15 Reasons You Should Visit Chicago over New York City

Lake Michigan provides Chicagoan with 24 unique beaches.
Lake Michigan provides Chicagoan with 24 unique beaches. | © Roman Boed / Flickr
Photo of Sarah Ashley
3 May 2018

As two of the three largest urban destinations in the United States, Chicago and New York City often find themselves competing against one another for tourists. Los Angeles gets off easy, basking in a sunny category of its own. Both the Windy City and the Big Apple offer visitors tall buildings, tons of culture, and rich history. But, for anyone on the fence, these are 15 reasons traveling to Chicago is your best bet.

More accessible airports

Getting to the city from Midway and O’Hare airports is as easy as pie. The Orange Line L train runs directly from Midway through downtown; the Blue Line takes passengers from O’Hare to the Loop and western neighborhoods. Tourists can hop off near their hotels or transfer to different L lines (for a $0.25 transfer fee), continuing on to neighborhoods around the city. It typically takes 45 minutes to an hour and a half to arrive at your destination from either airport. In comparison, the easiest method out of JFK or LaGuardia in New York requires tracking down a city bus on the street and transferring to a subway line. Expect travel on the New York side to take up to two hours, unless you shell out $50 for a taxi.

The Chicago Transit Authority runs L trains and busses throughout the city and neighboring suburbs. | © FTSKfan / WikiCommons

Cheaper public transportation

Speaking of the L, a single ride is $2.50 on the Chicago Transit Authority (CTA), versus $2.75 via the Metropolitan Transportation Authority (MTA) in New York. In addition, the CTA offers 1-day ($10), 3-day ($20) and 7-day ($28) unlimited ride passes. The MTA only offers a 7-day option ($32), which makes a single weekend on their subway $12 more expensive than Chicago’s.

More intuitive trains and buses

Chicago and New York love their superlatives. New York City is the biggest city in the country. Chicago has the world’s largest Tiffany glass dome. One superlative that doesn’t bode well for travelers? New York’s MTA is the most complicated transportation system in the world. Researchers at the University of Oxford and the French Atomic Energy Commission studied navigation maps from major hubs around the globe. They found the second most complicated to be Paris’ Metro, which was still about half as tricky to navigate as the MTA.

Forbidding trash bags on Chicago sidewalks allows more room for pedestrians and flowers. | © Center for Neighborhood Technology / Flickr

Less trash lining the streets

New York is notorious for its trash production, displays, and smells. Unlike Chicago, where trash goes into alleyway dumpsters behind businesses and homes, New Yorkers pile their garbage up along sidewalks throughout the city. Consider the stench part of the Big Apple experience – or just come to Chicago where breathing in doesn’t feel hazardous to your health!

Plenty of public restrooms

One thing travelers may not research ahead of time is the frequency and state of a city’s public restrooms. New Yorkers themselves advise against using public toilets, if there’s even one around. Businesses in both areas certainly limit bathroom use to customers only, but Chicago’s public restrooms are often cleaner and more widely available.

The burgers at Small Cheval alone are worth the trip to Chicago. | © Lou Stejskal / Flickr

Best burger in the country

In 2012, Bon Appetit declared Au Cheval’s burger the best in the nation. Since then, the restaurant has opened two additional locations dubbed Small Cheval that serve nothing but their signature hamburgers, cheeseburgers, fries, and shakes. Can’t bear to eat anything other than New York’s infamous Shake Shack burger? No problem – there are three locations in Chicago, too.

More pizza options

Not only does Chicago serve its signature deep-dish pizza, it also offers Quad Cities-style pies. Never heard of Quad Cities-style pizza? Check out Roots Handmade Pizza in Lincoln Square and West Town. The Quad Cities is an area in western Illinois and eastern Iowa, made up of five different towns that all connect where the Mississippi and Rock rivers meet. The pizza crust here is made with dark roasted malt, which makes for a chewier, sweeter pizza. It’s sliced with scissors into thin strips before serving.

Oak Street Beach offers up hot, sandy fun with a towering backdrop. | © Steven Kevil / WikiCommons

Chicago has beaches

Yes, New Yorkers can see the ocean from their windows. But, Chicagoans can actually go to the beach during the summer without venturing out of town. Chicago’s 28 miles of shoreline offer visitors a huge expanse to choose from when debating which beach to visit. Oak Street Beach with the towering skyline in the background or North Avenue Beach with volleyball nets? South Shore Beach behind the South Shore Cultural Center or Montrose Avenue Beach where visitors can bring dogs? Luckily, there’s no bad choice and tons of lake to swim in.

Chicago birthed the skyscraper

After the infamous fire of 1871 that destroyed 17,500 buildings in Chicago, the city wasted no time in rebuilding itself. Up until the 1880s, buildings taller than five stories were unheard of. Architect William Le Baron Jenney wanted to change that. Jenney designed the Home Insurance Company building, a 10-story structure on the corner of Adams and LaSalle Streets in downtown Chicago. Completed in 1884, it was the world’s first skyscraper and an architectural feat. Yes, New York now has Chicago beat in the skyscraper category, with taller, more numerous buildings. But Chicago’s where it all started.

Wrigley Field, built in 1914, is one of the most iconic baseball fields in the country. | © Rex Hammock / Flickr

Older baseball stadium

Wrigley Field is one of the oldest baseball stadiums in the country (the only one older is Fenway Park in Boston). The park opened in 1914 and has seen over 100 years of baseball. It’s also one of the last MLB parks using a hand-turned scoreboard. Since the Chicago Cubs won the 2016 World Series, breaking a 108-year curse, the area around Wrigley Field has blossomed. Visitors will not only get a taste of rich Chicago and American history, they can also bask in the new amenities, restaurants, and activities around Wrigleyville.

Best impressionist collection outside Paris

The Art Institute of Chicago boasts the most expansive, revered collection of impressionist paintings outside the Musée D’Orsay in Paris. The museum houses more than 30 paintings by Claude Monet including several Haystacks and Water Lilies works. Art lovers who aren’t able to make it across the pond to France can also check out Pierre-Auguste Renoir’s Two Sisters (On the Terrace), an iconic representation of 19th-century impressionism.

Kinky Boots got its start in Chicago before hitting Broadway. | © Broadway Tour / Flickr

See hits before they hit Broadway

Directors often select Chicago as a perfect location to debut new musicals, before sending shows to Broadway. Chances are, catching a show in the Loop’s theater district will be much easier on your wallet than waiting to see the same performances in New York several months down the road. For example, Kinky Boots started in the Windy City and went on to win the Tony Award for Best New Musical during its run in the Big Apple.

Touch the Great Pyramid

Tribune Tower on Michigan Avenue is the only place on the planet where tourists can get a taste of the Great Pyramids, Abraham Lincoln’s Tomb, the Great Wall of China, the Taj Mahal, and the Parthenon all in one sitting. Sections of rock from each of these (and more!) famous sites around the world have been folded into the building’s structure on the lower levels, with labels, allowing tourists to touch and admire many histories at once.

Lincoln Park Zoo is free to the public year-round. | © chascarper / WikiCommons

A zoo that is always free

The Lincoln Park Zoo in Chicago is free every day of the week. Sure, New York’s Bronx Zoo offers free hours sporadically, but why work around someone else’s schedule? Tourists and residents alike flock to the Lincoln Park Zoo every week to see animals from the world over, without paying a dime.

Quantity and quality

New Yorkers know there are pros and cons to living in the largest city in the U.S. One thing is clear though: it’s easier for tourists to see more great stuff in Chicago in a shorter amount of time. Chicago isn’t as sprawling as New York, so travelers on a budget (both financially and time-wise) can see and do more in a few days in the Windy City than they could in the Big Apple. World-class museums, Michelin-star restaurants, diverse neighborhoods, and rich history exist in both places – why not get more bang for your buck in the Midwest?

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