC vs. Chicago
City Aesthetics – New York
One of my favorite things about New York is how it feels like a dozen different worlds packed into one city. You have greenery in Central Park, upscale stores on 5th Avenue, and skyscrapers overlooking the Hudson River. Every neighborhood has its own style, and the more you visit, the more you pick up on what’s visually unique about each one. For instance, you’ll notice designer boutiques and old-time cafe signs in SoHo, whereas brownstones and tree-lined sidewalks make up the Upper West Side. Even the chaos feels curated here; there’s something effortlessly stylish about people rushing through the streets in trench coats and sneakers, coffee in hand.
Of course, I have to highlight the less glamorous side of things too. A lot of people say New York is dirty, and, well…they aren’t wrong. While there’s plenty of trash and graffiti, I like to think it makes the city feel real. NYC is always portrayed as glamorous in the movies, but the real life grunge reminds you this is also a city filled with millions of everyday people just trying to make it in the Big Apple. And besides, the graffiti can serve as an awesome photo backdrop…
City Aesthetics – Chicago
When I think of Chicago, I think of the gorgeous skyscrapers surrounding the Chicago River. In fact, one of the things I always tell people to do when they visit Chi is take an architecture cruise to see the city on the water. In fact…I might think Chicago’s skyline is prettier than NYC’s?? It’s quite the toss-up. A lot of this could be because the city feels wide open compared to New York; you can really take in the view from a lot of different angles.
Chicago is a very clean city for its size, which gives it a more sophisticated feel. This is because it has a lot of alleyways, so people put their trash in the back alleys instead of on the sidewalk. A lot of the buildings have a regal look to them, such as the Drake Hotel, the Wrigley Building, and the Tribune Tower. Neighborhoods like the West Loop and Wicker Park have that cool, creative vibe with exposed brick and string-lit patios, while the downtown area feels polished and powerful.
Comparing The Vibe of NYC vs. Chicago
What’s the Vibe in New York City?
As cliché as it sounds, there is nothing like the vibe of New York City to me. It’s the city of dreams, the city of opportunities, the city where if you can make it here, you can make it anywhere. There’s something for everyone: from arts, design, and entertainment to finance, healthcare, and hospitality. I TRULY feel like I am in a movie scene every time I visit.
NYC has a “swagger” and a confidence unlike any other city I’ve been to. I do love the challenge that it presents, but some find this city’s aggressive hustle culture very intimidating. People are always rushing to get somewhere, cars are always blaring their horns, and absolutely nothing is relaxed. Yes, it can be stressful, but I love it because it means things are happening here. Whenever I walk around NYC, I feel upbeat and energized. It makes me feel like my life could change in an instant (in the best way).
Of course, this intense city vibe also translates to its citizens. Some people say NYC locals can be rude or unfriendly. In a city of millions of people, you’ll likely encounter some rude folks…but I like to say that a lot of people embody the city’s tough, strong confidence. It’s expensive, it’s hectic, it’s chaos, and it’s arguably the hardest city in the world to live in. The locals know this, and wear it like a badge of honor. Call me crazy, but I honestly love people in New York for this reason. I respect the hustle and the dedication that it takes to call this city home. Having said all that, I’m also friends with some NYC natives who are nice, chill, and super friendly. One of the best things about a city this size is you’re sure to find people you vibe with.
What’s the Vibe in Chicago?
TBH, it’s hard for me to put the exact vibe of Chicago into words. While there’s definitely art, culture, and creativity, I don’t get that city-of-dreams feel that I get in NYC. Despite its size and heavy traffic, Chicago has a more relaxed, laid back vibe. That’s not to say it isn’t busy; it definitely is…but I don’t feel like people on the street are rushing to get everywhere. Areas like the Magnificent Mile, Millennium Park, and the Loop will likely be crowded, and other streets come alive after work between 5:00-9:00pm. Overall, you could say the vibe is more local and less tourist. But my biggest takeaway from being here is that Chicago has a very proud energy. You can practically feel the emotions from the Michael Jordan era still lingering as you walk down the sidewalk.
Chicago’s proud, confident energy translates directly to its people. Chicagoans love their city, and they want you to understand why so you can love it just as much. People love telling you about things Chicago is known for, where the best pizza spots are, the coolest neighborhoods to check out, their favorite bar, why you need to go to a Cubs game, etc. Hearing how the locals hyped this place up really won me over when I first visited. Having said all that, there’s a mix of friendliness and grit. I’ve met some of the nicest, coolest people here, but others have an edge that comes from living in a city that’s been through things. Chicago is great, but it’s also a “tough” city, and locals have had to learn to adapt.
The Food Scene in NYC vs. Chicago
Let me preface this section by saying the food in both cities is to die for. I am every bit as obsessed with restaurants in New York as I am restaurants in Chicago. Both places have incredible food staples: Italian restaurants, sushi, and steakhouses…along with other local foods they’re famous for.
Famous Food in NYC
- New York-style pizza – Thin, foldable slices with a crisp crust and classic tomato sauce
- New York-style bagels – Rich and chewy; try one with Lox and cream cheese
- Hot dogs – Especially from street carts or spots like Gray’s Papaya and Nathan’s Famous
- New York cheesecake – Dense, creamy, and typically served plain or with a fruit topping
- Cronut / trendy pastries – NYC is known for starting viral food trends, such as Dominique Ansel’s cronut – a croissant/donut hybrid that is worth every. single. calorie.
- Black and white cookie – Flat, shortbread cookie iced with half chocolate and half vanilla fondant
Famous Food in Chicago
- Deep-dish pizza – Characterized by an extra thick, buttery crust layered with cheese and chunky tomato sauce. 2 of the most popular places to get deep dish pizza are Lou Manalti’s and Giordano’s
- Chicago-style hot dog – “Dragged through the garden” with mustard, relish, onions, tomato slices, sport peppers, a pickle spear, and celery salt (no ketchup allowed!)
- Garrett Popcorn mix – A sweet-and-salty blend of caramel and cheese popcorn
- Jibarito – Puerto Rican sandwich made from sliced and fried plantains, protein, lettuce, mayo, and cheese
- Italian beef sandwich – Try one from Al’s Italian Beef
The Style: How To Dress in NYC vs. Chicago
When I travel, I like to mesh my own personal style with the vibe of the city I’m going to. It almost becomes a creative challenge!
Dressing for New York City
If I could compare my personal style to a city, it would be New York. There’s an equal mix of sophisticated glam and street style, and my outfits usually revolve around one of the two aesthetics. In New York, fashion is a second language. People dress with intention: whether it’s sleek and minimalist in SoHo, edgy and experimental in Brooklyn, or timelessly chic on the Upper East Side. The city thrives on individuality, and even casual outfits tend to look curated. You’ll see neutral tones, structured pieces, and statement accessories that feel effortlessly cool. Personally, there are few things I love more than an all-black ‘fit, and you’ll see more black here than anywhere else.
(but I’ve never met a pop of color I didn’t like)
Now, don’t get me wrong: you’ll also see plenty of people who look a little more casual or thrown together. New York moves fast, and not everyone is stepping out of a Vogue shoot every day. Between commuting, long work hours, and unpredictable weather, practicality sometimes wins out over polish. It’s part of the city’s charm—you get a mix of effortless style and total chaos, often on the same block.
Dressing for Chicago
Again, I’m gonna be honest with you: I can’t quite come up with a word for the overall fashion vibe in Chicago. It’s definitely more laid-back than New York’s…practical, but still polished. In the winter, locals balance fashion with unpredictable weather, dressing in layers and leaning toward cozy, classic pieces that still look put-together. You’ll see tailored coats, denim, knitwear, and lots of boots in the colder months. Summer brings breezy dresses, Cubs caps, and lakefront athleisure. It’s less about making a statement and more about looking stylish in a way that feels approachable and comfortable.
When I visit Chicago, I still tend to dress like I do in New York, because for me the vibe is still “girl in the big city.” But I’ll be honest and say that it’s harder for me to nail down the trends here. Because Chicago doesn’t have the same level of reputation for fashion that New York does, I feel like there’s less pressure to dress a certain way. Having said that, I like the pressure that New York puts on me to level up my style. It’s almost like a personal challenge every time I visit!
How Safe is NYC Compared to Chicago?
In today’s world, “safe” is somewhat of an arbitrary term. To quote one of my best friends, “shit can go down anywhere.” I think the key with any city is knowing where the safe areas are, or more importantly, knowing which areas to avoid.
Safety in New York
As large and intimidating as New York City can be, statistically it’s relatively safe in terms of its size. There are constantly people walking everywhere, so you never really feel like you’re by yourself. This tends to make me feel safer. In terms of which areas to avoid, I have always been told to steer clear of East Harlem. Also, areas that are extra-crowded (Times Square, etc) increase the likelihood for getting pickpocketed, despite being a must-visit.
Safety in Chicago
Chicago has a reputation for being a very UNsafe city, and a lot of this is due to its history of gangs and gang violence. The city has a lot of reported shootings, robberies, and assaults. The main areas to AVOID are the South Side as well as anything further west than the West Loop. Areas like River North, Streeterville, Gold Coast, and the West Loop are reported to be safer. In contrast to New York’s busy streets, some of Chicago’s streets can be desolate, depending on the day and time you’re out and about. While Chicago is statistically more dangerous, it’s important to keep your eyes peeled in both cities.
How Expensive is NYC vs. Chicago?
As you’ve probably guessed, while both cities are expensive, New York is definitely worse. New York is iconic for a reason, but it comes at a cost…literally. Hotels and dining can add up quickly, and even casual meals are often pricier than their Chicago equivalents. On the flip side, Chicago generally gives you more city for your money. Hotels, restaurants, and attractions tend to be noticeably cheaper, so you can still enjoy a big-city experience without the same price tag.
Additionally, both cities have popular attractions you can explore for free. In Chicago, Millennium Park, the lakefront, and Lincoln Park Zoo cost nothing to visit, and same for the Brooklyn Bridge, Central Park, and Grand Central Terminal in NYC. Additionally, major NYC museums such as the Metropolitan Museum of Art, Guggenheim, and Whitney offer free or “pay-what-you-wish” hours on certain days.
If you are reading this post with the idea of moving to either NYC or Chicago, you likely already know rent is pricier in New York. In Chicago, $3,000-4,000 per month will get you a nice apartment with a rooftop pool, gym, doorman, and other amenities. But in New York, you’d likely need to pay at least $6,000/month for all of the above.
What is the Weather Like in NYC vs. Chicago?
Weather in New York
One of my favorite things about New York is that it’s a vibe no matter what season you visit. Spring and fall will bring you comfortable weather, golden light, and fewer crowds. Spring can be rainy, but the flowers in Central Park make up for it. And fall in the city is beautiful. Summers can be hot and humid, and a lot of locals leave and go to the Hamptons or upstate NY. This isn’t to say it’ll be less crowded, but that you’ll likely have to contend with more tourists than residents.
Winter in NYC is cold but magical: think holiday markets, Rockefeller Center, and the city sparkling under twinkling lights. Seriously, if you’ve never been to New York City during Christmastime, put it on your list immediately. (Unless you absolutely despite crowds…then, maybe don’t.) But for the rest of us, walking around NYC at Christmas is an experience you will never regret. Even if it’s chilly, there’s no shortage of indoor attractions to keep you warm.
Weather in Chicago
If you’re a hip-hop loving millennial like me, you’ve likely heard Kanye West rap about Summertime Chi in a few of his songs. The rumors are true: Chicago shines in the summer. The city comes alive with rooftop bars, lakefront festivals, and long days that spill into warm nights by the water. It’s one of the best times to explore the Riverwalk, Navy Pier, or grab drinks with skyline views. When people ask me the best time to visit Chicago, I always say summer. Fall is also gorgeous, with crisp air and colorful parks.
Winters in Chicago are famously brutal, mostly due to the wind chill coming off of the lakes. I lived in Chicago for a month in November, and honestly, the temperatures were bearable. Locals told me the cold typically hits at the end of December and goes through February. I didn’t experience this, so I can’t give my 2 cents…but I completely believe those who tell me winter is a no-go. Interestingly, I’ve had some locals tell me that spring is their least favorite season in Chi. While it’s “supposed to” be warm, a lot of times the colder temperatures linger into May.
Getting To NYC and Chicago
New York City Airports
New York has 3 different airports close to the city: La Guardia, JFK, and Newark (in New Jersey). Having flown into and out of all 3, I prefer La Guardia, but that’s not the point. The point is, you have options. Any time I travel to New York, I love knowing that I can explore all 3 airports to find a relatively cheap flight at a relatively good time.
While you ARE able to take the subway from the airport into the city, this will usually tack on about 10 minutes to your travel time…but of course, it’ll be cheaper than Uber and taxis. Below, I’ve listed the time it takes to travel from each airport to Times Square by car:
- La Guardia: 35-40 minutes
- JFK: 50 minutes
- Newark: 45-50 minutes
Hotel recommendations
Where Should You Stay in New York City?
Anytime anyone asks me for hotel rec’s, I always advise staying in the Midtown area of NYC. This is a central location below Central Park, right near Grand Central Station. Notable hotels I’ve stayed in include Club Quarters Grand Central and Park Terrace Hotel.
Chicago Airports
Chicago has 2 different airports: Midway and O’Hare. O’Hare is usually touted to be the nicer of the 2, but Midway tends to be cheaper, so you can guess which one I’m usually flying into. If you plan on flying internationally, only O’Hare offers direct flights across the pond. Similar to NYC, you are also able to take the subway (or the “L”) into the city. The Blue Line connects to O’Hare, and the Orange Line connects to Midway. Keep in mind, these will take longer but will also be cheaper.
Below is the time it takes to travel from each airport to downtown Chicago (aka The Loop) by car:
- Midway: 25 minutes
- O’Hare: 40 minutes
Hotel Recommendations
Where to Stay in Chicago
- Low Budget: Freehand Chicago
- Mid-range: Residence Inn by Marriott: Magnificent Mile, Allegro Royal Sonesta
- 5 star: The Drake, The Langham Chicago, The Peninsula
