Eating Chicago in 2 Days – Vol. 2

Are you heading to Chicago for just a couple of days on business or for a quick getaway but have no idea where to find the best food and drink?  Don’t worry because I’ve got you covered with my new blog series, Eating Chicago in 2 Days.  I am creating short itineraries of Chicago’s must-visit restaurants, bars, coffee houses and specialty shops which will provide you with diverse culinary tours of this food mecca in the Midwest.  Please enjoy my latest installment of this new blog series about Chicago’s food scene which is easily accessible via our local trains and buses.  Ditch your car and let’s go Feeding Off The Rails! 


Day 1 – Eating Chicago in 2 Days – Vol. 2


Forget chain coffee shops such as Starbucks or Dunkin’ Donuts.  I have nothing against them but

Chicago has a tremendous coffee culture with many charming spots where you can fuel your day.  Check out Toni Patisserie in The Loop for your morning coffee, tea, and breakfast treat.  This stylish bakery will transport you to France even though it’s just steps from Michigan Avenue. – 65 E. Washington St. (Take the Orange, Brown, Green Purple or Pink Lines to the Washington/Wabash ‘L’ stop)


You can read more about the 30 Coolest Chicago Coffee Spots HERE on the blog.



Eating Chicago in 2 days Coolest Chicago Coffee Spots Toni Pastisserie in Chicago

Flattery or insult with my coffee?



When you’re ready for some lunch in a setting with a British vibe, head to Pilsen and stop into Pleasant House Pub.  I love this place!  The owners have their own farm and they even mill their own grains for the bread they make.  However, the English pot pies are what you want here.  Choose from steak and ale, mushroom and kale or the curry chicken balti pies.  Split one of the fresh salads and order a craft beer. – 2119 S. Halsted (Take the #8 Halsted bus. Transfer available at the Halsted ‘L’ stop on the Orange Line.)




Eating Chicago in 2 Days Chicago Bakeries Hibiscus tea at Pleasant House Pub in Pilsen




If you are looking for something sweet after lunch, walk a few blocks north to Kristoffer’s Bakery and get the super moist tres leches cake which comes in a few flavors including Kahlua, coconut, and caramel.  The chocoflan is also amazing.  Kristoffer’s Bakery sells its tres leches cakes to other several restaurants in Chicago but you can buy it by the slice or get a cake to take home.  Even celebrity chef, Rick Bayliss (Topolobambo, Frontera Grill, Xoxo) sings the praises of this Pilsen bakery. – 1733 S. Halsted St. (Take the #8 Halsted bus.  Transfer is available at the Halsted ‘L’ stop on the Orange Line.)




Eating Chicago in 2 Days Chicago Bakeries Coolest Chicago Coffee Kristoffer's Bakery tres leches cake

Caramel tres leches cake a Kristoffer’s Bakery



Read more about the Sensational Chicago Bakeries That Will Make You Drool



Later on, continue eating Chicago in 2 days with a ride to Uptown Pho in the Uptown neighborhood.  This Vietnamese restaurant is part of the section in Chicago’s north side known as “Asia On Argyle.”  The food here is bright, fresh and comforting. – 1010 W. Argyle St. (Take the Red Line to the Argyle ‘L’ stop).




Eating Chicago in 2 days Tofu and veggie pho at Uptown Pho

Super fresh tofu and veggie pho!



After dinner, walk a few blocks over to Green Mill Cocktail Lounge which was an old haunt of Al Capone.  The rich history here is truly haunting as you can sit in the same booth as the legendary mob boss!  Stay for the cocktails and nightly jazz acts.  Green Mill is where the original poetry slam began and It takes place on Sunday nights.  Go check it out!  – 4802 N. Broadway (Take the Red Line to the Lawrence ‘L’ stop.)




Eating Chicago in 2 days Green Mill Lounge in Uptown

Historic speakeasy and Al Capone hangout, Green Mill Lounge


Day 2 – Eating Chicago in 2 Days – Vol. 2



Perhaps you are in Chicago for a convention at the McCormick Convention Center.  You may even be staying at the Hyatt McCormick Place.  I understand that those conventions can be long days and you may want to keep your dining options close by for the sake of time.  Enjoy a taste of New Orleans with some chicory coffee, pralines, and beignets at Akhira Praline Candy & Coffee House in the South Loop.  The owners are super friendly and great jazz and Cajun tunes fill the air.  – 1845 S. State St. (Take the #21 Cermak bus or the Green Line to the Cermak/McCormick Place ‘L’ stop)




Eating Chicago in 2 Days Ahkirah's Praline in the South Loop in Chicago

A taste of New Orleans at Akhirah’s Praline Candy and Coffee House



Eating in Chicago is as diverse as the American landscape and there are several wonderful Southern restaurants from which choose.  One of my favorite establishments for a taste of soul food is Pearl’s Place Restaurant in Bronzeville.  The fried green tomatoes, sweet potato pie, and shrimp ‘n grits are to die for!  You can order food off of the menu or choose the buffet which is a great bang for your buck! – 3901 S. Michigan Ave. (Take the Green Line to the Indiana ‘L’ stop or Take the #4 Cottage Grove bus to Indiana and 35th St.).




Eating Chicago in 2 Days Southern food in Chicago Chicago comfort foods Pearl's Place Restaurant fried green tomatoes best restaurants of 2017

The crunchy and juicy fried green tomatoes at Pearl’s Place Restaurant in Chicago




Eating Chicago in 2 Days Southern food in Chicago comfort foods Pearl's Place Restaurant shrimp 'n grits

Creamy shrimp ‘n cheesy grits at Pearls’ Place Restaurant in Chicago



Hyde Park is home to the University of Chicago, the Obamas, and Muhammad Ali to name a few famous folks.  And this south side neighborhood also has some delicious places to eat such as Ja’ Grill which specialize in Jamaican cuisine.  Enjoy some jerk and curry cuisine while sipping on some tropical drinks.  The atmosphere at this spicy place is colorful, warm with an island vibe.  DJs spin tunes in the evenings. – 1510 E. Harpur Ct. (Take the Red or Green Lines to Garfield and transfer to the #55 Garfield Bus)




Eating Chicago in 2 Days Ja' Grill in Hyde Park

I need to come back for some DJ spins very soon




Eating Chicago in 2 Days Ja' Grill menu

Jerk shrimp entree with cabbage-carrot escabeche and rice & beans



If you’re still ready to continue Eating Chicago after your Jamaican dinner, head north to Simone’s in Pilsen for a craft beer or cocktail in the lively restaurant/bar with DJs spinning groovy tunes karaoke and burlesque shows.  – 960 W. 18th St. (Take the #8 Halsted bus and #18 Indiana buses) 




Eating Chicago in 2 Days Simone's

Simone’s in Chicago’s Pilsen neighborhood



If you missed my first installment of Eating Chicago in 2 Days – Vol. 1, check it out.

In keeping with the spirit of Feeding Off The Rails, I encourage you to leave your car at home and ride the CTA trains and buses as you begin Eating Chicago in 2 Days.  Save on gas. Avoid traffic, road rage and parking.  Reduce pollution. Don’t drink and drive!