top of page
me hiking in colter bay close up.jpeg

Hi, I'm Georgina! A coffee-loving adventure enthusiast here to share my favorite travel tips with you! My goal is to inspire others to get out and explore this wild planet by camping, hiking, or wandering around a fun new city!

Travel Resources & a Free Planner

Join our newsletter to receive the 3 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf! Bi-weekly travel tips 🙂

Free Travel Planner Printable!

Travel Planner Preview.png

Grab your FREE travel planner printable below and get planning your next trip with Alpacka My Bags!

  • Georgina D'Angelo

Chicago vs New York: Plan an Epic City Trip

Updated: Jan 29

The United States is a popular travel destination for people from all over the world, even for those who live in the country. There are so many incredible places to visit here, two of the most popular places being Chicago and New York City. And with good reason!

These two big cities are both worth visiting, so how do you choose where to plan your trip when it comes down to Chicago vs New York? Each has so much to offer, from a wide array of activities for every type of travel style, food options from all around the world, and city views on every block.

Plan a City Trip - Chicago vs New York

New York is famous for its Broadway Theater, Statue of Liberty, unreal cuisine options, and bustling Times Square. Miles away, Chicago is known for its architectural styles, lakefront views, variety of food options, and iconic neighborhoods.

Picking which city to visit might be a tough choice, I totally agree. It would be hard to pick if you could only visit one, so let’s dive into Chicago vs New York so you can narrow it down and plan your own trip!

Disclosure: This article may contain affiliate links, meaning we get a small commission at no extra cost to you if you make a purchase through one of them. Read our affiliate disclosure.

In this article...

New York vs Chicago - Manhattan Bridge
Manhattan Bridge - New York City

Location: New York vs Chicago

One of the most important things to take into consideration when picking between Chicago vs New York is location. Where is each city geographically located in the United States?

The good news is that because both are very large cities, they both have great international airports to fly into. Meaning, flights to both cities will generally be around the same price, but obviously, you might be able to find a great deal to one of them from your home airport.

My favorite flight-finding resources are and Google Flights. Take a look at flights and compare prices for both cities. This might be a good starting point for you.

Chicago vs New York - Buckingham Fountain
Buckingham Fountain - Chicago

Chicago is in the Midwest US, in Northern Illinois situated right on the edge of Lake Michigan. New York City is located on the east coast, not quite as far north as Chicago, but right next to the Atlantic Ocean.

Five boroughs famously make up New York City, the Bronx, Brooklyn, Manhattan, Queens, and Staten Island. In each borough, you will find smaller neighborhoods, each with its own unique vibe and local feel.

In Chicago, many different neighborhoods complete the diverse city. You have luxury neighborhoods like Lincoln Park and River North, quirky ones like Wicker Park and Boystown, and bustling ones like the Loop and Lakeview.

Population and Size

New York is the largest city in the US with a population of over 8.4 million people. Chicago sits as the third largest US city with a population of nearly 2.7 million people. While NYC has a larger population, it is not as proportionately big in land size, making it more densely populated than Chicago.

Because it is larger than Chicago, New York is a little bit busier. But this doesn’t make it more daunting. It is super easy to get around if you utilize public transportation. And it just means there is more to see and do!

Being slightly smaller, Chicago is more laid back than New York. This often attracts travelers visiting with kids or larger families. There is still so much to see and do here, you truly couldn’t run out of fun things to do in Chicago.


New York vs Chicago - Transportation
Penn Station - NYC

The great part about being huge cities is the reliable public transportation you’ll find in both Chicago and New York. You can easily visit both places without renting a car which will save you money.

You will also find taxis and rideshare options like Uber in both cities, but these will be more expensive. If you plan on utilizing public transportation, make sure you have a tap credit card, and you’ll be good to go.

This is essentially your train and bus ticket. In Chicago, you can also buy longer-term tickets, such as 24-hour tickets, that have unlimited rides for that amount of time. If you’re staying for multiple days, a longer-term ticket might be a better option.

History and Culture

Both New York and Chicago have been popular travel destinations for quite some time. While both are very large cities, NYC is bigger than Chicago. Each city has its own unique history, making for different experiences in both cities.

New York City Vibes
NYC Vibes

New York began growing into the city it is today by being the main entrance city for immigrants entering the United States, mainly from Europe. Because it is situated right on the coast, ships were able to dock here allowing for more people to enter the city. This is where the famous Ellis Island is located.

Today, NYC is popular for those seeking a fast-paced, ever-changing vibe. It is known for the arts, high-end hotels, nightlife, museums, restaurants, and shopping.

Chicago began growing later than New York, when westward expansion started in the US and railroads were built around the Midwest. Chicago also became a trading hub with Canada as it is located next to Lake Michigan which connects to Canada.

Chicago vs New York - Lake Michigan
Lake Michigan - Chicago

While Chicago is a little more laid back, it is still a very busy city, but you’ll find many quiet neighborhoods, family-oriented restaurants, and more relaxed atmospheres just outside of downtown. But downtown, or the Loop, is only a train ride away and offers all the nightlife, sightseeing, shopping, and vibrance you could want.

What to Do: Chicago vs New York

Each with a unique history, these two famous cities offer a variety of fun things to do. From sightseeing to museums, trying new foods to watching a show, there is no shortage of activities in either place.

Chicago vs New York - WNDR Museum
WNDR Museum - Chicago

You’ve got the Statue of Liberty, Broadway, Empire State Building, Chelsea Market, etc. in New York City. In Chicago, there’s Navy Pier, lakefront beaches, the Willis Tower, the Bean, etc.

Wherever you decide to visit, there will be plenty of activities to enjoy, sights to see, and food to eat. Being two of the most populated and popular cities in the US, Chicago and NYC have entertainment down pat.

New York vs Chicago
Walking the High Line - New York

If you’ve never been, however, there are some things every first-time visitor has to do in each city. Check out my top picks below.

Food and Dining

If you’re a foodie who loves trying new foods, you can’t go wrong with either city. When it comes to Chicago vs New York for best restaurants, I’d say they’re neck in neck. The options are endless in both cities; you won’t be disappointed.

This also goes for picky eaters. Because there are so many options, you’ll be able to find something you like in either city! Food halls are great options too as they’re one building with multiple restaurants to choose from. And you can usually have a nice sit-down meal at them.

Birthday Cake Bagel - New York
Birthday Cake Bagel - New York

The food is still delicious, and you can try multiple restaurants with ease. Just order what you want from each place, and there you go.

A couple of my favorite food halls are:

Chicago: TimeOut and Aster Hall

New York: Urban Space W 52nd and Chelsea Market

Chicago vs New York - Restaurants
Time Out Market - Chicago

Chicago vs New York Pizza

If you didn’t know already, pizza is a staple in both New York and Chicago. You have the thin crust, large slices that’s the famous New York style pizza, and Chicago is known for its deep dish pizzas. The Chicago vs New York pizza feud runs deep, and most people are very particular about their favorite.

Chicago Pizza: Known for deep dish style pizza, but you’ll find thin crust options too. The best pizzerias here are Lou Malnati’s and Giordano’s. You’ll find plenty of others, but these are the best two in my opinion.

Chicago vs New York Pizza
Chicago Deep Dish

New York Pizza: Giant slices of thin-crust pizza is the famous New York style pizza. You can find all kinds of topping options, and can also buy a whole pizza if you’re feeling like it. They’re just generally gigantic. Head to Joe’s Pizza Broadway for the best.

Chicago vs New York Pizza
New York Style Giant Slices

Have you tried either Chicago or New York pizza?


This might be a very important factor for you. While they’re both up north and get cold, these two cities have slightly different climates.

New York is located on the northeast coast, bringing in cold winters and hot, humid summers. It generally doesn’t drop below freezing for too long in New York, with the coldest temperatures occurring in January and February.

Chicago in Winter
Chicago in Winter

Chicago is further inland and right next to Lake Michigan. Winters are quite harsh here, but gorgeous when there’s freshly fallen snow blanketing the already pretty city. Summers in Chicago are perfect, with temperatures generally staying in the 70s and low 80s (°F).

Best Time to Visit: Chicago vs New York

Along with the weather, the best time to visit each depends on what you’re wanting to do. This might also affect where you visit if you have set vacation dates.

New York is great to visit any time of year, but if you want to enjoy more outdoor activities, like bike riding in Central Park, I recommend visiting NYC in May or September. The weather is cool, but not cold, and the crowds are much smaller than in the middle of summer.

New York vs Chicago
New York in February - Not Too Freezing

But the fall is also a really nice time to visit New York. The foliage is very pretty here, and there are tons of parks around the city to enjoy the turning of the leaves in the fall.

I love Chicago every time of year, but winters can be bitterly cold here. However, the holiday season is a very fun time to visit Chicago. There are many fun things to do in Chicago in December that make the cold worth it.

But if you’re not a fan of this, I recommend visiting Chicago in the summer, from June through August. It’s such a gorgeous time of year in the city, and you can comfortably enjoy walking around downtown and some of the best neighborhoods, as well as relaxing on a lakefront beach.

Chicago vs New York
Summer in Chicago

Spring and fall are great options too, as the crowds will be smaller. The weather is cooler, and slightly rainier these times of the year, but it’s still pleasant enough for enjoying time outdoors.


This doesn’t have to be a stressful part of your vacation planning anymore! Packing for a trip can be difficult because the weather is often unpredictable. So I’m here to help.

My tried and true packing tips and travel essentials are:

  • Layers - It’s better to have some warmer layers you can take on and off than to be freezing. Being northern cities, the evenings will be chilly even in the summer.

  • Packing cubes - You can fit much more in a small bag with compression packing cubes.

  • Mix and Match Outfits - Pack tops and bottoms that match with each other so you can have multiple outfits without bringing your whole wardrobe with you.

  • Rain Jacket or Compact Umbrella - Always, always, always bring one with you. Then the unpredictable rain can’t interfere with your adventures!

  • Sunglasses - Just like a rain jacket, I don’t recommend going on any trip without a pair of sunglasses. They hardly take up any space either.

  • Comfortable Walking Shoes - These are big cities, and there is a ton to see. So pack your most comfortable walking shoes and get ready for all-day exploring.

  • Sunscreen - A small bottle of face sunscreen is a must for me. If you’re going to be outside a lot, this is always a good idea. Protect your skin!

If you’re visiting New York or Chicago in the winter, you will definitely want a winter coat with you. Northern winters are no joke. In the summer you should be comfortable in shorts, dresses, tank tops, etc. If you choose to visit the Windy City, I have a detailed packing list for what to wear in every season in Chicago.

Chicago vs New York - Packing
Winter in Chicago

You will find all kinds of fashion styles and trends in both cities, so don’t worry about following certain clothing customs. This is one of my favorite parts about these cities, everyone’s just going on and living their own lives! So wear what you please, just pay attention to the weather.

Trip Cost: Chicago vs New York

Because these are popular US cities, costs are going to accumulate. Overall, Chicago will most likely be slightly cheaper than New York. You can find slightly more budget-friendly accommodation in Chicago, but if you’re looking for luxury, you can find high-end hotels in both cities. Splurging on a Times Square hotel in New York is amazing and so worth it.

Transportation costs are about the same; NYC averages about $2.75 per ride and Chicago at about $2.50. Food will be about the same depending on what you choose to eat. You can find expensive high-end restaurants in both cities, as well as mom-and-pop restaurants with much cheaper, yet still delicious, options.

New York City Brooklyn Bridge
Brooklyn Bridge - New York City

While in general, New York is slightly more expensive than Chicago, the cost of your trip will come down to what you want to spend. You can stay at a luxury hotel or a budget Airbnb. You can dine in only high-end restaurants or you can save money and find cheaper spots or even cook some meals in your accommodation.

It is possible to plan a luxury trip, a budget trip, or anywhere in between to either New York or Chicago.

How do you choose: New York vs Chicago?

I truly believe both Chicago and New York are well worth visiting. Each city is unique with its own feel, local finds, famous monuments, delicious restaurants, and fun experiences. So how do you choose when it comes to planning a trip to Chicago vs New York?

I recommend starting by looking at flights from your home airport. You might find a great flight deal to one of these cities that will automatically help you decide. If that’s not the case, take into consideration the other Chicago vs New York factors.

Are you wanting to experience a world-renowned theater experience at a Broadway show in New York? Do you enjoy museums and architecture that you can find plenty of in Chicago?

If you’re having a tough time picking, I recommend visiting Chicago first. It is slightly smaller and easier to navigate, especially if you’re not used to the hustle and bustle of a large city. In total, it can easily be cheaper, yet there’s no shortage of fun to be had here.

The Bean Chicago
The Bean - Chicago

Maybe the Chicago vs New York Pizza will be a deciding factor. Or the time of year you are able to travel will help you decide. Wherever you decide to go, don’t discount the other city. Try to plan a future trip there!

There is so much to see, do, eat, and experience in both Chicago and New York, I promise you, you don’t want to miss out on either.

You might also like to read:

Save this for later!

Chicago vs New York | Alpacka My Bags - Pinterest Cover


Post: Blog2_Post

Ready To Book Your Trip...

Planning a vacation can be time-consuming and a little overwhelming. To help smooth this process for you, we've compiled our favorite travel planning resources.

From finding the best flights and hotels to the essentials you need to make the most of your trip, check out the Alpacka My Bags travel resources page.

Travel Resources & a Free Planner

Join our newsletter to receive the 3 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf! Bi-weekly travel tips 🙂 

me hehe Large.jpeg


Hi, I'm Georgina, adventure enthusiast and creator of Alpacka My Bags. I'm here for all of your travel and adventure planning needs! 


I've been exploring this beautiful planet since I was a child, so I decided it was time to share my travel tips with others to enjoy. After college, I knew the "traditional career path" was not for me.


I needed to travel and explore what this world has to offer. It sounds cliché but you do only live once. So I made going on adventures a priority, and soon realized that I wanted to share them with others so you can enjoy them too! 

My passion is spreading the travel bug and showing others that travel is attainable and so worth it. From itineraries to camping tips to packing lists, Alpacka My Bags has you covered!

Join me, and often my partner and my dog, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as I have, I hope you find my tips useful for all of your future travels.

bottom of page