6 Things For Homesick Chicagoans To Do In NYC

Devin Booth

Moving from the Windy City to the Big Apple can be a difficult adjustment, and feelings of nostalgia are bound to come up. Are you longing for the days when you could walk on garbage-free sidewalks, bike along the lakefront, or eat as many Chicago dogs as you want? Don’t fret, we present six things to do and see in New York City that will transport you back home.

Hudson River Sunset V

Manhattan Waterfront Greenway

Are you missing the refreshing feel of Lake Michigan’s breeze when walking along the lakefront? No worries, NYC offers that same relaxing calm that only large bodies of water can bring you. The Hudson River Greenway stretches 11 miles, starting beneath the George Washington Bridge and continuing to Battery Park in Manhattan’s southern-most point. You can bike, jog or walk along the Hudson River and take in the gorgeous view. For the East siders, the East River Bikeway offers a similar, albeit shorter bike and running path along the East River, with a particularly quaint section from Governor’s Island Ferry Terminal to East 63rd street. Although the Hudson and East Rivers are no Lake Michigan, these walking paths can revitalize a homesick Chicagoan in need of some peaceful, scenic beauty.

the dog

2. Brooklyn


When Manhattan’s densely-packed skyscrapers and cutthroat, fast-paced energy becomes overwhelming, take a quick subway ride across the river to Brooklyn. In many parts of the borough, a Chicago-like vibe permeates the streets. Brooklyn has a slower pace, more locally-owned establishments and a friendlier vibe. The neighborhood of Williamsburg parallels Chicago’s Wicker Park/Logan Square area, with hipsters omnipresent, unique restaurants and bars as well as artsy coffee shops. Other Brooklyn neighborhoods such as DUMBO, Bushwick and Clinton Hill also share similarities with Chicago.

Brooklyn, NY, USA

Potbelly Sandwich Shop

Chicago’s original toasted sandwich shop, Potbelly, has now opened over 15 locations, scattered throughout Manhattan. One bite of a hot ‘wreck’ or ‘pizza sandwich’ will evoke all of those warm memories from your first Potbelly experience. Tasting Potbelly’s homemade oatmeal chocolate chip cookies will transport you back to Lincoln Avenue.

Potbelly Sandwich Shop, 150 East 44th Street, New York, NY, USA +1 646 289 4202

3. Chicago Sports Bars

Pub, Pub Grub

Central Park NYC Winter
© Tobias Schreiber/Flickr
It always helps to meet and surround yourself with other Chicagoans if you’re homesick, especially while watching Chicago sports. Sports bars include Overlook, Triona’s, The Gael Pub and Tavern on Third. Strewn throughout New York City, these Chicago sports bars will make you feel right at home as you cheer and cry with the Bears, Blackhawks, Bulls, Black Sox and Cubs.

Brutal New York City Winters

Cold is pretty much a guarantee once winter hits in New York City. Snow storms and freezing temperatures are sure to give you flashbacks to the bone-chilling days of trying to survive in ‘Chibera’ – perhaps then you’ll take solace in not being in Chicago anymore.

landscape with balloons floating in the air


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